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The Perfect 5-Days Family Itinerary to Italy in May (with kids)

Imagine stepping hand-in-hand with your family into a living storybook, where every corner pulses with the timeless magic of Italy. In the gentle warmth of May, ancient cities awaken with vibrant colors, enchanting aromas, and the laughter of children discovering wonders that have shaped the world. From the sun-dappled piazzas of Rome to the serene canals of Venice, this journey invites your family to wander through history, art, and culture in a way that sparks curiosity and togetherness unlike any other. This is more than a trip—it’s a shared adventure where eyes widen with the awe of monumental cathedrals, where little hands try their skill in artisan workshops, and where sweet moments of gelato and laughter create a tapestry of memories that will forever tie your family to a place of wonder and warmth. With every step, you’ll feel Italy’s rich spirit weaving its way into your hearts, igniting imaginations and gifting you not just sights, but enduring stories to treasure. Prepare to embark on a remarkable family journey bursting with joy, discovery, and the kind of magic that only Italy in spring can bring.

Why You'll Love This Trip

  • Experience the awe and imagination of ancient Roman wonders, where history comes alive under the springtime sun and every piazza bursts with vibrant local life.
  • Dive into the world of Renaissance art and architecture in Florence, inspiring both adults and children while strolling through storybook streets and engaging in hands-on artisan traditions.
  • Glide through Venice’s enchanting canals, where colorful alleys, mask-making magic, and lively piazzas create a captivating playground for the whole family.
  • Connect with Italy’s soulful flavors during interactive cooking experiences set amidst scenic Tuscan hills, blending learning, laughter, and delicious memories.
  • Bask in the unique blend of culture, nature, and gentle spring weather that invites relaxed exploration, shared wonder, and moments of pure delight for travelers of all ages.
  • Watch your family’s curiosity and bonds grow stronger as you uncover Italy’s timeless treasures together—transforming a vacation into an unforgettable journey of connection and joy.

Your Trip Map

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Your Journey

1
Main activity for day 1

Roman Family Gateway

Step into the heart of ancient Rome where history bursts into life with every cobblestone and fountain. May’s gentle warmth invites your family to explore the marvels of the Colosseum, where gladiators once battled, and nearby Imperial forums whisper stories of emperors long gone. Wander through piazzas buzzing with life and discover gelato shops perfect for cooling down while watching lively street performers. This is an immersive introduction to Italy’s eternal city, rich with layers of history, culture, and family-friendly charm that blend seamlessly in the Roman springtime air.

Begin your Roman adventure at the breathtaking , where the atmosphere resonates with echoes of ancient crowds and heroic gladiators. As you explore this vast amphitheater, watch your children marvel at the sheer scale and imagine the grand spectacles of centuries past. Early morning visits help you dodge the midday crowds and heat, making it a comfortable experience for the whole family. Next, stroll a few minutes to the , winding through crumbling temples and arches that once formed the center of Roman life. Engage your kids with stories of mythology and emperors, transforming ruins into a living history lesson. By midday, head toward the , a masterpiece of baroque artistry; here, your family can toss coins together to pledge a return visit, joining a timeless Roman tradition under the May sun. Continue to , where lively street performers and artists create an enchanting sensory experience, perfect for kids who love to watch and interact with local culture. End your day with a treat at nearby, savoring creamy gelato made from traditional recipes—an ideal refreshing reward that captures the authentic flavors of Italy and delights all ages.

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 family-friendly hotel overlooking the Colosseum, perfectly located for early visits to the Colosseum and Roman Forum, minimizing travel with children while offering spacious suites.

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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
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 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.
Top Activity
Giolitti Gelateria
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 Taverna dei Fori Imperiali Rome
Located near the Colosseum and Roman Forum, this family-friendly trattoria offers authentic Roman cuisine in a warm setting perfect for families. It complements the day’s ancient Roman landmarks with traditional dishes that children and adults can enjoy after a day of sightseeing, and its proximity fits well into the walking itinerary around the historic center.
Located near the Colosseum and Roman Forum, this family-friendly trattoria offers authentic Roman cuisine in a warm setting perfect for families. It complements the day’s ancient Roman landmarks with traditional dishes that children and adults can enjoy after a day of sightseeing, and its proximity fits well into the walking itinerary around the historic center.
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 Wonders and Trastevere Charm

Today brings the family closer to the artistic and spiritual heartbeat of Rome with the awe-inspiring Vatican Museums and the Sistine Chapel’s divine ceiling. Afterwards, dive into the colorful neighborhood of Trastevere, where narrow cobbled streets and lively piazzas brim with authentic Roman life and kid-friendly trattorias. May’s mild weather encourages leisurely exploration, letting you soak up Italy’s rich faith, art, and vibrant street scenes amidst fragrant lemon trees and the gentle hum of Sunday street musicians.

