Custom vacations to ItalyExpertly planned just for you

Experience the best of Italy with our custom vacation packages. Featuring more destinations than any other travel site & expert trip planning to fit your needs and budget.

  • 100% customized itineraries

  • Exclusive, locals-only experiences

  • More destinations than any travel site

Custom Italian vacations

Is the only thing we do

Since 2003, our Italian-born founder and his team of travel experts have been designing one of a kind, custom Italian vacations.


Trips Booked

We have over 20 years of experience crafting custom Italian travel packages.


Unique Destinations

We've crafted vacations and honeymoons to over 100 locations in Italy just this year.


Trip Support

Our staff is on call 24/7 during your trip, so you can relax and enjoy Italy.

Vacationing to Italy

Has never been easier

For over two decades we have been working with brides, grandparents, friends, parents or anyone with an adventurous spirit to plan the ultimate Italian vacation. Unlike internet travel sites or even our competitors, our team consists of first generation Italians who know where to go and what to do. Don't just see Italy. Live it.

Describe your dream vacation

Talk directly to our Italian-born founder, or fill out a short questionnaire, so we can better understand your interests, preferred locations and ideal activities while in Italy.

You get a completely customized itinerary

Crafted specifically for you with absolutely everything you'll need for a perfect trips to Italy including travel, accommodations, food & activities and more.

Take your once in a lifetime trip

With every detail in you custom travel itinerary planned to perfection, you'll be on your way to visit only the places you want to see, and do only the things you want to do.

More Italian destinations

Than any travel site

Whether you want to travel to a world-renowned city, or a picturesque village (or both) we'll make sure you see the real Italy.


A city of romance

Naples is a city that exudes romance and charm at every turn. From the winding streets of its historic center, filled with stunning Baroque architecture and lively street performers, to the breathtaking views of the Bay of Naples and Mount Vesuvius, this city is a true feast for the senses. Stroll hand in hand along the colorful streets, stopping to sample delicious local cuisine and sip espresso at a charming outdoor cafe. Or, venture out to the breathtaking Amalfi Coast, where you can lose yourselves in the beauty of the Mediterranean Sea and the picturesque, cliffside towns. No matter what you choose to do, Naples is the perfect destination for a romantic getaway filled with adventure, culture, and romance.

Discover Naples


Past & present meet in the canals

Venice is a city unlike any other. Nestled among the canals of the Venetian Lagoon, it is a place where the past and present come together in perfect harmony. As you wander through the streets and over the charming bridges, you can't help but feel as though you have been transported back in time. The stunning architecture and art that adorn every corner are a testament to the city's rich history and cultural heritage. But it's not just the sights that make Venice so special. It's the way the city comes alive at night, with music filling the air and the soft glow of the streetlights reflecting off the water. It's the way the gondoliers navigate the narrow canals with ease, singing sweet melodies as they go. There is a sense of romance and magic in the air in Venice, a feeling that draws people in and captures their hearts. It's a place where dreams are made and memories are created, a true gem of Italy that will stay with you forever.

Discover Venice


A land of culture & food

Tuscany is a romantic region in Italy known for its natural beauty, cultural heritage, and cuisine. It has rolling hills, vineyards, and ancient villages, and is surrounded by fields of wheat, sunflowers, and olive groves. The air is perfumed with lavender, rosemary, and thyme, and the sound of cicadas fills the air. At the heart of Tuscany is Florence, a city with Renaissance art and architecture, including the Uffizi Gallery and the Accademia Gallery with works by Michelangelo, Leonardo da Vinci, and Botticelli. A romantic dinner in a trattoria with Chianti and pasta alla carbonara is a perfect way to end a day of exploring this magical region.

Discover Tuscany


Breathtaking history & beauty

Wander through the city, and you'll be transported back in time to a world of gladiators and emperors. Rome is filled with iconic landmarks, such as the Colosseum, the Pantheon, and the Trevi Fountain, each one more breathtaking than the next. As the sun sets over the city, the streets come alive with the sound of music and laughter. The restaurants and cafes are filled with the scent of freshly baked bread and the sizzle of grilling meats. A glass of wine and a plate of pasta, enjoyed al fresco at a candlelit table, is the perfect way to end a day of exploring this magical city. With its rich history, stunning architecture, and delicious cuisine, Rome is a city that truly captures the heart and soul. It's no wonder that it's considered one of the most romantic cities in the world, and it's the perfect place to celebrate love with your special someone.

Discover Rome


Renaissance architecture & art

Florence is a city that exudes romance with its stunning Renaissance architecture and beautiful art. The city is filled with charming piazzas, cozy cafes, and picturesque bridges. The Arno River winds its way through the city, and a romantic walk along its banks is the perfect way to take in the beauty of this magical city. As the sun sets, the streets come alive with the sound of live music and the aroma of freshly baked bread. With its rich cultural heritage, stunning art, and delicious cuisine, Florence is a city that truly captures the heart and soul.

Discover Florence


Modern fashion & historic art

Milan is the capital of the Lombardy region in northern Italy and is known for its rich history, art, and fashion. It is home to many famous landmarks, including the Duomo di Milano, a gothic cathedral with stunning architecture, and the Galleria Vittorio Emanuele II, an upscale shopping center housed in a glass-domed arcade. Milan is also home to several world-class museums, such as the Brera Art Gallery and the Leonardo da Vinci National Science and Technology Museum. In addition to its cultural attractions, Milan is a bustling city with a vibrant nightlife and an excellent dining scene, making it a popular destination for travelers.

Discover Milan

Thoughtfully crafted itineraries

For any type of trip

No matter what type of trip you want, Trips 2 Italy can build you the perfect itinerary.

Our clients have been saying

The nicest things

Don't take our word for it, read what families, couples, seniors and solo adventurers who travel with us have to say.


Robin and Michael

Venice, Florence, Rome

"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."


Allison and Joshua

Capri, Tuscany

"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."


Rachel and Chase

Rome, Venice

"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."

The latest musings and news

From our blog

We cover regions of Italy and what makes them so special as well as recipes, travel tips and much more.

Chris Hubbard Our Top 10 Italy Travel Destination Picks for 2022

Looking for some fresh destinations for your 2022 vacation to Italy? We’ve compiled a list of timeless classics and lesser-known gems in Italy....

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January 5, 2023
Chris Hubbard Italy Makes for the perfect graduation gift

Christmas is upon us, and you might still be looking for the perfect gift to give your new or soon-to-be graduate. Whether he or she is a high school...

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January 5, 2023
Chris Hubbard Italy’s La Befana Celebration

While Christmas might be more famous worldwide, Italian children have another special holiday to look forward to in early January. On the night of...

Tommaso De Poi
January 5, 2023

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.