Family Adventures in the Florida Keys on Islamorada

Travel Writers
Fri, 17 Apr 2026 21:00:00 -0700
Lifestyle

By Candyce H. Stapen

Just the thin green lines of mangrove islands separated the vast expanse of glistening turquoise waters from the blue sky. Our boat ride from Islamorada, Florida, gifted us with this colorful perspective and gave us a sense of the area's expansiveness. Just 81 miles southwest of Miami, laid-back Islamorada measures 20 miles long and in some places is barely 150 feet wide.

Islamorada encompasses Plantation, Windley, and Upper and Lower Matecumbe keys and offshore Indian Key and Lignumvitae Key. Some 160 to 190 acres of water are part of official Islamorada, which is surrounded by the 3,800-square-mile Florida Keys National Marine Sanctuary.
Updated: Sat Apr 18, 2026

By Candyce H. Stapen

Just the thin green lines of mangrove islands separated the vast expanse of glistening turquoise waters from the blue sky. Our boat ride from Islamorada, Florida, gifted us with this colorful perspective and gave us a sense of the area's expansiveness. Just 81 miles southwest of Miami, laid-back Islamorada measures 20 miles long and in some places is barely 150 feet wide.

Islamorada encompasses Plantation, Windley, and Upper and Lower Matecumbe keys and offshore Indian Key and Lignumvitae Key. Some 160 to 190 acres of water are part of official Islamorada, which is surrounded by the 3,800-square-mile Florida Keys National Marine Sanctuary.

Vacationers kayak, canoe, paddleboard, snorkel and fish — Islamorada is known as a major sport-fishing destination. Anglers match wits with sailfish, marlin, tuna and mahi-mahi. Getting out on the water is a must, and a boat ride is the best way with young children. My son, Josh, and his wife, Susan, who live in Miami, invited my husband and me to enjoy some family time with them and their 15-month-old daughter and 3-year-old son. Islamorada put us in a laid-back watery playscape.

Captain Mike of Mykeys tours picked us up at the dock at our oceanfront resort, en route to the mangroves in the Florida Bay, he told us to look for dolphins and manatees in the crystal-clear water. Even though we didn't see any, the 3-year-old loved the wind-in-his-hair boat ride. He waved to the pelicans roosting on rocks, to the snowy egrets perched on mangrove branches and to the cormorants plunging into the bay. He pointed to the flat-bottom boats, shallow draft vessels suited to fishing in the bay's flats where water can be just knee-deep. We caught sight of a juvenile shark before it zigzagged into the mangrove roots.

Captain Mike also showed us such Islamorada landmarks as Lignumvitae Key known for its tropical hardwood hammock, a part of Lignumvitae Key Botanical State Park. Kayaking or canoeing the offshore flats might reveal bonefish, snooks, mangrove snappers and other shallow-water fish.

Islamorada served as the location for many scenes in "Bloodline," the Netflix thriller about a dysfunctional family that operates a Keys inn. As series fans, we enjoyed the seaside views of Robbie's Marina, the setting for some boat and dock scenes; Coral Bay Marina, the stand-in for Kevin Rayburn's boat-repair yard; Morada Beach Cafe, an exemplar of the Keys' ambience with its toes-in-the-sand setting and colorful chairs; and Pierre's Restaurant, the location of many dock and porch scenes. Before your trip, fast-forward through "Bloodline" for a visceral sense of the region. Mykeys private charters include sunset cruises, snorkeling outings and trips to Islamorada's sandbar.

Another day, we visited Theater of the Sea, a prettily landscaped marine mammal park. Along with delivering educational tidbits about dolphins, sea lions and parrots, the trainers and guides explained that these animals were either born in captivity or rescued and rehabilitated but deemed unable to live in the wild.

Although we arrived ready to be a bit judgmental about performing animals in captivity, we came away entertained and encouraged by the kids' wide-eyed wonder at the dolphins' jumps, flips and speedy swims as well as the colorful macaws' prancing at the parrot show. It turned out to be a no-pressure way to teach children how to appreciate and care for animals. Book ahead if you want to swim with dolphins or engage in other animal interactions.

In the afternoon, we returned to our four-bedroom villa for naps — the kids' and ours — followed by splashing with the children in the resort's pool and playing bocce and cornhole on the lawn. The family-friendly resort offers 22 four-bedroom villas and eight hotel rooms.

The relaxed atmosphere extends to Islamorada's restaurants. At upscale French-inspired Pierre's, we dined on Key West pink shrimp and perfectly cooked branzino. Our table on the back veranda overlooked the palm-tree-lined beach and the distant mangroves. At Marker 88, we chose to sit on the deck shaded by gumbo limbo trees or on the beach. Not to miss are the marinated tuna nachos with crispy wonton chips.

We came to Lorelei for sunset views and live music. We munched on fried shrimp and cracked conch, but the real show, for us, was my grandson stepping, twisting and twirling to the music. He paused only long enough to catch his breath and look at the pelicans. I joined him, delighted to share in his joy.

WHEN YOU GO

Visit Florida, Islamorada: visitflorida.com/places-to-go/southeast/islamorada

MykeysTours of Islamorada: mykeystours.com

The Islands of Islamorada: theislandsofislamorada.com

Theater of the Sea: theaterofthesea.com

Pierre's Lounge & Restaurant: moradabaykeys.com/dining/pierres-restaurant

Marker 88: marker88.net

Lorelei Cabana Bar and Restaurant: loreleicabanabar.com

Snorkeling near Alligator Reef Lighthouse is just one of the pleasures of Islamorada, Florida. Photo courtesy of Visit Florida Keys.

A family dines on the sand at popular Marker 88, where fish tacos are the order of the day. Photo courtesy of Visit Florida Keys.

Family paddleboarding is popular in Islamorada, Florida. Photo courtesy of Visit Florida Keys.

Candyce H. Stapen is a writer at www.greatfamilyvacations.com. Follow her on Twitter and Facebook @Familyitrips and Instagram @CandyceStapen and discover www.HennysKids.org, Stapen's non-profit that brings educational items to rural schools in Africa.