Multigenerational & Retired Travelers
Because your time together deserves more than a standard itinerary.
From grandparents to grandchildren, we create seamless Italian journeys designed for comfort, connection, and unforgettable shared memories.
Best Multigenerational Destinations in Italy
Rome remains a favorite, where interactive tours of ancient wonders and food-focused strolls please both history buffs and picky eaters. In Florence, art and artisanship come alive with hands-on workshops and private museum visits. Tuscany offers space, serenity, and villas perfect for shared meals under the stars.
For something fresh, we love Puglia, with its whitewashed towns, seaside farmhouses, and warm southern hospitality—ideal for slow travel and multi-room stays. The Italian Lakes, from Garda to Como, offer breezy elegance, gentle landscapes, and boat days that feel like a dream. And in Venice, our guests enjoy exclusive access to private palazzi and cultural corners hidden from the crowds.
With over 15 years of experience crafting tailor-made trips for American families, we know how to balance comfort, culture, and connection—at every age.
Let’s build something your family will remember forever.
Why Dragonfly Is Ideal
for Multigenerational Travel
Post-COVID, many families have rediscovered the true value of time together.
That’s why we’ve created a dedicated service for multigenerational and retired travelers—luxury journeys designed to slow down, reconnect, and experience Italy in ways that speak to everyone in your group.
At Dragonfly Tours, we design with intention. That means planning for varied energy levels, pacing that feels effortless, and experiences that every generation can enjoy.
Whether it’s an anniversary, milestone birthday, or long-awaited reunion, we turn your vision into a seamless and meaningful journey—without logistical stress.
You’ll enjoy private guides, first-class transfers, curated cultural experiences, and accommodations selected for both comfort and charm.
Every member of your family will feel seen, included, and cared for.
Ready to turn your travel dreams into reality?
Schedule a call with one of our expert travel designers to discuss your journey!
Your journey
step by step
Our Signature Travel Process
Stories from
Our Guests
Over 12,000 American travelers served. 100% 5-star reviews.
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FAQ – Everything You Need to Know
In this section, you’ll find answers to the most common questions our travelers ask.
Every journey is unique, and while this page covers the essentials, we’re always here for anything more specific or personal.
If your question isn’t listed—just ask. We’ll be happy to help shape your perfect Italian experience.
Is Italy a suitable destination for multi-generational travel?
Absolutely. Italy is ideal for families of all ages. From toddler-friendly gelato tours to museum visits with expert guides for grandparents, we balance each itinerary to include experiences for children, adults, and seniors alike.
How do you adapt the itinerary for retired travelers or older family members?
We tailor the rhythm, transportation, and experiences based on mobility, comfort, and interests. This means avoiding long walks, adding more downtime, choosing hotels with elevators, and offering private transportation door to door.
Can you organize experiences that appeal to both kids and grandparents?
Yes! Imagine a hands-on cooking class where three generations cook pasta together, or a private boat tour along the Amalfi Coast with something for everyone—relaxation for adults, fun for kids, and scenery for all.
Can you provide accommodations that suit both kids and older adults?
Yes. We hand-select accommodations with easy access, family-friendly options, and comfort-focused amenities. Some include pools for kids, wellness areas for adults, and step-free access for older guests.
Is it possible to plan some “free time” in the itinerary for different family members?
Of course. We can design days where younger guests go on a Vespa tour while others enjoy a spa treatment, a quiet art visit, or a relaxing aperitivo at a historic café. Italy offers something for every generation.
One of our family members has mobility issues. Can you accommodate this?
Absolutely. We frequently design trips for travelers with reduced mobility. We select wheelchair-accessible hotels, organize vehicles with low steps or lifts, prioritize step-free access to attractions, and arrange for private assistance when needed. Just let us know in advance so we can plan accordingly.
Can you help with special needs or accessibility requests?
Yes. Whether it’s dietary requirements, medical equipment, or slow-paced days with minimal walking, we plan every detail to ensure safety, comfort, and peace of mind for every guest.
What destinations in Italy are best for multi-generational travel?
Great options include:
- Tuscany for villa stays and relaxed pace
- Rome for iconic sights and layered history
- Puglia for sandy beaches and family-friendly villages
- Lake Como for nature and elegance
- Sicily for culture, sunshine, and slower rhythms
Do you offer a local travel assistant during the trip?
Yes. You’ll have a dedicated travel designer and a local contact available 24/7 throughout your stay—ideal for larger families or retired guests who appreciate extra peace of mind.
Our Trusted Partners
Our trusted network of five-star hotels and exceptional hospitality partners sets the standard for every journey.
