6 days, 5 nights · Best for Families seeking ancient history and Tuscan hill towns
Family Vacation Rome and Under the Tuscan Sun Vacation Packages
Experience ancient Rome and charming Tuscany as a family. Explore, taste, and connect on an unforgettable Italian adventure.
Your Adventure Starts Here
This is a starting point. Change the nights, choose the style of hotel, add the experiences you want. Your planner takes it from there.
Stop 1Rome, Lazio
Rome
Three days of emperors, popes and catacombs
We hold three nights in the historic center, where your family walks to the Trevi Fountain, Piazza Navona, and trattorias serving pizza al taglio and supplì. A private guide leads you through the Basilica of Santa Maria Maggiore, St. John Lateran, and the catacombs south of the walls, where tunnels and ancient burial niches bring early Christian Rome into focus.
On the third day, another guide meets you at the Vatican Museums. She walks you through the Tapestry Gallery, Raphael Rooms and Sistine Chapel, then into St. Peter's Basilica. Families with older children climb the dome for views across the Tiber and the city's terracotta rooftops.
Arranged for you: We arrange three nights' accommodation, private guided tours of the catacombs and the Vatican Museums with St. Peter's Basilica, and family dinners at local restaurants.
Your hotel
Styles, not names. We name the property once we know your dates and your party.
Interests in Rome
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Gladiator school for kids Day Trips · Half day
Children don tunics and learn sword drills from a historian in costume near the Colosseum.
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Private Colosseum and Forum tour Day Trips · Half day
A guide trained in engaging young learners brings emperors, gladiators and senators to life.
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Pizza-making class in Trastevere Day Trips · Half day
The family shapes dough, tops pies and bakes them in a wood oven at a neighborhood pizzeria.
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Borghese Gallery skip-the-line visit Day Trips · Half day
Reserved entry and a guide who explains Bernini sculptures and Caravaggio paintings in the villa galleries.
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Ancient and Old Rome Walking Tour, Skipping the line at Colosseum Guided Tours and Sightseeing · Tour in a DayUnlock the secrets of the Eternal City, skip the lines and step into the world of emperors, gladiators, and gods on this lively, story-filled Roman adventure.
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Full Day Rome Tour Guided Tours and Sightseeing · Tour in a DaySee Rome your way in one unforgettable day. Vatican treasures, Imperial ruins, and iconic monuments with the ease of a dedicated tour escort.
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Papal Audience in Saint Peter’s, Vatican City Guided Tours and Sightseeing · Tour in a DayWitness a truly unforgettable moment in Rome, attend a Papal Audience and receive the Pope’s blessing.
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Rome by Bicycles Tour with English Speaking Guide Guided Tours and Sightseeing · Tour in a DaySee more of Rome with less effort, cruise past iconic landmarks on a fun, guided bike ride made for everyone.
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Rome by Night Guided Tour Guided Tours and Sightseeing · Tour in a Day
See Rome at its most magical, an evening stroll through illuminated fountains, grand piazzas, and ancient ruins.
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Rome by Night guided Tour with Dinner & Show Guided Tours and Sightseeing · Tour in a Day
Fall for Rome after dark. Glowing landmarks, a romantic evening stroll, and dinner with live music to seal the moment.
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Rome: The Eternal & Ancient Rome Tour Combo Guided Tours and Sightseeing · Tour in a DayExperience the magic of the Eternal City with a full-day tour showcasing Rome’s most iconic historical sites.
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Rome: The Eternal City Tour Guided Tours and Sightseeing · Tour in a Day
Discover Rome’s most iconic monuments in comfort on this tour.
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Skip the Line: Vatican Museums and Sistine Chapel Guided tours Guided Tours and Sightseeing · Tour in a Day
Skip the lines and step straight into the Vatican’s greatest masterpieces. Museums, Sistine Chapel, and St. Peter’s Basilica with an expert guide.
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The Ancient Rome Tour Guided Tours and Sightseeing · Tour in a Day
Walk in the footsteps of emperors and gladiators, discover the power, passion, and innovation that shaped the world in Ancient Rome.
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The Ancient Rome Walking Tour, Skipping the line at Colosseum Guided Tours and Sightseeing · Tour in a Day
Experience the ancient highlights of the Eternal City with a guided walking tour that takes you through Rome’s most iconic landmarks.
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The Christian Rome & Catacombs Tour with Hotel Pick Up Guided Tours and Sightseeing · Tour in a DayJourney through Rome’s spiritual heart, explore ancient basilicas, sacred relics, and the origins of Christianity in the Eternal City.
Day by day in Rome
Upon arrival in Rome, head to your centrally located 4-star hotel and complete the check-in process. Once you’re settled, begin exploring the city center, where ancient monuments and lively piazzas will captivate travelers of all ages. Take a relaxed walk through the historic streets, letting the family soak in Rome’s vibrant atmosphere. In the evening, enjoy a delicious family dinner at a local restaurant within walking distance of your hotel, then return for your first overnight stay in the Eternal City.
Start your day with breakfast at the hotel before setting out to explore Rome’s iconic city center. Visit family-friendly highlights such as the stunning Piazza Navona and the Trevi Fountain. Don’t forget to toss coins for good luck! After lunch at a local eatery, embark on an afternoon guided tour that brings you to the impressive Basilica of Santa Maria Maggiore and the Basilica of St. John Lateran. Continue to the Catacombs just outside Rome, where a local guide will lead you through ancient underground passages, bringing history to life for young travelers. Return to the city center for dinner at a cozy trattoria, then enjoy a magical evening stroll and a scoop of gelato before heading back to the hotel.
