Live Italy, Don't Just See It!
Our team consists of first-generation Italians who know where to go, what to do, and how to truly experience Italy like a local. Not sure which kind of trip you want? Start with our Italy vacations by trip style, nine ways to travel Italy with a summary of each.
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. As Italians, we know all those unique places to show you throughout Italy that make a one of a kind Italy vacation experience. Our handcrafted custom itinerary creates memories that will last a lifetime.
As Recommended By:
A relaxed 10-day, land-only family journey through Italy’s south: Rome by electric tuk-tuk, seaside Gaeta, the ruins of Pompeii, the island of Capri, the street food of Naples, and
See Italy’s three iconic cities your way on an 8-day guided journey. Explore the Colosseum, the Vatican, and Florence’s cathedrals, then glide through Venice by gondola. Private driver, premium
From the peaks of the Dolomites to the shores of the Italian Riviera, an escorted 16-day journey through Northern Italy: Cortina, Venice, Verona, Lakes Garda, Como and Maggiore, Milan,
Your Italy honeymoon deserves more than a standard itinerary; it should be the beginning of your own Italian love story. At Trips 2 Italy, we believe every couple’s journey is unique, and so is every Italian honeymoon we design. Imagine sharing your first sunset as newlyweds overlooking the rolling hills of Tuscany, wandering hand-in-hand through romantic Venetian canals, or savoring a private dinner on the Amalfi Coast. We listen to your honeymoon dreams and custom build a one-of-a-kind Italian adventure, filled with moments you’ll cherish forever.
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 organizes 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!
Italy is meant to be experienced together, through the wonder in your child’s eyes at ancient ruins, the joy of grandparents sharing family stories over gelato, and the laughter echoing through sunlit piazzas. At Trips 2 Italy, we craft immersive Italian family vacation itineraries that delight every generation, blending hands-on adventures, authentic flavors, and seamless logistics so you can focus on making memories. Whether you’re traveling with toddlers, teens, or grandparents, your family’s Italian vacation will be uniquely yours, filled with discovery, connection, and moments you’ll cherish forever.
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.
Savor Italy with all your senses. Immerse yourself in Italy vineyard tours and private tastings in the country’s most celebrated wine regions, roll up your sleeves for hands-on cooking lessons with local chefs, and discover the secrets of Italy’s culinary heritage with exclusive visits to artisanal producers. At Trips 2 Italy, we design Italian food and wine journeys that go far beyond the table, inviting you to taste, create, and connect with the flavors, the people, and traditions that make Italy unforgettable. Each Italy culinary experience is crafted just for you, so every meal becomes a memory, and every glass tells a story.
Your Italy honeymoon deserves more than a standard itinerary; it should be the beginning of your own Italian love story. At Trips 2 Italy, we believe every couple’s journey is unique, and so is every Italian honeymoon we design. Imagine sharing your first sunset as newlyweds overlooking the rolling hills of Tuscany, wandering hand-in-hand through romantic Venetian canals, or savoring a private dinner on the Amalfi Coast. We listen to your honeymoon dreams and custom build a one-of-a-kind Italian adventure, filled with moments you’ll cherish forever.
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!
Italy is meant to be experienced together, through the wonder in your child’s eyes at ancient ruins, the joy of grandparents sharing family stories over gelato, and the laughter echoing through sunlit piazzas. At Trips 2 Italy, we craft immersive Italian family vacation itineraries that delight every generation, blending hands-on adventures, authentic flavors, and seamless logistics so you can focus on making memories. Whether you’re traveling with toddlers, teens, or grandparents, your family’s Italian vacation will be uniquely yours, filled with discovery, connection, and moments you’ll cherish forever.
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.
Savor Italy with all your senses. Immerse yourself in Italy vineyard tours and private tastings in the country’s most celebrated wine regions, roll up your sleeves for hands-on cooking lessons with local chefs, and discover the secrets of Italy’s culinary heritage with exclusive visits to artisanal producers. At Trips 2 Italy, we design Italian food and wine journeys that go far beyond the table, inviting you to taste, create, and connect with the flavors, the people, and traditions that make Italy unforgettable. Each Italy culinary experience is crafted just for you, so every meal becomes a memory, and every glass tells a story.
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.
See Italy Through Our Eyes
They say all roads lead to Rome, unless of course you had the privilege to grow up there and simply call Italy 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 ingredient we carefully craft into each vacation we create. 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.
Traveling isn’t just about places; it’s about stories.
At Trips 2 Italy, we believe the magic of travel is found in the moments you can’t plan: sharing homemade pesto with a Ligurian chef, learning family traditions in a Tuscan vineyard, or wandering Rome’s quiet backstreets with a local friend. Founded by Italians, our mission is to craft journeys that immerse you in the heart of Italy, so you don’t just see it, you live it.
Rome, Venice, Florence, Naples or a snowy Alpine village? Our Italy specialists compare the best places to spend New Year's Eve in Italy and the traditions that make Capodanno special.
From La Scala and La Fenice to the Verona Arena and Puccini's lakeside festival, our Italy specialists share how to plan a trip around opera in Italy, season by season.
Planning Italy with kids? Italy insiders share the best regions, how to pace the days, and how a custom family itinerary keeps every age happy.
Plan a private Amalfi Coast honeymoon with Italy insiders. Where to go, when to travel, and how a custom itinerary turns the coast into your own.
A guide to the best ski resorts in Italy, from the Dolomites to the Aosta Valley, and how to build a custom Italian ski trip that pairs the slopes with...Read More
