Cities & Regions

We've custom-crafted vacation itineraries to more cities and regions in Italy than any other travel site.



Italy isn't just a hobby, it's our birthplace, and we know the country inside and out. Let us help you live Italy.


Happy Customers

We've been crafting Italian vacations for over 20 years. Trust the team with the most Italian travel experience.

About Trips 2 Italy

Above all else, we're on a mission to help people see and experience the wonders of Italy just like a local would.

Why lovers of Italian travel

Love Trips 2 Italy

We don't want you just to see Italy, we want you to live it - just like a local would.

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

Live Italy

Ready to experience Italy like a local?

Just tell us about where you want to go, or what you like to do and our team will start crafting your custom Italian vacation itinerary


Our clients say

The nicest things

Adventurers, families and honymooners all love working with Trips 2 Italy, but don't just take our word for it.

Robin & Michael
Rome & FlorenceHoneymoon

Our trip was fabulous. All the plans were set up perfectly, everything went off like clockwork. We really appreciated the special service we received everywhere we went. Walking out to the canal in Venice and having the water taxi drive up at exactly the scheduled time was perfect. Our favorite tour of all was the food and wine tour in Rome. The food was authentic and locals were unique and memorable.

Mary & Greg
Venice & FlorenceItalian Vacation

We had the most wonderful trip to Italy with Mary and Martin C. and we wanted to thank you personally for putting together such a fabulous itinerary. Too many favorite things to list! Such a beautiful place and we want to go back in a few years and hit Rome and the Amalfi Coast. When the time comes, we will make sure and contact you! Many, many thanks to you again Tommaso!

Tuscany & FlorenceFood & Wine Tour

Tomasso promised us a unique, wonderful traveling experience and he exceeded our expectations. We are so grateful for his care to every detail and selection of activities. The cooking class was an especially wonderful. I never dreamed it would be in an outside kitchen surrounded by the beauty of Italy. Making our own pasta was so much fun and topping the meal off with “chocolate salami” was heavenly.


Our mission:

Don't see Italy, live it

Most travel sites sell one-size-fits-all trips. We're on a mission to help travelers experience Italy like a local.

The story

of Trips 2 Italy

When most people think of Italy and it's people, they think of people who are passionate for the things they love. Trips 2 Italy founder, Tommaso De Poi along with his sister Giulia, have that passion for Italy. Since 2003, they have been helping customize vacations for their guests that truly embrace the Italian experience. Their mission is simple yet ambitious. They want to create that dream vacation. They understand that each trip, your trip, is a once in a lifetime event. Combining their first-hand knowledge of Italy with their years of vacation planning helps make each trip special. They are uniquely in tune with each client and their unique needs. They take the time to listen to find those small but important details that help transform the trip from a vacation that can be planned anywhere, to a truly personal experience.

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Our founder

Tommaso De Poi

Tommaso De Poi, founder of Trips 2 Italy, was born at the foot of the Alps in Lake Como, Italy. He developed a love of skiing, but as he grew, the waters of Lake Como became his passion. Growing up in Italy made him uniquely qualified to be able to share the love of his country with anyone who asks. In 1999, Tommaso's job brought him to Houston. In 2003, he decided that he wanted to share his love of Italy and help people see the beauty of his beloved homeland. Tommaso serves on the board of the Italian Cultural and Community Center in his adopted hometown of Houston. He has taken a large interest in the center because he wanted to make sure his children, although born in America, kept their heritage.

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The core values

Guiding us

We believe providing a quality vacation experience is the most important part of a Trips 2 Italy vacation. We hand-select each hotel or service to ensure that we provide the best quality to our guests. Our quality does not stop during business hours, either. We understand that unique circumstances can arise, therefore we offer 24/7 assistance to ensure that we are available to help. Quality planning is going beyond simply planning a vacation. Having the vision to create the perfect vacation starts with listening to our guests and what their dreams are. Vision also requires knowledge of how to make those dreams a reality, by using our experience and vision to create the perfect Italian vacation.

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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.