Directory
Pick how you want to go sailing: a boat you rent and skipper yourself, a captained private charter, a seat on a day sail, or a membership that keeps a fleet on call. Start with the way that fits, then filter by region and type.
Bareboat, in charter talk. Beach cats by the hour from Pensacola Beach to Key West, and cruising boats by the day or the week from Cape Coral, Naples, Fort Lauderdale, Key Largo and Marathon. Most of the beach rentals ask for no certificate; for a cruising boat, expect a certification, a sailing résumé or a checkout sail.
Rent a sailboat in FloridaA private charter for your group, captain included, from an afternoon on Biscayne Bay to a week in the Keys or a crossing to the Bahamas. No certificate and no résumé needed.
Captained chartersSunset sails, snorkel and shelling trips, dolphin watches and harbor tours sold by the seat: schooners in Key West and St. Augustine, catamarans from Naples to Pensacola.
Day sailsA fleet on call instead of a boat of your own: a day-block club in Naples with a checkout sail in place of a certificate, or Key Largo cottages that come with a sailboat at the dock.
Membership chartersWhere: Tampa Bay & Gulf Coast (Charlotte Harbor bareboat fleets, Naples and Clearwater day sails) The Keys (Key West schooners, Key Largo and Marathon rentals) Miami & Southeast (Biscayne Bay, Fort Lauderdale, Bahamas crossings) Northeast (St. Augustine and Amelia Island) Panhandle (Pensacola Bay, Destin and Choctawhatchee, Panama City) Inland Lakes & ICW (the Space Coast lagoons and Ponce Inlet)
How to choose. Two questions settle most of it. Do you want to run the boat? If you want the helm with nobody else aboard, start with the rentals; everything else comes with a captain. And when are you coming? The prime season is November to May, when the wind is steady and the storm risk is lowest. Hurricane season runs June 1 to November 30, with the real risk from August to October, and a few operators close or haul out for part of the summer, so read the listing before you plan around a summer date. The when-to-sail guide has the month-by-month picture. Coming from abroad? Florida issues no skipper's license. A rental operator judges you on your sailing résumé or a checkout sail, so have the résumé ready; the bareboat requirements guide covers the one state card that does apply.
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.
Featured Daysail The Keys · Marathon
Sirius is a Coast Guard inspected 36-foot sailing catamaran carrying 24 guests from Safe Harbor Marathon Marina, running two-hour sunset cruises by the seat and private charters. Capt. Dale Kamerzel has run the company since 2000. Siriusly Nauti is a motor boat.
Featured Daysail Northeast · St. Augustine
76-foot replica blockade-runner schooner sailing out of the City Marina in St. Augustine. Day sails, sunset sails, and moonlight sails. The city's longest-running tall-ship daysail.
Featured Daysail The Keys · Key West
Crewed daysails on Hindu, a 1925 gaff-rigged schooner designed by William H. Hand Jr. as a half-scale Grand Banks fisherman, later a WWII Navy patrol boat and Provincetown whale-watcher. Winter sunset and daytime sails out of the Historic Seaport.
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.
Featured Daysail Tampa Bay · Naples
Naples's longest-running sailing catamaran by its own account, a 53-foot Gold Coast cat carrying 44 passengers from the Naples City Dock since 1991. Daily sunset, shelling and sightseeing seat sails and private charters. The company's Sweet Tiki is a motor boat.
Northeast · St. Augustine
Sailboat rentals on Salt Run, the tidal lagoon inside Anastasia State Park, run by the park's concessionaire. Three fourteen-foot Hobie Waves and three single-sail Aqua Finns, reserved by phone. Previous sailing experience is required and renters must be over 21.
Daysail The Keys · Key West
Year-round crewed sails on a 75-foot Key West-built catamaran from Sunset Pier at the foot of Duval Street. Public sunset cruises and Sunday brunch sails, private daysails and events, with food and drink included in every fare.
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.
Crewed Miami / Southeast · West Palm Beach
Private sails for up to six on Carpe Vita, a 42-foot Fountaine Pajot Venezia catamaran, from the City Docks in downtown West Palm Beach. Sunset and celebration charters, a summer anchorage off Peanut Island for swimming and snorkelling, and longer runs down to the Keys.
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.
Daysail Inland & ICW · Merritt Island
Two Maine Cat 30 sailing catamarans, Endless Summer and Dolphin Breeze, working the Indian River Lagoon from Cape Crossing Marina on Merritt Island. Dolphin sails, sunset sails and island runs, six guests at a time. Groups of seven to twenty take both boats.