Start your morning immersed in the hallowed halls of the , where the youngest family members can marvel at thousands of years of human creativity and devotion. To fully appreciate the masterpieces without feeling overwhelmed, pace your visit with breaks before entering the , whose breathtaking ceiling painted by Michelangelo captures the imagination of all ages with scenes from Genesis. Following this, step outside to visit , where children will enjoy the grandeur of the dome and the sprawling piazza, offering spectacular views of Vatican City and beyond. In the afternoon, wander over to , a charming Roman neighborhood bursting with character. Its maze of cobbled streets invites exploration, while lively piazzas reveal street artists and fresh market stalls that bring Italian culture to life. As sunset approaches, gather the family for an authentic pizza meal at , where thin-crust Roman pies are served in a warm, casual setting loved by locals, allowing the children to taste one of Italy’s most beloved dishes and soak up the neighborhood’s convivial spirit.

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

Luxury hotel close to Vatican Museums with expansive grounds and family-friendly amenities such as spacious rooms and a pool, perfect for resting after a busy cultural day.

Book
Highlights of the day
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.
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
Trastevere
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 Activity
Pizzeria Ai Marmi
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 Ai Marmi Trastevere Rome
Situated in the heart of Trastevere and already part of the itinerary, this beloved family-friendly pizzeria is ideal for enjoying authentic thin-crust Roman pizza in a lively, casual atmosphere. It perfectly complements the day’s exploration of Vatican art and the charming Trastevere neighborhood, offering a relaxed meal that suits families with kids.
Situated in the heart of Trastevere and already part of the itinerary, this beloved family-friendly pizzeria is ideal for enjoying authentic thin-crust Roman pizza in a lively, casual atmosphere. It perfectly complements the day’s exploration of Vatican art and the charming Trastevere neighborhood, offering a relaxed meal that suits families with kids.
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

Florence’s Renaissance Treasures

Venture north to Florence where the Renaissance awakens the senses with breathtaking art, architecture, and storybook streets. May’s blossoming gardens and warm breezes bring the city’s piazzas to life, inviting children and adults alike to stroll along the Arno River, climb the Duomo’s terracotta dome, and explore the Uffizi’s glittering masterpieces. The family will savor traditional Tuscan flavors and can enjoy hands-on artisan workshops, making this day a rich tapestry of Italian creativity, history, and joyful discovery in a city where the past and present dance beautifully together.

Begin your Florentine journey at the Cathedral of Santa Maria del Fiore, where the striking terracotta dome dominates the skyline and invites adventurous family members to climb its 463 steps for sweeping views of the city’s red roofs and rolling Tuscan hills. The cathedral’s intricate facade and the Baptistery’s golden doors provide a feast for the eyes that captures the spirit of Renaissance Italy. After this, stroll to the to encounter artworks that shaped Western art history. To keep children engaged, focus on iconic pieces like Botticelli’s ‘The Birth of Venus,’ sharing stories about the myths behind the paintings that spark their imagination. Break for a lively walk through , where kids can delight in spotting the replicas of Michelangelo’s David and other grand statues, perfect for photos and daydreams. Cross the historic , a unique medieval bridge brimming with boutique jewelry shops, enjoying the river views and the lively atmosphere. To cap off the day, immerse the family in an authentic artesanal leather workshop nearby, where hands-on crafting sessions offer both learning and a memorable souvenir-making experience, an exciting way for kids to engage with local tradition while creating something truly special.

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

Luxury family-friendly hotel located a short walk from the Duomo and Uffizi Gallery, providing spacious suites suitable for families and amenities tailored to comfort after a day exploring Renaissance treasures.

Book
Highlights of the day
Top Sight
Cathedral of Santa Maria del Fiore (Florence Duomo)
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
Piazza della Signoria
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.
Top Activity
Florentine Leather Workshop
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 classic Florentine family-friendly eatery near the city center and the Duomo, Trattoria Mario serves traditional Tuscan dishes with a welcoming atmosphere ideal for families. It complements the day’s Renaissance art and cultural immersion by providing hearty local flavors in a convivial setting, conveniently located to fit into the busy touring schedule.
A classic Florentine family-friendly eatery near the city center and the Duomo, Trattoria Mario serves traditional Tuscan dishes with a welcoming atmosphere ideal for families. It complements the day’s Renaissance art and cultural immersion by providing hearty local flavors in a convivial setting, conveniently located to fit into the busy touring schedule.
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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4
Main activity for day 4

Venice’s Enchanting Canals

Enter the magical world of Venice’s waterways, where gondolas glide beneath ancient bridges and piazzas buzz with Venetian charm. May’s pleasant springs weather is perfect for wandering along narrow alleys, visiting the Doge’s Palace and Saint Mark’s Basilica, and watching mask-makers handcraft Carnival treasures. The children will thrill at spotting pigeons in St. Mark’s Square and tasting freshly made cicchetti in cozy bacari, making this day a dreamlike blend of history, art, and family-friendly adventure.

