Scuba Diving

Diving is the primary recreational activity around Islamorada, and there are dozens of shops and charters that cater to divers. Key Dives (79851 Overseas Hwy., 305/664-2211, two-trip single-tank dives from $80, snorkeling excursions from $35 per person) is routinely cited as one of the best, and the company’s concierge approach to expeditions is designed to minimize headaches and maximize memorable underwater experiences.

Ocean Quest Dive Center (85500 Overseas Hwy., 305/664-4401, full-day dive trips from $98 per person, snorkeling excursions from $43) runs a great operation, and their decades of history in the area means they’ve got more than a few “secret” dive sites that will be considerably less crowded.

Also, nearby Tavernier—about halfway between Islamorada and Key Largo—has good dive shops and charter boats in the form of Conch Republic Divers (90800 Overseas Hwy., Tavernier, 305/852-1655, half-day trips from $60) and the Florida Keys Dive Center (90451 Overseas Hwy., Tavernier, 305/852-4599, two-tank trips from $50, snorkeling excursions from $35).

Beaches

As is the case throughout most of the mangrove-thick coast of the Keys, sandy beaches are few and far between in Islamorada. The small ocean-side swimming area at Anne’s Beach (mile marker 73, sunrise–sunset daily) is about as good as they come; there are covered picnic pavilions, two parking areas, and restrooms. The water is fairly shallow and quite calm.

Fishing

There are several sportfishing charters operating out of Islamorada. Captain Mike Bassett specializes in backcountry trips for snook, redfish, mangrove snapper, tarpon, and more; he runs a 19-foot skiff under the name of Born & Raised Charters (84000 Overseas Hwy., 305/853-5541).

Reef Runner Charter (83413 Overseas Hwy., 305/852-3660) operates a 40-foot boat out of Whale Harbor Marina that can take out fishing groups of up to six people. Captain Bill Bender (85932 Overseas Hwy., 305/664-8232) runs a smaller 22-foot boat for light-tackle fishing a little closer to shore and specializes in sniffing out sharks. Islamorada Sport Fishing (www.islamoradasportfishing.com) is a good resource for anglers looking for more information on Islamorada charters.