Custom Trips

Your Custom Trip To Italy

Our name says it all and our specialty is planning a custom trip to Italy – vacation packages that are one of a kind, featuring itineraries filled with destinations and activities that are hand selected by our guests. We understand that planning a vacation abroad can be stressful, time-consuming, and often confusing, and that pre-packaged vacations don’t always offer everything one might be looking for. We offer customizable packages to take the stress out of travel and provide a more personalized experience for each guest.

Not only do custom trips to Italy allow travelers to personalize their vacation, but because our Italian travel experts blend their insider knowledge of the country with over 15 years of experience they are able to create an incomparable getaway. No matter what type of vacation one has in mind, planning a customized trip to Italy creates a vacation that has memories that will last a lifetime.

Art and Culture

Possibly Italy’s biggest draw is its incredible amount of art, architecture, and culture. With roots that can be traced back to one of the world’s earliest empires, Italy’s history makes it a travel destination with unprecedented culture at every turn.

Between almost 40 UNESCO World Heritage sites, countless legendary cathedrals and churches, and numerous art museums, travelers have endless options to choose from when planning a customized trip. Unlike a pre-packaged vacation, our personalized art and culture trips are unique to each traveler’s interests, ensuring certain works of art or historic sites are prioritized.

Another benefit to creating a custom trip to Italy that is a culture-focused package is the ability to schedule additional time to experience local life. If traveling during a specific time of year, our staff can recommend unique, local cultural activities, events, and festivals to include in the itinerary. Whether an internationally famed event like the Carnival of Venice or a more local ritual like shopping at open-air farmer’s markets, there is no better way to fully immerse in the culture of Italy than joining Italian residents in traditional events.


Of all the trips one may take in their lifetime, one of the most important and memorable is the honeymoon. Whether celebrating for the first time as newlyweds or marking a monumental anniversary with a second honeymoon, a honeymoon vacation should be a romantic time of bonding, and above all – personal.

Since no two couples are alike, we believe that no two honeymoons should be either. The best honeymoon experience begins with custom trip to Italy,  that includes destinations and activities that are hand-selected by the couple. From riding in a gondola in Venice to savoring Tuscan wines to enjoying water sports in Italy’s Lake District, our honeymoon packages cater to each couple’s unique interests. Trips 2 Italy can help couples curate a customized honeymoon guaranteed to evoke romance and create memories that will last a lifetime.

Hiking, Biking and Skiing

Featuring a varied geography which includes everything from sand and surf to snowcapped mountain peaks, Italy is the perfect destination for active travelers who wish to experience mother nature, Italian style.

By choosing a custom vacation package, travelers can decide what types of outdoor activities to enjoy and how best to balance their active time with sightseeing, free time, and relaxation. Enjoy hiking the famed trails of Cinque Terre, biking through the small villages in the Italian countryside, or skiing fresh snow powder in the Italian Alps – all without missing out on any of the other sites and activities on one’s wish list.

Family Trips to Italy

Traveling is one of the most exciting ways for families to bond. Trips 2 Italy’s customized family vacations allow for families of all sizes to enjoy once-in-a-lifetime moments together via an itinerary that meets their unique desires and needs.

Traveling with Children

While traveling with kids can be difficult at times, our travel experts can streamline the process by helping parents create an itinerary that is fun and child-friendly without sacrificing the culture, history, and sightseeing that one comes to Italy for.

Special Occasions

Whether gathering the entire family for a wedding, engagement, anniversary, or monumental life event, our custom vacations are the perfect way to celebrate with the entire family. Unlike pre-packaged vacations, our customized trips are personal, making family events even more special.

Family Reunions

One of the most daunting events to plan for families is a reunion. We make the process easier and more exciting by helping families create a custom trip that is as unique as their family is – complete with events, tours, and experiences that are sure to bring everyone closer together.

Heritage Tours

For families with Italian heritage, Trips 2 Italy can create a custom heritage tour which helps trace Italian roots, helping travelers explore small towns and walk the same streets as their ancestors.

Food and Wine

Each of Italy’s 20 regions is home to a unique style of cuisine and varied selection of local wines, all of which is deeply influenced by the area’s history and culture. For lovers of fantastic food and excellent wines, there is no better destination than Italy.

With pre-packaged trips, guests are limited to certain areas and activities that may or may not interest them. However, Trips 2 Italy’s custom food and wine vacations allow the travelers to select which aspects of Italian cuisine are most important to them. Whether one wishes to take part in hands-on cooking classes and in-depth winery tours or would rather sit back, relax, and be served course after course of Italian delicacies, we can customize a food and wine itinerary that is personal and authentically Italian.

Travel Groups

Along with groups of family and friends gathering to travel for a special occasion, we can create a custom trip to Italy for travel groups consisting of members from organizations or clubs. For special interest groups, there is no better way to meet the needs of large parties like a customized itinerary. Pre-packaged trips may not accommodate large sizes or meet the unique needs of a niche interest. In addition, our insider knowledge of Italy can help groups reach off-the-beaten path locations and participate in activities that only locals are privy to.

To fully enjoy the depth of culture, history, and sightseeing that Italy has to offer, a custom vacation is the best way to please every member of the group. Types of travel groups include, but are not limited to:

  • Religious & Spiritual Groups
  • Food & Wine Clubs
  • Travel Clubs
  • Businesses
  • Sport Clubs
  • Photography Clubs

Your Custom Trip to Italy

Individuals, families, or groups have unique needs or multiple interests that don’t fit into a specific category. Our team of travel experts can create custom trip to Italy that meet a variety of special requests and cater to any size group. From traveling with small children to longer vacations which feature multiple destinations within Italy, our goal is to ensure each of our guests’ expectations are exceeded.

Some of the unique travel options we offer include:

  • Shore Excursions – Ideal for travelers visiting Italy via a cruise ship.
  • Fly and Drive Packages – Allows travelers to visit multiple locations during one trip.
  • Escorted Tours – Whether individuals or groups, our knowledgeable guides can bring unique insight into Italy’s history and culture
  • Luxury Vacations – Incredible Italian getaways with an added touch of decadence

Creating a custom trip to Italy   makes planning any vacation simple and personalized. Simply choose your trip type and length and let our experts do the rest. Our guests always receive assistance before and even during their vacation if needed to ensure their experience is everything they expected an