Daysail Panhandle · Pensacola Beach
Two-hour sails from Pier One Marina on Pensacola Beach aboard Dare II, a Condor 40 trimaran, one of twenty-one built in Annapolis from 1985 to 1991. Daily 11am and 2pm sails and a sunset cruise, six guests at most, booked online. Captain Kirk has owned her since 2002.
Daysail Tampa Bay · Naples
Champagne sunset and daytime dolphin sails by the seat aboard Cool Beans, a Coast Guard-inspected 42-foot sailing catamaran for 20, from the dock at Osteria Capri on the Isles of Capri, plus private charters. The sister Lil' Beans is a pontoon; the shelling runs go under power.
Daysail Tampa Bay · Fort Myers Beach
Copacetic is a 36-foot sailing catamaran her captain spent years building by hand in Fort Myers, now carrying 24 guests off Fort Myers Beach and Sanibel. Day and sunset sails by the seat, a Saturday yoga sail, and private charters to Lovers Key and Upper Captiva.
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.
Crewed Panhandle · Fort Walton Beach
No trips for the rest of 2026 after hurricane damage in the area; the owners plan to resume in March 2027. Private crewed catamaran daysails on a Stiletto 27 from Adventure Marina on Okaloosa Island, with Crab Island, sunset and snorkel runs for up to six guests.
Crewed Miami / Southeast · Coconut Grove
A 40-foot Beneteau on Biscayne Bay, skippered by Rodrigo Burgos from South Bayshore Drive in Coconut Grove, with pickups at Key Biscayne or South Beach. Private day trips for up to six; overnight and multi-day sails down to the Keys take four, with reef snorkeling on the way.
Crewed Tampa Bay · Dunedin
Daily captained sails from the Dunedin Marina aboard Miracle, a 41-foot Morgan Out Island skippered by Captain Herman. Sunset and dolphin cruises and full days at the barrier islands. A separate business from Wind Star Sailing, which keeps a similar Morgan at the same marina.
Crewed Panhandle · Destin
Space Dancer, a 45-foot Beneteau sloop, leaves the AJ's Seafood and Oyster Bar dock on Destin Harbor, then out East Pass into the Gulf with Captain Chris. Two- to four-hour private sails, sunset and fireworks cruises, time at the helm on request, and overnight trips year round.
Crewed Tampa Bay · Goodland
Easy Breezy, a 30-foot Stiletto sailing catamaran, launched from the Goodland Boat Park ramp on the Ten Thousand Islands side of Marco Island, Nick Rezac at the tiller. Private two-hour, half-day and full-day sails and a sunset cruise for up to six, with an island stop.
Daysail Tampa Bay · Holmes Beach
Capt. Kit Baxter sails Flip Flops, a Maine Cat 30 catamaran, out of Holmes Beach on Anna Maria Island, six guests at most. Public sails go with two aboard, private sails need three spots. Sunset and day sails on the bay, and four- to six-hour runs to Passage Key and Egmont Key.
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.
Crewed Tampa Bay · Port Charlotte
Courageous, a 1983 Hunter 37 Cherubini, sails Charlotte Harbor from a Port Charlotte dock with Captain Curtis. Private day and sunset sails for up to six, with informal instruction for anyone who wants the helm. Closed for summer 2026 until November, per the operator.
Crewed Northeast · Fernandina Beach
Private cruises on a Lagoon 410 catamaran from Amelia Island Marina, past Fort Clinch and the wild horses of Cumberland Island. Three-hour sunset sails and longer sightseeing runs, plus overnights to St. Marys and Jekyll, and to St. Simons and St. Augustine on request.
Daysail Inland & ICW · Ponce Inlet
Arabella is a 50-foot cold-molded catamaran carrying up to 48 guests on the Ponce Inlet and New Smyrna waterway. Social swim-and-sail and sunset cruises need 14 passengers to sail; private charters do not. Her 64-foot mast takes her to 15 knots with the wind behind.
Daysail Northeast · St. Augustine
Atlantic Fury, a 65-foot sailing catamaran, sails from Beaches Marina on Vilano Beach into St. Augustine's harbor past the Castillo de San Marcos. Live-music sunset sails and dolphin-watch harbor sails by the seat, plus private charters. Their Island Cat is a power catamaran.
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.
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.
Daysail Panhandle · Panama City Beach
Two sailing catamarans, the 50-foot Island Time and the 53-foot Island Time II, out of Grand Lagoon in Panama City Beach. A three-hour snorkel sail to Shell Island with gear and paddleboards aboard, and a two-hour sunset dolphin sail, both sold by the seat.
