Wander Freely, Plan Smartly

The Tailored 14-Days Adventure Itinerary to Italy in September (for couples)

Imagine embarking on a journey where every heartbeat echoes the timeless romance and vibrant spirit of Italy—where ancient stones hold whispered secrets of empires past, sun-dappled vineyards invite you to savor life’s simple pleasures, and cobalt seas sparkle under endless September skies. This is not just a trip; it’s a passage into a world rich with art, adventure, and intimate moments that kindle the soul. From the thrill of exploring grand ruins steeped in legend to the quiet magic of a gondola gliding through Venice’s serene canals at twilight, each day unfolds like a love letter to discovery and connection. Picture yourselves wandering hand in hand along winding cobblestone streets, breathing in the aroma of fresh espresso and Tuscan herbs, feeling the warm embrace of golden sunlight on your skin, and sharing laughter over glasses of Chianti beneath a vast expanse of stars. This 14-day adventure will transform the familiar into the extraordinary, inviting you to lose yourself in breathtaking landscapes, vibrant cultures, and the tender moments that await beyond every corner. Together, you’ll create memories etched in time—stories to carry home as cherished treasures long after the journey ends.

Why You'll Love This Trip

  • Experience Italy’s rich history and vibrant culture in a deeply immersive and adventurous way that connects you both to the past and present.
  • Savor the romance of intimate moments shared on sunlit Tuscan hills, tranquil Venetian canals, and the breathtaking Amalfi coastline.
  • Feel the thrill of exploring iconic landmarks like the Colosseum and Pompeii alongside hidden gems and charming medieval villages.
  • Relish the sensory delights of authentic Italian cuisine, wine tastings amidst rolling vineyards, and lively street markets pulsating with local life.
  • Bask in the warm, welcoming embrace of September’s perfect climate—balancing sunny days and cool evenings ideal for exploration and relaxation.
  • Craft a shared story filled with awe-inspiring moments, heartfelt connection, and the transformative spirit of Italy’s enduring allure.

Your Trip Map

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Your Journey

1
Main activity for day 1

Roman Beginnings and Ancient Marvels

Dive straight into the heart of Italy's ancient empire as you wander the timeless streets of Rome. Feel the powerful pulse of history beneath your feet while exploring legendary ruins and grand piazzas, where each stone whispers stories of gladiators, emperors, and Roman gods. The vibrant atmosphere of September’s mild climate blends seamlessly with Rome's grandeur, inviting you to savor every moment of your first Italian adventure.

Begin your Italian adventure by immersing yourself in the iconic grandeur of the , where the light of early September casts a warm glow over the ancient stone arches. Wander through the amphitheater’s labyrinth of passageways, imagining the roar of the crowds and the fierce spectacle of gladiatorial battles; the air vibrates with a sense of monumental history. Take advantage of the early morning to avoid the crowds, and pause to admire views of the surrounding Palatine Hill from the upper tiers. From there, easily stroll to the adjacent , where the remnants of temples, basilicas, and public squares draw you into the political and social vigor of ancient Rome. Surrounded by olive trees and the gentle hum of the city, let your mind wander to the bustling marketplaces and triumphal processions that once animated this space. Conclude your explorations at Piazza Venezia, gazing up at the dazzling Vittoriano Monument, whose marble façade gleams under the afternoon sun and offers sweeping views of the city rooftops. This day is the perfect blend of awe-inspiring ruins and vibrant urban life, setting an adventurous tone for the journey ahead.

Where to Stay
Accommodation
Hotel Palazzo Manfredi – Small Luxury Hotels of The World
Full starFull starFull starFull starEmpty star
4.3
(Very Good)

A luxury hotel directly overlooking the Colosseum, providing stunning views and immediate access to the key ancient sites, perfect for adventure travelers eager to immerse themselves in Roman history.

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Highlights of the day
Top Sight
Colosseum
This is a highlight of your day—an experience designed to immerse you in the local culture and create lasting memories during your trip.
Top Sight
Roman Forum
This is a highlight of your day—an experience designed to immerse you in the local culture and create lasting memories during your trip.
Top Sight
Piazza Venezia and Vittoriano Monument
This is a highlight of your day—an experience designed to immerse you in the local culture and create lasting memories during your trip.
Where to Eat
Top Restaurant
Trattoria Luzzi Rome
Located just a 10-minute walk from the Colosseum and Roman Forum, Trattoria Luzzi offers authentic Roman cuisine in a lively, casual setting perfect for adventurous couples eager to savor classic dishes like carbonara and cacio e pepe after a day exploring ancient Rome’s iconic landmarks.
Located just a 10-minute walk from the Colosseum and Roman Forum, Trattoria Luzzi offers authentic Roman cuisine in a lively, casual setting perfect for adventurous couples eager to savor classic dishes like carbonara and cacio e pepe after a day exploring ancient Rome’s iconic landmarks.
Bookable Activities
Bookable Activity
Rome: VIP Colosseum & Ancient Rome Small Group Tour
Full starFull starFull starFull starHalf star
4.7
(150 reviews)
Clock icon3 hours
$75.96per person

Get the most out of the Colosseum, Palatine Hill and Roman Forum with the VIP Small Group Tour, allowing you to visit the most important areas of Ancient Rome with your guide and group of maximum 12 people. Enter the Amphitheater and explore the first and second levels, learning about its structure, engineering, history, and functions. After visiting the Colosseum you will enter the Palatine Hill and Roman Forum with your guide, who will lead you to the most fascinating and historically important areas of this era. This and even more to be discovered along the path! Don't loose the chance to have the most amazing and unforgetable experience ever! Your guide will be at your complete disposal for any question or curiosity guaranting an interactive visit tailored on your needs!

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2
Main activity for day 2

Baroque Elegance and Timeless Fountains

Step deeper into Rome’s soul by embracing the charm of its Baroque masterpieces and romantic fountains. The ornate artistry and spirited piazzas exude a vibrant energy, setting a poetic rhythm to your day. As the evening falls, revel in the magic of softly lit streets where locals and travelers converge for gelato and impromptu serenades under the September skies.

