Custom Italian Vacations

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

Bespoke itineraries
First-class accommodations
Locals-only experiences

Start now - for free

Takes just 3 minutes to complete

Custom ItalianVacations

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

Bespoke itineraries
First-class accommodations
Locals-only experiences

Start now

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 aboutyour ideal 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'llperfect 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'll receive 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.

We've crafted trips to over 101 regions in 475 cities and towns. View all destinations

Personalized itineraries

For every type of trip

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

Custom Vacations

Italy captivates with its fusion of history, aesthetics, culture, and breathtaking outdoor adventures, inviting you to explore ancient ruins, admire artistic treasures, and wander romantic canals.

Honeymoons

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

Family Vacations

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

History & Architecture

Experience the enchantment of Italy, where architectural grandeur and rich history create a unique canvas for unforgettable exploration and adventure.

Cruise Excursions

Embark on a captivating cruise journey through Italy, sailing from the romantic canals of Venice to the breathtaking Amalfi Coast, the rich heritage of Sicily, the enchanting Old Town of Bari, and finally, the chic, picturesque Portofino, each offering a unique taste of Italy's vibrant history, aesthetic marvels, and rich culture.

Group Trips

Italy offers the best balance of historical allure, breathtaking beauty, and vibrant culture to make your group trip truly unforgettable.

Personalized itineraries

For every type of trip

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

Custom Vacations
Italy captivates with its fusion of history, aesthetics, culture, and breathtaking outdoor...
Honeymoons
No country offers a better combination of romance, beauty, and culture to make your honeymoon...
Family Vacations
Create lasting memories and bond with your loved ones in a beautiful and enriching setting....
History & Architecture
Experience the enchantment of Italy, where architectural grandeur and rich history create a...
Cruise Excursions
Embark on a captivating cruise journey through Italy, sailing from the romantic canals of Venice...
Group Trips
Italy offers the best balance of historical allure, breathtaking beauty, and vibrant culture to...