Renting a sailboat you skipper yourself is called a bareboat charter: the boat is yours for the day or the week, with no captain aboard. It's the most freedom, and the best value per person, for cruising the Keys, Biscayne Bay, or the Gulf coast. Here are the 22 Florida companies that rent sailboats this way.
What you need depends on the size of the boat. For a big cruising boat, expect the company to want a certification, a sailing resume, or a checkout sail, and the bar varies: MidBay Sailing on Choctawhatchee Bay asks for ASA 103 or equivalent, Southwest Florida Yachts in Cape Coral wants a cruising resume and a demonstrated checkout, and Florida Keys Sailing in Marathon runs a checkout and a signed bareboat agreement instead of asking for paperwork. For a small boat by the hour or the day, most of the companies below are beach-cat rentals that ask for no certificate at all: some bundle a short lesson, and some, like Navarre Beach Ski & Sail, rent only to sailors who can already handle the boat; the Hobie cat rentals guide walks the beaches and the boats. New to a bigger boat? See bareboat charter requirements, or book a crewed charter that comes with a captain. Planning the trip itself? Start with the Keys cruising itinerary.
Featured Tampa Bay · Cape Coral
Charlotte Harbor and Pine Island Sound bareboat operator working out of Tarpon Point Marina in Cape Coral. Sister to Florida Sailing & Cruising School. The same fleet runs ASA instruction one week and bareboat charter the next.
Tampa Bay · Bradenton Beach
Gulf-front beach rental on Anna Maria Island, family run for forty years and, by its own account, the only place on the island renting sailboats. Hobie Wave and Hobie Getaway catamarans by the hour or half day, first come, first served, with a short lesson for first-timers.
Tampa Bay · Fort Myers Beach
The same Fort Myers Beach family has run the beach stands at the Diamond Head and Best Western resorts on Estero Boulevard since 1991, and the Hobie 14s and 16s go off the sand there by the hour, booked online, with safety gear and a short orientation included.
Tampa Bay · Naples
Island Dreams, a 31-foot Catalina, goes out bareboat by the half day, full day or night from the Naples City Dock, with a checkout sail in place of a certificate. Captained charters for six as well, and a members-only club that sells sailing in blocks of days.
Tampa Bay · Sarasota
One-boat bareboat operation at Sara Bay Marina, renting a Catalina 30 by the half day, the day or the week on Sarasota Bay. No certificate is asked for. The bar is experience instead, extensive for a day charter and two recent years to take her overnight, and renters must be 25.
Tampa Bay · Naples
Naples City Dock operation running since 1985. Public and private sails on Danmark, a 40-foot sloop the company says is the only Coast Guard inspected sloop in Southwest Florida, plus bareboat rental of a smaller Beneteau by the half day or the week.
Tampa Bay · Captiva
The one sailboat rental on Sanibel or Captiva as of September 2026. Fourteen-foot Hobie Waves from the shop on Andy Rosse Lane, the Captiva village street that ends on the Gulf beach, by the hour up to a full day and reservable in person, online or by phone.
The Keys · Key Largo
Leopard catamaran fleet working the Keys out of Marina Del Mar in Key Largo since 1988, with further docks in Key West and on Stock Island. Bareboat or captained, by the day, the sunset or overnight, to the Keys and the Bahamas. Bareboat asks for time on a comparable catamaran.
The Keys · Marathon
Bareboat and captained charters from Keys Fisheries Marina, gulfside Marathon at mile marker 49. 27- to 36-foot Catalina and Irwin cruisers and a Beneteau 51, by the day or in three-day, two-night packages within 50 miles, Key West included; a checkout stands in for paperwork.
The Keys · Key Largo
Cottage-and-sailboat package on the bayside of Key Largo. Rent a cottage and, if you are a qualified sailor with recent time on the water, the 22-foot Catalina at the dock is yours to sail inside Florida Bay at no charge. Larger boats and captained trips cost extra.
