Florida’s chain of subtropical isles is an ideal spot for multigenerational families and leisure groups to gather and make memories

The Florida Keys archipelago is well known for its incredible natural beauty, stunning turquoise waters, outstanding boating and fishing and spectacular sunsets. The 125-mile-long island chain is loaded with history, wildlife and opportunities for outdoor adventure. There are plenty of things to do in the Florida Keys for all ages and interests throughout this gorgeous string of islands.

Finding the right spot to reconnect in the Florida Keys is essential. There are a number of choices. For us, it was important to travel far enough down the island chain to capture the true feeling of the Florida Keys without spending too much time driving to our destination. We also wanted to be in the middle of the action, with plenty of options for activities and adventures. That’s why a basecamp in the Middle Keys works well. There’s plenty to experience on Duck Key, and the attractions of Key West, Marathon and Islamorada are just a short drive away.

Exploring the Florida Keys

The Florida Keys offer a Caribbean-like vibe, but these islands can be easily reached by car. Driving down the Florida Keys Overseas Highway was the perfect way to start our trip. This southernmost section of U.S. Highway 1 includes more than 40 bridges, including the Seven Mile Bridge at Marathon, one of the longest segmented bridges in the world. We enjoyed taking in the spectacular sea views, spotting boats and wildlife along the way.

Another of the advantages of road tripping through the Keys is the wealth of appealing spots to stop for shopping, sightseeing and sampling the destination’s famed key lime pie. Popular places to stop on the Florida Keys Overseas Highway drive include Key Largo, Tavernier, Islamorada and Marathon.

Florida Keys Blond Giraffe Key Lime Pie Photo Courtesy of Nancy Schretter

Luscious key lime pie is the official state pie of Florida. Photo courtesy of Nancy Schretter

The small town of Tavernier is home to the Blond Giraffe Key Lime Pie Factory and its outstanding key lime pies. The company’s delectable desserts have won numerous awards and have been featured on multiple television shows, including Travel Channel’s “Food Wars” and multiple Food Network programs. We sampled key-limeade and several varieties of key lime pie in the Key Lime Pie Factory’s Secret Garden, a secluded outdoor area filled with tables and greenery that’s perfect for groups.

Suitably refreshed, we made our way down the island chain to our next set of stops in Islamorada. Known as the “Village of Islands,” Islamorada offers a number of appealing attractions. Adventurers can rent a kayak and paddle over to Indian Key State Park, an 11-acre deserted island listed on the National Register of Historic Places. The uninhabited island contains the ruins of an early 1800s town that was once home to Jacob Housman’s salvaging empire. Snorkeling at Indian Key State Park can be excellent, too.

Florida Keys Betsy the Lobster Rain Barrel Village Photo Courtesy of Nancy Schretter - things to do in the florida keys

Betsy the Lobster, a 30-foot-tall Florida Keys Spiny Lobster sculpture, provides a memorable photo-op for visitors to Rain Barrel Village in Islamorada. Photo Courtesy of Nancy Schretter

Islamorada offers plenty of appeal for shoppers as well, including the open-air complex of galleries and boutiques at Rain Barrel Village. For decades, the stores at Rain Barrel Village have featured an extensive variety of paintings and sculptures, ceramics, custom jewelry, clothing and gifts crafted by local artisans. It’s also a great place to take a group picture with Betsy the Lobster, one of the Florida Keys’ most photographed landmarks.

Families and groups alike will want to make their way to Robbie’s, a must-go detour off the highway in Islamorada. Scores of hungry tarpon (and sneaky pelicans) circle the dock there, just waiting to be fed. Years ago, I lay flat on the dock at Robbie’s, dangling a silvery bait fish in my fingers. Large gray-green shapes moved in the water beneath me, eyeing the bait. I watched and waited – until a massive tarpon exploded out of the water to grab the bait fish in its gaping mouth before returning to the depths. There’s a good reason why tarpon have earned the “silver king” nickname. Some tarpon can be as long as 8 feet and weigh up to 280 pounds. Hand-feeding the wild tarpon at Robbie’s is an unforgettable Florida Keys adventure that’s well worth experiencing. Kayak rentals are available at Robbie’s for those wishing to visit Indian Key State Park.

Florida Keys Aerial Island View of Duck Key Photo Courtesy of Hawks Cay Resort

Idyllic Duck Key is perfectly situated in the Middle Keys and is home to award-winning Hawks Cay Resort. Photo courtesy of Hawks Cay Resort

Once we arrived at our amenity-filled basecamp on the small island of Duck Key, it was hard to leave. Our Hawks Cay Resort home-away-from-home was packed with activities, adventures and dining venues. Still, there are a number of attractions that can tempt guests away from their secluded Duck Key paradise.

Families and nature lovers often make the short drive to tour Marathon’s famed Turtle Hospital, a non-profit organization that rescues, rehabilitates and releases injured sea turtles. The Turtle Hospital offers daily Guided Educational Experiences, offering visitors the opportunity to tour the organization’s facilities and learn about their work. Other popular experiences in Marathon include feeding sharks and stingrays at Aquarium Encounters and sampling a delicious lobster reuben sandwich at Keys Fisheries.

Florida Keys Key Deer Photo Courtesy of Nancy Schretter - things to do in the florida keys

Visitors can catch a glimpse of tiny wild Key deer on Big Pine Key and other islands in the Lower Keys. Photo courtesy of Nancy Schretter

Just a little farther down the Florida Keys Overseas Highway is Big Pine Key, home to Bahia Honda State Park. The beautiful white sand beach here earned the #1 spot on Dr. Beach’s yearly rankings of the top beaches in the United States. The area is a birder’s paradise, and the historic trestle-style Bahia Honda Bridge is fascinating to view as well. While on Big Pine Key, we were thrilled to spot indigenous Key deer, the endangered smallest subspecies of the North American white-tailed deer. The National Key Deer Refuge is located on Big Pine Key.