Begin your day with a relaxed walk to the legendary , where early September light turns the cascading water into shimmering silver streams. Join locals and travelers in tossing a coin over your shoulder, making a wish to return someday to this Eternal City. Let the ornate statues and intricate carvings captivate you as you linger, savoring the sounds of flowing water mixed with lively chatter. As afternoon arrives, amble towards the Spanish Steps at Piazza di Spagna, where the bustling atmosphere is tinged with an air of elegance. Climb these famous steps slowly, pausing to absorb the view and indulge in a creamy gelato from a corner vendor, sharing the space with Romans and visitors alike in a joyous mingling. Continue on to , a lively open-air gallery where monumental fountains such as Bernini’s Fountain of the Four Rivers stand proudly amidst street musicians and artists. Sit at a café, sipping a cappuccino in the mellow climate, allowing yourself to fully feel the pulse of Rome’s Baroque flair before the evening gently rolls in under a warm September sky.

Where to Stay
Accommodation
InterContinental Rome Ambasciatori Palace
Full starFull starFull starFull starEmpty star
4.4
(Very Good)

Situated in the historic Ludovisi area near Piazza di Spagna and Trevi Fountain, perfect for exploring Baroque landmarks and enjoying evening strolls in lively piazzas.

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Highlights of the day
Top Sight
Trevi Fountain
This is a highlight of your day—an experience designed to immerse you in the local culture and create lasting memories during your trip.
Top Sight
Piazza di Spagna and Spanish Steps
This is a highlight of your day—an experience designed to immerse you in the local culture and create lasting memories during your trip.
Top Sight
Piazza Navona
This is a highlight of your day—an experience designed to immerse you in the local culture and create lasting memories during your trip.
Where to Eat
Top Restaurant
Osteria dell’Ingegno Rome
Situated near Piazza Navona, this stylish yet welcoming osteria specializes in Roman and Italian flavors with a modern twist, ideal for a romantic evening following your exploration of Trevi Fountain, Spanish Steps, and lively piazzas, allowing the couple to indulge in refined local dining in the Baroque heart of Rome.
Situated near Piazza Navona, this stylish yet welcoming osteria specializes in Roman and Italian flavors with a modern twist, ideal for a romantic evening following your exploration of Trevi Fountain, Spanish Steps, and lively piazzas, allowing the couple to indulge in refined local dining in the Baroque heart of Rome.
Bookable Activities
Bookable Activity
Pastamania in Rome
Full starFull starFull starFull starHalf star
5.0
(85 reviews)
Clock icon3 hours
$58.16per person

Learn how to make homemade fresh pasta easily and successfully. If you have flour and eggs you can make pasta and we will teach the secrets. We will teach you to make pasta in different shapes in a place in the centre of Rome. We will cook all the pasta we have prepared with 2 different sauces, we will then taste all together the pasta. We will offer you organic Tuscan wine produced with natural methods and bottled in our cellar "Dalle Nostre Mani". Every participant will receive English instructions for making pasta at home, easily and successfully at the end of the experience.

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3
Main activity for day 3

Vatican Splendors and Spiritual Grandeur

Today invites you into the spiritual and artistic heart of the Catholic world, where centuries of faith and creativity converge in awe-inspiring masterpieces. Navigating through grand basilicas, resplendent chapels, and vast museums, you’ll discover intimate frescoes and monumental art that define the Renaissance and beyond. The crisp September mornings bring a contemplative peace to these sacred spaces, enriching the sense of reverence and wonder.

Start early to enter , where the morning sun illuminates the gleaming marble floors and soaring dome, creating a transcendent atmosphere. Wander slowly past Bernini's magnificent colonnades and step inside the cavernous interior that holds priceless works like Michelangelo’s Pietà, where the delicate sculpture evokes profound emotion. Feel the weight of centuries of faith around you, and if you're adventurous, climb the dome for a breathtaking panorama over St. Peter’s Square and the terracotta roofs of Rome. Then progress to the , a vast labyrinth of galleries showcasing treasures that span millennia. Navigate the halls filled with ancient sculptures, Renaissance tapestries, and the Raphael Rooms, savouring the quiet awe that surrounds each masterpiece. End your Vatican visit in the , where Michelangelo’s ceiling envelops you in vibrant Biblical scenes, a spiritual and artistic summit for any traveler. Early September offers moderate crowds and temperate weather, ensuring your visit feels intimate and contemplative amidst these grand spaces.

Where to Stay
Accommodation
Villa Agrippina Gran MELIá
Full starFull starFull starFull starHalf star
4.5
(Great)

Luxurious resort located near Vatican City, perfectly positioned for early access to St. Peter's Basilica and the Vatican Museums for an immersive spiritual adventure.

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Highlights of the day
Top Sight
St. Peter's Basilica
This is a highlight of your day—an experience designed to immerse you in the local culture and create lasting memories during your trip.
Top Sight
Vatican Museums
This is a highlight of your day—an experience designed to immerse you in the local culture and create lasting memories during your trip.
Top Sight
Sistine Chapel
This is a highlight of your day—an experience designed to immerse you in the local culture and create lasting memories during your trip.
Where to Eat
Top Restaurant
Hostaria Costanza Rome
Just minutes from the Vatican Museums and St. Peter’s Basilica, Hostaria Costanza serves traditional Roman cuisine in an elegant setting, perfectly complementing a day focused on spiritual grandeur and Renaissance masterpieces, offering a refined yet cozy dining experience for a cultured and adventurous couple.
Just minutes from the Vatican Museums and St. Peter’s Basilica, Hostaria Costanza serves traditional Roman cuisine in an elegant setting, perfectly complementing a day focused on spiritual grandeur and Renaissance masterpieces, offering a refined yet cozy dining experience for a cultured and adventurous couple.
Bookable Activities
Bookable Activity
Rome: Photo Shoot in Rome with Professional Photographer
Full starFull starFull starFull starHalf star
5.0
(253 reviews)
Clock icon1h 30m
$71.22per person

Professional Photography: Our experienced photographers will capture your best angles and candid moments. Iconic Locations: Explore Rome's most famous landmarks and make them the backdrop of your memories. Quick Delivery: Your beautifully edited photos will be sent within 24 hours. Sweet Ending: Enjoy the most exquisite ice cream Rome has to offer. Unforgettable Memories: Our goal is to provide you with a unique, fun, and hassle-free experience, resulting in photos that will make you smile for years. Join us for this unforgettable journey through Rome's history and charm, and book your experience now! Be ready to create beautiful memories and savor Rome's sweetest treats. NEW: We have an option with a Vespa Scooter, instead of walking we will go with a Vespa (only for adults).

