Custom Vacations to Italy
Live Italy, Don't Just See It!

Handcrafted journeys for travelers who seek authentic experiences, local insight, and unforgettable memories across all 20 regions of Italy.

Discover the True Italy, Tailored Just for You

For over 23 years, Trips 2 Italy has created deeply personal journeys for travelers who want more than a typical vacation. Our custom Italy vacations are designed for the curious, for those who wish to experience Italy as an expert traveler, not a tourist.

We believe in authentic connections, local insight, and turning every trip into a story worth telling. Founded by a native Italian with a passion for hospitality, our team brings first-hand knowledge and genuine love for Italy to every itinerary we craft.

Your Italy, Your Way

Imagine walking the ancient streets of Rome with a local historian. Learning to make pesto in a sun-drenched Ligurian kitchen. Sipping Amarone in a grand 16th-century noble villa as the Veneto hills stretch to the horizon.

Whether you dream of vibrant cities, peaceful countryside escapes, coastal adventures, or charming villages untouched by time, your trip is as unique as you are.

Types Of Custom Italy Vacations We Specialize In

Family Adventures: Multi-generational trips designed for all ages
Romantic Getaways: Intimate experiences for couples
Cultural Explorations: Art, history, architecture, and beyond
Culinary Journeys: Wine tours, cooking classes, and local flavors
Special Interests: Photography tours, ski trips, graduation celebrations, and more

Special requests? Dietary needs? Accessibility considerations? We take care of everything – so you can focus on living Italy.

Why Travelers Trust Trips 2 Italy

Personalized Itineraries

Every journey is handcrafted to your interests, pace, and dreams. Whether you're passionate about art, cuisine, history, or hidden gems, your itinerary is built around you.

Local Knowledge, Real Connections

Led by native Italians, our team's personal relationships open doors to authentic experiences: private tastings, artisan workshops, and off-the-beaten-path adventures that guidebooks can’t propose.

23+ Years of Expertise

With more than two decades of experience and hundreds of trusted partners across all 20 Italian regions, we navigate Italy's rich diversity so you can travel with confidence.

Dedicated Support, Every Step of the Way

From your first call to your return home, our team is by your side. We work tirelessly behind the scenes to ensure every detail is flawless, and we're always just a call away if you need us even while you travel.

Live Italy, Don't Just See It!

How Your Custom Vacation Comes to Life

Personal Consultation

Share your vision, interests, and travel style with our Italian travel experts. We listen first because your trip starts with your story.
Tailored Proposal

Receive a detailed, personalized itinerary crafted around your vision. No cookie-cutter packages, just a journey designed entirely for you.
Refinement

We fine-tune every detail together until your trip feels perfect. Most travelers need just one or two revisions; we make it easy.
Travel with Confidence

Depart with our exclusive travel advice and insider tips, plus 24/7 support. From arrival to farewell, we're with you every step of the way.

Tommaso and his team have outdone themselves again by planning a fabulous vacation to Italy for us and 12 family and friends. We have used Trips to Italy three times now and never have been disappointed. From the beginning of planning the trip throughout the course of the trip, every detail was covered. From hotels, drivers/transfers, tour guides, restaurant recommendations and the book they put together for all the places you will travel is always incredible. We highly recommend Trips to Italy for your Italy trips!

Jennifer DiPrisco

This was our second time using Trips 2 Italy and we will definitely use them again. We just returned from a week on Lake Como, staying in a villa in Torno. Magnificent is an understatement! Tommaso and his team did a fantastic job of arranging one-of-a-kind experiences with ease. They are extremely attentive, providing personal coaching and helpful advice and materials along every step, in and out of country. I highly recommend Trips 2 Italy if you love a first class travel itinerary and experiences. Ciao!

Susan Asimakis

Trips2Italy is the gold standard for others who specialize in Italy travel. I have been a client since 2006 and each of the eleven trips since that first one (most recently in April/May 2025) have been arranged by Tommaso and his wonderful team of Italy specialists. Details matter to them. Wishes matter to them. Budget matters to them. Phone conversations to get to know you and your vision for your trip are the standard. Conversations with them may lead to destination suggestions you didn’t expect.

Jo Hoeppner

Ready to Experience the Real Italy?

Your perfect Italian journey is just a conversation away. Contact our team today and discover why thousands of travelers have trusted Trips 2 Italy for over 23 years.

Custom Vacations to ItalyLive Italy, Don't Just See It!