Begin with a hearty breakfast, then enjoy a free morning for sightseeing. Consider taking the kids to the Colosseum and Roman Forum for an unforgettable lesson in ancient history (optional tour, advance booking suggested). Sample Roman street food like pizza or supplì for lunch. In the afternoon, join a family-friendly guided tour of the Vatican Museums, where an engaging guide will share stories in the Tapestry Gallery, Raphael Rooms, and Sistine Chapel before visiting St. Peter’s Basilica. Adventurous families can climb the dome for sweeping city views or visit the nearby Castel Sant’Angelo. After a full day, return to your hotel to unwind and head out for your final dinner in Rome.
Stop 2Cortona, Tuscany
Cortona
Hill town days and Etruscan heritage
Your driver collects you after breakfast and heads north, stopping in Tarquinia and Tuscania to visit Etruscan necropolises where painted tombs show scenes of feasting and daily life from three thousand years ago. In Caprarola, you tour Villa Farnese, a pentagonal Renaissance palace with frescoed halls and terraced gardens that children explore at their own pace.
By evening you reach Cortona, a walled town perched above the Valdichiana. We hold two nights in the center, steps from the eleventh-century cathedral, the Etruscan Academy Museum, and artisan workshops selling ceramics and linen. On your second day, the family walks the cobbled lanes, climbs to the fortezza for valley views, and gathers for a final dinner at a trattoria where the owners greet you by name.
Arranged for you: We arrange private transfer from Rome with stops in Tarquinia, Tuscania and Caprarola, two nights' accommodation in Cortona's historic center, and dinners at local trattorias.
Your hotel
Styles, not names. We name the property once we know your dates and your party.
Interests in Cortona
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Cooking class at a countryside farmhouse Day Trips · Half day
The family rolls pici pasta and prepares ribollita under the guidance of a Tuscan cook.
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Private wine estate visit with grape juice tasting Day Trips · Half day
Tour cellars and vineyards, then sample estate wines while children taste fresh-pressed grape juice.
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Guided hike to hermitages above Cortona Day Trips · Half day
A local guide leads the family on stone paths to Le Celle, a Franciscan hermitage founded in the thirteenth century.
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Ceramics workshop in a studio Day Trips · Half day
An artisan teaches hand-building techniques and the family decorates tiles to take home.
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Private Tour Excursion to Cortona & Montepulciano Guided Tours and Sightseeing · Tour in a DayExperience the magic of Tuscany on this all-day tour of two of its most enchanting towns, complete with hotel pick-up for your convenience!
Day by day in Cortona
After breakfast, say “Arrivederci Roma!” and set off for the Tuscan countryside. Along the way, stop in the ancient towns of Tarquinia and Tuscania, where the family can explore Etruscan necropolises and learn about Italy’s oldest civilizations. Continue to Caprarola to visit the Renaissance-era Villa Farnese, discovering its grand interiors and gardens. Journey onward to Cortona, a picturesque Tuscan town. Check into your hotel in the city center and savor your first taste of Tuscan cuisine at dinner.
Share breakfast with your family at the hotel before spending the day exploring the enchanting town of Cortona. Wander its ancient winding streets, admire the city walls, and stop in at artisan shops or local museums. Notable sites include the 11th-century Cathedral and the Etruscan Academy Museum, where children and adults alike can deepen their understanding of the region’s history. As evening falls, enjoy a farewell dinner at a welcoming trattoria, where you’ll be treated like family by the friendly owners.
Day 6
CORTONA, FLORENCE (or ROME)
Enjoy your last breakfast in Cortona, then check out of your hotel and transfer to either Florence or Rome (city center or airport), depending on your post-tour plans. With hearts full of memories and a deeper appreciation for Italy’s rich history and culture, your family adventure concludes as our services come to an end.
Why plan with Trips 2 Italy?
Designed around you by Italian-born planners
Guides, drivers and boats for your party alone
Hand-selected hotels in every destination
Local English-speaking guides who know their city
Met at the airport, private transfers throughout
Testimonials
Hear from travelers who have planned Italy with us
They took the time to understand our preferences and designed an itinerary that was comfortable, personalized, and enjoyable. They offered thoughtful recommendations while never being pushy.
We missed our connecting flight in Munich. I had just got through customs and was looking up the number to call when Trips 2 Italy called me. They told me exactly what to do and they already knew what flight we had been rebooked on.
Ready to make it yours?
Send us this adventure with your changes. An Italian-born planner builds the first full draft and calls you to walk through it.
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Questions travelers ask
Where will we travel on this itinerary?
Over 6 days this journey brings you to Caprarola, Rome, Tarquinia, Tuscania, Cortona, and Florence. Each stop is woven into the itinerary with time for the landmarks, the views, and the local flavor that make it special.
How will we get around during the vacation?
Transportation is arranged as part of the itinerary, with comfortable train segments between the cities and vehicle transfers where they serve you best. Every connection is planned for you, so you can focus on the scenery instead of the logistics.
What kind of traveler is this package for?
It works beautifully for families, with a pace and a mix of experiences that every generation can enjoy together.
Can we customize this itinerary?
Absolutely. Every Trips 2 Italy itinerary is designed to inspire and can be tailored end to end, from the number of nights and hotel categories to the experiences along the way. A minimum of 2 travelers applies.
What is the best season for this itinerary?
The package is available all year around on request. Spring and fall offer mild walking weather and lighter crowds at the major sights, summer brings long lively evenings, and winter rewards travelers with quieter museums and festive streets.