Best Romantic Things to Do in Islamorada
Why Islamorada works for a wedding weekend: championship golf and 27 oceanfront acres at Cheeca Lodge, plus properties we hold stay notes on like Amara Cay Resort and Three Waters Resort and Marina.
Islamorada sits on US-1 a short drive south of Key Largo, officially incorporated as the "Village of Islands" and known for generations, on marina charter boards up and down the Overseas Highway, as the Sport Fishing Capital of the World. That heritage shows up in the wedding weekend itself, not just the postcards -- this is the stretch of the Keys built around doing things together, not just watching the water.
Cheeca Lodge and Spa is the anchor of that reputation and the real reason most wedding parties consider Islamorada at all: 27 oceanfront acres on the Atlantic side, a private beach, a championship golf course, and a full-service spa, all under what is, by its own long standing, the most recognized name in Florida Keys hospitality. It is built for a full weekend rather than a single ceremony day -- golf for the groomsmen that morning, spa appointments for the wedding party that afternoon, a private-beach ceremony that evening.
The rest of Islamorada's real bench fills in around that anchor rather than competing with it. Three Waters Resort and Marina sits on 15 waterfront acres where the Atlantic Ocean, the Gulf of Mexico, and Florida Bay all meet -- a working marina with 72 slips and four restaurants, the honest, unpolished side of the Keys, and a good fit for a rehearsal dinner or welcome party that doesn't want resort formality. Amara Cay Resort brings a livelier, more modern waterfront pool scene and waterfront dining, better suited to a day-after brunch or a group that wants energy over hush. And Coconut Palm Inn, a short drive north in Tavernier, is the pick for a smaller, quieter guest list -- an adults-only garden retreat built around exactly that kind of hush.
All of it sits on the same short run of US-1 that connects north to Key Largo, which is the practical case for Islamorada: a wedding weekend here can borrow the reef-and-bay quiet of Key Largo for the morning and still come home to a livelier pool scene and a real golf course by afternoon, without a long drive between the two.
Stays we have notes on near Islamorada, Florida Keys
Guide last updated Aug 25, 2026.
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