Wander Freely, Plan Smartly

The Perfect 7-Days Adventure Itinerary to Italy in May (for couples)

Imagine stepping hand in hand into a canvas painted with the golden light of autumn—where ancient stones whisper timeless love stories and every breath is filled with the aroma of fresh espresso, rich wine, and crisp mountain air. This seven-day adventure through Italy in November invites you and your partner to lose yourselves in the magic of vibrant cities, serene countryside, rugged coastlines, and majestic alpine peaks. Each moment pulses with romance and excitement, weaving a tapestry of shared discoveries that will deepen your connection and awaken your senses. From the velvet evenings beneath Rome’s illuminated ruins to the tranquil gardens hidden within the Vatican’s heart; from winding Tuscan roads lined with fiery cypresses to the intoxicating hues of Liguria’s cliffs meeting the sea—this journey is an invitation to experience Italy not just as a place, but as an emotion. It’s an intimate escape where history, art, nature, and adventure blend seamlessly, creating a story you and your loved one will carry forever. Prepare to be enchanted, exhilarated, and transformed as you embark on a romance that transcends time and place.

Why You'll Love This Trip

  • Feel the electric romance of ancient Rome and the intimate charm of its lively neighborhoods as you explore together in the soft glow of autumn light.
  • Experience awe and tranquility side by side in the Vatican’s sacred art-filled halls and secret gardens, a perfect balance of wonder and peaceful reflection.
  • Wander hand in hand through Tuscany’s golden harvest landscapes, medieval towns, and world-renowned vineyards, where every view feels like a timeless postcard.
  • Discover Florence’s Renaissance heartbeat interwoven with quiet artisan streets, inviting moments of connection amid its artistic and cultural treasures.
  • Immerse yourselves in the breathtaking colors and coastal breezes of Cinque Terre’s cliffside villages, forging memories along romantic seaside paths.
  • End your adventure surrounded by the awe-inspiring Dolomites—crisp mountain air, panoramic ridgelines, and rustic alpine warmth offering a breathtaking finale to your journey.

Your Trip Map

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Your Journey

1
Main activity for day 1

Rome: Ancient Wonders and Romantic Aura

Step into the eternal city where every street whispers stories of emperors, gladiators, and lovers. The golden hues of October bathe the ancient ruins in a warm glow, making your first day in Rome a breathtaking plunge into history and passion. From the grandeur of the Colosseum to the serene corners of Trastevere, the city’s blend of adventure and charm will sweep you into a whirlwind of discovery and intimate moments.

Begin your Roman adventure immersed in the majesty of the , arriving early in the morning to beat the crowds and enjoy the soft, golden light that makes the ancient stone glow warmly. Imagine the roar of thousands of spectators as you explore the labyrinth beneath the arena floor, uncovering secrets of gladiatorial contests and wild beast hunts. The atmosphere is thick with history, thrilling your adventurous spirit as you wander through one of the greatest engineering feats of the ancient world. From here, a short stroll brings you to the , where you can trace the footsteps of Julius Caesar and Cicero amid temple ruins and triumphal arches. The autumn air carries a subtle crispness, ideal for leisurely, immersive exploration while you absorb the echoes of civilization's grand past. In the afternoon, venture over to Trastevere, a neighborhood that offers a welcoming maze of narrow streets lined with vibrant murals, ivy-clad buildings, and a spirit of bohemian romance. Here, let your senses indulge in an aperitivo on a piazza terrace, watching as day melts into twilight while locals play lively music or gather for evening passeggiata. The blend of historic grandeur and intimate, lively charm makes your first day in Rome a captivating adventure that sets the perfect 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)

Luxury hotel overlooking the Colosseum, ideal for early morning visits and immersion in ancient Rome’s atmosphere with romantic and adventure style suitable for couples.

