Getting away on a multi-gen trip, one that includes a variety of ages and friends and family members with different interests, can be a fun way to spend some quality time before the end of summer, but a bear to plan.
When considering different travel interests and age-appropriate activities, organizing a multigenerational trip is easier done with accommodations offering a little bit of everything in diversely entertaining destinations. Enter this list.
Enjoy the cooling air of the city or lingering long sunsets of the beach on your next family stay.
The Rittenhouse in Philadelphia
For an easy-to-please destination with shopping, history, incredible dining, fun nightlife and an entertaining theater scene, Philadelphia has it all. Stay in the heart of the action in the Rittenhouse neighborhood of Center City at the stunning hotel of the same name: The Rittenhouse. Located along Rittenhouse Square, guests can take advantage of the park’s green spaces, pop-up markets, art shows and events hosted regularly in the summer.
Enjoy easy walking distance to the park, shops, high-end dining and Philadelphia musts like The Philadelphia Art Museum and The Franklin Institute. After a long day exploring the city, filling up on cuisine and culture, head back to your hotel’s indoor glamping scene. Kids can cozy up in sleeping bags and tent-enclosed mattresses with homemade s’mores. The little ones in your group will also find robes and slippers, just their size, to match the adults, along with a welcome gift from the hotel.
The Ritz-Carlton Resorts of Naples in Naples, FL
For the last-minute beach seekers in your group, Naples, Florida, boasts some stunning vistas along the Gulf of Mexico. Located right on the shore, The Ritz-Carlton, Naples offers all the 5-star luxury services and amenities travelers can ask for (literally), but with the casual, relaxing vibes of a beach resort. Lounge by the pool or on the beach, or set up a tee-time at the golf course. When you get hungry, stop by any of the resort’s 10 dining establishments, or split up to accommodate everyone’s palates.
Kids Tent. Photo: The Ritz-Carlton Resorts of Naples
The kids will love the Nature’s Wonders program with hands-on activities and exploring 11 different aquariums. The young adults and teens can check out the Virtual User Experience and play virtual reality games on a break from the beach. Adult children, parents and grandparents can unwind with a spa treatment with something for everyone, including CBD enhancements, anti-aging and sleep treatments. Families staying at the golf resort add on to the experience with an in-room camp site — perfect for the end of the season. This amenity comes with a space-themed tent, glow-in-the-dark galaxy, lantern and space discovery book.
Read This Next
#WhereverFamily
Insta FeedNorth America
Sep 3, 20266 Winnipeg, Canada, Destinations for Family Travel
It’s time to start dreaming of your next family trip. Here’s some destination inspiration for you. Take a visual journey through Winnipeg, Canada, with us.
Sponsored Content
Best of Both Worlds
Enjoy the best of both worlds when you fly with TAP Air Portugal thanks to the Portugal Stopover program. With the program, TAP passengers, whether traveling for business, leisure or both, can stop in Portugal for up to 10 days at no additional airfare on the way to their final destination. What does this mean for travelers wishing to explore by both land and sea? It means after flying to Portugal with TAP and experiencing the country in an entirely new way, travelers can then embark on scenic river and ocean cruises from Portugal’s port cities, or fly with TAP to another European destination.
Hotels
Sep 3, 20263 Caribbean, Latin American Marriott Hotels for Multigen Trips
Multigenerational travel continues to grow in popularity, with family travelers moving away from traditional getaways for meaningful trips with family members of all ages. The Caribbean and Latin America are growing destinations of interest for this type of travel, and three Marriott properties offer opportunities for multigen families to create lifelong memories.
Destinations
Sep 2, 2026Look Past the Traditional Classroom with Scott Dunn’s Back-to-School Itineraries
Parents looking to provide their kids with hands-on learning experiences going beyond textbooks by visiting unique destinations with family-centric approaches will find that and more with Scott Dunn's private, expert-led itineraries. These experiences provide lessons the classroom cannot.
Sponsored Content
GET TO KNOW TAP FORBIZ
Unlock flexible, refined business travel with TAP Air Portugal’s program, TAP FORBIZ. Developed for small, medium and large Companies, with options for corporate events, TAP FORBIZ offers exclusive advantages adapted to each type of business.
Destinations / North America
Sep 2, 2026Visit an Old-Fashioned County Fair in Maine
Celebrate autumn with a family trip to a traditional New England county fair. These annual celebrations of agriculture and country life are filled with sights and activities for the whole family to enjoy, from admiring prize pumpkins and meeting live animals to witnessing horse shows, listening to country music and dancing, and doing craft demonstrations. Most fairs also have carnival rides and hands-on activities for kids.
ShareThis