Custom Italian Family Vacations for Every Generation

Thoughtfully Planned for Your Family, From Kids to Grandparents

This holiday season, turn “maybe someday” into memories in Italy. We craft stress‑free itineraries for families, big and small, that fit everyone’s pace, interests, and budget.

Let Us Plan The Perfect Italy Vacation For Your Whole Family

We listen to what matters most to your family, whether that’s grandparents revisiting favorite cities, teens discovering something new beyond the usual tourist spots, or little ones seeing Italy’s wonders for the first time. We weave it all together into a custom Italy vacation where everyone feels included, relaxed, and truly cared for.

Why Families Of All Sizes Love Our Custom Trips To Italy

Stress Free Trip Planning

Enjoy Italy together while we manage the details: centrally located hotels, reliable transport, and thoughtfully planned tours, activities, and skip the line reservations.

Kid Approved Fun

From hands on pizza and gelato experiences to city walks, museum treasure hunts, and family friendly boat excursions, we match activities to your children’s ages and interests throughout the trip.

Planning For Every Generation

We thoughtfully pace your itinerary, recommend routes, experiences, and stays with comfort in mind so grandparents and grandkids can enjoy Italy’s historic streets together.

Custom Itineraries

Every itinerary is built from scratch around your family’s timing, interests, and travel style, no generic templates, just a trip that feels personal and meaningful.

Insider Knowledge of Italy

We combine regional, cultural, and on the ground know how, from trains to timing, to suggesting activities, dishes, and restaurants so your family experiences Italy like an insider.

First Class Accommodations

We hand select accommodations that reflect your family’s style, whether that’s charming boutique stays, family friendly hotels, or luxury properties. We keep comfort, character, and location in mind.

Zero Stress Logistics

From key transfers and activities to thoughtfully sequenced days, we coordinate the practical details of your trip so you can relax and focus on time together.

Support While You’re In Italy

While you’re in Italy, our team is just a call or email away for urgent needs and unexpected questions, so you never feel alone when you’re far from home.

Live Italy, Don't Just See It!

How It Works – A Journey Crafted With Heart

With Trips 2 Italy, you’re not just booking a tour, you’re entrusting your family’s memories to passionate Italy travel experts who treat your trip with the same care we would give our own.

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  Share Your Family's Dream Italy Experience With Us

  Tell us who’s traveling, what everyone hopes to see and feel, and any milestones you’re celebrating. We listen carefully to design a trip that truly reflects your family’s story.

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  We Design Your Authentic Italian Experience

  With over 22 years of experience, our team crafts each itinerary with passion and precision. We don’t believe in “one size fits all”. From handpicked hotels to immersive experiences, every detail reflects our commitment to authenticity, quality, and genuine connection.

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  Relax — We Take Care of Everything

  We coordinate accommodations, private transportation, and select experiences so your family can simply arrive and enjoy. For extra large family groups, additional on the ground support can be arranged when needed.

Thank you again for all your help in organizing our fantastic family trip to Italy.
As promised, everything went smoothly which made the trip even more enjoyable. We didn’t have to worry about anything thanks to your planning and organizing every last detail in advance. It truly made the trip even more memorable Thank you again for everything. I will definitely be recommending Trips 2 Italy to others!

Susan R. and Family

Here we are raising our glasses toasting to Tommaso for planning such a fantastic trip for our family! Everything was amazing – the trip exceeded all of our expectations! We truly could not have done this many things and coordinated all 17 people without you. Everything ran very smoothly – all drivers and tour guides were exactly where they were supposed to be at the time they were supposed to be there and we loved one tour guide better than the next!

Jill T. Family

Our family trip to Italy could not of turned out anymore spectacular than it did, from drivers to the private tour guides, we couldn’t have been set up any better. Your itinerary worked perfectly and we got a small taste of Italy (especially Lucios cooking) that will last us a lifetime or until Jennie and I decide to go back. Your attention to detail was magnificent and afforded us such a great opportunity to see the Amalfi coast and Rome in the short time that we had.

Richard M. Family

Ready to Start Planning Your Family’s Italian Story?

Whether you’re dreaming of a once‑in‑a‑lifetime trip with grandparents and grandkids, or a relaxed escape with your immediate family, we’re here to guide you every step of the way. Share your ideas with us, and we’ll transform them into a custom Italian journey filled with authentic experiences, thoughtful pacing, and memories your family will talk about for years to come.