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Madison & Timothy

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Things To Do

If you know us well, you know we are some big foodies! Here is a list of our favorite dining options in the area or those that were highly recommended to us! We’ve also added some fun things to do while in Islamorada.

Pierre's Restaurant

81600 Overseas Highway, Islamorada, FL 33036

This restaurant was the set for the show "Bloodlines" if you've ever seen it! We love their French cuisine and the views of the sunset are amazing! Make sure you make reservations ahead of time though, as it books up fast!

Square Grouper Islamorada

80460 Overseas Highway, Islamorada, FL 33036

Our favorite dinner spot. Island dining including seafood, steaks and craft cocktails!

Lorelei Restaurant & Cabana Bar

96 Madeira Road, Islamorada, FL 33036

Great live music, beach eats and cocktails located on the water with a beautiful sunset view!

Mangrove Mike's Cafe

82200 Overseas Highway, Islamorada, FL 33036

Breakfast served all day, need we say anything else? This is our favorite little cafe and breakfast spot in Islamorada!

Midway Cafe & Coffee Bar

80499 Overseas Highway, Islamorada, FL 33036

Funky, counter-serve nook with an outdoor patio serving all day breakfast & lunch, baked goods, smoothies & coffee.

Islamorada Brewery & Distillery (Islamorada)

82229 Overseas Highway, Islamorada, FL 33036

A favorite spot of ours! This place has pub style bites, food trucks, a beer garden and distillery.

Papa Joe's Waterfront

79786 Overseas Highway, Islamorada, FL 33036

A beloved treasure reborn in 2024 on the historic grounds of the original 1938 site. Modern dining experience with a lively Tiki Bar (21+) to the family-friendly lawn and elegant dining room with sweeping ocean and bay views.

Marker 88

88000 Overseas Highway, Islamorada, FL 33036

Enjoy some coastal sunset dining overlooking the Florida Keys bay, with a wide variety of food and drink options!

Wahoo's Seafood Bar and Grill Restaurant

83413 Overseas Highway, Islamorada, FL 33036

Located on the water and perched above the world-famous Whale Harbor Marina, Wahoo's Bar and Grill offers locally caught fish and seafood that comes from right off the dock!

Chef Michael's

81671 Overseas Highway, Islamorada, FL 33036

Restaurant with fresh fish and seafood, steaks, and chops!

Lazy Days

79867 Overseas Highway, Islamorada, FL 33036

Low-key dining destination for seafood & more with ocean views from the dining room, porch & beach.

Islamorada Fish Company

81532 Overseas Highway, Islamorada, FL 33036

Owned by Bass Pro Shops, this open-air space under a tiki hut serves seafood with waterfront views.

Clearly Unique Charters

81801 Overseas Highway, Islamorada, FL 33036

Boat charters for snorkeling, sandbar trips, sunset cruises, private charters and more!

Bud N' Mary's Marina

79851 Overseas Highway, Islamorada, FL 33036

World famous fishing marina! They offer offshore/ inshore fishing charters

Florida Keys Boat Charters

85920 Overseas Highway, Islamorada, FL 33036

Boat charters for fishing, snorkeling, or sandbar trips!

Theater of the Sea

84721 Overseas Highway, Islamorada, FL 33036

A marine mammal park located in the Village of Islamorada. Theater of the Sea lagoons and lush, tropical gardens are home to dolphins, sea lions, sea turtles, fish, sharks, stingrays, alligators, and birds.

For all the days along the way
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