Boat speeding on water with people cheering, under a clear blue sky.

Boating & On The Water

In The Florida Keys, life flows with the tide. Rent a skiff for backcountry exploring, hop on a sunset cruise, or join locals at a sandbar party where the water is the dance floor. Paddleboards and kayaks slip quietly through mangroves, while sailboats and charters head offshore for bigger adventures. With marinas, rentals, and tours across the islands, getting on the water is easy—and unforgettable. Sunshine, salt air, and stories worth retelling are all included.

Filters
Keys Season Deals
Destination
Category
Key Largo

American Sailing Academy

Learn to sail in paradise: ASA-certified courses in Key Largo.

Key West

Sigsbee Marina

Navy MWR Key West: Your go-to hub for family recreation, fitness, dining, lodging, and tickets on Naval Air Station Key West.

Key Largo

Morning Star Sailing Charters

Morning Star Sailing Charters offers personalized sailing experiences in the Florida Keys, including captained and bareboat charters, sunset cruises, and snorkeling tours.

Marathon

Faro Blanco Resort Marathon Florida Keys, Curio by Hilton

Waterfront resort in Marathon offering coastal luxury, a full-service marina, spa, dining, four pools, and a sister property, Courtyard by Marriott.

Weddings Max
130
Meetings Max
130
Total Space
1820 sq ft
Largest Room
1820 sq ft

Marathon

Coco Plum Beach and Tennis Club

Charming family-friendly beachfront resort in Marathon featuring tennis, marina access, and relaxing coastal villas.

Key West

Aloha Sailing Key West

Personalized sailing charters aboard a Fountaine Pajot catamaran, exploring the Florida Keys and Dry Tortugas.

Key West

Cow Key Marina

Cow Key Marina is a full-service waterfront hub in Key West offering boat and jetski rentals, watersport tours, a waterfront restaurant, and even daily manatee sightings.

Key Largo

Calypso Sailing

Calypso Watersports offers private sailing charters aboard Leopard Catamarans in Key Largo and Key West, providing unforgettable journeys tailored to suit every need.

Marathon

Blackfin Resort & Marina

Escape to Blackfin Resort & Marina in the Florida Keys—relax, fish, boat, and enjoy stunning sunsets!

Marathon

Tropical Boat Rentals

Explore the Florida Keys with top-quality, well-equipped boat rentals!

Key West

No Doubt Fishing Charters

No Doubt Charters is a family-owned Key West fishing charter offering sportfishing, snorkeling, and trips to the Dry Tortugas.

Marathon

Captain Hook’s Marina and Dive Center

Explore award-winning Florida Keys adventures with Captain Hook’s Marina & Dive Center!

Key Largo

Key Largo Princess Glass Bottom Boat

Glass-bottom cruises over Molasses Reef—see the reef without getting wet.

Islamorada

Whale Harbor Marina

Whale Harbor Marina — premier full-service marina and charter hub in Islamorada, Florida Keys.