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4
Main activity for day 4

Florence: Renaissance Heartbeat

Step off the train into Florence’s Renaissance embrace, a vibrant city where art, architecture, and culture bloom in every piazza and narrow lane. This day awakens your senses with breathtaking sculptures, magnificent cathedrals, and intimate artisanal workshops. As you explore under September’s golden light, the Tuscan air hums with centuries of creativity and passionate innovation.

Arrive in Florence and let the city’s Renaissance spirit enfold you as you make your way to the Florence Cathedral, affectionately called Il Duomo di Firenze. Marvel at Brunelleschi’s colossal red-tiled dome soaring above the city skyline, and step inside to admire Giotto’s frescoes and the intricate marble façade that tells stories etched in stone. Climb the dome’s narrow, winding stairwell to stand atop this architectural triumph, where panoramic views reveal Florence’s terracotta rooftops and the surrounding Tuscan hills bathed in golden September light. Following this, ease into the cultural riches housed within the , where Botticelli’s ethereal 'The Birth of Venus' and da Vinci’s enigmatic works await. Meander through a treasure trove of Renaissance art, occasionally pausing to feel the reverent hush that hangs in these storied halls. Conclude your day with a sunset visit to the , wandering across the medieval bridge dotted with glittering jewelers’ shops. Lean over the parapet with your loved one to watch the sun’s fading glow dance on the Arno River, imprinting a romantic memory that will linger long after the day fades.

Where to Stay
Accommodation
Suite del Brunelleschi
Full starFull starFull starFull starFull star
5.0
(Outstanding)

Luxury hotel in the heart of Florence, steps from the Duomo and Uffizi Gallery, offering a historic yet modern stay perfect for Renaissance exploration.

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Highlights of the day
Top Sight
Florence Cathedral (Il Duomo di Firenze)
This is a highlight of your day—an experience designed to immerse you in the local culture and create lasting memories during your trip.
Top Sight
Uffizi Gallery
This is a highlight of your day—an experience designed to immerse you in the local culture and create lasting memories during your trip.
Top Sight
Ponte Vecchio
This is a highlight of your day—an experience designed to immerse you in the local culture and create lasting memories during your trip.
Where to Eat
Top Restaurant
Trattoria Mario Florence
A famed local spot a short walk from the Duomo, Trattoria Mario provides hearty Tuscan dishes such as bistecca alla fiorentina, perfectly matching the adventurous spirit for a full day of Renaissance art and architecture exploration, giving the couple an authentic and vibrant Florentine dining experience.
A famed local spot a short walk from the Duomo, Trattoria Mario provides hearty Tuscan dishes such as bistecca alla fiorentina, perfectly matching the adventurous spirit for a full day of Renaissance art and architecture exploration, giving the couple an authentic and vibrant Florentine dining experience.
Bookable Activities
Bookable Activity
Florence Walking Tour
Full starFull starFull starFull starHalf star
4.8
(552 reviews)
Clock icon2h 30m
$3.55per person

First of all this is a tour based on a voluntary tip at the end of the tour, that's why the booking is cheap. Welcome to the Original Florence walking tour, a complete tour of the main landmarks of the cradle of renaissance. A tour made by only certified and expert guides, delivering a friendly tour, they will introduce the city to you. You will learn about art, Medici family, history, food, anecdotes, secrets and culture of Florence; with tips about the city, restaurants , museums, night life, told from the perspective of a local. The meeting point is in Piazza dell'unità italiana. Then we will walk through the beautiful streets and squares of one of the most iconic cities of the world.

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5
Main activity for day 5

Tuscan Countryside and Wine Trails

Escape the city buzz to the rolling hills and golden vineyards of Tuscany, where the landscape blends with centuries-old traditions to create postcard-perfect scenes. Savor rustic countryside charm as you meander through quaint villages, taste bold Chianti wines, and share moments beneath endless skies that stretch warmly in September’s embrace.

Leave the bustle of Florence behind for a day immersed in the idyllic Tuscan countryside. Your first stop is , an enchanting medieval village where narrow cobblestone streets wind past ancient stone houses and rustic wineries. Explore the town’s Etruscan tombs and charming piazza, soaking in the warm light reflecting off terracotta roofs and abundant vineyards that stretch to the horizon. Relish an early lunch of hearty Tuscan fare, pairing fresh local bread and Pecorino cheese with a glass of Chianti Classico. Next, continue to the fairytale , a storied castle set amidst fragrant vineyards overlooking the rolling hills. Here, enjoy a guided wine tasting in the estate’s historic cellars, savoring robust reds as a local expert shares tales of the land, terroir, and winemaking traditions. Conclude your day in , a hilltop haven where artisan shops and wine bars invite leisurely exploration. Walk the town walls for views of vineyards kissed by September’s mellow sun and let your hearts delight in the serene landscape before returning to Florence’s embrace.

Where to Stay
Accommodation
Villa le Barone
Full starFull starFull starFull starHalf star
4.7
(Amazing)

A charming countryside villa offering authentic Tuscan ambiance and prime location amidst Chianti vineyards, perfect for immersive wine trail adventures.

