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3 Destinations for Skip-Generation Travel

by Eugenia Lazaris

May 12, 2026

Anna Maria Island, Florida © Thomas X De Wever | Dreamstime.com

Multigenerational

Summer is on its way and that means many parents are looking for creative ways to keep kids entertained while keeping up busy work schedules. Grandparents are often a great solution — parents can send the kids off on a trip with someone they trust, and both kids and grandparents get to have fun together. Finding the right trip to keep each generation entertained and happy can be a bit tricky, so we’ve put together a list of some of the best destinations in the country to do just that.

 

Anna Maria Island, Florida
Not far from Tampa you’ll find Anna Maria Island, a charming destination that cherishes its small-town vibe. None of the buildings are taller than three stories, you won’t find a chain restaurant and there are plenty of vacation rentals to give different generations the space they need, all under one roof. The island is home to award-winning beaches with calm waters that make beach days the perfect blend of fun, relaxing and safe. Boat tours, water sports, museums and festivals, along with great food and shopping, give you plenty of ways to either spend your days packing in the sites or exploring at the relaxed pace of island time.

 

Carlsbad, California
Carlsbad is the quintessential California beach town, perfect for a skip-gen getaway. The vibe is laidback and, despite great weather, beautiful beaches and a top-notch culinary scene, it never gets that overcrowded feeling. In other words, great beach time for kids and grandparents in a safe, laidback environment that everyone can relax in. You’ve got plenty of options for places to stay, from connected rooms in a hotel to a vacation rental with plenty of privacy and room to stretch out. Downtown Carlsbad, known as the Village, is walkable and filled with fun shops to explore, but there is also Legoland, as well as one of the town’s quirkiest spots, The Camp Store, a beach-front spot for food; drinks; live music; and a random collection of items like dinosaurs, aliens and Bigfoot that the owner displays throughout the year.

 

San Antonio, Texas
San Antonio is a favorite for families, solo travelers, girls trips and more, but it’s especially ideal for a skip-gen vacation. The city is home to iconic sites like the Alamo, where grandparents will appreciate the history, and kids can see firsthand what they’ve learned about in school. In the same part of town you’ve got plenty of other family-friendly attractions, like Ripley’s Believe It Or Not! and Legoland Discovery Center. Booking a stay in a hotel along the city’s Riverwalk, a walkable route that follows the San Antonio River through downtown, puts you right in the heart of the action. There is plenty to see and do along the river (including a river boat ride so you can see the city from the water), and great spots to eat, but the Riverwalk also makes getting around the city incredibly easy.

#WhereverFamily

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