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Highlights of the day
Top Sight
Colosseum
HistoricLandmarkIconic
The grand amphitheater of ancient Rome, where epic battles and spectacles once captivated thousands.
Top Sight
Roman Forum
HistoricArchaeologicalOutdoor
The heart of ancient Roman political, commercial, and religious life, full of ruins and evocative arches.
Top Sight
Trastevere Neighborhood
NeighborhoodCulturalRomantic
A charming, lively district known for winding cobblestone streets, authentic trattorias, and vibrant nightlife.
Where to Eat
Top Restaurant
Trattoria Da Enzo al 29
Located at Via dei Vascellari, 29, 00153 Roma RM
Located in Trastevere, this authentic trattoria offers traditional Roman cuisine in a rustic, cozy ambiance perfect for couples seeking a romantic yet adventurous dining experience after exploring ancient 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

Vatican’s Sacred Art and Serene Gardens

Delve into the spiritual and artistic treasures of the Vatican, where awe-inspiring art and peaceful gardens create moments of transcendence. October's mild weather invites tranquil exploration of the Vatican Museums, crowned by Michelangelo's Sistine Chapel frescoes, and a quiet stroll through the Vatican Gardens, offering a reflective oasis hidden within the bustling city.

Start your day with an early entrance to the , allowing you to wander through vast galleries filled with masterpieces spanning millennia without the larger crowds that gather later. Feel your breath catch as you approach the , where Michelangelo's vivid depiction of creation and judgment surrounds you in breathtaking color and emotion, an encounter that transcends mere sightseeing to become a moment of deep awe. After soaking in this artistic grandeur, join a reserved guided stroll through the , a hidden gem often missed by casual tourists. Here, the serenity of perfectly manicured lawns, ancient trees, and ornate fountains invites you to slow down and reflect in botanical beauty, a contrast to the city’s hustle. The fresh autumn air and softer afternoon light make this an idyllic time for intimate conversations amid nature and history, creating a perfect balance of spiritual and sensory delight. Complete your day with a quiet walk around St. Peter’s Square as the sun dips, witnessing the piazza’s grand baroque architecture come alive under the evening glow.

Where to Stay
Accommodation
Bio Hotel Raphael - Relais & Châteaux
Full starFull starFull starFull starHalf star
4.5
(Great)

Luxury boutique hotel within walking distance to Vatican Museums and St. Peter’s Square, providing peaceful, artistic ambiance matching the spiritual adventure of the Vatican day.

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Highlights of the day
Top Sight
Vatican Museums
MuseumArtHistoric
A vast complex housing one of the world’s richest art collections, culminating in the breathtaking Sistine Chapel.
Top Sight
Sistine Chapel
HistoricArtReligious
Michelangelo’s masterwork ceiling and Last Judgment frescoes that symbolize the height of Renaissance art.
Top Sight
Vatican Gardens
GardenPeacefulHistoric
A beautifully landscaped sanctuary with fountains, sculptures, and lush greenery reserved for peaceful Vatican retreats.
Where to Eat
Top Restaurant
Ristorante Arlù
Located at Borgo Pio, 135, 00193 Roma RM
Located near the Vatican, Arlu offers refined Roman and Lazio dishes in a cozy setting, perfect for a relaxing lunch after the intellectual and spiritual immersion in the Vatican Museums.
Bookable Activities
Bookable Activity
Vatican City: Skip the Line Access to St Peter Basilica
Full starFull starFull starFull starEmpty star
4.3
(23 reviews)
Clock icon1h 10m
$20.65per person

Gain exclusive access to St. Peter's Basilica, a cornerstone of Catholic faith and an architectural masterpiece, with reserved entry that allows you to bypass the crowds. Marvel at Michelangelo's Pietà and Bernini's grand Baldachin, each showcasing unparalleled artistry. Explore the stunning mosaics that adorn the Basilica's walls and ceilings, immersing yourself in a space rich with history and spiritual significance. Built over the tomb of St. Peter, this iconic church invites you to connect with centuries of artistic achievement and profound religious heritage.

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3
Main activity for day 3

Tuscany’s Timeless Countryside Escape

Escape the city’s pace to the rolling hills of Tuscany, where cypress-lined roads, medieval towns, and aromatic vineyards invite adventurous souls to enjoy rustic beauty and genuine local experiences. October’s harvest season colours the landscape with amber and gold, enriching your journey of exploration and flavors in the heart of Italy’s most romantic countryside.

