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Custom Italy Group Vacations For Senior Travelers

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Fully customized Italy group trips designed for travelers 55+, with a comfortable pace, thoughtful planning, and 24/7 support during your vacation.

Let Us Plan The Perfect Italy Vacation For Your 55+ Group

Travel Italy with ease, comfort, and great company. We design custom vacations for mature travelers and senior groups, from retirement communities and 55+ neighborhoods to church groups, clubs, and circles of lifelong friends.

From active itineraries to slow, scenic days, we’ll tailor every detail to your group’s comfort while still highlighting the very best of Italy’s culture, food, and history.

Retirement Communities

Share Italy with your neighbors through easy-paced tours, shared meals, and authentic experiences that deepen friendships and memories.

Church Groups

Journey through Italy’s sacred sites with gentle pacing, meaningful pilgrim stops, and shared moments of prayer, reflection, and fellowship.

Senior Centers/Clubs

Transform your club’s next outing into a relaxed Italian escape, tailored to your group’s pace, interests, and comfort.

Share a few details about your travelers, and we’ll design a custom, no-obligation itinerary for your group.

Plan My Group’s Italian Getaway
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 unlocking the soul of Italy, guided by passionate experts who treat your group like family. Every itinerary is custom-made for your travelers’ interests, pace, and comfort.

  • Share Your Group's Dream Italy Experience With Us

    Tell us about your group: who you are, how you like to travel, and what Italy means to you. We’ll discuss must-see sights, preferred pace, and any comfort considerations so we can design the right experience for your travelers.

  • We Design Your Authentic Italian Experience

    With over 22 years of expertise, 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.

  • Relax — We Take Care of Everything

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

Start Planning My Group Trip Today!

Why Seniors Love Our Italy Group Trips

100% Private Tours

Your group, your tour. No strangers, no generic bus routes. Travel at your own pace with people you know and trust.

Pace Designed For Your Group

We design each day around your group’s comfort level. No rushed schedules, just reasonable walking, well timed breaks, and plenty of time to explore and enjoy Italy.

Comfort Focused Planning

We know not everyone travels at the same pace, so we plan routes, hotels, and activities with your group’s comfort and walking needs in mind.

First Hand Knowledge & Local Insight

We live and breathe Italy. Our planning is based on real experience and trusted local partners, so your group can travel with confidence and enjoy truly memorable experiences.

Fully Customizable

Prefer more wine tastings? Want to focus on art, history, or culinary experiences? Need extra downtime built into the itinerary? We customize every detail to match your group’s interests, comfort level, and energy.

Dedicated Tour Director

An English-speaking Italian tour director travels with your larger group, bringing Italy to life through stories, local insight, and on-the-ground support. Their role is to keep everyone comfortable, informed, and enjoying each day.

Ready To Start Planning Your Vacation?

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Still Have Questions About Your 55+ Italy Group Trip?

We’re here to help. Share your group’s ideas, needs, and concerns, and we’ll walk you through every step of planning a comfortable, authentic Italian vacation.

Common Questions From Group Trip Organizers

What's the minimum group size?

We typically create custom vacations for groups of 10 or more travelers and can comfortably handle larger groups as well. Each itinerary is designed to keep the experience intimate, well‑organized, and enjoyable for everyone.

How far in advance should we book our group trip?

For the best choice of dates, hotels, and flight options, we recommend planning 9–12 months in advance. This also gives your travelers plenty of time to prepare. If your timeline is shorter, let us know, we’ll let you know what’s realistically possible.

What if someone needs to cancel?

Trips 2 Italy always recommends purchasing an optional travel protection plan. In many cases, these plans can offer protection if you need to cancel for covered reasons (such as medical issues or family emergencies) and may also provide benefits for trip interruptions or unexpected medical needs while traveling. During the planning process, we’ll walk you through the available options so you can choose the coverage that best fits your needs.

Can you accommodate special dietary or health needs?

We regularly work with travelers who have dietary restrictions or health considerations, and we do our best to accommodate these during planning. Please share any needs (such as gluten‑free, vegetarian, or low‑sodium diets) as early as possible so we can coordinate with our local partners.

Is airfare included?

Yes. We include roundtrip airfare from a U.S. gateway as part of the package. This helps keep the group together and simplifies logistics from departure to return.

How much walking is involved?

Walking levels can be adjusted based on your group’s needs. Italy’s historic centers often include cobblestones, stairs, and uneven streets, so we’ll discuss your group’s general comfort level in advance and design a pace that feels reasonable, building in rest time and convenient transportation wherever possible.

Who helps us during the trip?

Your group is supported by our local Italian partners and, in many cases, a dedicated English‑speaking tour director who travels with the group. They help with day‑to‑day logistics, share local insight, and make sure everyone feels informed and cared for, so group leaders can relax and enjoy the journey too.