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Highlights of the day
Top Sight
Castellina in Chianti
This is a highlight of your day—an experience designed to immerse you in the local culture and create lasting memories during your trip.
Top Sight
Castello di Brolio
This is a highlight of your day—an experience designed to immerse you in the local culture and create lasting memories during your trip.
Top Sight
Radda in Chianti
This is a highlight of your day—an experience designed to immerse you in the local culture and create lasting memories during your trip.
Bookable Activities
Bookable Activity
Monteriggioni San Gimignano and Castellina in Chianti Fullday from Rome
Full starFull starFull starFull starFull star
5.0
(1 reviews)
Clock icon12 hours
$854.58per person

Enjoy a day exploring the landscapes and artistic small towns that Tuscany can offer: • Monteriggioni • San Gimignano • Castellina in Chianti Lunch and WineTasting Included. Pick up and drop off will be at your accommodation in Rome. Local licensed Tour Guide if option selected. Worry-Free and Safe Private Tour Experience, operated only with: • Expert Professional English-Speaking Drivers • Selected local Expert Licensed Tour Guides (when booked) • Welcoming by private licensed fully-insured air-conditioned comfortable Vehicles

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6
Main activity for day 6

Adventurous Amalfi Coast Drive

Set off on a breathtaking drive along the Amalfi Coast’s cliff-hugging roads, where jagged cliffs tumble into turquoise seas, vibrant lemon groves perfume the air, and colorful villages cling dramatically to the landscape. This day is an adrenaline-charged blend of stunning vistas, hidden coves, and sensory indulgence, all heightened by the crisp September breeze and clear skies.

Launch your adventure from Naples in the early morning, taking the coastal road that snakes along cliffs edged by the sparkling Tyrrhenian Sea. Each curve unfurls awe-inspiring vistas of pastel villages that seem to cascade toward the waves, lemon groves waving gently in the sea breeze. Your first destination is , where vibrant houses stacked on steep slopes create a mosaic of colors glowing warmly in September’s golden light. Wander narrow lanes filled with artisan shops, then descend to the pebbly beach where the sea laps softly at your feet—perfect for a refreshing dip or a moment of tranquility. Next, continue to historic , where the magnificent Cathedral of Saint Andrew towers over a lively piazza buzzing with markets and cafés. Enter the cool cathedral interior, marvel at its Byzantine-style mosaics, and soak in the town’s maritime history. Finish your drive in , perched high above the coast with sprawling terraced gardens at Villa Rufolo and Villa Cimbrone where every viewpoint offers postcard-perfect panoramas of the coastline. A concert in the gardens or a sunset stroll here is the ideal romantic crescendo to this exhilarating day.

Where to Stay
Accommodation
Le Sirenuse
Full starFull starFull starFull starHalf star
4.8
(Amazing)

Iconic luxury hotel in the heart of Positano offering spectacular cliffside views and immediate access to beach and village explorations.

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Highlights of the day
Top Sight
Positano
This is a highlight of your day—an experience designed to immerse you in the local culture and create lasting memories during your trip.
Top Sight
Amalfi
This is a highlight of your day—an experience designed to immerse you in the local culture and create lasting memories during your trip.
Top Sight
Ravello
This is a highlight of your day—an experience designed to immerse you in the local culture and create lasting memories during your trip.
Where to Eat
Top Restaurant
La Pergola Positano
Perched above Positano’s beach with stunning coastal views, La Pergola offers fresh Amalfi Coast seafood and Mediterranean flavors in an intimate yet lively atmosphere, perfectly complementing a thrilling day of scenic coastal drives and village exploration for a couple seeking both adventure and romance.
Perched above Positano’s beach with stunning coastal views, La Pergola offers fresh Amalfi Coast seafood and Mediterranean flavors in an intimate yet lively atmosphere, perfectly complementing a thrilling day of scenic coastal drives and village exploration for a couple seeking both adventure and romance.
Bookable Activities
Bookable Activity
Private Transfer from Positano to Naples
Full starFull starFull starFull starFull star
5.0
(27 reviews)
Clock icon1 hour
$118.69per person

Our car service company is operating for more than 10 years. All our vehicles are new comfortable Mercedes cars. Drivers are professional, and will make your trip enjoyable.

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7
Main activity for day 7

Capri’s Sea Grottos and Coastal Charms

Indulge in a day of coastal elegance on the island of Capri, where azure waters, fragrant lemon groves, and dramatic cliffs beckon exploration. This day blends intimate boat rides through glowing sea grottos with leisurely village strolls, pastel facades, and the simple joy of watching sun-drenched fishing boats bobbing in the harbor. The early autumn warmth creates a serene atmosphere perfect for romantics and adventurers alike.

Upon arrival at Capri’s via a scenic ferry ride from the Amalfi Coast, start your day wandering among the vibrant fishing boats bobbing peacefully in the harbor. The air is fragrant with salt and lemons, and the gentle hum of vendors and café chatter creates an inviting ambiance. Next, embark on an intimate boat excursion to the famed Blue Grotto, a cavern where sunlight filters beneath the water to produce an otherworldly blue glow that shimmers on the rocky walls. As your skiff slips silently into the cave, marvel at the magical light dancing across ancient limestone and the silky water surface beneath your fingertips. Returning to shore, stroll up to the Piazzetta, Capri’s bustling little square, where outdoor cafés spill onto cobbled streets alive with local charm. Sip espresso alongside locals and travelers, enjoy people-watching, and savor the sensation of time slowing down in this gem of the Mediterranean. The early autumn sun bathes the island in warm, inviting light, making every moment here a serene, romantic treasure.

Where to Stay
Accommodation
J.K. Place Capri
Full starFull starFull starFull starHalf star
4.8
(Amazing)

Luxury hotel near Capri’s Piazzetta offering elegant rooms and easy access to Blue Grotto excursions and island exploration.