Board a morning train from Rome to Siena, letting the landscape unfold in vibrant autumn hues as you journey north. Arriving in Siena, lose yourself in the medieval magic of , a uniquely shell-shaped square that pulses with local life and history. Watch as artisans showcase crafts and residents enjoy cafes, feeling the deep connection between place and time. Wander up the narrow streets to Hagia Sophia’s Duomo with its stunning striped marble and intricate mosaics, soaking up the town’s artful heritage. In the afternoon, take a scenic drive into the Chianti region, where rows of vineyards stretch across golden hills and quaint wineries invite you for intimate tastings of robust Sangiovese grapes paired with local pecorino cheese and truffles. Engage with passionate winemakers, learning their ancient techniques amidst breathtaking panoramas. Continue to , whose medieval towers pierce the sky, a fairy-tale setting where you can stroll through the winding stone streets, discover artisan shops, and savor gelato made with locally grown saffron as the fading sun casts a warm light over red tile roofs. The day’s blend of history, nature, and epicurean delights nourishes both body and soul as you embrace Tuscany’s timeless romance.

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

Located just outside Siena’s historic center, offering panoramic views and easy access to Piazza del Campo, perfect for adventurers wanting countryside comfort and quick city visits.

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Highlights of the day
Top Sight
Piazza del Campo
HistoricSquareMedieval
Siena’s famed shell-shaped medieval square, known for its striking brickwork and vibrant public life.
Top Sight
Chianti Vineyards
CountrysideWineScenic
Famous rolling vineyards producing world-renowned wines, dotted with traditional wineries and tasting rooms.
Top Sight
San Gimignano
HistoricTownScenic
A medieval hill town famous for its skyline of ancient towers and charming cobblestone streets.
Where to Eat
Top Restaurant
Osteria Le Logge
Located at Via del Porrione, 33, 53100 Siena SI
A historic osteria near Piazza del Campo offering elevated Tuscan dishes with an intimate ambiance, perfect for fueling adventures exploring medieval Siena.
Bookable Activities
Bookable Activity
Siena: A Wine Tour and Tasting Experience
Full starFull starFull starFull starHalf star
5.0
(328 reviews)
Clock icon3 hours
$100.89per person

In the hills of the gorgeous Tuscan countryside,  just 2kms away from the medieval center of Siena, this Educational Wine Tour and Tasting 'Vine, Wine and Life' is a 3-hour tour held in an organic winery. Learn about the different stages of wine making through the seasons and enjoy tastings and a light lunch.

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4
Main activity for day 4

Florence’s Artistic Heartbeat and Hidden Alleys

Discover the Renaissance jewel of Florence, where monumental art and intimate local life beat side by side. October brings mild weather perfect for wandering the Arno’s banks, exploring fresco-filled churches, and uncovering colorful artisan workshops off the beaten path. This day promises endless discoveries and moments that connect you deeply to the creative spirit of Tuscany’s capital.

Begin your morning marveling at the Florence Cathedral’s magnificent dome, a fifteenth-century engineering marvel that dominates the city skyline. Ascend the spiral staircase to the top for a moment of exhilaration and a sweeping view of the ochre rooftops and distant Tuscan hills. Inside the cathedral, the intricate frescoes of the Last Judgment and the gleaming marble floors invite reverence and quiet contemplation. From this spiritual pinnacle, stroll a few minutes to the , where you can lose yourself amid masterpieces by Botticelli, Leonardo da Vinci, and Michelangelo. Let your gaze be captured by the ethereal 'Birth of Venus' and the dramatic 'Medusa,' feeling the pulse of Renaissance genius that shaped Western art. After a fulfilling art immersion, cross the iconic Ponte Vecchio, alive with jewelers' shops and the soft murmur of the Arno River below, to the . This bohemian quarter invites you to stroll through artisan workshops where traditional goldsmiths and leatherworkers create beautiful crafts passed down through generations. Stop at a quiet café for espresso and watch locals weave the fabric of everyday life, from open-air markets to friendly greetings on the streets. The day ends here, blending awe-inspiring art with authentic local rhythms, a perfect harmony for adventurers and romantics alike.

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

Located right by the Duomo, this luxury hotel offers immediate access to Florence Cathedral and Uffizi, perfect for art-loving adventurers wanting to delve into Renaissance treasures.

