Whether you're hiding behind a Carnival mask, crafting your own gelato flavor, or cruising around Lake Como, Italy has a new experience for your family waiting around every corner. With two weeks to explore, you've got plenty of time to design your ideal itinerary. Hit all the highlights, take it easy on a road trip, go for a more active path down the coast, or slow down with a sling-bound baby with these options that will have you gesturing wildly with excitement in no time.

Itinerary #1: Highlights of Italy

Get in all the hotspots on this itinerary that's ideal for school-age children. Search for secrets in the Venetian lagoon, create your own gelato flavor in Florence, reconstruct ancient Rome, and make pizza in its birthplace, Naples.

Pose in front of the iconic Ponte Vecchio Bridge in Florence
Day Highlights Overnight
Day 1 Arrive in Venice, Private Gondola Ride, Walking Tour in Marco Polo's Footsteps Venice
Day 2 Venetian Mask Painting & Family Scavenger Hunt in the Doge’s Palace Venice
Day 3 Boat Tour To Venice Islands & Murano Scavenger Hunt For Families Venice
Day 4 Family Foodie Scavenger Hunt & Transfer to Florence Florence
Day 5 Free Morning in Florence & Gelato-Making Class Florence
Day 6 Day Trip to Pisa & Lucca Florence
Day 7 Florence to Rome & Family-Friendly Rome by Golf Cart Rome
Day 8 Treasure Hunt in the Colosseum & Roman Forum Rome
Day 9 Mosaic & Fresco Workshop, Vatican Highlights Treasure Hunt Rome
Day 10 Family Food Tour & Pasta-Making Class, Parks & Hills of Rome Rome
Day 11 Rome to Naples, Afternoon Tour & Local Dinner Naples
Day 12 Pizza Cooking Class & Naples Walking Tour Naples
Day 13 Pompeii for Kids Naples
Day 14 Depart Naples  


Your tour through the most-visited cities in Italy starts in Venice, with visits to a mask-making atelier, the secret passages of the Doge's Palace, and the islands of the Venetian Lagoon, all of which will be explored via scavenger hunts for their hidden treasures. Hop over to Florence next, where you'll create your own gelato flavor and day trip out to Pisa, home of the famous leaning tower, and the medieval walls of Lucca.

After that, it's off to the city where all roads lead: Rome. See the sights in the easiest fashion with a spin around on a guided golf cart tour, then get in-depth in the Colosseum and Roman Forum with the help of 3D reconstruction glasses that let you see the buildings as they once were. Craft a mosaic, see the arts by the masters in the Vatican museums, and learn to make pasta like a pro before you head to your last stop in Naples. You'll sample local specialties like seafood and pizza—and make your own—while touring the city and nearby sites such as the ancient city of Pompeii, once buried by volcanic eruption, before you head home. Learn more

Itinerary #2: Family Road Trip Through Northern Italy

You've got six cities to see in this itinerary, which will still let you move at your own pace with its easy road trip design that's ideal for families with school-age children who need some flexibility. You'll get plenty of free days as well as guided introductions to spots like Lake Como, the cities and villages of Tuscany, and the coast along the Italian Riviera.

Exploring Cinque Terre
Day Highlights Overnight
Day 1 Arrive in Milan, Transfer to Lake Como, and Como, Bellagio & Villas Boat Tour Lake Como
Day 2 Free Day in Lake Como Villages Lake Como
Day 3 Lake Como to Lake Garda, West Lake Garda & Sirmione Boat Tour Lake Garda
Day 4 Free Day on Lake Garda Lake Garda
Day 5 Lake Garda to Chianti, Chianti Wagon Ride & Picnic Chianti
Day 6 Explore Tuscany Chianti
Day 7 Chianti to San Gimignano & Monteriggioni San Gimignano
Day 8 Day Trip to Volterra San Gimignano
Day 9 San Gimignano to Siena & Explore Siena Siena
Day 10 Day Trip to Florence Siena
Day 11 Siena to Italian Riviera & Explore Genoa Italian Riviera
Day 12 Free Day on the Italian Riviera Italian Riviera
Day 13 Sunset Boat Trip & Cinque Terre Villages Italian Riviera
Day 14 Italian Riviera to Milan & Depart  


You'll fly into Milan and immediately hit the road up to Lake Como. Its glitzy shores can still be navigated on a budget as you ride a boat tour around the lake and its historic villas, browse the boutiques of Bellagio, and explore the gardens of the rich and famous along the lake's edge. Next up is Lake Garda, considered one of Italy's most family-friendly lakes for its many easy hiking trails and amusement parks. It even has its own castle. You'll tour the western side of the lake via boat to give you plenty of inspiration for how to spend a free day on its shores.

From there you'll head to the sunny countrysides of Tuscany, starting off with a wagon ride through the hills of the Chianti Valley. Enjoy the gentle pace of the horse-drawn wagon as your guide introduces you to this famous region, which has much more to offer than its eponymous wine. Explore the tall medieval towers of San Gimignano, hillside fortress of Monteriggioni, and walled town of Volterra with your wheels. Siena is up next, Italy's "open-air museum," with its expansive plaza and city walls and a day trip to Florence, where you can catch a look at Michelangelo's "David" or lounge in the Boboli Gardens where the Medici family once walked.

