Things To Do

Lorelei Restaurant

Lorelei Restaurant & Cabana Bar is a classic Islamorada spot right on the water with beautiful sunset views, live music, and a fun, laid-back Keys atmosphere. It’s perfect for a casual afternoon or sunset cocktail.

Papa Joe's Waterfront

Papa Joe’s Waterfront is another great option while you’re in town. We love heading up to the rooftop tiki bar for a drink and some conch fritters, the sunset views here are incredible. They serve fresh seafood in a relaxed yet polished waterfront setting.

Square Grouper Islamorada

Stop at Square Grouper for dinner. It’s a little more elevated than the typical beach bar — great food, craft cocktails, and beautiful waterfront views overlooking Florida Bay.

Islamorada Fish Company

Islamorada Fish Company is just a quick 2-minute drive from the Islander Resort and an easy, laid-back spot right on the water. Great seafood, beautiful sunset views, and a relaxed Keys vibe — perfect for a casual lunch or dinner while you’re in town.

Robbie's of Islamorada

Robbie’s is a classic Keys experience — you can hand-feed the giant tarpon right off the dock, walk through the little open-air market, or grab a casual bite by the marina. It’s fun, easy, and very “Old Florida Keys”, especially if you’re looking for something to do during the day.

Rain Barrel Village

Founders Park

Sundance Watersports

Spray Watersports

Windley Key Fossil Reef Geological State Park

Long Key State Park

Bahia Honda State Park