Daysail Panhandle · Pensacola Beach
Jolly Mon is a 27-foot American Mariner sloop, the boat this Pensacola Beach family business started with in 2011 and still its only sailboat. Two- to four-hour sailing, snorkelling and sunset tours from Pier One Marina. The rest of the Jolly fleet is powered tritoons.
Daysail Tampa Bay · Sarasota
Three 30-foot sailing catamarans, two Maine Cat 30s and a Stiletto 30, on Sarasota Bay and the Gulf passes since 2007. Public seat sails from Marina Plaza downtown, private charters from there or Longboat Key, and custom six-hour days out of Holmes Beach on Anna Maria Island.
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.
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.
Daysail The Keys · Key West
Three wooden schooners sailing from the Historic Seaport. The 86-foot windjammer Appledore II in Key West winters, champagne sunset sails and backcountry eco tours on the bugeye Appledore Star, sunset and dolphin sails and private charters on the 43-foot Valora.
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.
Daysail Tampa Bay · Fort Myers Beach
Husband-and-wife operation sailing Orion's Child, a 2004 Hunter 386 monohull, from slip C-18 at Salty Sam's Marina on Fort Myers Beach since 2009. Sunset sails and daytime trips into the Gulf off Fort Myers Beach and Sanibel, six guests at most, sold private or by the seat.
Daysail The Keys · Marathon
Chao Lay is a 2006 Bavaria 50 that has sailed around the world, now running day and sunset sails from Yacht Haven Marina in Marathon. Six guests at a time through Boot Key Harbor, Hawk Channel and the Florida Keys Marine Sanctuary. Capt. Mike goes out in calm weather only.
Crewed Tampa Bay · Marco Island
Mariah is a 40-foot catamaran at Riverside Marina on the Marco Island Yacht Club property, and Captain Ron sails her one group at a time. Private day sails and sunset cruises for up to six, about three hours on the Gulf off Marco, with fifty years of sailing behind the skipper.
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.
Daysail Tampa Bay · Naples
A 48-foot catamaran built to a Kurt Hughes design, carrying up to 48 from Port O Call Marina on Naples Bay. Narrated shelling, sightseeing and sunset trips daily, year-round, sailing into the Gulf when the weather allows. Private charters too. Sister boat to the Naples Princess.
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.
Crewed Northeast · Jacksonville
Private sails on the St. Johns River from Ortega in Jacksonville aboard Now and Zen, a 42-foot catamaran, six guests at most and every charter yours alone. Sunset and day sails, and multi-day trips north to Cumberland and Jekyll or south to St. Augustine.
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 · 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.
Daysail Panhandle · Panama City Beach
Daydreams is a 47-foot Beneteau monohull sailing out of Grand Lagoon to Shell Island, six guests on a shared snorkel or sunset sail and twelve on a private charter. The company's Privateer, Footloose, Lazy Daze and tiki boat are all powered, so Daydreams is the one that sails.
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.
Daysail Northeast · Fernandina Beach
Daysail and private charter on Amelia Island, Florida's northernmost barrier island. Two-hour to half-day sails on a 40-foot J/40 sloop out of Fernandina Beach, with Nassau Sound and the Amelia River both reachable in a session. Not sailing as of September 2026, per its own site.
Daysail Tampa Bay · Venice
Two-hour sails into the Gulf from the Crow's Nest Marina at the Venice jetties aboard Inspiration, with Captain Dove and mate Tim. Six passengers at most, by appointment, guests welcome at the wheel. Hauled out for maintenance July 14 to October 15, 2026, per the operator.
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.
Daysail Tampa Bay · Clearwater Beach
A 52-foot steel staysail schooner built in Clearwater in 2016, sailing daily from the Clearwater Beach Municipal Marina. Two-hour afternoon and sunset sails by the seat, 22 guests at most, plus private charters. The course follows the wind, and guests can help raise sail.
Daysail The Keys · Key West
74-foot topsail schooner built 1982–83, long the unofficial flagship of the Conch Republic and, since 2023, flagship of Key West. Currently laid up at a Key West boatyard and not sailing. Her nonprofit is fundraising a full restoration.
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.
Crewed Tampa Bay · Naples
One captain, one boat, every trip. Jeff Gage runs private charters for up to six from the Naples City Dock aboard Sea Suite, his 2011 Leopard 39 catamaran, the route set by the guests. Sunset sails, days on the Gulf, afternoons at anchor, and informal instruction on request.
