Custom Italian VacationsCrafted for Your Family

Embark on a magical journey, orchestrated by our native Italian travel experts.

  • Stress Free Planning

  • Local Insider Knowledge

  • Family Friendly Itineraries

Why lovers of Italian travel

love Trips 2 Italy

We don't just plan vacations; we craft once-in-a-lifetime experiences.

Personalized Vacations

No two vacations are alike, which is why we start by listening, and then tailor each trip into the most unique Italian travel experience.

Custom Itineraries

We plan your perfect Italian vacation down to the smallest detail, including hidden dining suggestions and sites that only an Italian would know.

Italy Obessed

Our founder Tommaso De Poi was born and raised in Lake Como, and he has made it his life work to share the wonders of Italy with the world.

Decades of Experience

For nearly 20 years, Trips 2 Italy has perfected the art of creating the most memorable Italian vacations for our thousands of happy clients.

Family Vacations

From Trips 2 Italy

No more scrolling through travel sites looking for the perfect fit. Let our experts craft your dream Italian vacation, made exclusively for families.

Stress Free Planning

Just tell us where you want to go, or what you want to do.

We cover every detail: Flights, hotels, accommodations, & excursions

Simply relax and savor your perfectly planned getaway

Local Insider Knowledge

Crafted by native Italians with over 30 years of experience

We know all the off-the-beaten paths & tourist traps to avoid

See why 5,000+ customers refer us to their friends & family

Customized For You

One-of-a-kind experiences you can’t get anywhere else

A travel itinerary filled with family-friendly things to do

Backed by our exclusive Flexible Travel guarantee

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We take care of every detail

You get the perfect trip

Custom
Itineraries
Itineraries

Boutique
Hotels
Hotels

Local
Food & Wine
Food & Wine

Private
Guided Tours
Guided Tours

Flights +
Transportation
Transportation

Flexible
Scheduling
Scheduling

We take care of every detail

You get the perfect trip

Custom
Itineraries

Boutique
Hotels

Local
Food & Wine

Private
Guided Tours

Flights +
Transportation

Flexible
Scheduling

Why more people travel

With Trips 2 Italy

We know you have options when booking your trip. Find out what truly sets Trips2Italy apart from the rest.

One of a Kind

Family Vacations to Italy

Just as every family is wonderfully unique, so should be their holidays, and that's what we aspire to achieve at Trips 2 Italy. We are dedicated to curating personalized Italy family vacation packages that are as distinctive as your family's dynamic. While standard vacation packages may offer some enjoyable experiences, they fall short of the truly bespoke experiences that a custom Italy family vacation can provide. In planning a custom trip with us, we pay attention to every detail, ensuring that each itinerary is meticulously tailored to match the diverse interests, needs, and dreams of each family member. Embrace the joy of discovering Italy's cultural riches, culinary delights, and scenic beauty, all at a pace that suits your family, creating unforgettable memories to be cherished for a lifetime.

Discover One of a Kind

Crafted by a Team

That Specializes in Italian travel

Trips 2 Italy is fueled by a team of dedicated Italian-born travel experts, all led by our founder, Tommaso. Our intimate, firsthand knowledge of our homeland enables us to offer you exceptional recommendations for hotels, must-visit places, engaging activities, and remarkable sights. We don't just suggest; we personally select and book flights, provide transportation throughout your stay, and manage every detail in between. This hands-off approach is designed to ensure that every moment of your journey is enjoyed without the hassle of logistics. Our commitment is to offer you an Italian experience that reflects our love for the country, while ensuring your trip is as seamless and memorable as possible.

Discover Crafted by a Team

Book your Family Vacation

With Complete Peace of Mind

Exclusively from Trips 2 Italy, we offer our new flexible travel plan, tailored to provide peace of mind for our family travelers. This plan allows you to reschedule your family vacation up to 30 days before your scheduled departure date without incurring any fees or costs. We understand that plans can change, especially when traveling with family, and we want to ensure your experience is stress-free. If changes occur to your itinerary or the international travel situation after your family trip is booked, we will promptly contact you to discuss any alterations and your options, which can include modifying or postponing your trip. Should you decide to delay your journey, Trips 2 Italy will issue a letter of credit, ensuring 100% of your payment towards the booking is preserved. This way, you and your family can look forward to exploring the beauty of Italy, knowing you're in flexible and caring hands.

Discover Book your Family Vacation

Family Activities in Rome

A family trip to Rome, the 'Eternal City', presents a remarkable blend of historical marvels and engaging activities for all ages. Begin your adventure at the iconic Colosseum, where you can step back into ancient times and imagine the thrilling gladiator battles that once took place. For a hands-on experience, enroll the family in a Roman Gladiator School where you can learn about ancient Roman history and even train in gladiator combat techniques. In Vatican City, make sure to visit the awe-inspiring St Peter's Basilica, an architectural masterpiece that holds centuries of religious significance. The combination of ancient history, timeless architecture, and engaging experiences makes Rome an exceptional destination for a family trip filled with education, adventure, and unforgettable memories.

