Slide 1
Your Custom Italy Vacation Starts Here
Live Italy! Don't Just See It

Creating a One Of A Kind Italy Vacation Has Never Been Easier

1. Choose Your Italy Destination

No matter what type of Italy vacation you are looking for, Trips 2 Italy is able to create that unique travel experience, customized just for you. 

2. Create a Custom Itinerary 

As Italians, we know all those unique places to show you throughout Italy that make a one of a kind memorable Italy vacation experience. Our handcrafted custom itinerary creates memories that will last a lifetime. 

3. Book Your Trip to Italy

Book your trip with peace of mind. Trips 2 Italy locks in your price and guarantees that there will be no unexpected price changes. Complete peace of mind that allows you to book today, only available from Trips 2 Italy. 

Popular Italy Vacation Destinations

See Italy Through our Eyes

They say all roads lead to Rome, unless of course you had the priveldge to grow up there and call Italy simply home. As children we walked the cobblestone streets. As adults we married in the vineyards of Tuscany;  prayed in the Sistine Chapel;   sailed Lake Como and skied the Italian Alps. Italy has made us who we are. As any Italian knows, there is a passion for what we love. And, our love of Italy is the ingrediant we craft each vacation we create with. Our goal  for our guests is simple really; experience Italy with the same passion we do.

For nearly two decades we have been working with brides, grandparents, friends, parents or anyone with an adventurous spirit to plan the ultimate Italian vacation. From the encounter, with us, you will feel our commitment to providing the best Italy vacation and our pride in designing it uniquely for you.  Unlike internet travel sites or even our competitors, our team is comprised of first generation Italians who know where to go and what to do. Don't just see Italy. Live it. 

Sample Italy Vacation Itineraries

Italy Honeymoon Vacations

Planning an Italy honeymoon is not like planning any other trip. If done right is an experience that will last a lifetime. For that reason, planning an Italy honeymoon trips needs to be done with extra planning and care. It is not the type of trip that you can copy an itinerary and expect to have the travel experience that should accompany such an important trip. Being specific at the types of experiences you want will help Trips2Italy we work with our couples to create a custom vacation tailored right to their dreams.

 Plan My Honeymoon

Group Travel to Italy (more)

When traveling as a group, whether with business colleagues, with friends, or as part of an organization or club – one of the most difficult tasks can be organizing a travel itinerary that fulfills the needs of everyone while maintaining the group’s central goal. And when it comes to international travel, ensuring all the arrangements are made correctly can be a struggle.

Luckily, Trips 2 Italy organized group travel to Italy and custom escorted group tour packages that alleviate the tremendous stress of planning and allows for a relaxing, exciting, and unforgettable vacation for all. We get to know what aspects of your vacation are most important and plan tours and activities based on the exact desires of the group. Our custom escorted group tour packages are fully customizable and allow for the entire group to fully immerse themselves and enjoy the wealth of culture that Italy is so famous for!

 Plan My Groups Trip

Family Vacations to Italy

Just like families, family vacations come in all types and sizes. From a heritage tour, to a graduation trip that will create memories of a lifetime,  Trips 2 Italy will create the perfect Italy family vacation. Have smaller children or babies? We are experts at traveling with children and creating things that both parents and children can enjoy. From the deep history and culture of Italy  to the experiencing the foods, that let children know italian food is more than pizza, we can create the perfect travel experience for your family.

 Plan My Family Vacation to Italy

Escorted Group Tours Of Italy

While we all dream of traveling to a foreign land and exploring the culture and sights of a place like Italy firsthand, there can be some anxiety about navigating the unknown and fear of missing out on the best attractions. For first-time visitors or those who want a completely stress free vacation, Trips 2 Italy recommends escorted group tours of Italy. One of our knowledgeable Tour Escorts will lead you and a large group of likeminded travelers on an organized Italian itinerary of exciting proportions. We eliminate any stress travelers may have regarding navigating Italy’s roads, railways, or walking paths by handling all of the travel arrangements and scheduling. With the comfort of knowing reputable guides will lead you through your trip, you can truly relax, enjoy your adventure and experience the best that Italy has to offer.

 Plan My Group Tour

Food and Wine Trips to Italy

Nothing encapsulates the true heart and spirit of Italy quite like exploring the high-quality wines and native cuisine that has made Italy legendary. Meals in Italy are crafted with time and attention to every detail. The average meal in Italy can last up to three hours, giving diners the chance to truly enjoy every single bite. The crown jewel of the culinary world, Italy offers travelers a food-centric experience unlike any other.

