Where do cruises depart from?

Cruises depart from Stock Island, near Key West; exact meeting details are provided after booking.

How many people fit on board?

The passport 40 'Leona' accommodates up to six guests for a private charter.

Is swimming or snorkeling included?

Swim stops are possible when conditions and captain discretion allow; bring your own mask and snorkel if you want to snorkel.

What happens in bad weather?

Trips are subject to captain discretion and local weather; charters may be rescheduled or rerouted for safety.

Are beverages or food provided?

What is included is determined at booking; guests commonly bring snacks and drinks—confirm details with the operator.

Is there an age limit or accessibility info?

There is no posted age minimum; boarding may require stepping down to a dock or into a dinghy—contact the operator for accessibility concerns.

Private Sailing Cruise: 3-Hour Key West Charter Aboard Leona

Adventure Brief

A three-hour private sail from Stock Island aboard Leona offers an intimate way to experience the Florida Keys—choose morning, afternoon, or sunset for wildlife, reef views, and easy cruising. Perfect for small groups who want a relaxed, captain-led boat experience.

3 hours

easy

From $634.94

Private Sailing Cruise launches from Stock Island, just east of Key West in the southernmost reaches of Florida. For three hours aboard Leona, a classic Passport 40, small groups of up to six people slip away from the bustle of the harbor into the clear, shallow waters of the Florida Keys. Island Sailing and Excursions has been running charters for decades, and their private sail is built around an unhurried, personal rhythm: morning calm when the light is soft, afternoon thermals that fill the sails, or the slow burn of a Key West sunset. The Passport 40's spacious decks and traditional lines make Leona a comfortable platform for watching coastal geology - coral limestone outcrops, low mangrove keys, and broad seagrass flats that cradle juvenile fish and sea turtles. Key features on a typical cruise include colorful shallow reefs that fringe the Keys, mangrove tunnels carved by tides, and wide vistas of open ocean framed by distant islands. Wildlife sightings are common: pods of bottlenose dolphins often race the bow, green and loggerhead sea turtles forage in the flats, and migrating terns and pelicans wheel overhead. The waters you sail are part of the Florida Reef, the third-largest barrier reef system on Earth, and the hard limestone and coral formations give the coastline its distinctive low, jagged profile. Beyond scenery, the cruise taps into local maritime history. Key West's economy once revolved around wrecking and salvage in the 19th century, and the islands' channels and shallow banks still tell that story in submerged wrecks and scattered artifacts. Your captain can point out historic harbors and modern conservation efforts that protect reef and mangrove habitat. A Private Sailing Cruise is distinct here because it favors intimacy and seamanship over crowding - no mass tour boat, just a small group, a knowledgeable captain, and a well-handled sailboat. It's ideal for couples, families, and small groups who want a gentle adventure with time to swim, photograph, or simply breathe on deck. Expect flexible routing - your captain chooses the safest, most scenic course based on wind and weather - and a relaxed pace that highlights both nature and local culture. Practical notes: departures are from Stock Island near Key West, trips last three hours, and the vessel accommodates up to six guests. Weather can affect routing; for the best light bring polarized sunglasses and a light jacket for sea spray. For a short window on the water that feels like a proper escape, this private sail delivers an authentic, expert-led taste of the Florida Keys. Book a morning for glassy seas and snorkeling, an afternoon to chase the breeze, or a sunset to watch flaming skies melt into the sea—each departure promises small-boat intimacy and genuine island character daily.

Private Sailing Cruise: 3-Hour Key West Charter Aboard Leona

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