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Highlights of the day
Top Sight
Blue Grotto (Grotta Azzurra)
This is a highlight of your day—an experience designed to immerse you in the local culture and create lasting memories during your trip.
Top Sight
Marina Grande
This is a highlight of your day—an experience designed to immerse you in the local culture and create lasting memories during your trip.
Top Sight
Piazzetta di Capri
This is a highlight of your day—an experience designed to immerse you in the local culture and create lasting memories during your trip.
Where to Eat
Top Restaurant
Da Paolino Lemon Trees Capri
Set amid fragrant lemon groves near Capri’s Piazzetta, Da Paolino provides a unique dining experience featuring fresh local seafood and island specialties, ideal after visiting the Blue Grotto and Marina Grande, capturing Capri’s coastal charm and relaxed elegance for a romantic, adventurous couple.
Set amid fragrant lemon groves near Capri’s Piazzetta, Da Paolino provides a unique dining experience featuring fresh local seafood and island specialties, ideal after visiting the Blue Grotto and Marina Grande, capturing Capri’s coastal charm and relaxed elegance for a romantic, adventurous couple.
Bookable Activities
Bookable Activity
Boat Tour of the Caves on the Island of Capri
Full starFull starFull starFull starEmpty star
4.3
(449 reviews)
Clock icon2 hours
$92.58per person

Are you ready to set off to discover the island of Capri? You will be able to travel aboard a Capri gozzo, a typical comfortable and pleasant boat. The journey will be followed by an expert guide who will explain everything you need to know about the island and its main attractions. Furthermore, the goiter will stop to allow you to BATH in the crystalline waters of Capri. Simply put, you will have a FANTASTIC experience! The surprises don't end there. You can also taste the traditional LIMONCELLO CAPRESE and enjoy some snacks. If you want to explore Capri in the best way, this is the TOUR FOR YOU! What are you waiting for to book this tour? You won't regret it and you will see Capri like you've never seen it before! ATTENTION: the visit to the Blue Grotto is not guaranteed due to weather and other conditions which may prevent the correct execution of the tour

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8
Main activity for day 8

Naples: Ancient Streets and Fiery Flavors

Feel the raw energy of Naples as you navigate its vibrant streets, historic centers, and intimate pizzerias. This city pulsates with life, where ancient ruins, Baroque churches, and bustling markets form a backdrop to passionate Neapolitan culture. The temperate September air carries the aroma of fresh pizza crusts, fried street food, and the sea breeze—inviting a full embrace of Naples’ spirited charm.

Step into Naples’ historic center and be instantly enveloped by a vibrant mosaic of energy and history that pulses through narrow alleys and piazzas. Explore , the lively artery cutting through the city’s core, where the air is filled with the scent of espresso, fresh bread, and frying street food. Meander with locals weaving through bustling markets and artisan shops, pausing at centuries-old churches adorned with dramatic Baroque art that tell stories of Naples’ complex past. Take time to savor an authentic Neapolitan pizza, the city’s prized culinary gift, where thin crusts, fresh buffalo mozzarella, and sun-ripened tomatoes blend perfectly in fiery wood-fired ovens. Afterwards, delve deeper into the ancient world at the , where astonishing artifacts from Pompeii and Herculaneum reveal preserved echoes of Roman life. September’s cool light and gentle breeze make wandering these streets a thrilling and sensory day of discovery.

Where to Stay
Accommodation
Grand Hotel Vesuvio
Full starFull starFull starFull starHalf star
4.5
(Great)

Historic luxury hotel on the waterfront, near Naples port and historic districts, a perfect base for the dynamic city exploration.

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Highlights of the day
Top Sight
Naples Historic Center
This is a highlight of your day—an experience designed to immerse you in the local culture and create lasting memories during your trip.
Top Sight
Spaccanapoli
This is a highlight of your day—an experience designed to immerse you in the local culture and create lasting memories during your trip.
Top Sight
Naples National Archaeological Museum
This is a highlight of your day—an experience designed to immerse you in the local culture and create lasting memories during your trip.
Where to Eat
Top Restaurant
Pizzeria Gino Sorbillo Naples
Located in Naples historic center near Spaccanapoli, this world-renowned pizzeria serves traditional Neapolitan pizza baked in wood-fired ovens, perfect for an adventurous foodie couple to experience the city’s iconic flavors after a day immersed in Naples’ vibrant culture and streets.
Located in Naples historic center near Spaccanapoli, this world-renowned pizzeria serves traditional Neapolitan pizza baked in wood-fired ovens, perfect for an adventurous foodie couple to experience the city’s iconic flavors after a day immersed in Naples’ vibrant culture and streets.
Bookable Activities
Bookable Activity
Naples Sightseeing Boat Tour
Full starFull starFull starFull starHalf star
4.7
(992 reviews)
Clock icon1h 30m
$63.81per person

Experience the beauty of Naples, Florida while cruising on the iconic Double Sunshine.  This 90-minute sightseeing cruise takes you from historic Tin City Shops out to the Gulf of Mexico. Along the way you will see southwest Florida wildlife, Keewaydin Island, enjoy historical narration provided by our Pure Florida Captains and see some of the most beautiful mansions in Port Royal, an incredibly exclusive neighborhood home to well-known millionaires.  Guests love easily moving throughout the boat to get the best view, unique photo opportunities and relaxing on the water. The price of this trip includes a flexible cancellation policy, allowing you to cancel and receive a full refund up to 2 hours before the trip's departure time

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9
Main activity for day 9

Pompeii and Mount Vesuvius Adventure

Travel back 2,000 years as you explore the hauntingly preserved streets of Pompeii, frozen in time by volcanic ash. The day culminates with an exhilarating hike up Mount Vesuvius to gaze out over the Bay of Naples from the rim of the famous volcano. The fresh September air and clear skies provide a perfect contrast to the ancient ruins, creating an unforgettable blend of history and natural wonder.