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Highlights of the day
Top Sight
Florence Cathedral (Duomo)
HistoricArchitectureReligious
An iconic symbol of Florence, famous for Brunelleschi’s massive red dome and intricate façade.
Top Sight
Uffizi Gallery
MuseumArtHistoric
Home to one of the world’s most important collections of Renaissance art.
Top Sight
Oltrarno District
CulturalArtisanNeighborhood
Florence’s artisan quarter with workshops, quaint cafes, and a lively bohemian atmosphere.
Where to Eat
Top Restaurant
Trattoria Mario
Located at Via Rosina, 2r, 50123 Firenze FI
A beloved, vibrant spot near San Lorenzo that serves traditional Florentine dishes with a friendly, informal vibe, perfect after visiting the Duomo and Uffizi for a hearty, authentic meal.
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

Cinque Terre: Rugged Coastline and Vibrant Villages

Experience Italy’s dazzling Ligurian coastline where colorful cliffside villages nestle against turquoise seas. October’s mild weather and softened tourist crowds invite you to hike coastal paths, savor fresh seafood, and embrace the lively charm of this UNESCO World Heritage site. The fusion of sea, sky, and village life creates a breathtaking adventure full of sensory wonders and heartfelt encounters.

Arrive early in the enchanting village of Riomaggiore, where the vibrant pastel buildings tumble dramatically toward the Ligurian Sea, offering picture-perfect views at every turn. Breathe in the salty air and let your feet wander along narrow cobbled streets lined with arches bursting with bougainvillaea and local shops selling handwoven goods. Embark on the famous , a path carved into cliffs along the sea, where the gentle breeze mingles with the soft sound of waves crashing below. This romantic trail promises breathtaking panoramas of rugged coastline, ideal for couples to share quiet moments and vibrant memories. Upon reaching Manarola, take time to explore its tiny harbor, watching fishermen bring in the day’s catch while local cooks prepare fresh anchovies and seafood delicacies. Enjoy a leisurely lunch at a seaside trattoria, savoring Ligurian specialties like trofie al pesto or stuffed mussels, accompanied by crisp white wine from nearby vineyards. The day’s blend of invigorating hiking, mesmerizing scenery, and authentic village life embodies Italy’s coastal magic, leaving you both exhilarated and enchanted.

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

Clifftop luxury hotel with spectacular sea views strategically located near Riomaggiore and hiking trails suitable for adventurous travelers wanting comfort and access to the coast.

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Highlights of the day
Top Sight
Riomaggiore Village
CoastalVillageScenic
The southernmost village of Cinque Terre, known for its steep terraced vineyards and pastel houses cascading to the sea.
Top Sight
Via dell’Amore
HikingRomanticScenic
A famous and scenic seaside walking trail connecting Riomaggiore to Manarola.
Top Sight
Manarola Village
CoastalVillageGastronomy
A charming village famous for its bright homes and seafood restaurants perched above the waves.
Where to Eat
Top Restaurant
Trattoria La Grotta
Located at Via Colombo, 247, 19017 Riomaggiore SP
A family-run seaside restaurant serving fresh seafood and Ligurian specialties, ideal for couples looking to experience authentic coastal cuisine after hiking Via dell’Amore.
Bookable Activities
Bookable Activity
Ferry boat tour to the Cinque Terre with stop in Riomaggiore and Monterosso
Full starFull starFull starFull starEmpty star
4.2
(90 reviews)
Clock icon8 hours
$79.52per person

Discovering the Cinque Terre coast, a UNESCO heritage site, and two of its pearls appreciating the shape and the design that the nature has gifted to this area.

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6
Main activity for day 6

Venice: Labyrinth of Canals and Intimate Wonders

Dive into Venice’s captivating maze of waterways and bridges, where every corner reveals artistic treasures and quiet moments of romance. October’s gentle light softens the city’s enchanting atmosphere, making a gondola ride and exploration of hidden sestieri an immersive, unforgettable adventure for two.

Step off the train into the enchanting atmosphere of Venice, where the hum of footsteps and lapping water replaces the clatter of cars. Begin a thoughtful exploration at , where golden mosaics shimmer above you and the blend of Byzantine, Gothic, and Renaissance elements feels almost dreamlike. Spend time admiring the delicate marble floors and serene chapels, letting the golden light that filters through stained glass windows fill your soul with reverence. As midday approaches, board a vaporetto to glide along the , observing opulent palazzi and hidden courts with frescoed façades that hint at Venice’s glorious mercantile past. This waterborne journey is unforgettably romantic, the gentle rocking of the boat and the reflections on the water carrying you through centuries of beauty. Later, seek out the , where the crowds thin and local life thrives amid art galleries and cozy cafes. Cross little bridges to quiet canals where you can savor a spritz alongside Venetians while watching gondolas drift by in the soft October light. The day balances iconic grandeur and intimate discovery, a perfect Venetian embrace.