Kick off your enchanting day in Venice at the stunning , where shimmering gold mosaics and intricate Byzantine domes transport your family into a world of artistic wonder. Children will gaze upward in awe at the dazzling artwork while you soak in the basilica’s centuries-old spiritual beauty. Just steps away, explore the Doge’s Palace with its grand halls and intriguing history, captivating imaginations with stories of Venetian rulers and secret prisoner passages beneath the Bridge of Sighs. As your family crosses the bustling , the lively shops and views of the Grand Canal provide vibrant scenes perfect for curious minds and cameras alike. Embrace an authentic Venetian experience in the afternoon with a mask-making workshop, where kids and parents can design and decorate traditional Carnival masks, connecting with Venice’s rich cultural heritage through hands-on creativity. To round the day, discover cozy bacari bars serving cicchetti—Venetian small plates—and indulge in flavors like fried seafood or olives in a relaxed, informal atmosphere where the family can refuel and mingle with locals.

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

A prestigious family-friendly hotel overlooking the lagoon near Saint Mark’s Square, offering easy access to major sights like the Doge’s Palace and a luxurious setting for families.

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Highlights of the day
Top Sight
Saint 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
Doge’s Palace (Palazzo Ducale)
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.
Top Activity
Venetian Mask Workshop
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 Activity
Bacaro (Venetian Tapas Bars)
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 Squero Venice
Located near the Rialto Bridge, this cozy bacaro-style osteria offers a family-friendly introduction to Venetian cicchetti (small plates), complementing the day’s mask workshop and canal-side explorations. Its informal and authentic atmosphere allows families to enjoy local flavors and mingle with locals, fitting well into the afternoon sampling of Venetian snacks.
Located near the Rialto Bridge, this cozy bacaro-style osteria offers a family-friendly introduction to Venetian cicchetti (small plates), complementing the day’s mask workshop and canal-side explorations. Its informal and authentic atmosphere allows families to enjoy local flavors and mingle with locals, fitting well into the afternoon sampling of Venetian snacks.
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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5
Main activity for day 5

Tuscan Countryside and Culinary Delights

Escape into the idyllic Tuscan hills for a day of nature, history, and irresistible flavors. May’s mild climate enhances your walk through idyllic vineyards and medieval hill towns like San Gimignano, where towers pierce the sky and gelato is a local pride. The family gathers to partake in a cooking class amid olive groves, learning to craft fresh pasta and sauces. This day of rustic beauty and hands-on culinary fun leaves a lasting taste of Italian tradition and countryside tranquility that kids and adults savor alike.

Begin this perfect Tuscan day with a scenic drive to the medieval jewel of San Gimignano, a hilltop town famed for its preserved towers and winding alleyways that invite families to step back into the Middle Ages. The town’s charming piazzas and artisan shops offer a magical atmosphere as kids hunt for hidden nooks and enjoy the town’s renowned gelato, considered some of Italy’s best and a must-try treat under the bright May sun. Following your exploration, immerse the family in a lively cooking class nestled in a rustic countryside setting, where you all learn the art of making pasta from scratch alongside a seasoned local chef. This interactive experience is rich with laughter and learning as recipes unfold and tastes evolve—with kids delighting in the sensory joy of fresh dough and the fragrance of simmering sauces. To savor the breathtaking surroundings, take a gentle stroll through nearby vineyards and olive groves, the quintessential Tuscan landscape, where rolling hills and fresh air create tranquility and inspiring views that linger in your memory as much as the flavors you’ve created together.

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

Family-friendly hotel located in the heart of San Gimignano near the historic towers, providing spacious rooms and easy access to gelato shops and artisan boutiques.

Book
Highlights of the day
Top Sight
San Gimignano 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 Activity
Tuscan Cooking Class
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 Activity
Vineyards and Olive Groves Walk
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
A highly recommended family-friendly restaurant in San Gimignano’s historic center, Cum Quibus offers refined Tuscan cuisine in a welcoming atmosphere. It perfectly complements the day’s exploration of medieval San Gimignano and the cooking class by providing a superb local dining experience that can accommodate families after a day outdoors, ensuring an authentic taste of the Tuscan countryside.
A highly recommended family-friendly restaurant in San Gimignano’s historic center, Cum Quibus offers refined Tuscan cuisine in a welcoming atmosphere. It perfectly complements the day’s exploration of medieval San Gimignano and the cooking class by providing a superb local dining experience that can accommodate families after a day outdoors, ensuring an authentic taste of the Tuscan countryside.
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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5-Day Family With Kids Itinerary to Italy in may | Wandio