Begin the day exploring the vast ruins of Pompeii, arriving early to wander through streets where life was suddenly halted in AD 79 by the powerful eruption of Mount Vesuvius. Walk past well-preserved villas adorned with intricate frescoes, bustling marketplaces, and the remains of theatres and baths, all silent witnesses to a vibrant ancient city frozen in volcanic ash. The September weather is often clear and mild, enhancing your ability to absorb every detail without the summer heat. Immerse yourself in the stories of everyday Romans through the casts of victims, mosaics, and artifacts scattered across this archaeological marvel. After exploring Pompeii, head to Mount Vesuvius for a thrilling ascent along the crater rim. Feel the lush scents of Mediterranean vegetation as you climb, reaching the summit where the vast active crater yawns before you. From this vantage point, gaze out over the sparkling Bay of Naples, the city skyline below, and the rugged coastline stretching endlessly. The rush of this natural adventure paired with Pompeii’s haunting history makes for a profound and invigorating day.

Where to Stay
Accommodation
Resort & Winery Bosco De Medici
Full starFull starFull starFull starHalf star
4.5
(Great)

Comfortable and well-located hotel near Pompeii archaeological site, providing rest and spa facilities after intense exploration and hikes.

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Highlights of the day
Top Sight
Pompeii Archaeological Site
This is a highlight of your day—an experience designed to immerse you in the local culture and create lasting memories during your trip.
Top Sight
Mount Vesuvius National Park
This is a highlight of your day—an experience designed to immerse you in the local culture and create lasting memories during your trip.
Where to Eat
Top Restaurant
Ristorante Kad Nishta Pompeii
Close to the Pompeii archaeological site entrance, this charming restaurant offers Mediterranean and Campanian dishes with fresh local ingredients, providing a relaxed setting for couples to unwind and savor authentic flavors after a day of exploring ancient ruins and hiking Mount Vesuvius.
Close to the Pompeii archaeological site entrance, this charming restaurant offers Mediterranean and Campanian dishes with fresh local ingredients, providing a relaxed setting for couples to unwind and savor authentic flavors after a day of exploring ancient ruins and hiking Mount Vesuvius.
Bookable Activities
Bookable Activity
Explore Pompeii with an Archaeologist
Full starFull starFull starFull starHalf star
4.9
(454 reviews)
Clock icon2 hours
$42.73per person

Ready to go back to the 79 AD? This tour consists of a marvelous throw-back walk around the ancient city of Pompeii, the Roman city that was covered by vulcanic ashes in 79 AD. A walk in Pompeii is a very intense experience: it will be like wandering through an ancient living city! During the tour, the guide will explain the history of the city and how the Romans lived, showing you the most important public buildings and private homes. Don't miss the chance to visit the most famous archaeological site, you will feel like you are wandering around a living ancient city!

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10
Main activity for day 10

Venice: Canals and Timeless Romance

Step into a dreamlike city where waterways substitute streets, gondolas glide under ancient bridges, and Renaissance palaces hold centuries of secrets. Venice in September offers a peaceful respite from summer crowds, allowing you to lose yourself in labyrinthine alleys and sun-dappled piazzas. The interplay of light and water creates a magical atmosphere perfect for lovers seeking a unique blend of adventure and romance.

Awake in Venice to a serene September morning where water gently laps against centuries-old palazzi, creating a timeless lullaby. Make your way to the heart of the city, , where intricately golden mosaics and onion-shaped domes invite you to explore layers of Byzantine and Gothic artistry. Step inside to admire the gleaming interiors and the evocative Pala d’Oro altar, alive with jewels and gold leaf. Afterwards, glide along the aboard a vaporetto or a private gondola, passing palatial homes and bustling markets that define Venice’s unique rhythm. The light dances on the water’s surface, creating a kaleidoscope of reflections that enchant and inspire. Wander over the , pausing to shop for Murano glass or leaf through artisan stalls as you admire the perfect vista down the canal. As evening falls, find a quiet spot by a canal side café to savor cicchetti and a spritz, letting the magic of Venice’s labyrinthine waterways and intimate atmosphere envelop you completely.

Where to Stay
Accommodation
Hotel Danieli, Venice
Full starFull starFull starFull starHalf star
4.6
(Great)

Iconic luxury hotel overlooking the lagoon near St. Mark’s Basilica, perfect for romantic and adventurous days exploring Venice’s finest landmarks.

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Highlights of the day
Top Sight
St. Mark’s Basilica
This is a highlight of your day—an experience designed to immerse you in the local culture and create lasting memories during your trip.
Top Sight
Grand Canal
This is a highlight of your day—an experience designed to immerse you in the local culture and create lasting memories during your trip.
Top Sight
Rialto Bridge
This is a highlight of your day—an experience designed to immerse you in the local culture and create lasting memories during your trip.
Where to Eat
Top Restaurant
Osteria alle Testiere Venice
A small, romantic seafood osteria near St. Mark’s Basilica, Osteria alle Testiere features Venetian specialties such as fresh catch and cicchetti, matching perfectly with a day spent exploring Venice’s iconic landmarks and waterways, offering an intimate dining experience suited to an adventurous couple.
A small, romantic seafood osteria near St. Mark’s Basilica, Osteria alle Testiere features Venetian specialties such as fresh catch and cicchetti, matching perfectly with a day spent exploring Venice’s iconic landmarks and waterways, offering an intimate dining experience suited to an adventurous couple.
Bookable Activities
Bookable Activity
Venice Gondola Experience
Full starFull starFull starEmpty starEmpty star
3.5
(168 reviews)
Clock icon30 minutes
$52.00per person

A gondola ride is the most traditional, enchanting and unique way to explore Venice and experience its unique atmosphere. A tour through the canals and inner waterways of this city which will make us feel as stepping into a far, old time, still alive and pulsing in this magic corner of the Earth. Let yourself slide along the peaceful canals of Venice, enjoying the silence away from the crowds and the picturesque views which can be admired only from this one-of-a-kind perspective. By no doubt, a tour to come into contact with the deepest side of Venice.

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11
Main activity for day 11

Murano and Burano Island Escapes

Venture beyond Venice’s main islands to the colorful jewels of Murano and Burano, where traditional crafts and vibrant village life create a lively, charming day trip. Witness centuries-old glassblowing techniques in action and stroll along canals flanked by rainbow-hued houses. The soft September light enhances every color and reflection, making these islands a photographer’s and adventurer’s dream.

