Custom Italian VacationsCustomized Just for You

Experience the beauty of Italy like a local, not a tourist.

  • 100% custom itineraries

  • Crafted by native Italians

  • More locations & things to do

Why lovers of Italian travel

love Trips 2 Italy

We don't just plan vacations; we craft once-in-a-lifetime experiences.

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.

Describe your ideal trip

Tell us what you like
  • Starts with a simple, 4 question survey that takes only minutes to complete

  • Designed around your interests like ideal locations, activities & food

  • Each trip we build is 100% custom-crafted for you, and no one else

Get a custom itinerary

Designed exclusively for you
  • Including everything you'll need for a perfect trip to Italy

  • Crafted by experts in Italian travel with over 30 years of experience

  • With an itinerary designed just for you and your interests

Take the perfect honeymoon

With every detail handled
  • One of kind experiences you can't get anywhere else

  • A Travel itinerary based on exactly the things you want to do

  • Backed by our exclusive Flexible Travel guarantee

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We take care of every detail

You get the perfect trip

Custom
Itineraries
Itineraries

Boutique
Hotels
Hotels

Local
Food & Wine
Food & Wine

Private
Guided Tours
Guided Tours

Flights +
Transportation
Transportation

Flexible
Scheduling
Scheduling

We take care of every detail

You get the perfect trip

Custom
Itineraries

Boutique
Hotels

Local
Food & Wine

Private
Guided Tours

Flights +
Transportation

Flexible
Scheduling

Why more people travel

With Trips 2 Italy

We know you have options when booking your trip. Find out what truly sets Trips2Italy apart from the rest.

One of a Kind

Custom Vacations to Italy

At Trips 2 Italy, we believe that every journey is as unique as the individuals embarking on it, and we specialize in crafting personalized travel experiences to Italy. Our expertise lies in creating custom itineraries that cater to your specific preferences, ensuring that every aspect of your trip is tailored to your interests and desires. Whether you want to delve into Italy's vibrant culture, savor its renowned cuisine, or immerse yourself in its stunning landscapes, we are dedicated to designing a memorable vacation that exceeds your expectations. With Trips 2 Italy, you can look forward to creating cherished memories that will stay with you for a lifetime.

Discover One of a Kind

Crafted by a Team

That Specializes in Italian Travel

With our unparalleled Italian-born expertise, Trips 2 Italy specializes in hassle-free vacations that cover every aspect of your journey. From flights and transportation to handpicked accommodations and restaurant reservations, we ensure a seamless travel experience. Our dedicated team selects the finest accommodations, tailored to your preferences, and arranges reservations at top-notch restaurants, so you can savor Italy's exquisite flavors. Whether it's a romantic honeymoon, group trip, beach getaway, or ski adventure, our curated itineraries cater to your desires. With Trips 2 Italy, you can relax and immerse yourself in Italy's beauty, from idyllic coastlines to magnificent Alps. Plus, enjoy the peace of mind of our 24/7 assistance, ensuring a worry-free trip. Create cherished memories that will last a lifetime, while we handle the logistics.

Discover Crafted by a Team

Book Your Custom Vacation to Italy

With Complete Peace of Mind

Introducing our new flexible travel itinerary, exclusively offered by Trips 2 Italy. With this option, you have the freedom to change your departure date for your Italian vacation up to 30 days in advance, with no penalties or registration costs. We understand that circumstances can change, and flexibility is crucial, especially for individual travelers. If there are changes to your itinerary or travel conditions, we will reach out to discuss necessary adjustments and explore your options, including rescheduling or canceling the trip. Rest assured, Trips 2 Italy will provide a letter of credit that covers the full amount paid for your reservation if you choose to postpone, ensuring complete protection for your investment.

Discover Book Your Custom Vacation to Italy

Custom Vacations

With Trips 2 Italy

Just tell us a little bit about where you'd like to go, and what you'd like to do. Our Italy travel experts will do the rest.

Food & Wine Trips

Italy beckons to culinary enthusiasts and food lovers alike, enticing them with its world-renowned cuisine and exceptional wines. From the vibrant street food scene in Rome to the succulent steaks of Florence, the iconic pizzas of Naples, and the gastronomic treasures of Emilia Romagna, each region offers a distinct culinary experience. Whether you find yourself amidst the picturesque hills of Tuscany or the coastal charm of the Amalfi Coast, prepare to indulge in a feast of delectable flavors and savor local specialties. Immerse yourself in the passion and artistry of winemaking as you explore the renowned wine regions of Tuscany, Piedmont, and Veneto, where tastings and vineyard tours will unveil the secrets behind Italy's extraordinary vintages. Embarking on a culinary adventure in Italy guarantees unforgettable moments, inviting foodies and wine enthusiasts to partake in an unforgettable exploration of the country's culinary delights.

Historical & Cultural Trips

Embark on an enchanting journey through Italy, a land brimming with culture, history, and architectural marvels. Immerse yourself in the breathtaking beauty of Rome's Colosseum, the artistic treasures of Florence's Uffizi Gallery, and the romantic charm of Venice's picturesque canals. Experience the vibrant energy of Italy's renowned festivals, from the dazzling Venice Carnival to the exhilarating Palio di Siena. Uncover the secrets of ancient civilizations as you explore the captivating ruins of Pompeii and be in awe of the majestic splendor of the Vatican City. Italy's rich cultural tapestry awaits, offering a captivating blend of history, art, and celebration that will leave an indelible mark on your soul.

Active Italian Adventures

Italy's diverse landscapes enchant nature enthusiasts with its captivating beauty, from stunning coastlines to majestic mountains and endless hiking trails, creating the perfect backdrop for unforgettable outdoor adventures. Indulge in epic ski escapades in the Italian Alps or embark on exhilarating hikes along the picturesque Cinque Terre and Amalfi Coast, offering awe-inspiring vistas for all skill levels. Immerse yourself in the tranquility of the Tuscan countryside through horseback rides, while walking and biking tours throughout Italy allow you to explore cities and embrace the captivating outdoors. Whether your passion lies in skiing, biking, hiking, or leisurely strolls, Italy presents a plethora of active vacation options to satisfy your desires.

Custom Vacation packages

We've crafted for clients

Curious about what a custom itinerary from Trips 2 Italy is like? Explore these Custom Vacation packages to see what we do.

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.