Islamorada, Fl Itineraries

The Perfect Islamorada Escape

Whether you're seeking a quick weekend getaway or a full week of sun-drenched adventure, our custom itineraries make it easy to experience the best of the Florida Keys. From sunrise paddles in clear kayaks to sunset cruises on floating tiki bars, each day offers the perfect mix of relaxation and island discovery. Choose your ideal stay 2, 3, or 5+ nights — and let Islamorada’s charm, flavors, and coastal beauty set the pace.

A boat dock with a "Boat Rentals" sign and palm trees, by a turquoise sea under a blue sky with fluffy clouds.

Weekend Escape in the Keys

2-Night Stay

Escape to Islamorada for two unforgettable nights filled with Champagne welcomes, sunset tiki cruises, beachfront yoga, and clear kayak paddles. Savor fresh seafood, enjoy live music, play beach games, and soak in breathtaking ocean views.

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A coastal area with turquoise waters, white buildings, palm trees, and a parking lot, viewed from above.

Keys Discovery Getaway

3-Night Stay

Experience three nights in Islamorada with sunset cruises, dolphin encounters, sunrise paddles, and relaxing beach time. Enjoy island dining, spa afternoons, and a sandbar adventure the perfect balance of exploration, indulgence, and laid-back tropical charm.

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Chesapeake Beach Resort

The Full Islamorada Experience

5+ Night Stay

Dive into the ultimate island escape with six days of sunrise paddles, snorkeling reefs, sunset cruises, and sandbar adventures. Enjoy spa time, local eats, live music, and beachside bonfires a perfect blend of relaxation and discovery.

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