In Islamorada, winter is measured less by the calendar than by time spent on the water. Set in the heart of the Florida Keys, the Islamorada Resort Collection brings together Three Waters Resort & Marina, Amara Cay Resort and La Siesta Resort & Villas, giving travelers a choice of accommodations while keeping the surrounding islands, beaches and waterways at the center of the experience.

Known as the Sportfishing Capital of the World, Islamorada lends itself naturally to an outdoors-focused winter escape. Guests can head offshore with a local captain, snorkel the reefs, paddleboard, kayak or boat out to the Islamorada Sandbar. A complimentary Rum Runner water taxi connects the three resorts, making it possible to move between properties for dining and drinks. At Three Waters, Kindler centers its menu around wood-fired cooking, while the legendary Tiki Bar is associated with the creation of the Rum Runner cocktail. For travelers who prefer a slower afternoon, private beaches and pools provide another way to settle into the Keys’ relaxed rhythm.

The Curated Take: Islamorada’s appeal is its relationship with the water. Rather than treating the Keys simply as a place to escape cold weather, the destination invites travelers to experience the landscape through fishing, boating, reefs and sandbars. That makes it a particularly natural choice for a winter trip where being outdoors is the point, not merely a bonus.