The Keys · Key Largo
Baker's Cay, the resort on the bayside of Key Largo, keeps 14-foot Hobie Waves on its beach through Scuppers, by the hour, briefing and life vest included, open to beginners and old hands alike. The same company runs a second base on St. Pete Beach.
The Keys · Key West
Hobie Wave and Hobie Getaway rentals from two huts on Smathers Beach, the sailing half of a Key West watersports operation running since 1984. Walk-up only, daily 9 to 5, with paddleboards and kayaks on the same beach.
Featured Miami / Southeast · Fort Lauderdale
Fort Lauderdale bareboat operator working from its own docks on the Middle River, chartering sailing catamarans since 1979. A Lagoon 45 and a Bali Catspace 40, bareboat or captained, by the week to the Keys and the Abacos. A boating resume stands in for a certificate.
Miami / Southeast · Delray Beach
Beach cats rigged on the sand at Casuarina Road and A1A, Hobie Wave, Getaway and Hobie 16, pushed straight into the Atlantic. Walk up and sail, with a refresher from the staff if you want one, a captain if you would rather be driven, and dry storage for your own boat.
Miami / Southeast · Riviera Beach
Riviera Beach's rental stand at Blue Heron Boulevard on the Lake Worth Lagoon keeps a Hobie 16 and a Hobie Wave alongside its jet skis, kayaks and paddleboards. Booked by phone, and sailing lessons are sold separately for anyone starting out.
Miami / Southeast · Key Biscayne
Beach-cat rentals on Hobie Beach, the Rickenbacker Causeway strand named for the boats still rented there. Hobie Waves and Getaways by the hour, booked online, with a briefing before you push off and staff watching from the sand. No prior experience needed in settled conditions.
Panhandle · Pensacola Beach
Pensacola Beach watersports operation on Santa Rosa Sound, in business for more than fifty years. Hobie Wave and Hobie Getaway beach-cat rentals by the half or full day, first come first served, for sailors who can already sail; pontoons, Sea-Doos and parasailing alongside.
Panhandle · Niceville
Bareboat rentals and crewed sails from Bluewater Bay Marina on Choctawhatchee Bay. J/80s by the day, a Beneteau 331 and a Jeanneau 389 by the day or up to three nights aboard, for skippers with ASA 103 or equivalent; captained sunset, dolphin and Crab Island trips for up to six.
Panhandle · Navarre Beach
Navarre Beach Ski & Sail has launched Hobies from the sand at Juana's Pagodas since 1989. Thirteen-foot Hobie Waves for up to four, sailed on Santa Rosa Sound between Navarre Beach and Pensacola Beach, by the hour. Prior sailing experience is required.
Panhandle · Panama City Beach
Beach concession along Panama City Beach renting 16-foot Hobie Getaways you sail yourself, for up to four, by the hour or the day. Booked by phone, March through October, from a stand that also does chairs, kayaks, pontoons and jet skis.
Panhandle · Panama City
Bareboat and captained charters on a Vagabond 42 ketch from the CSS Yacht Basin in St. Andrews, Panama City's old waterfront. Rentals go out in four-hour blocks to skippers with ASA 104 or equivalent; the same boat does lessons and captained half and full days for up to six.
In the Upper Keys, Key Lime Sailing Club on the bayside of Key Largo rents cottages with Catalina sloops included, sailed day-by-day inside Florida Bay, with no bareboat resume required for the sub-25-foot fleet, and Scuppers Watersports rents Hobie Waves by the hour off the beach a mile up the highway. For a cruising boat, the Keys option is Florida Keys Sailing at Marathon, which sends Catalinas, an Irwin 34 and a Beneteau 51 out for three-day, two-night packages within 50 miles of the dock, Key West included. In Key West itself, Sunset Watersports rents beach cats off Smathers Beach. The Keys cruising itinerary maps the anchorages and distances; the Florida Keys region hub has the local clubs, schools, and weather.
Want a captain, a day sail, or a membership instead? See all Florida sailboat charter companies, or browse by place: Key West, the Florida Keys, or the Gulf coast.
