Couple descending wooden ship-themed stairway with nautical decor.

Things to Do

In The Florida Keys, adventure is just a footstep (or paddle, or fin) away. Whether you’re chasing sunrise paddle-trips, sunset sails, or discovering hidden mangrove tunnels, there’s always something new to try. Museums, wildlife tours, water sports, quirky local events—every destination brings its own flavor of fun. These listings span every kind of experience: rugged and wild, soft and serene, absurdly beautiful. So map out some time, pack your curiosity, and let the Keys pull you in.

Filters
Keys Season Deals
Destination
Category
Islamorada

Lazy Days Islamorada

Award-winning oceanfront dining with fresh seafood, steaks, and stunning views.

Islamorada

Islamorada Spearfishing Adventures

Islamorada Spearfishing Adventures is Islamorada's premier spearfishing charter led by Captain Jordi, a Florida Keys-raised PADI Scuba Instructor with 16 years of diving experience, offering private spearfishing, lobster hunting, scuba diving, freediving, and snorkeling charters with a 5.0-star rating across 100-plus reviews.

Islamorada

Islamorada Boat Rentals

Center consoles and a twelve seat pontoon, bookable online with instant confirmation for a half day, a full day, or up to a month. GPS, VHF and safety gear come aboard, and you need to be 25 to rent.

Islamorada

Islamorada Honey Company

Islamorada Honey Company — raw, unfiltered Florida Keys honey & live bee-relocation services in Islamorada, where sustainability meets sweetness.

Islamorada

Islamorada Candle Co.

Hand-poured vegan, clean-burning candles made in Islamorada.

Islamorada

Whale Harbor Marina

Whale Harbor Marina — premier full-service marina and charter hub in Islamorada, Florida Keys.

Islamorada

Amiga Mia Home - Boutique

Amiga Mia Home is a women-owned boutique in Islamorada built inside a redesigned vintage travel trailer. It stocks artisanal, boho-chic home decor and personal accessories, from ceramic planters to woven macrame crossbody bags and other handcrafted pieces.

Islamorada

Latitude Charters

Private boat charters in the Upper Keys — sandbar trips, sunset cruises, snorkeling & special-occasion charters.

Islamorada

The Trading Post

The Trading Post of Islamorada — a 24/7 deli, grocery, and local market hub with fresh food, full deli, and essentials.

Islamorada

Drop Anchor Resort & Marina

Drop Anchor Resort & Marina offers oceanfront accommodations with full kitchens, a heated pool, complimentary kayaks, paddleboards, and bicycles, all set in a tropical garden atmosphere. Ideal for couples and families seeking a relaxing Florida Keys getaway.

Islamorada

Pelagic Raptors Charters

Captain Mike runs a 39 foot Contender with triple 300s and a Seakeeper stabilizer out of Islamorada, for up to six anglers. Trips run from four hours to a ten hour swordfish expedition, with tackle and your fishing license included.

Islamorada

Miss Monroe Boutique

Shop Miss Monroe showcases chic, island-inspired women’s fashion, accessories & resort wear in the Keys.

Islamorada

Florida Keys Fishing and Eco-Tours

Tarpon specialists delivering snag-free charters & gear to reel in the Silver King.

Islamorada

Cayo Vida Marina

A small working marina on Old Highway at the top end of Islamorada, open from 6 in the morning for people who are actually going fishing. Live and frozen bait at the counter, charter boats on the dock, and Cayo Vida shirts on your way out.