Sail, snorkel, paddle and fish the Florida Keys with guides who have spent their lives on this water.
Most trips leave from our own dock. Prices are sample prices per guest unless noted, and our guest experiences team can tailor anything private.
2 hoursCast off from the resort dock on our 48-foot catamaran and sail west past Sunset Key as the sky turns tangerine.
From $95 per guest
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3.5 hoursSwim with parrotfish, nurse sharks and brain coral at Sand Key, the only living coral reef in the continental United States.
From $115 per guest
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2.5 hoursPaddle quiet backcountry channels where baby lemon sharks, rays and herons hunt among the mangrove roots.
From $79 per guest
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Half or full daySight-fish for bonefish, permit and tarpon with a licensed Keys captain. Driftwood will cook your catch for dinner.
From $650 per boat
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Half dayFly 70 miles west over turquoise shallows to Fort Jefferson, then snorkel the moat wall before flying back.
From $445 per guest
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2 hoursCruise past Hemingway's house, the Southernmost Point and hidden lanes with a local historian and a key lime pie stop.
From $55 per guest
Add to my stayTheo and the guest experiences team plan every trip, from which reef is clearest this week to where the tarpon are running.
Born in Key West and raised on the docks of Stock Island, Marisol ran boutique resorts in Tulum and Nassau before coming home to lead Azure Bay in 2019.
Jonah trained at a Palm Beach grand hotel and now oversees every room, from housekeeping standards to the key lime cookies waiting on your pillow.
Theo is a certified dive master who has logged 900 dives on the Florida Reef. He plans every snorkel, sail and seaplane trip we offer.
Andre cooked in Miami and Port-au-Prince before settling in the Keys. He buys fish at 6 am and changes the Driftwood menu daily.
Add experiences when you book your stay, ask the concierge on arrival or call us before you travel. Popular trips like the sunset sail and seaplane book out in spring.
If a trip is cancelled for weather, we rebook you on the next available departure or refund in full.
The sunset sail, kayak tour and bike ride welcome all ages. Snorkel trips suit confident swimmers aged 8 and up.
Book direct for our best rate, a welcome drink at Salt and Lime and free cancellation on most stays.
Rated 4.8 from 2,146 guest reviews
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