The Boston Globe Spotlights Multigenerational Magic at The Islands
In a recent Boston Globe article, Pamela Wright shares her unforgettable “gramping” escape to The Islands with her two young grandchildren. From early morning pool adventures and dolphin kisses to beachfront s’mores and island explorations, the piece beautifully illustrates how The Islands of Islamorada is the perfect backdrop for multigenerational memories.
"ISLAMORADA, Fla. — Daniel, age 7, and Lucca, age 4, came down the stairs dressed in their bathing suits, sun hats, and sunglasses. They were carrying “Paw Patrol” towels and squirt guns, and sporting huge smiles. “Can we go to the pool?” they shouted in unison. It was 6 a.m.
We delayed them with pancakes and a walk on the beach, but by 8 a.m., when the pools opened, they were jumping in the water. Their enthusiasm and delight were contagious. Such are the joys of traveling with children (forgetting the early morning wake-up).
This trip was a skip-gen getaway — we had the kids while their parents stayed home — to Islamorada in Florida’s upper Keys. The village, dubbed “the best-kept secret in the Keys,” is made up of six islands: Plantation Key, Windley Key, Upper Matecumbe Key, Lower Matecumbe Key, and the offshore islands of Indian Key and Lignumvitae Key, strung between Everglades National Park and the Florida Strait. It was sunny, warm, beachy gorgeous, with a slew of fun activities nearby.
We’re not alone in pursuing and enjoying “gramping” travel. A recent Travel Market Report revealed that family and multigenerational travel is the second-leading travel category sold by US and Canadian travel advisers. And the trend of grandparents investing in shared travel experiences is growing.
According to Booking.com’s Travel Predictions 2025 Research, multigenerational trips are increasing in 2025, with 80 percent of boomers happy to fund their children’s and grandchildren’s holidays.
“It’s about creating lasting memories, but it’s also about learning together, being curious together, experiencing the world together — all of which create a unique and lasting bond between a grandparent and grandchild that lasts a lifetime,” says Road Scholar president and CEO James Moses. Road Scholar has been offering grandparent adventures for over 40 years and has more than 75 programs designed specifically for grandparents and grandchildren.
“As families become more geographically spread out, we expect even more interest in experiences like this — where grandparents can spend intentional, quality time with their grandchildren,” says Moses.
We were giving it a whirl with a trip to Islamorada, about a 90-minute drive from Miami airport, after a direct flight from Boston. We checked into the Islands of Islamorada resort, an oasis of 22 pure white, stand-alone villas and eight one-bedroom suites, offering the perfect setup for our visit. The property sits on 7.61 acres, surrounded by gardens and mature trees, set well back from the busy Florida Keys Overseas Highway. The spacious, 4,000-square-foot villas, decked out in chic nautical hues, had everything we needed, including a well-appointed kitchen, roomy dining and living areas, laundry room, balconies overlooking the ocean, and outdoor seating areas. There are two pools on the property, a marina, a playground, tiki bar, a private beach, pickleball court, kayaks, sailboats, and paddleboards. The kids would have been happy staying here for the duration of our getaway, and that’s what we did our first afternoon and evening. We walked the small beach; we swam in the pool; we had take-out pizza and roasted s’mores at one of the resort’s firepits.
Rise and shine! It was off to the pool early the next morning, before heading to the nearby Theater of the Sea. This fun, throw-back attraction, open and family-owned since 1946, is filled with dolphins, sea lions, turtles, alligators, fish, and birds. Basically, you go from one show to the next. We started with the parrot show, and moved on to the sea lion show, and the dolphin show; all were big hits with the kids, especially the jumping, diving, and dancing dolphins. We peeked at the alligators and sea turtles (rescued animals) and fed hungry fish at the small beach area. There are several “swim with the dolphin” programs, and we splurged for the Shallow Water Swim. Weeks later, the kids still pointed at their cheeks where they were kissed by the dolphin.
“They’re starving!” Daniel shouted as a large tarpon jumped to snag a fish from his hands. Lucca jumped back and laughed. Pelicans swarmed overhead, occasionally diving near our bucket of fish. We were at Robbie’s of Islamorada, a colorful and popular marina, restaurant, and market. Islamorada is considered the Sportfishing Capital of the Keys, and Robbie’s is the center of the action, offering a variety of fishing charters. We dined on casual island fare, including crispy fried cracked conch and grouper sandwiches, while watching the charter boats come and go, and captains cleaning the catch. After dinner, we bought a bucket of baitfish to feed the “silver kings” — some bigger than Daniel and Lucca — that hang around the dock looking for an easy meal.
Our days took on an easy rhythm. We spent the mornings at the resort and then headed out for an activity. One day we drove to Marathon to visit the Turtle Hospital, a small nonprofit rescue, rehab, and release care facility for sea turtles. After a rather dry talk on sea turtles (the kids fidgeted), we entered the hospital where we could observe a turtle being operated on, and visited the tanks that house a variety of rehabilitating turtles. After, we walked (the kids ran) a portion of the Seven Mile Bridge, connecting Knights Key in the Middle Keys to Little Duck Key in the Lower Keys. Another day, we went to John Pennekamp Coral Reef State Park, where the kids enjoyed the aquariums and shipwreck displays at the Visitor Center, and the beach. There’s also kayaking, canoeing, scuba diving, and snorkeling within the park. With our youngsters in tow, we opted for the glass-bottom boat tour out to Molasses Reef, where we saw tons of fish darting through the coral reef, stingrays, jellyfish, and more.
After a last-minute swim on our final day, and negotiation on what shells to bring and what to leave on the beach, we headed to the airport, wet suits and all. Ten minutes after takeoff, we were all fast asleep.
Diane Bair and Pamela Wright can be reached at bairwright@gmail.com."