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The Best Resorts for a Multigenerational Family Vacation and How to Plan

The soft rumble of ambient music and poolside splashing try to lull me to sleep as the blistering Mexican sun beats down on my pale New England skin. Before I drift off, I peer over my sunglasses to do a quick kid check.

As I scan the Ambassador pool of the Grand Velas Riviera Maya, I spy the gaggle of cousins at the swim-up bar, sucking down their daily infusion of tropical fruit smoothies. Another glance to my right shows my father-in-law enjoying his daily indulgence, a poolside massage — a brief interruption to an ongoing Scrabble tournament with his wife. The smile on my mother-in-law’s face captures her joy at seeing her entire family, usually separated by over thousands of miles, gathered together in one place.

When my youngest nephew approaches her to ask if he can order pizza, it doesn’t even take his charming smile to twist her arm. There is nothing she loves more than spoiling her grandchildren and to get that opportunity for a full week is absolutely priceless.

Of course, it took over a year of planning and much negotiation to make this week of zen a reality. Planning a multigenerational trip can be a challenge, but these tips, followed by five of our family favorites, will get you on your way.

How To Plan An Multigenerational Trip

1.) Plan Early
Coordinating the schedules of multiple families requires an effort in organizational planning, between schools, camps, sports, and work schedules. This may require traveling over particularly busy times such a Christmas break, summer vacations, or popular long weekends, like Memorial Day weekend.

2.) Be Prepared To Compromise
If half of your party would like to trek the glaciers in Argentina and the other half prefers ordering cocktails by the pool, it can be hard to find a middle ground — but you must. Maybe a nice resort in Costa Rica with optional day trips into the jungle is the way to go.

3.) Make Sure There Is Something For Everyone
Your teens are not going to want to hang out with your toddlers and your toddlers are not going to spend all day sitting on the edge of the pool. Make sure there are activities and amenities for everyone — fine dining for the foodies, family activities for all ages, and a kids’ club (or teen club).

4.) Give The Kids Some Independence
Many resorts that cater to families also offer kids a degree of independence, which can be incredibly important. Cousins have a chance to bond without the constant watchful eyes of parents, and the adults can relax and enjoy their limited time together without the weight of other responsibilities.

5.) Plan Your Room Configurations
When kids get to bunk together, it’s like a multi-day slumber party. Of course it can also be easy to forget the rules observed so closely at home and these may vary from family to family. It’s good to set some group guidelines and also keep a connecting room to at least one set of parents.

Playa del Carmen, Mexico


It may be the daily restocking of snacks in the mini-bar, but the children in our family have been clamoring to return to the Grand Velas Riviera Maya. This is one of those rare all-inclusive resorts that can satisfy both the foodies and the pickiest of eaters. Activities abound from pool games to separate kids’ clubs and a teen club, karaoke bar, beach buggy, Mayan performances, dive-in movie nights, and a truly spectacular spa.

Those that enjoy more than sunbathing can visit the nearby Mayan ruins in Tulum and the adventure seekers can zip line, go tubing through cenotes, and learn about Mayan culture in the nearby Xcaret Parks.

Grand Velas Riviera Maya - All Inclusive

Top rated
Playa del Carmen
9.7 Excellent (2185 reviews)

Guanacaste, Costa Rica


For those that want to steer clear of the all-inclusive resorts, but still fancy a place where everyone from Grandma to little Johnny will be happy, the Four Seasons Resort Costa Rica at Peninsula Papagayo goes above and beyond to cater to family groups.

Children are greeted with their own set of amenities, including kid-friendly bath products and their names written on the bathroom mirrors. The kid’s club can entertain parents that want to relax or family activities from kayaking and stand up paddling boarding to surf or golf lessons can be arranged. Even teens can have fun at evening events on the beach or dive-in movie nights at the pool. During school vacation weeks, the hotel even sets up a special game room for extra entertainment options.

Of course, for those adventurers, zip lining is nearby or day trips can be arranged to a national park and hacienda for a local lunch and wildlife boat tour, or longer trips to the Cloud Forest are possible. Our crew got a real kick out of seeing the real-life monkeys frolicking in the trees around the resort.

Four Seasons Costa Rica at Peninsula Papagayo


North Conway, New Hampshire


The Red Jacket Mountain View Resort is that quintessential New England hotel that attractions families for generation after generation. Walking through the corridors and passing through connecting doors marking additions that have been added over the years feels like a passage through time. North Conway offers a charming small-town base for exploring New Hampshire’s White Mountains and nearby attractions such as Story Land amusement park or the Mount Washington Cog Railway.

After days spent hiking and exploring, families are welcomed back with unpretentious suites overlooking the mountains. The daily calendar of activities will keep everyone busy and all generations enjoy outdoor s’mores by the fire. However, it can be hard to tear kids away from the Kahuna Laguna indoor water park, which really makes the Red Jacket a year-round destination.

Red Jacket Mountain View Hotel

North Conway
8.4 Very good (187 reviews)

Amelia Island, Florida


Located off the Northeastern Coast of Florida, Amelia Island offers southern charm, which is in sharp contrast to splashier resorts further down the Florida coast. The Ritz-Carlton Amelia Island extends its southern hospitality to families in ways that go above and beyond, starting with the first impression at the kid’s check-in.

The amenities for young guests continue with the famous Ritz Kids program, which teaches guests about the pirate lore that surrounds the island and the ecology of the beach from sea turtles to searching for shark’s teeth. Programs also include astronomer-led stargazing sessions on the beach, bonfires, kid’s nights out, and pirate tuck-ins.

All ages can enjoy the multiple on-site dining options and fabulous on-site spa, or downtown trolley tours, kayaking, and shopping.

The Ritz-Carlton, Amelia Island

Top rated
9.2 Excellent (1016 reviews)