17 Best Things to Do in Islamorada

The sandbar sits in Florida Bay a short run from the marinas: knee-deep water, a sand bottom and a crowd of boats on weekends. Shared trips run about 3 hours and cost $80–$130 per person; private charters start around $300 for the boat. Morning trips get glassier water, afternoons get the party. Bring water shoes, the bottom has shell.

The 1873 iron lighthouse marks a reef 4 miles offshore with 10–20 ft of water, parrotfish, snapper and the occasional nurse shark. Shared catamaran trips from Tavernier run $60–$80 per adult with gear; two-hour private charters start at $300. Summer visibility is best; winter cold fronts can blow it out for a day.

Robbie's at Mile Marker 77.5 has been hand-feeding tarpon off its dock since 1976. Admission is a couple of dollars and a bucket of bait a few more; the fish are 60–150 lb and come up out of the water for it. Pelicans will try to steal the bait. Go early or late to avoid the mid-day crush, and walk the flea-market stalls while you are there.

Islamorada's bayside mangrove creeks are flat, shallow and sheltered, which is why clear-bottom kayak tours work here. A guided 90-minute sunset paddle runs about $79 per person; morning eco-paddles through the mangroves and manatee channels from Tavernier are $64. No experience needed, and the clear hulls make the nurse sharks and rays under you the whole point.

If you would rather stay dry, a two-hour glass-bottom boat trip over the patch reefs runs $75 per adult and works for kids and grandparents alike. The same operator runs a 2.5-hour night tour with lights under the hull, which is when the lobster and octopus come out.

Islamorada sunsets happen over Florida Bay, so the best seat is a boat on the bayside. Shared sunset cruises run $65–$90 per adult for about 90 minutes; private sunset charters for up to six start around $300–$380 for the boat. Lorelei's and Morada Bay are the bars to watch it from if you stay on land.

The bayside flats and Everglades edge hold bonefish, tarpon, redfish and snook. A half-day on a flats skiff with a guide runs $500–$700 for one or two anglers, full days $900–$1,000. Tarpon season is April through July; bonefish are year-round but best in spring and fall. Guides supply tackle and licenses are covered on the boat.

Sailfish, mahi, tuna and wahoo run off Islamorada in winter and spring; half-day reef and wreck trips for snapper and grouper run year-round. Private charters for up to six start around $450 for a half-day and $800–$2,000 for a full day offshore. Many local restaurants will cook your catch for a per-person fee.

A 10-acre island a half-mile offshore that was the Dade County seat in 1836 until it was burned in the Second Seminole War. You reach it by kayak or boat only; the foundations and streets are still laid out and there is a short loop trail and a swimming spot. Rent a kayak at Robbie's (about 30 minutes each way) or join a guided paddle.

Across the highway on the bayside, Lignumvitae Key is the highest point in the Keys at 16–18 ft and holds one of the last virgin tropical hardwood hammocks in the US. Access is by boat or kayak with ranger-led tours on a set schedule; check the park calendar before you paddle out. Mosquito repellent is not optional.

A former quarry at Mile Marker 85.5 where the 1900s railroad cut blocks out of fossilized coral. The 8-ft quarry walls show star and brain coral in cross-section. Small entry fee, self-guided trails, about an hour.

Mile Marker 83, bayside. Hard-hat helmets, rebreathers, treasure-salvage gear and the Keys' own diving history across a dozen rooms. Plan 60–90 minutes; it is the best rainy-day stop in the Upper Keys.

A 1946 marine park at Mile Marker 84.5 with dolphin, sea lion and parrot shows plus swim-with programs. General admission runs under $50; dolphin swims are priced separately and sell out in season. Shows run on a loop, so two to three hours covers it.

In Tavernier at Mile Marker 93.6, a rehab sanctuary with a boardwalk through the mangroves past pelicans, hawks, owls and herons that can't be released. Donation entry, guided sanctuary tours about $25, and the wild pelicans show up for the afternoon feeding.

A guided four-hour walk-and-ride through the town's fish houses and bars with tastings at each stop, about $119 per person. There is a golf-cart version and a happy-hour version for groups that would rather not walk. Good first-day orientation if you are staying a few nights.

Mile Marker 81.5 oceanside. The brewery's beer garden anchors a two-block strip of galleries and studios that hosts an Art Walk on the third Thursday of each month. Hogfish sandwiches at Islamorada Fish Company and Lazy Days are the two classic lunches within a mile.

Bayside at Mile Marker 82, the sunset bar everyone ends up at. Live music nightly, a dock you can tie a boat to, and the sun goes down directly in front of the tables. Arrive 45 minutes before sunset in season for a seat.