A group of people is enjoying a sunny day on a boat with an American flag, relaxed and conversing with a bright blue sky in the background.

Day Trip Ideas at The Islands Of Islamorada

Published on June 1, 2021

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The Islands of Islamorada is centrally located so you can head north and south for a day’s adventure in paradise — and we make it easy by handling the arrangements for you. Our staff is eager to help our guests immerse themselves in the natural surroundings and unique experiences of The Florida Keys. Our on-site concierge can connect you with trusted locals and help coordinate your activities. Here are some of our favorite experiences.

A serene coastal scene with calm waters, a rocky shoreline, lush palm trees, and a partly cloudy sky during sunset or sunrise.

Islamorada

Just a three-minute drive from The Islands of Islamorada is Theater of the Sea, a small, family-owned marine park. Enjoy dolphin, sea lion and parrot shows; meet sea turtles; and ride in a bottomless boat. For many, the highlight of their visit is swimming with dolphins, sea lions, stingrays or sharks. Learn about marine wildlife while being amazed during the many animal interactions.

A school of yellow fish swims near the ocean floor, while a diver observes from above, amidst clear blue waters and scattered coral.

Key Largo

Farther north, off Key Largo, is John Pennekamp Coral Reef State Park, the first undersea park in the country. The most popular way to explore is to take a boat ride out to the reef for snorkeling and diving among colorful fish, coral and an iconic sunken statue. Keep an eye on the water as you travel to and from the reef and you just might see dolphins playing in their natural habitat! Not up for swimming? Kayaking through the mangroves or taking a glass-bottom boat tour are other ways to see this attraction.

A serene sunset over calm waters with silhouettes of poles and distant trees against an orange and blue gradient sky.

Marathon

Heading south into Marathon, you’ll see the Old Seven Mile Bridge, which runs parallel to the Overseas Highway. The two-mile section of the bridge is closed to vehicles and has become a great place to walk, run, bike ride, and see sea life. You can take a leisurely walk to Pigeon Key, home to eight buildings on the National Register of Historic Places, in the middle of the channel.

Two deer stand on a peaceful, tree-lined path surrounded by dense greenery, creating a serene natural scene.

Big Pine Key

At the National Key Deer Refuge on Big Pine Key, you’ll find the elusive and endangered Key Deer. They are tiny compared to other species of deer — no more than 32 inches tall — and only found in the Lower Keys. You can hike, bike or kayak through the preserve, and the visitor center is chock full of information. The Key Deer are most active in the morning and evening.

An aerial view of a coastal resort with white buildings, green landscapes, and a deep blue ocean horizon in the background.

Key West

A visit to Key West just has to start with a photo at the Southernmost Point of the continental United States. After a stop at the oversized buoy, head to the Ernest Hemingway Home and Museum to walk through the legendary writer’s house and pet the six-toed cats that are descendants of Hemingway’s felines. You won’t want to miss the nightly sunset celebration in Mallory Square that features jugglers, tightrope walkers and sword swallowers. Afterward, stroll along the famed Duval Street, which comes alive at night with restaurants and bars galore. And when you’re tired, your luxury villa or suite is waiting for you with everything you need for a good night’s sleep.