Things to Do

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

Walk into Purple Pineapple Boutique in Islamorada and you'll immediately feel like you've found your people. Owner Lisa has filled this Village Square gem with breezy resort wear, dresses, rompers, two-piece sets, the best denim in the Keys, tarnish-free waterproof jewelry with select locally made styles, exclusive Purple Pineapple candles, Marlin's Cocktail Co. products, and a heartfelt Crafts Against Cancer collection handmade by Lisa's mom Peggy — all in a warm, kid-friendly space with a play area for little ones and a shave ice truck just steps away.

Explore reef, sandbars, and waves with jet skis, boats, and snorkeling adventures by Seahorse Water Adventures.

Anchors Away Boat Rentals & Tours offers a diverse fleet of over 30 boats, including center consoles, deck boats, and pontoons, available for flexible rentals ranging from 2-hour to monthly durations, with GPS-equipped vessels and optional add-ons like snorkeling gear and GoPro cameras.

Clothing store in Islamorada, Florida

Coconut Cove Beach Resort & Marina is a family-friendly, waterfront resort in Islamorada, offering a zero-entry pool, private beach, and event spaces for weddings and private functions. Located on a 7-acre tropical estate, it's ideal for both relaxation and special events.

Upscale clothing and fly fishing store with swimwear and brands such as Pelagic, Salt Life, Huk, and Columbia.

The Tipsy Octopus — quirky souvenir & specialty shop in Islamorada, where island‑style treasures, art pieces and fun gifts meet a roadside stop filled with character.

Peaceful tropical hammock preserve with short trails and bayside views in Islamorada.

Escape to Amara Cay Resort for luxe island vibes, ocean views, and pure relaxation.

Blue Marlin Jewelry is a family-owned fine jewelry boutique in Islamorada, Florida, offering a curated selection of designer pieces, custom creations, and nautical-themed designs.

Otherside Boardsports in Islamorada offers lessons, rentals, and retail gear for paddleboarding, kiteboarding, winging, wake, foil & more.

Se La Vie Beach Boutique is your go-to island-vibe boutique for chic, seaside-inspired fashion and lifestyle essentials.

Island Adventures is a veteran-owned charter company running private snorkel, sandbar, and sunset trips from 80500 Overseas Highway in Islamorada. Each outing is your own group on the boat, with snorkel gear, floating mats, and life jackets aboard, so beginners, non-swimmers, and kids can all get in the water.

Explore Rain Barrel Village: Florida Keys' vibrant artisan shops, tropical gardens, and iconic Betsy the Lobster!