A Guide to Islamorada: The Sweet Spot of the Florida Keys

In Islamorada, you’ll often be surrounded by water - the ocean on one side and the bay on the other! Some of our favorite ways to experience that perfectly azure water:

• Snorkel: Cheeca Rocks is a shallow reef perfect for beginning snorkelers. You’ll often see sea turtles and sting rays, and as the kids say, “you’ll feel like you’re in Finding Nemo!”

• Alligator Lighthouse and Alligator Reef are matchless: The water there looks like shockingly blue KoolAid, and under the lighthouse are clouds of literally thousands of fish. An unforgettable snorkeling experience – we always recommend booking with Wild Dolphin Tours, the kindest captains around.

• Famous Islamorada Sandbar: Wild Dolphin Tours will also take you out to the sandbar, where boats park all day to swim and party in waist-deep water on the sandbar. Bring a floatie for a relaxing afternoon!

• Kayak/paddle-board: The water is so calm that you’ll feel like you’re in a pool, but one with iconic mangroves and teeming wildlife. For two very different but perfect paddles, we recommend renting equipment at Robbie’s to explore the nearby mangroves or head out to Indian Key, a historic state park where you can explore an abundance of tide pools, climb a tower with an amazing view of surrounding islands or roam the footpaths and ruins of a 19th-century town. You’ll feel like a pirate with an uninhabited island all to yourself.

• Founder’s Park beach and pool: An idyllic, often sparsely populated little beach with a marina and gorgeous pool and splash pad perfect for kids.

• Fishing: Our favorite spot by far was Capt. Jon with Drop Back Charters – he will work tirelessly to bring you back with a boat full of fish after an unforgettable day.

• For a more inexpensive experience for novices, a half-day fishing trip on Bud N' Mary’s party boat is perfect.

Other recommendations for fun Islamorada activities

• Feed tarpon at Robbie’s: An experience not to be missed; you'll feed smaller fish to gigantic tarpon who hang out by Robbie’s dock.

• Theater of the Sea: A family-owned park filled with rehabilitated dolphins, sea lions, turtles, alligators, sharks and rays. The landscaping here is so lush that you feel like you’re in a jungle, and kids adore and never tire of the shows because you’re seated so close to all the animals. You can swim and interact with all the animals through special programs, and insiders know that if you follow a path all the way through the park to the lagoon beach in the back, the school of rainbow and blue parrotfish who live there will become your best friends if you feed them – literally, they will rub up on your legs like puppies, but they’re actually some of the most beautiful fish you’ll ever see.

Recommendations for shopping in Islamorada

• Ocean Gardens

• Miss Monroe Boutique

• Banyan Tree

• Drift

• Sea Aire

• Rain Barrel Village: Take your photo with Betsy, the giant lobster outside this quaint village of shops.

• Worldwide Sportsman: Tour a replica of Ernest Hemingway’s boat Pilar docked inside the shop and watch for the manatees that are often hanging out by the docks outside the store!

Day Trips

Key West is a two-hour drive, but it’s one of the most stunning drives in the world, including crossing over the iconic Seven Mile Bridge.

The perfect full day in Key West includes:

• Exploring the lush Butterfly House.

• Marveling at where Hemingway clacked away at his typewriter, still displayed in his treehouse.

• Taking a photo at the Southernmost Point.

• A quick stop at the delicious Cuban Coffee Queen.

• Dinner at El Siboney for incredible authentic Cuban food off the beaten path.

The Everglades National Park makes for another wonderful day trip from Islamorada. We recommend taking an airboat and seeing the shows at Everglades Alligator Farm, skipping lunch in favor of a gigantic fresh tropical fruit ice cream shake at the iconic Robert is Here, and if it’s a Saturday, taking a free tour of the private gardens of Robert Fuchs at the beautiful RF Orchids.

Also within driving distance of Islamorada, we recommend spending a day at Bahia Honda, the best beach in the Florida Keys, and touring the Turtle Hospital in Marathon, where you can feed and view rescued sea turtles, from tiny hatchlings to gigantic loggerheads.

Eat

Almost every restaurant in Islamorada is on the water. You’ll be able to watch sunsets from the bayside.

• Lazy Days: Order the catch of the day served “Lazy Days Style”- it will ruin you for all other fish forever.

• Marker 88: Swing tables on the beach. We recommend the tuna steak!

• Morada Bay: A wonderful upscale tropical vibe.

• Lorelei Restaurant and Cabana Bar: Live music for sunset celebrations every night – a more casual atmosphere.

• Bayside Gourmet: A gem the locals rave about – not on the water but perfect for takeout. Extremely affordable: the grouper reuben is our very favorite dish here, but the Islamorada sandwich, pizzas, and salads are all wonderful and an amazing deal.

Drink

• SandBar at Whale Harbor: Overlooking the famous sandbar, this is the place to come for happy hour on a sunny afternoon for an incredible view.

• Postcard Inn Tiki Bar: Home of the original rum runner – they’re delicious and this tiki bar offers vintage charm.

• Islamorada Fish Company: Perfect view of sunset over the mangroves.

• Midway Cafe: Best local coffee spot.