Key West is another popular hub-and-spoke sightseeing destination for groups visiting the Florida Keys. Located just 60 miles from Duck Key, it’s a great choice for a day trip. Visitors enjoy strolling down Duval Street, a tourist venue lined with shops and restaurants. At one end of Duval Street is Mallory Square, and at the other is the Southernmost Point buoy, a much photographed symbol that’s said to mark the southernmost spot in the continental United States.

Key West is home to attractions for all ages and interests. Travelers interested in history and culture like the restored Harry S. Truman Little White House, Ernest Hemingway Home and Museum, Fort Zachary Taylor State Park and Audubon House and Gallery. Filled with valuable artifacts and treasures recovered from shipwrecks, the Mel Fisher Maritime Museum is another fascinating place to explore.

There’s plenty of fun for families in Key West as well. At Key West Butterfly and Nature Conservatory, adults and children alike enjoy walking through the glass conservatory featuring more than 50 species of colorful butterflies and numerous species of exotic birds. Riding the Conch Tour Train can be a good way for families to learn about Key West’s history and take in the sights.

A Luxurious Home Base

Set on 60 waterfront acres on secluded Duck Key, award-winning Hawks Cay Resort is a superb choice for multigenerational vacations, family reunions and group trips. The AAA Four Diamond destination resort provides all of the sought-after Florida Keys activities in one location while still offering easy access to the Keys’ most popular attractions. At Hawks Cay, guests can enjoy a wide variety of accommodations, top-notch restaurants, excellent recreational and watersports facilities, and a wealth of activities for all ages.

Florida Keys Hawks Cay Resort Photo Courtesy of Nancy Schretter

Hawks Cay Resort features a wealth of amenities for guests including a massive saltwater lagoon, five swimming pools and an extensive array of watersports. Photo courtesy of Nancy Schretter

Hawks Cay Resort features 427 villas and hotel rooms, six restaurants, five swimming pools and an immense saltwater lagoon, eight lighted tennis courts, a full-service spa, a wide variety of watersports, fishing charters, and the Dolphin Connection facility where guests can interact and swim with resident dolphins. The resort’s 250 two- and three-bedroom villas provide plenty of room, and most offer kitchens, making them perfect for groups and families. Hawks Cay’s newly renovated hotel guest rooms are convenient to the resort’s pools, restaurants and the saltwater lagoon – making them an excellent choice for those who want to be close to the action.

Dining is always a memorable part of leisure group travel experiences. Outstanding restaurant choices at Hawks Cay Resort range from the casual Hawks Cay Marketplace and poolside Tiki Grill to fine dining at Sixty-One Prime. Restaurant menus focus on showcasing the dishes and flavors of South Florida with a signature farm-to-table approach. One of my favorite dining options was Angler & Ale, a casual Keys-style dining venue overlooking Hawks Cay Marina. The restaurant offers a terrific selection of fresh seafood, meats, burgers and craft beers. Anglers can bring in their fresh catch as part of the restaurant’s “Hook and Cook” special, and the chef will prepare their fish fillets exactly to their liking.

Florida Keys Hawks Cay Pirate Pool Photo Courtesy of Nancy Schretter

Hawks Cay Resort’s Coral Cay activities and adventure center for younger guests includes a cool Pirate Ship Pool. Photo courtesy of Nancy Schretter

Hawks Cay Resort is an exceptional vacation destination for families and multigenerational groups. The property was named Best Multigenerational Resort in Parents’ Family Travel Awards 2021 and Best Family Resort in the United States in the USA TODAY 10Best Readers’ Choice Awards 2020. The resort’s Coral Cay activities and adventure center offers a wide array of programs and amenities for kids of all ages, including a soccer field, basketball courts, a mini-golf putting course, an indoor game room, a cafe, and two kid-friendly pools, including a fun Pirate Ship Pool. Bicycle rentals, which are free for resort guests, are available at Coral Cay as well.

Coral Cay’s activities calendar also features lots of fun family programs, including kickball, dodgeball, a Pirates Invasion Show and visits with Koral the Mermaid. Hawks Cay Resort’s drop-off kids programs for guests ages 5-12 include Camp Hawk Environmental Education Program, which focuses on the Florida Keys ecosystem. Camp Hawk’s acclaimed Camp Adventure program provides tons of supervised activities and fun for 5-12-year-olds during day and evening hours.

Watersports and aquatic adventures are a highlight at Hawks Cay Resort. Free kayak and stand-up paddleboard usage in the saltwater lagoon is included as part of Hawks Cay’s resort fee. Guests can also choose from an extensive array of watersports activities, snorkeling excursions, sandbar boat tours, sunset cruises and other eco-adventures offered by Solé Watersports at the Hawks Cay Marina. Half-day and full-day private boat charters are available, too.

Florida Keys Charter Fishing at Hawks Cay Resort Photo Courtesy of Nancy Schretter

Sport fishing charters are popular at Hawks Cay Resort. Photo courtesy of Nancy Schretter

The Florida Keys rank as one of the top places for deep-sea fishing. Hawks Cay Resort is home to two fishing shows, Discovery Channel’s “Saltwater Experience” television show and “Into the Blue,” both filmed on property. Anglers are lured by the resort’s outstanding marina and famed sport fishing experiences, all based at a full-service resort with plenty of amenities to keep non-fishing family members happy. For groups of families and fishing enthusiasts alike, it’s the best of all worlds.

For more information visit Hawks Cay Resort.


By Nancy Schretter

Header photo courtesy of Nancy Schretter