Board a waterbus leaving Venice for Murano, a short ride that gradually reveals the serene lagoon and floating architecture unique to this region. Arriving in Murano, immerse yourself in the legendary glassmaking tradition by visiting the Museo del Vetro, housed in a medieval palace where delicately crafted glass artworks showcase centuries of Venetian innovation and skill. Witness glassblowers creating fiery masterpieces in live demonstrations, intricate the balance of artisanal tradition and creative passion. After the museum, explore Murano’s peaceful canals lined with charming cafes and shops offering exquisite glass treasures. Continuing on, ferry to Burano, an island that greets you with a kaleidoscope of brightly colored fishermen’s houses reflecting vivid shades onto the gently rippling water. Stroll along quiet lanes dotted with lace shops, a centuries-old craft kept alive by dedicated artisans. Let yourself be swept away by the cheerful atmosphere and the soft September sun, creating perfect light for photos and lingering memories before a gentle return to Venice as twilight descends.

Where to Stay
Accommodation
Hotel Villa Del Mar
Full starFull starFull starFull starEmpty star
4.2
(Very Good)

Charming guesthouse on Burano offering colorful surroundings and easy access to lace shops and scenic canal walks.

Book
Highlights of the day
Top Sight
Murano Glass Museum (Museo del Vetro)
This is a highlight of your day—an experience designed to immerse you in the local culture and create lasting memories during your trip.
Top Sight
Burano Island
This is a highlight of your day—an experience designed to immerse you in the local culture and create lasting memories during your trip.
Where to Eat
Top Restaurant
Osteria Al Duomo Murano
Close to the Murano Glass Museum, this cozy osteria serves Venetian and lagoon-inspired dishes, providing an authentic local atmosphere after a day discovering traditional glassblowing and the colorful charm of Murano and Burano, ideal for adventurous couples interested in culture and local flavors.
Close to the Murano Glass Museum, this cozy osteria serves Venetian and lagoon-inspired dishes, providing an authentic local atmosphere after a day discovering traditional glassblowing and the colorful charm of Murano and Burano, ideal for adventurous couples interested in culture and local flavors.
Bookable Activities
Bookable Activity
Murano, Burano and Torcello Half-Day Sightseeing Tour
Full starFull starFull starEmpty starEmpty star
3.5
(7.8k reviews)
Clock icon4h 30m
$35.61per person

Explore three famous islands in the Venice Lagoon--Murano, Torcello and Burano--on a half-day sightseeing excursion by motorboat. You'll stop at a blown glass factory on Murano, visit Venice's first cathedral on the peaceful island of Torcello, and taking lots of pictures of Burano's coloured houses. This morning or afternoon tour is an excellent introduction to the magical islands surrounding the city of Venice and its enclosed bay in the Adriatic Sea. Deaprtures every day from San Marco Giardinetti or Venezia Santa Lucia Railway Station (departure time in Santa Lucia Railway Station is set 30 minutes before the indicated departure time from San Marco Giardinetti).

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12
Main activity for day 12

Cinque Terre Coastal Wonders

Discover a rugged stretch of Ligurian coastline where multicolored villages cling to cliffs above the sea, vineyards grow on terraces, and hiking trails wind through wild landscapes. September’s perfect weather balances warm sun and cool breezes, inviting you to explore dramatic coves, taste fresh seafood, and absorb the tranquil charm that radiates from each of the five unique towns.

Arrive in , the largest and most accessible of the Cinque Terre villages, its sandy beach inviting you to dip your toes in the Ligurian Sea after your adventure-packed journey. Wander ancient cobbled streets where shuttered pastel houses stand proudly, and sample local focaccia bread infused with Ligurian herbs at a traditional bakery. Embark on a scenic coastal hike or catch a short train to , a poetically perfect village framed by craggy cliffs and a small harbor where fishing boats bob gently. Lose yourself in its narrow lanes lined with artisan shops and seafront cafés serving freshly caught seafood accented with basil and garlic — flavors emblematic of the region. Finally, continue to , the southernmost jewel, where colorful terraces climb steep cliffs and sunset hues paint the sky in romantic tones. Each town offers breathtaking views blending sea, sky, and history in a way that only Cinque Terre’s rugged charms can provide.

Where to Stay
Accommodation
Hotel Porto Roca
Full starFull starFull starFull starEmpty star
4.4
(Very Good)

Seaside hotel with stunning views and convenient location, ideal for exploring Monterosso and the Cinque Terre hiking trails.

Book
Highlights of the day
Top Sight
Monterosso al Mare
This is a highlight of your day—an experience designed to immerse you in the local culture and create lasting memories during your trip.
Top Sight
Vernazza
This is a highlight of your day—an experience designed to immerse you in the local culture and create lasting memories during your trip.
Top Sight
Riomaggiore
This is a highlight of your day—an experience designed to immerse you in the local culture and create lasting memories during your trip.
Where to Eat
Top Restaurant
Ristorante Miky Monterosso al Mare
Located in Monterosso al Mare, Miky offers fresh Ligurian seafood and regional dishes in a refined yet relaxed setting, fitting perfectly after hiking and exploring the Cinque Terre villages, giving the couple an authentic taste of coastal Ligurian cuisine in a memorable seaside atmosphere.
Located in Monterosso al Mare, Miky offers fresh Ligurian seafood and regional dishes in a refined yet relaxed setting, fitting perfectly after hiking and exploring the Cinque Terre villages, giving the couple an authentic taste of coastal Ligurian cuisine in a memorable seaside atmosphere.
Bookable Activities
Bookable Activity
Horse ride on the coast of Monterosso al Mare Cinque Terre
Full starFull starFull starFull starHalf star
4.9
(131 reviews)
Clock icon1h 40m
$94.95per person

For those who love nature and horses, you can ride admiring the sea, cross woods, admire the scents and colors of the Cinque Terre, it is a unique experience on the Ligurian coast, thanks to its location in Monterosso al Mare.

