Trip Types
Packages
Regions
Blog
About Us
Testimonials
Custom Vacations to Italy
Crafted for Your Family
With more destinations, accommodations & things to do, your family will experience Italy like a local, not a tourist.
Tell us your preferences and ideal locations
Our clients say
The nicest things
We've helped thousands of happy travelers experience the beauty and culture of Italy
-
"Thank you all so much for creating such an unforgettable experience. It was full of flavor and wonder and was just what we wanted. You helped create the best first impression of Italy. We are already discussing what we want to do the next time we visit."
Megan and Stephen H.
Florence Naples
-
"Oh my goodness, Peter and I had a magnificent time! Our hotel in Verona was fantastic...very comfortable and quiet. We ate at two of the restaurants that your team recommended and both were fabulous. The only thing wrong was that our trip went by too quickly."
Laura & Peter C.
Venice Verona Lake Como Parma
-
"Our trip was so lovely, and we thoroughly enjoyed the food tour! The coliseum tour was fantastic as well and our guide was so accommodating. Italy definitely has our heart - we will definitely reach out to you for our next Italian adventure."
Shannon S.
Rome
-
"Thank you, once again, for another unforgettable trip to Italy! We don’t know how you do it, but you designed this trip to be exactly what we wanted. The food, wine, sites, drivers and tour guides made for the most amazing trip."
Barbara & Michael B.
Every single detail
Planned to perfection
Each custom itinerary includes flights, accommodations, dining, activities and more
Custom
Itineraries
Explore Italy your way with personalized, bespoke travel itineraries
First-class
Accommodations
Exceptional lodging options when it's time to unwind & relax
Incredible
Food & Wine
Indulge in the best regional cuisine & award-winning wines
Local
Guided Tours
Intimately explore Italy's most renowned and iconic sites
Effortless
Travel
Relax knowing flights and transportation are seamlessly coordinated
Flexible
Planning
Effortlessly modify and customize your travel itinerary
Based entirely on how you want to see Italy
A completely fresh take on
Planning a trip
Custom itineraries with personalized travel experiences crafted for you by local Italians
We make it easy
You tell us What you want to see and do Rather than trying to sell you a "package" designed for the masses, we start every trip by discovering exactly how you want to see Italy.
A vacation to Italy designed exclusively for you Every detail of your trip, including the cities, food, tours, and nightlife, will be crafted to your exact preferences
Helping you discover the hidden wonders of Italy We want you to see Italy from a local's perspective. Our native team will help you avoid tourist traps and uncover the authentic Italy.
By the team that does travel to Italy And nothing else You deserve a unique, one-of-a-kind honeymoon experience from a company focused exclusively on Italian travel - not a pre-built "package".
The Italy vacation of your dreams
Starts Right Here
Just tell us your preferences and must-do's. Our Italian-born travel experts will take care of the rest.
The perfect trip
For any occasion
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.
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.
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.
Custom, one-of-a-kind vacations to Italy made easy
Exclusively crafting
Custom Trips to Italy
Bespoke Italian vacations are the only thing we do, and we'd be honored to do yours next.
8,444
Trips Booked
We have over 20 years of experience crafting custom Italian travel packages.
130+
Unique Destinations
We've crafted vacations and honeymoons to over 100 locations in Italy just this year.
24/7
Trip Support
Our staff is on call 24/7 during your trip, so you can relax and enjoy Italy.
Dive in & explore
This custom itinerary
Explore each day of this custom-crafted itinerary to Italy we crafted for our client
- 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.
The next custom vacation itinerary to Italy we make can be yours
5701 Woodway Dr.
Suite 220
Houston, TX 77057 USA
Company
Top Pages
Traveling
Learn About Italy
Trips 2 Italy | Custom Italian Vacations | Est. 2003
Copyright © Trips 2 Italy LLC.