Daysail The Keys · Key West
Long-running Key West daysail outfit operating large cruising catamarans out of the Historic Seaport. Sunset, reef-snorkel, and full-day sail-and-snorkel itineraries crewed by USCG-licensed captains. Sister operation Key West Schooners covers the wooden-schooner side.
Daysail Panhandle · Pensacola
Sirena is a 48-foot sailing catamaran working out of Southwind Marina on Pensacola's south shore, certified for 49 and held to 12. Sunset and dolphin sails, a half-day run to Fort McRee and Johnson Beach, a snorkelling trip, and a Blue Angels practice cruise on flying days.
Crewed Panhandle · Destin
Private charters on the trimaran Nice Tri from Destin Harbor behind the Marina Cafe, run by Capt. Pam. Two-hour scenic sails, snorkelling over the grass flats and the second sandbar, dolphin runs and Crab Island afternoons, with sunset and fireworks cruises in season.
Crewed Miami / Southeast · Coconut Grove
Kyle and Brianna Brown's 2018 Lagoon 42 catamaran, captained out of Dinner Key Marina in Coconut Grove. Half-day, full-day and sunset sails on Biscayne Bay for six, overnights as far as Bimini. Groups of seven to twelve contract the boat and engage the captain separately.
Crewed Panhandle · Pensacola
A 47-foot Leopard catamaran on Pensacola Bay, boarding at the Maritime Park docks downtown. Half- and full-day charters with paddleboards and kayaks aboard, swim calls at Deadman's Island and Fort McRae, an overnight to Orange Beach, and an ASA 114 course on the same boat.
Crewed Tampa Bay · St. Petersburg
Captained sails on Tampa Bay from the Harborage Marina, run by a couple who cruised the Caribbean aboard the boat that is now the fleet's flagship. Three boats, a Morgan 44, a Catalina 355 and a Leopard 45 catamaran, out for one to four hours with six aboard.
Crewed Miami / Southeast · Stuart
Luna Cat, a 2019 Lagoon 42 skippered by Erinn Hennessy, at the Fish House District marina on Manatee Pocket. Captained private sails for up to six on the Indian River Lagoon and offshore; parties of seven to thirteen charter the boat and hire the captain separately.
Daysail Tampa Bay · Treasure Island
Gaff-rigged topsail schooner sailing from Treasure Island out through John's Pass into the Gulf. Suncoast Horizon is 55 feet, built in 2000 to a Merritt Walter design, certified for 28 guests and held to about 21. Sunset and day sails by the seat, plus private charters.
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.
Crewed Tampa Bay · St. Petersburg
Sweet Escape is a 2023 Bali 4.2 catamaran running private all-inclusive charters for up to six on Tampa Bay out of St. Petersburg. Captain and first mate, paddleboards, kayaks, snorkelling gear and refreshments come with every booking. Sunset, swim and full-day sails.
Daysail Tampa Bay · St. Petersburg
Between boats. Hawkeye, the 47-foot sailboat behind these two-hour sunset sails from downtown St. Petersburg, was sold in June 2026, and the sails are on hold until the company finds another vessel.
Crewed Tampa Bay · Gulfport
Private sails for up to six on Boca Ciega Bay and Tampa Bay from the Gulfport waterfront aboard Cay Michele, a 1981 Hardin Voyager 45 staysail ketch, hull 92 of the 130 built. Sunset sails, barrier-island runs with a dinghy ashore, and sandbar afternoons, every trip yours alone.
Daysail Miami / Southeast · Stuart
Classic boats on the St. Lucie River from Sunset Bay Marina in downtown Stuart since 2010. Daily seat sails and private charters on Resolute, a Friendship sloop for twelve, and Margot, a Marshall 22 catboat for six. The flagship, the scow schooner Lily, is laid up for rebuild.
Daysail Miami / Southeast · Fort Lauderdale
Two sailing catamarans in two cities. Spirit of Lauderdale works out of Bahia Mar in Fort Lauderdale, and the 125-passenger Caribbean Spirit sails Biscayne Bay from Bayside in Miami. Sail-and-splash trips with a swim stop, sunset sails, private charters.
Crewed Tampa Bay · Dunedin
Wind Star is a 41-foot Morgan Out Island ketch at slip 8 in the Dunedin Marina, with Captain Harry at the helm. Half days on St. Joseph Sound, full days to Anclote Key or Three Rooker Bar, sunset and dolphin cruises, and overnight to week-long charters for up to four.
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.
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