Custom ItalianVacations

Experience the best of Italy with a custom-crafted trip built entirely for you.

  • Bespoke itineraries

  • First-class accommodations

  • Locals-only experiences

Vacationing to Italy

Has never been easier

Our team consists of first-generation Italians who know where to go, what to do, and how to truly experience Italy like a local

1) Tell us about yourideal trip
Your trip to Italy should be built for you, not the masses. That's why every itinerary we create is customized around our client's unique preferences.
2) Together, we fine-tune the details
Once you've shared what your ideal trip looks like, the team at Trips 2 Italy works with you to help make that dream a reality.
3) You received acustomized itinerary
From flights and accommodations, to activities and where to eat, you'll receive a completely customized itinerary with everything covered.

Exclusively crafting

Vacations to Italy

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

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.

To the most destinations

throughout Italy

From the world-renowned cities to the picturesque villages and sun-swept beaches, we'll help get you anywhere you want to go.

Naples

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.

Venice

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.

Tuscany

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.

Rome

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.

Florence

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.

Milan

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.

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Personalized itineraries

For every type of trip

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

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    Custom Vacations

    Italy captivates with its fusion of history, aesthetics, culture, and breathtaking outdoor...

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    Honeymoons

    No country offers a better combination of romance, beauty, and culture to make your honeymoon...

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    Family Vacations

    Create lasting memories and bond with your loved ones in a beautiful and enriching setting....

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    History & Architecture

    Experience the enchantment of Italy, where architectural grandeur and rich history create a...

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    Cruise Excursions

    Embark on a captivating cruise journey through Italy, sailing from the romantic canals of Venice...

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    Group Trips

    Italy offers the best balance of historical allure, breathtaking beauty, and vibrant culture to...

Our clients say

the nicest things

We've worked with thousands of wonderful clients, from honeymooners to group travelers and solo adventures.

Dear Emily,<br />
<br />
Our trip to the Amalfi Coast Cities was wonderful. Our driver, Mareo, was very courteous and informative. He was also a very safe driver. The hotel in Sorrento is beautiful and the staff is very friendly. The breakfast buffet is amazing - such a large selection.<br />
<br />
Thank you!<br />
Dear Trips 2 Italy,<br />
<br />
Thank you so much for planning us such a wonderful vacation! Rome and Florence were amazing! Our hotels and tours have been perfect, and the food and wine were better than we imagined!<br />
<br />
Ciao! Ciao Tomasso!<br />
<br />
As always, things are perfect. The girl's trip is all that we thought it would be & more. Perfecto! <br />
<br />
Grazie mille Hello Emily,<br />
<br />
This journey is coming to an end, and I really enjoyed myself. I want to thank Trips2Italy for planning a wonderful trip for us. Every detail went as expected, and we couldn't ask for anything more. We look forward to our next trip.<br />
<br />
Thanks again! Tommaso and Ana,<br />
<br />
We are having a wonderful time in Italy! It truly has been the perfect honeymoon. Thank you for all of your hard work in making this trip special - you have thought of everything! You have made traveling in Italy simple and easy and have provided us with some unforgettable experiences. We will be sad to leave in a few days.<br />
<br />
Thank you again for everything! Dear Tommaso,<br />
<br />
We are in Roma, surrounded by Catholics (like ourselves). The historical structures are breathtaking, and the narrow streets near-death experiences (American humor). Our bus tour put it all together after the two great walking tours. We are doing our fair share of strolling, wine, and great food!<br />
<br />
Marty and Gene Ciao Tommaso,<br />
<br />
We have walked an unforgettable experience - thank you and your team for helping us make it happen.<br />
<br />
Grazie! Hello Emily,<br />
<br />
This journey is coming to an end, and I really enjoyed myself. I want to thank Trips2Italy for planning a wonderful trip for us. Every detail went as expected, and we couldn't ask for anything more. We look forward to our next trip.<br />
<br />
Thanks again! Dear Emily, Giulia & Trips 2 Italy team,<br />
<br />
Thank you for making our trip to Amalfi Coast & Taormina a memorable trip. We will never forget our wonderful trip celebrating our 25th wedding anniversary with our son. Your planning & coordination made our trip relaxing & worry free.<br />
Love,<br />
<br />
With love

View all postcards

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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.