 Plan My Culinary Trip to Italy

Italy Outdoors

From boating to hiking to skiing, Italy offers so many opportunities for those who like the great outdoors. Our beaches are known world wide. The Italian Alps offers world class skiing and snowboarding.  And, as you travel the hidden gems throughout the countryside, our hand crafted custom Italy vacation packages give each of our outdoor enthusiasts the perfect vacation experience.

 Plan My Outdoor Italy Vacation

Experience the Trips 2 Italy Difference

Why Trips 2 Italy?

It’s all about the passion.

There are many ways to plan a customized trip to Italy and many different choices; what sets Trips 2 Italy apart is our passion for both our country and our clients. As Italians, we are the ultimate insiders. We are proud of our country and want to share that with each of our guests.  We believe that everyone should experience Italy the way we do when we travel back home; this means we customize each Italian vacation to allow our clients to not just see Italy the way any tourist would, but to live it!

Italy Customized To You

Each vacation we plan is hand-crafted to exceed your expectations. From a Honeymoon to an Anniversary, a graduation to a reunion, Trips 2 Italy creates the perfect Italian getaway for you.

You Have A Friend In Italy

We offer 24/7 service directly to our clients so you always have a friend just a phone call away.

Easy

Most of all we make your vacation planning easy. We listen to what you would like and make that happen for you!

Experience Our Italian Experts

We have planned thousands of vacations in our 15 years of creating lifelong memories for our clients. We also have the kind of experience not everyone has; we have first-hand experience with Italy. We grew up there, and we still have family there. Anyone can book a trip to Italy, but not everyone can plan a vacation to Italy.