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13
Main activity for day 13

Tuscan Hill Town Enchantment

Return inland to the Tuscan hills for a day among ancient villages that evoke a slower, sweeter time. Surrounded by vineyards, olive groves, and sweeping views, you’ll soak in palpable history and enjoy intimate encounters—local markets, craft shops, and warm hospitality. September’s soft light and cooling evenings provide the perfect backdrop for this romantic exploration.

Journey deeper into Tuscany’s timeless hills to reach , where soaring medieval towers punctuate a skyline that has remained unchanged for centuries. Wander the narrow lanes lined with artisan shops showcasing local ceramics and saffron products, absorbing the palpable historic atmosphere that embraces every stone. Visit the Collegiata di Santa Maria Assunta to admire frescoes that tell vivid stories of medieval faith and artistry. Along quiet city walls, take in expansive views over rolling vineyards bathed in September’s golden haze, capturing moments of calm and beauty. Later, drive to , a town steeped in Etruscan mystery and alabaster craftsmanship. Explore the Roman theatre ruins and engage with local artisans shaping translucent alabaster into delicate artworks, connecting with living traditions. This day offers a perfect blend of history, culture, and serene landscapes — quintessentially Tuscan.

Where to Stay
Accommodation
Hotel la Cisterna
Full starFull starFull starFull starEmpty star
4.4
(Very Good)

Located in the medieval center with rooftop views of towers, capturing the essence of Tuscan hill town charm.

Book
Highlights of the day
Top Sight
San Gimignano
This is a highlight of your day—an experience designed to immerse you in the local culture and create lasting memories during your trip.
Top Sight
Volterra
This is a highlight of your day—an experience designed to immerse you in the local culture and create lasting memories during your trip.
Where to Eat
Top Restaurant
Cum Quibus San Gimignano
Situated near the historic center of San Gimignano, Cum Quibus is renowned for innovative Tuscan cuisine using local ingredients, ideal for a romantic and culinary adventurous couple concluding a day exploring medieval hill towns and artisan crafts in an intimate, charming setting.
Situated near the historic center of San Gimignano, Cum Quibus is renowned for innovative Tuscan cuisine using local ingredients, ideal for a romantic and culinary adventurous couple concluding a day exploring medieval hill towns and artisan crafts in an intimate, charming setting.
Bookable Activities
Bookable Activity
San Gimignano: Chianti wine tasting
Full starFull starFull starFull starHalf star
4.5
(8 reviews)
Clock icon1 hour
$35.49per person

A few steps from San Gimignano, there is a splendid family-run winery. Here you can taste the typical Tuscan products: starting from the wine up to tasty local croutons. You will visit the cellar, the vineyards, and all the places where the wine comes to life. You will listen to stories, and curiosities, and you will learn the winemaking processes that make Tuscany and Chianti areas to be protected and loved. You will discover the secrets of wine and grapes and the best combinations with strictly typical foods. Do not miss the opportunity to combine Tuscan wine with appetizing foods (such as cheese and ham) and find out how wines are produced in a real cellar. You can have a lovely tasting of 4 wines accompanied by snacks of typical products preceded by a tour of cellars and vines.

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14
Main activity for day 14

Farewell with Venetian Twilight

Conclude your Italian adventure under the shimmering twilight of Venice, where your last evening blends peaceful gondola rides, glittering canals, and heartfelt reflection. As the September dusk lengthens, the city’s magical aura invites you to savor a final embrace of Italy’s enduring enchantment, weaving memories that will forever glow in your heart.

Spend your final day and evening back in Venice, immersing in the city's unique magic one last time. As the afternoon light softens, embark on a private gondola ride along the , gliding past historic palaces, arched bridges, and quays alive with stories stretching back centuries. Feel the gentle sway of the boat beneath you, the splash of oars, and the lyrical song of your gondolier as you pass under dreamy light. After the ride, savor an aperitivo at a quiet spot overlooking the water, where local cicchetti and a glass of Prosecco mingle with the scent of the lagoon. Wander hand in hand through lantern-lit alleys leading back to St. Mark’s Square, where the fading light makes the basilica's golden mosaics shimmer like a fairy tale. September’s cool evening air invites slow steps and heartfelt conversation. Here, in Venice’s enchanting twilight, your Italian adventure finds its perfect, unforgettable close.

Where to Stay
Accommodation
Bauer Palladio Hotel and Spa
Full starFull starFull starFull starEmpty star
4.4
(Very Good)

Centrally located luxury hotel on the Grand Canal, ideal for concluding the journey with easy access to gondolas and evening strolls.

Book
Highlights of the day
Top Sight
Grand Canal
This is a highlight of your day—an experience designed to immerse you in the local culture and create lasting memories during your trip.
Where to Eat
Top Restaurant
Ristorante Quadri Venice
Facing St. Mark’s Square near the Grand Canal, Quadri offers exquisite Venetian fine dining with gourmet local dishes, perfect for a luxurious and romantic farewell dinner after a sunset gondola ride, letting the couple savor Venice’s enchanting atmosphere one last time in style and elegance.
Facing St. Mark’s Square near the Grand Canal, Quadri offers exquisite Venetian fine dining with gourmet local dishes, perfect for a luxurious and romantic farewell dinner after a sunset gondola ride, letting the couple savor Venice’s enchanting atmosphere one last time in style and elegance.
Bookable Activities
Bookable Activity
Venice: Explore Venice on Electric Boat
Full starFull starFull starFull starHalf star
4.6
(24 reviews)
Clock icon1h 30m
$118.69per person

Enjoy a cruise around Venice to admire the unique landmarks and “breath” the characteristic atmosphere of the city comfortably on board of a fully electric boat. An exclusive experience that allow you to relax and immerse into the Venetian atmosphere while cruising around the city and its close islands. The silent boat, sophisticated yet comfortable is equipped with a full open space that will let you live a true and luxurious experience.

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