Family Activities in Florence

Embark on a captivating family trip to Florence, where a wealth of activities awaits. Explore iconic landmarks like the Duomo and Ponte Vecchio, immersing yourselves in the city's rich history. Unleash your creativity in interactive art workshops and indulge in delightful food tours, savoring authentic Tuscan cuisine. Discover artistic treasures in renowned museums such as the Uffizi and Accademia, including Michelangelo's David. Whether strolling through charming streets or enjoying the beauty of Boboli Gardens, Florence offers an unforgettable family adventure filled with history, art, and culinary delights.

Family Activities in Venice

Experience the magic of a family vacation in Venice. Glide along picturesque canals on a gondola, taking in the iconic sights of Rialto Bridge and St. Mark's Square. Immerse yourselves in the rich history at Doge's Palace and Basilica di San Marco. Wander through charming streets, uncovering hidden gems, and indulge in the flavors of Venetian cuisine. Embrace the vibrant culture with a mask-making workshop, capturing the essence of Venice's Carnival tradition. Explore nearby Murano for its glass-blowing heritage and Burano for its colorful houses. Venice promises an enchanting family adventure, creating cherished memories that will last a lifetime.

A Family Vacations experience Like no other

Curious what honeymooning with Trips 2 Italy is like? Here's an actual itinerary from a recent honeymoon we crafted.

  • Day 1

    Rome

    Your family adventure begins

    As you step out of the airport, take a deep breath and let the magic of Italy snare your senses. After a ride to your lodging for the next few days, opt to unpack later and instead take advantage of the daylight and explore the city. A few landmarks of Rome you will not want to miss include the Borghese Gallery which is home to an extensive private collection of art from various time periods, the Basilica di Santa Maria Maggiore for gorgeous frescoes and mosaics, and the Piazza del Popolo for a taste of local culture. Spend the evening however you like, but begin it with dinner at a cozy Italian restaurant for an amazing local dinner.

  • Day 2

    Rome

    Lose yourself in the piazzas

    Rome is a large city filled with historic and architectural treasures that cannot be seen in the space of one day, much less three. So today, explore the city at your leisure making sure to stop at the Fontana di Trevi, or Trevi Fountain, to witness one of the most beautiful fountains in Europe that features a number of stunning statues that give the fountain a regal touch. Next wander through Piazza Navona, a famous public square featured in many films including Dan Brown’s Angels & Demons which is fabulous for people watching. If time allows, be sure to visit the famous Spanish Steps adjacent to the Piazza di Spagna and take in the sunset at the majestic Vitoriano.

  • Day 3

    Rome

    Explore St. Peter’s Basilica

    Breakout your best clothes for today as you and your love will be visiting the Vatican. This religious complex sometimes referred to as one of the world’s smallest countries, is packed with internationally recognized art and history inside the walls of St. Peter’s Basilica, on St. Peter’s Square, and in the Vatican museums and Sistine Chapel. A visit to the Vatican is said by religious and non-religious visitors alike to be a very moving experience. If you are visiting on a Wednesday when the Pope is in Rome, you may even be able to attend a Papal Audience at the Vatican. Traditionally the Pope appears to visitors and gives a Papal Blessing. This will certainly be a very special memory.

  • Day 4

    Rome

    Trace the steps of gladiators at the colosseum

    Today you will be visiting one of the most iconic symbols of Rome, the Roman Colosseum. This dramatic structure traces centuries back to the early Roman period. These ruins are still intact enough that to stand in the middle of the arena and picture a crowd going wild as a gladiator and his opponent step into the ring to battle for survival feels eerily realistic. A guided tour will also provide a visit to the underground Colosseum where you can virtually trace the steps of gladiators as they waited for their turn in the spotlight.

  • Day 5

    Rome

    Hold your family tight in the catacombs

    For a truly unique view of Rome, visit the catacombs or underground burial sites that date as far back as the second century. Although only a handful are open to the public, an estimated sixty or more catacombs can be found in Rome and stretch hundreds of kilometers. Traveling these subterranean passageways is an adventure unlike any you’ve experienced here so far. Some of the more popular catacombs you may want to visit include San Sebastiano, Domitilla, Priscilla, and Sant’Agnese. This activity is both exciting and fascinating and gives you an excuse to hold on extra tight to your love.