What Our Clients Say

Filter
1 - 5
Review for
Lucca Anphiteather Square Tuscany
Tommaso,Thank you and your team for everything. We had a wonderful trip. I can't tell you have terrific everyone was - Damiano, Simone, Raph
Review for
Venice Bridge Sight San Giorgio View
The room we got with your help ,was all we could ask for There is no way we were going to get the room we did if we had tried to book it our
Review for
Parma Batptistery Cathedral Square
We cant thank you enough for the great job you did scheduling every thing with No issues Arrival after a great Italia flight was good and dr
Review for
Portovenere Cinque Terre San Giorgio Cathedral
" Tommaso, Denis and I just got into Sheraton hotel at Milan airport. Trip was great and all of your arrangements worked out very well. The
Review for
Florence Santa Maria del Fiore Cathedral
Emily, Sorry for the delay in replying. We have been busy getting settled back into our trip. Congrats and I hope you had a good Honeymoo
Review for
Agrigento Scala dei Turchi Sicily Unesco Site
Overall we had a great time. All the Guides were great and we really enjoyed all the places that we visited. The first Hotel, in Sorrento al
Review for
Palermo Mondello Beach Coast Sicily
"Tommaso, we are having a wonderful time on our trip. We just left Sicily and are enjoying our day in Sorrento."
Review for
Rome Viale Riconciliazione St Peter Vatican
"Tommaso, the trip is wonderful, driving out of Rome is nerve whacking! The villa is beautiful it would have been perfect for my brother! Tu
Review for
Basilicata food Red Hot Pepper Sun dried
"Tommaso, The worst part of the trip was that I had to come home and start spending 12 hour days at work again. What the heck though - that'
Review for
Venice Book Store details
I want to thank you for the wonderful job you did planning our trip. I am really impressed with your knowledge about travel in Italy I wante
Review for
Tuscany Volterra Family Vacation
Ciao Tommaso, I hear from My Clients the B. Family. They having a wonderful time. Enjoyed their tours in Florence and Tuscany. They loved th
Review for
Amalfi Coast Positano View
"Dear Tommaso, thank you for setting up this wonderful vacation for us. We are having a great time.we have finally slowed down for a few hou
Review for
Venice Sign Rialto Bridge Directions
We enjoyed our vacation so much! Thank you all for planning our guides and excursions. All of our guides were very good. They were all very
Review for
Florence Tuscany Panoramic View
"Dear Tommaso & Co, thanks for the wonderful trip! Next time we'll ship Venice and go straight to Tuscany. what a magical place."
Review for
Piedmont Grinzane Cavour Castle Langhe
I wanted to let you know that we had a wonderful time! We can't thank you enough for everything. It was so organized, it made everything les
Review for
Rome Trevi Fountain Detail
Thank you for a wonderful planned precruise tour of your beloved Rome. We were able to walk or take the Hop On Hop Off everywhere we wanted
Review for
Veneto Soave Castle Town View
Good morning Emily Our trip to Italy and cruise was amazing and we thank you for your assistance and great organization. The way you had c
Review for
Milan Central Rail Station
Where do I begin? We enjoyed Italy so much. The hotels were a good choice. Rome is truly a walking city! The city was great and the food was
Review for
Florence Tuscany David of Michelangelo
"Buongiorno, Just wanted to thank you for your time spent with us in planning our trip and sharing with us all of the joys of Italy. The tri
Review for
San Gimignano Tuscany Medieval City View
"Buongiorno! The hotels in Rome Venice and Florence were all very nice. Giulia in your Milan office helped us with some issues, as Phill
Review for
Agrigento Scala dei Turchi Sicily Unesco Site
"Signore Tommaso, a wonderful trip, so far. The owner and the staff at Agriturismo Gigliotto have been extraordinary.Beautiful location and
Review for
Castel Del Monte Apulia
"Tommaso we are having a wonderful time! Everything has been great so far, thanks again for all your help! We look forward to the rest of th
Review for
Lombardy Lake Como Balbianello Villa
" To Tommaso and the Staff of Trips 2 Italy,Our recent trip to Italy was fantastic. The Lake Como region is as beautiful as we imagined. On
Review for
Sicily Food Arancini dish
What a trip! We hated to come home but were so tired that we needed to! We absolutely love Sicily, it's beautiful Thank you so much for the
Review for
Florence Loggia Dei Lanzi Tuscany Family
Hello Tommaso, Well we made it back from Italy and had a wonderful time! Everything went very well except for the small hiccup on the pick
Review for
Piazza Navona Rome Bernini Fountain Neptune Statue
We are now home and wanted to thank you for arranging such a wonderful trip. We had an amazing time!!! Everything you arranged for us worked
Review for
Venice Rialto Bridge view Gondola
Italy was amazing! We had so much fun. The history is evident everywhere you turn We were able to see so many facets of Italy: the Mediterra
Review for
Siena Duomo Cathedral Panoramic View
"Hi Tommaso + all, Italy is more beautiful than I remember. we are having a wonderful time eating and drinking at every opportunity. Spent t
Review for
Procida Campania Dock Amalfi Coast
Tommaso;We returned from our trip on a week ago Friday and I just wanted to thank you very much for everything.Everything turned out absolut
Review for
Rome Colosseum Panoramic City View
I just wanted to let you know how much our group enjoyed our tours of Rome with our guide... She was fantastic! Both days were so interestin
Review for
Liguria Cinque Terre Vernazza Dock View
We had a marvelous time in Italy... Our trip worked out just a planned. Our flights were all good, connections worked out. Rental car and dr
Review for
Ferrara Emilia Romagna Estense Castle
Hi Tommaso! Our trip was incredible! Even better than I envisioned- we all definitely want to return & absolutely did not want to leave
Review for
Florence Tuscany Areal View Duomo Cathedral
The trip you planned was perfect. We enjoyed staying in the countryside We loved exploring Tuscany. We loved the cooking class. And we total
Review for
Emilia Romagna Bologna food Mortadella
Hi Tommaso, ...I had a great vacation in Italy and really enjoyed the experience. The same applies for my mom too. As you know, we spent 5 n
Review for
Amalfi Coast People Family Vacation
Hello Tommaso,Our Italian adventure was absolutely, positively perfect in every way! The itinerary was filled with amazing experiences that
Review for
Cremona Cathedral Sunset View
This is music to my ears, when clients really enjoy their holiday, and this is what keeps them coming back. Tommaso, your people in Italy co
Review for
Venice Canal Grande Romantic Gondola Raid
"...our honeymoon was INCREDIBLE! We had the time of our lives... a trip we will remember forever and will look back on throughout our marri
Review for
Herculaneum Mosaics House of Nepture
Emily, You did a great job organizing our trips. I can't thank you enough! Peggy A.
Review for
Lake Maggiore Borromean Islands
Thank you for arranging such a memorable trip. The hotels were very nice and conveniently located and the tour guides and drivers very profe
Review for
Piacenza Central Square View
Italy was great, full of history and warm people and of course the food was delicious. Milan- Big city with the main attraction the Duomo
Review for
Rome Trastevere Restaurant Tables
"Hi Tommaso, just wanted to send you a card + say thanks. Not just for the travel arrangements Rome tours were great. Thanks again!"