Had your fill of cities? Your trip ends on the Italian Riviera. Dip into the port city of Genoa before you head to the pebbly beaches and fishing villages near Portofino. Hike between the villages of Cinque Terre and board a boat to watch the sun set over their roofs from the sea as you toast to your trip. Learn more

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Itinerary #3: Active Family Adventures 

Find an adventure ideal for teens in Veneto and Tuscany with this itinerary. Your family can paddle, bike, hike, and even hot air balloon through these two dynamic regions, with plenty of stops on the way for the perfect selfie.

Balloon over Chianti
Day Highlights Overnight
Day 1 Arrive in Venice & Gondola Paddling for Families Venice
Day 2 Venetian Mask Painting, Doge's Palace & St. Mark's Basilica Secret Passages Tour Venice
Day 3 Bike Tour on Lido Island & Visit to Murano & Burano Islands Venice
Day 4 Venice to Verona & Verona Guided Bike Tour Verona
Day 5 Dolomites Day Trip Verona
Day 6 Verona to Lake Garda, West Lake Garda & Sirmione Boat Tour Lake Garda
Day 7 Free Day on Lake Garda Lake Garda
Day 8 Sigurtà Park Bike Ride & Picnic Lake Garda
Day 9 Lake Garda to Siena Siena
Day 10 Ballooning Over Chianti Siena
Day 11 Drive Through Tuscany Siena
Day 12 Siena to Florence Florence
Day 13 Parks of Florence & Gelato-Making Class Florence
Day 14 Depart Florence  


Start your trip in Venice by paddling your own gondola over the canals and wandering the alleys to find the perfect ciccheti stop. Create Carnival masks so your teens can hide their faces once you start to be too embarrassing, sneak through secret passages in the Doge's Palace, and bike past the 1920s hotels that line the beaches of Lido Island and its San Nicolò Natural Reserve.

Your next stop is fair Verona, which anyone who paid attention in English class will hopefully recognize as the home to the story of Romeo and Juliet. Day trip into the Dolomites mountain range and ride a panoramic funicular past alpine villages. The park-lined shores of Lake Garda are next, where the biking continues through Sigurtà Park's gardens, along with a boat ride around the lake and its castle.

Your trip wraps in Tuscany, with the medieval city of Siena serving as your base for a hot air balloon ride over the Chianti Valley. Drive through the countryside to check out the villages and vineyards before you head to Florence, the region's capital. Lounge in the city's parks and create your own gelato flavor to celebrate your trip before you head home. Learn more

Itinerary #4: Southern Italy With Small Children

Smooth out your trip with your baby or toddler with this itinerary. Private tours, beach days, and easy boat cruises will make managing your armful a breeze, whether you're at sea or skipping the line at the main attractions.

Explore the Vatican City with your little one
Day Highlights Overnight
Day 1 Arrive in Rome & Family-Friendly Rome By Golf Cart Rome
Day 2 Private Colosseum & Roman Forum Tour Rome
Day 3 Parks of Rome & Private Vatican Guided Tour Rome
Day 4 Rome to Sorrento Sorrento
Day 5 Beach Day in Sorrento Sorrento
Day 6 Free Day in Sorrento Sorrento
Day 7 Day Trip to Capri Sorrento
Day 8 Sorrento to Amalfi Coast Amalfi Coast
Day 9 Free Day on the Amalfi Coast Amalfi Coast
Day 10 Private Amalfi Coast Boat Tour Amalfi Coast
Day 11 Amalfi Coast to Naples With Guided Pompeii Tour Naples
Day 12 Pizza-Cooking Class in Napoli & Explore Naples Naples
Day 13 Ischia and Procida by Ferry Naples
Day 14 Depart Naples  


Start off in Rome, where private tours and early access will help you navigate famous sites like the Colosseum, Roman Forum, and the Vatican with minimal disruptions to your sleep schedule. From there you'll head to Sorrento, home of terraced lemon groves, stony beaches, and a historic town center. Browse at your own speed with two days at your discretion to check out the beaches, shop the street markets, or just walk along the boulevards. A ferry will take you on a day trip to Capri, where you can start at the top in the town of Anacapri and slowly wind your way down the island under the gaze of Mount Vesuvius in the background.

From Sorrento, head to the narrow streets of the Amalfi Coast for another free beach day and private boat tour. Split your day between Amalfi and Positano on your boat tour, dropping anchor at grottoes, swim spots, and small towns ready to be strolled. Naples is up next, with a stop in the volcanic city of Pompeii on the way for a guided tour designed to keep smaller party members engaged while still showing parents the highlights. Once you arrive in Naples, you'll learn to make pizza in the city of its birth, and even toddlers can get in on the kneading. You'll wrap up your trip on the vacation islands of Ischia and Procida, popular for their picturesque landscapes and less-crowded ports, with views you may recognize from guidebook covers. Learn more

More Great 14-Day Italy Itineraries

Looking for more inspiration for your trip to Italy? Check out these other 14-day Italy itineraries, with history-focused trips, food & wine getaways, and best-of trips to hit the highlights. 

Or, describe your ideal trip and we will connect you with a local specialist to make it happen.


Map of 2 Weeks in Italy - 4 Family-Friendly Itineraries
Map of 2 Weeks in Italy - 4 Family-Friendly Itineraries