  • Day 6

    Assisi

    Enjoy a sunset dinner in rolling hills of Umbria

    Your time in Rome has now drawn to a close, so say Addio to the city and look forward to your journey to Assisi. This picturesque town who is said to have been the hometown of St. Francis, sits atop the rolling hills of Umbria and is a United Nations Educational Scientific Cultural Organization (UNESCO) World Heritage Site. Once you have arrived in Assisi and have had time to deposit your luggage at your new place of lodging, consider a stroll through this ancient town’s historic city center. As darkness begins to blanket the city, find a lovely restaurant for dinner and toast to a new adventure in Assisi.

  • Day 7

    Assisi

    Embark to medieval fortress from the 14th century

    After a leisurely breakfast, set out to explore the medieval fortress of Rocca Maggiore and some of the local churches. Rocca Maggiore is a fourteenth century castle that stands tall at the very highest part of the city and offers stunning views of Assisi, Perugia and beyond. The area is also home to a number of historical churches that are worth a visit including the famous Basilica of St. Francis, Santa Maria Sopra Minerva, Santa Maria degli Angeli, Duomo di San Rufino, Chiesa Nuova, San Damiano, and the Basilica di Santa Chiara.

  • Day 8

    Florence

    Be swept up by the charm of Florence

    This morning you will leave Assisi behind and travel to the gorgeous city of Florence. This beautiful but large town in the heart of Tuscany is full of amazing architecture, art, and cuisine. Once you have checked in to your new living quarters, take a little time to tour some of the main sights of Florence including Florence Duomo, Ponte Vecchio, and Piazza della Signoria. End your day with an evening cooking class that is sure to reveal the secrets of fine Italian cuisine and finish with a spectacular glass of wine.

  • Day 9

    Florence

    Marvel in great food and art

    You may want to eat light if at all this morning for breakfast because first on the agenda for today is a food tour through some of Florence’s most charming neighborhoods. You and your family will indulge in authentic Italian appetizers, first and second courses, and even desserts. After all that food, a lengthy walk through the Accademia Gallery is in order. Here you will behold famous masterpieces by renowned artists including David which was sculpted by Michelangelo.

  • Day 10

    Florence

    Tour San Gimignano finest winery

    Today you will be leaving the busiest part of Florence for a day excursion to San Gimignano, a medieval town well known for being a UNESCO World Heritage Site and its production of Vernaccia di San Gimignano wine. For lunch, visit a Chianti winery and do the hard work of taste-testing some of the finest Tuscan wines over a light but delicious Italian lunch. Then head to another medieval town, Siena, to take in the fabulous architecture and visit the site of the famous Piazza Il Campo horse race.

  • Day 11

    Florence

    Learn to cook, as a family

    After a leisurely breakfast and morning, attend an Italian cooking class. Here you will learn about the importance of fresh and quality ingredients in creating mouthwatering homemade meals. Once you’ve covered the basics, you and your family will go with the class to tour a Florence market to learn how to identify the best picks for assembling your meal. Learning how to cook here is a fantastic way to bring a little bit of Florence home with your loved ones.

  • Day 12

    Venice

    Unwind then explore the magic of Venice

    Alas, this morning you will conclude your time in Florence to leave for your final destination of Venice. Sometimes called the floating city, Venice is actually a series of islands separated by waterways and connected by bridges. Upon your arrival, simply take the day to explore the islands at leisure and stroll through this romantic and magical city hand in hand.

  • Day 13

    Venice

    An old-world gondola ride awaits

    Start your day with a visit to the beautiful St. Mark’s Basilica, one of the most visited churches in Venice. The church is sometimes nicknamed the Church of Gold because of the Byzantine glass mosaics that cover much of the inside and outside. After you’ve overcome the pleasant surprise of roughly eighty-five thousand square feet of mosaics inside the church, it is time for one of the most time-honored traditions of Venice, a gondola ride. Sail through the canals of the city with your gondola operator providing a brief history of important landmarks.

  • Day 14

    Venice

    Voyage to the Venetian islands

    Today is a day of choices between an excursion to the Venetian islands of Murano, Burano, and Torcello or an excursion to nearby Verona. A trip to Murano, Burano, and Torcello will yield glassblowing and lace-making demonstrations that make fabulous trip souvenirs that'll become family heirlooms. The most popular highlight for an excursion to Verona is visiting the setting of Shakespeare’s renowned literary work, Romeo and Juliet. Immerse yourselves in the star-crossed lovers’ story by touring Romeo’s house as well as Juliet’s house and tomb.

Family Vacation packages

We've crafted for clients

Curious about what a custom itinerary from Trips 2 Italy is like? Explore these Family Vacation packages to see what we do.

Your dream vacation starts here

No more endless scrolling through travel sites looking for the perfect fit. Tell us about your ideal trip and preferences, and let our Italian-born travel experts do the rest.

Your dream vacation starts here

Just share a few details about your ideal trip & let our travel experts do the rest.