Custom Italian Vacations Custom crafted just for you

With more destinations, accommodations & things to do, you'll experience Italy like a local, not a tourist.

Our clients say

The nicest things

We've helped thousands of happy travelers experience the beauty and culture of Italy

  • testimonial

    "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

  • testimonial

    "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

  • testimonial

    "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

  • testimonial

    "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

  • base imageoverlay image
    Custom
    Itineraries

    Explore Italy your way with personalized, bespoke travel itineraries

  • base imageoverlay image
    First-class
    Accommodations

    Exceptional lodging options when it's time to unwind & relax

  • base imageoverlay image
    Incredible
    Food & Wine

    Indulge in the best regional cuisine & award-winning wines

  • base imageoverlay image
    Local
    Guided Tours

    Intimately explore Italy's most renowned and iconic sites

  • base imageoverlay image
    Effortless
    Travel

    Relax knowing flights and transportation are seamlessly coordinated

  • base imageoverlay image
    Flexible
    Planning

    Effortlessly modify and customize your travel itinerary

Get your 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

Features Image

We make it easy

1

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.

2

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

3

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.

4

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

App screenshot
  • Food & Wine Trips

  • Historical & Cultural Trips

  • Active Italian Adventures

Italy beckons to culinary enthusiasts and food lovers alike, enticing them with its world-renowned cuisine and exceptional wines. From the vibrant street food scene in Rome to the succulent steaks of Florence, the iconic pizzas of Naples, and the gastronomic treasures of Emilia Romagna, each region offers a distinct culinary experience. Whether you find yourself amidst the picturesque hills of Tuscany or the coastal charm of the Amalfi Coast, prepare to indulge in a feast of delectable flavors and savor local specialties. Immerse yourself in the passion and artistry of winemaking as you explore the renowned wine regions of Tuscany, Piedmont, and Veneto, where tastings and vineyard tours will unveil the secrets behind Italy's extraordinary vintages. Embarking on a culinary adventure in Italy guarantees unforgettable moments, inviting foodies and wine enthusiasts to partake in an unforgettable exploration of the country's culinary delights.

Embark on an enchanting journey through Italy, a land brimming with culture, history, and architectural marvels. Immerse yourself in the breathtaking beauty of Rome's Colosseum, the artistic treasures of Florence's Uffizi Gallery, and the romantic charm of Venice's picturesque canals. Experience the vibrant energy of Italy's renowned festivals, from the dazzling Venice Carnival to the exhilarating Palio di Siena. Uncover the secrets of ancient civilizations as you explore the captivating ruins of Pompeii and be in awe of the majestic splendor of the Vatican City. Italy's rich cultural tapestry awaits, offering a captivating blend of history, art, and celebration that will leave an indelible mark on your soul.

Italy's diverse landscapes enchant nature enthusiasts with its captivating beauty, from stunning coastlines to majestic mountains and endless hiking trails, creating the perfect backdrop for unforgettable outdoor adventures. Indulge in epic ski escapades in the Italian Alps or embark on exhilarating hikes along the picturesque Cinque Terre and Amalfi Coast, offering awe-inspiring vistas for all skill levels. Immerse yourself in the tranquility of the Tuscan countryside through horseback rides, while walking and biking tours throughout Italy allow you to explore cities and embrace the captivating outdoors. Whether your passion lies in skiing, biking, hiking, or leisurely strolls, Italy presents a plethora of active vacation options to satisfy your desires.

Get your perfect trip

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.

Get started now

The next custom vacation itinerary to Italy we make can be yours

Trips 2 Italy | Custom Italian Vacations | Est. 2003

Copyright © Trips 2 Italy LLC.

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.