Italy Custom Tours and Vacations
Completely custom trips to Italy that offer more places to go, more sites to see, and more things to do than any other travel site.
Get a Custom ItineraryCompletely custom trips to Italy that offer more places to go, more sites to see, and more things to do than any other travel site.
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Simply tell us a little bit about where you'd like to go, and what you'd like to do. Our Italy travel experts will do the rest.
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Starts with a simple, 4 question survey that takes only minutes to complete
Designed around your interests like ideal locations, activities & food
Each trip we build is 100% custom-crafted for you, and no one else
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Including everything you'll need for a perfect trip to Italy
Crafted by experts in Italian travel with over 30 years of experience
With an itinerary designed just for you and your interests
Every detail planned to perfection
One of kind experiences you can't get anywhere else
A Travel itinerary based on exactly the things you want to do
Backed by our exclusive Flexible Travel guarantee
We know you have options when it comes to booking your Italian vacation. Find out what truly sets Trips2Italy apart from the rest.
Most travel sites sell a handful of the same pre-packaged vacations. At Trips2Italy, we custom design each trip with thoughtfully selected destinations, activities and itineraries so you get the vacation of your dreams - not someone else's.
You don't want to see Italy, you want to live it & no one can do that better than Trips2Italy. Our founder Tommaso & his 100% Italian-born team have dedicated their lives to building the most extraordinary, one of a kind Itailan vacation experiences.
From exquisite destinations like Rome & Florence to lesser-crowded yet breath taking regions like Piedmont & Umbria. Whether you want to be beach-side or country-side, spend time in vineyards or at monuments - Trips2Italy will build a vacation that's perfect just for you.
With an Italian vacation custom-crafted just for you and no one else, you won't just see Italy - you'll live it
From where you go, to the amazing sites you see while you're there, your custom Italian vacation from Trips 2 Italy will be personalized around the things you like to do. Our Italian-born travel experts blend their insider knowledge of the country with over 15 years of custom vacation experience to create trip that's incomparable to any vacation you've experienced before. No matter what type of vacation you have in mind, an Italian getaway by Trips 2 Italy will create memories that will last a lifetime.
The process of planning your getaway with us is personal from beginning to end. From hand-selecting destinations, activities, and tours during the planning process to utilizing our 24/7 assistance while on your honeymoon, our custom vacations offer couples the chance to be personally catered to. Packages can include a single destination or multiple cities and regions, exciting touring experiences or open time in the itinerary to relax, food and wine tours or fine dining – the choice is yours.
Exclusively from Trips2Italy, our new Flexible Travel Plan allows our guests to reschedule their trips up to 30-days before their scheduled departure date with absolutely zero fees or costs to enroll. Should changes occur to your itinerary or the international travel situation after you have booked your trip, we will contact you to discuss the changes to the itinerary and your options, which could include modifying or postponing the trip. If you decide to postpone your trip, Trips 2 Italy will issue a letter of credit valid for 100% of your payment made toward the booking.
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Rome
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 a romantic candlelit dinner.
Rome
Rome is large city filled with historic and architectural treasures that cannot hardly 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.
Rome
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 nonreligious 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.
Rome
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.
Rome
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.
Assisi
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.
Assisi
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.
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.
Florence
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 sweetheart 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.
Florence
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 fabulous architecture and visit the site of the famous Piazza Il Campo horse race.
Florence
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 love 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 you.
Venice
Alas, this morning you will conclude your time in Florence to leave for your honeymoon’s 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 city hand in hand.
Venice
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 and serenading you with a special Italian love song.
Venice
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 or even first anniversary presents to commemorate your honeymoon. 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.
"Thank you, thank you, thank you - the trip was fabulous! The plans were set up perfectly and everything went off like clockwork. The cooking class in Florence was an amazing, small-group group experience. The chefs were entertaining and really made the cooking a joy."
Robin and Michael
"Our Italian honeymoon was one we'll remember for a lifetime. Every detail of our trip was perfect from the guided tours, to the free wine and champagne at every hotel. The restaurant recommendations were done with such care and thoughtfulness too. The trip was just perfect."
Rachel and Chase
"Trips2Italy planned the honeymoon of our dreams - it was truly everything we could have asked for and we can't imaging a better trip, or an easier planning experience. Our favorite excursions were the boat trip to Capri and the wine tasting in the Chianti region of Tuscany."
Allison and Joshua
Italy Custom Tours and Vacations
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"We honestly had the most incredible trip ever - everything was perfect from start to finish. Tours were amazing, the hotels were charming, the transfers allowed us to feel safe and secure. We truly indulged in the Italian culture."
| Rome & Venice
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