Where to Stay
Accommodation
The Gritti Palace, a Luxury Collection Hotel, Venice
Full starFull starFull starFull starHalf star
4.7
(Amazing)

Iconic luxury hotel on the Grand Canal near St. Mark’s Basilica, ideal for romantic and adventurous travelers seeking historic grandeur and proximity to main sights.

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Highlights of the day
Top Sight
St. Mark’s Basilica
HistoricReligiousArtistic
Venice’s stunning cathedral famed for its opulent Byzantine mosaics and ornate architecture.
Top Sight
Grand Canal
ScenicHistoricTransport
The main waterway weaving through Venice, lined by Renaissance and Gothic palazzi.
Top Sight
Dorsoduro District
CulturalQuietRomantic
An artsy, quieter neighborhood filled with galleries, quaint cafes, and stunning views of the city’s rooftops.
Where to Eat
Top Restaurant
Osteria alle Testiere
Located at Calle del Mondo Novo, 5801, 30122 Venezia VE
A small, intimate Venetian seafood osteria near St. Mark’s Basilica offering exquisite traditional dishes, perfect for couples seeking an authentic, romantic culinary experience in the city.
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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7
Main activity for day 7

Dolomites Adventure: Alpine Majesty and Rustic Warmth

Complete your Italian odyssey with a breathtaking escape to the Dolomites, where jagged peaks, golden larch forests, and alpine charm create the ultimate outdoor adventure. October’s crisp air invites invigorating hikes and cozy mountain refuges, wrapping your journey in dramatic landscapes and heartfelt local hospitality.

Venture into the alpine splendor of the Dolomites, arriving in the delightful village of Ortisei where traditional wooden chalets and the scent of pine create an inviting atmosphere. Wander through its lively pedestrian streets, where local craftsmen display intricate woodcarvings, and stop to sip rich espresso at a sun-dappled café. Then ascend via cable car to the , a jaw-dropping panorama of jagged peaks softened by the golden hues of October’s larches. Standing here, surrounded by the dramatic landscapes that inspired poets and photographers, you’ll feel an exhilarating sense of freedom and awe. Lace up your hiking boots for a scenic trail descending to , a rustic mountain hut where hearty Ladin dishes like speck and canederli revive your energy. Enjoy your meal in the cozy warmth of the refuge’s wooden interiors while gazing out across valleys framed by towering cliffs. The crisp mountain air, stunning vistas, and welcoming hospitality combine to provide a thrilling finale to your Italian adventure—memories of rugged beauty and heartfelt connection to nature that will linger long after your journey ends.

Where to Stay
Accommodation
Hotel Angelo Engel
Full starFull starFull starFull starHalf star
4.7
(Amazing)

Charming mountain hotel close to cable car access with traditional styling and cozy atmosphere, great for hikers and explorers seeking alpine comfort.

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Highlights of the day
Top Sight
Seceda Ridgeline
MountainScenicOutdoor
A stunning jagged mountain ridge offering panoramic views over valleys and peaks in the Dolomites.
Top Sight
Ortisei Village
VillageCulturalMountain
Charming alpine village known for its woodcarving tradition and lively pedestrian streets.
Top Sight
Rifugio Firenze
RefugeRestaurantScenic
A cozy mountain hut offering hearty Ladin cuisine and panoramic views in the Dolomites.
Where to Eat
Top Restaurant
Regensburgerhütte
Located at Ciaulongh, 17, 39047 Santa Cristina Valgardena BZ
Cozy mountain hut offering hearty Ladin cuisine with breathtaking Dolomites views, perfectly matching the day’s alpine hiking and rustic adventure for a warm, inviting meal.
Bookable Activities
Bookable Activity
Private Luxury Transfer from Verona to Ortisei (or vice versa)
Full starFull starFull starFull starFull star
5.0
(2 reviews)
Clock icon2h 15m
$284.86per person

Exclusive transfer in first class with Luxury Mercedes Minivan with leather seats, air conditioned, wifi. Fresh water bottles included

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7-Day Adventure Couple Itinerary to Italy in may | Wandio