Key West Sailboat Charters
SEE ALSO: Florida Keys Sailboat Charters - Sailboat Charters throughout the rest of the Florida Keys.
SEE ALSO: Key West Motor Yacht Charters - Includes Power Boat Charters with a captain.
SEE ALSO: Key West Fishing Charters - Key West Fishing Charters are listed separately
Alphabetical Listings ~ 22 ~
Blue Ice Sailing Charters - Key West, Florida Keys, Florida - Monroe County - Explore the turquoise waters of Key West and sail the deep blue waters of the Gulf Stream on a private charter customized to your schedule. Sit back and relax and enjoy the sailing, take the helm or help the crew set the sails. If you do not know how to sail and would like to learn just let us know and we will take you through the basics, encourage you to take the wheel and help you with sail trim. Sailing is a wonderful family sport that people of all ages can enjoy and it is never too late to learn.
Breezin Sailing Charters - Key West, Florida Keys, Florida - Monroe County - There's no better way to spend a tropical evening in the Keys than on the water and onboard a beautiful 42 foot Catalina sailboat. Join us as the colors in the sky change and create a picture perfect Key West background.
Breezin Sailing Charters offers two hour charters, four hour half day charters or seven hour full day charters. Soft drinks and light refreshments are provided.
Catamaran Echo - Key West, Florida Keys, Florida - Monroe County - Catamaran ECHO is a fast and comfortable sailing machine, providing the most stable ride on the water. And with our big bimini top, you can get all the Key West sun or shade that you want. The fresh water shower on deck comes in handy on those hot days. A private bathroom in the cabin makes a day in the wildlife refuge civilized and helps protect our tropical waters. Specializing in comfortable private sailboat charters for groups of 2-6,7-14 and more.
Classic Harbor Line - Key West, Florida Keys, Florida - Monroe County - Classic Harbor Line, operators of a series of classic style vessels in Newport, RI and New York City. It’s Key West location includes the Schooner Adirondack III, an 80 foot wooden gaff-rigged sailboat and the Schooner America 2.0 a 105 foot replica of the original Schooner America that won the America’s cup race back in 1851. We offer Mangrove and Mimosa Cruises, Half Day Water Adventure, Day Sails, Champagne Sunset Sails, Full Moon, Star-Gazer Sails and private sailboat charters.
Danger Charters - Key West, Florida Keys, Florida - Monroe County - Danger’s Wind & Wine sunset sail features an array of fine wines and upscale beers from around the world, complemented by bountiful hors d’oeuvres that will arouse your palate. All this while sailing under a cloud of canvas aboard our Historic Key West Schooners. We also offer Sail, Snorkel and Kayak Day Trips. Come explore the backcountry in the Florida Keys with Danger Charters while we take you on a secluded island kayak tour among nature at it's best. We also offer private sailboat charters.
Florida Yacht Group - Key West, Florida Keys, Florida - Monroe County - The Florida Yacht Group sells, charters and services the world’s top brands of sailing yachts, sailing catamarans and power boats. We currently operate our bareboat charter fleet 365 days a year in three locations: Miami, Key West and Marsh Harbor-Bahamas with plans to expand to several other locations. Each location offers excellent cruising waters, a year round tropical climate, warm and clear seas, with hundreds of places to cruise to and things to do.
Floridays - Key West, Florida Keys, Florida - Monroe County - Floridays is a luxury 60 foot ketch rigged sailing yacht. Come with us snorkeling and sunset sailing and leave the crowds behind for affordable sailing adventures and personal service, drinks, margaritas, light snacks and FUN included. Snorkel the largest coral reef in North America. Famous for our Champagne Sunset Cruises and romantic weddings.
Fury Water Adventures - Key West, Florida Keys, Florida - Monroe County - Choose from a variety of watersports, reef snorkeling or sunset cruises and sails aboard the Fury Catamaran. Leave your worries behind and sail off into Key West’s famous sunset aboard a spacious state-of-the-art Fury Catamaran. The Fury cruises the tropical waters of Key West with a warm ocean breeze and a magnificent sunset as a backdrop. Private charters are also available.
Key West Sailing Adventure - Key West, Florida Keys, Florida - Monroe County - Enjoy the local favorites, a half day or full day sailing and snorkeling the reef with captain and mate, or just lay back and sail the sunset with us. We offer a Key West Boat and Breakfast Charter, the Stay/Sail Charter. This is a fun and memorable alternative to land lodging. Stay a weekend or a week. This Key West boat and breakfast charter can be designed to meet your needs and schedule. We also offer sailing getaways, snorkel charters, sunset cruises, Bahamas charters and more.
Lions Paw Life Sailing Charters - Key West, Florida Keys, Florida - Monroe County - The 45-foot Lions Paw is a first-class sailing vessel, and our crew are experienced and passionate about sailing. Our customizable sailboat charters offer you options for overnights at sea or in port and daytime excursions.
Our Key West sailing adventures include a stay on the boat and choose half, full and overnight sails, sailing, fishing, diving and snorkeling.
Namaste’ Sailing Adventures - Key West, Florida Keys, Florida - Monroe County - Namaste Sailing specializes in custom sailing adventures each carefully crafted to make your experience with us special, unique and most of all fun. Whether you are a Boy Scout troop form Iowa or a family on spring break we can accommodate your passion for a quality, crowd free, sailing adventure in the beautiful Florida Keys.
Restless Native Key West, LLC - Key West, Florida Keys, Florida - Monroe County - Sailing excursions, boat & breakfast stays, day sails, sunset sails, weddings, term charters and memorials at sea aboard our luxurious 42' Lagoon 420 catamaran. Reserve your private charter aboard our luxurious vessel and experience the tranquil beauty of Key West's waters. Our private charters allow you to choose your own adventure. For a Boat & Breakfast experience, Our 2007 42' luxury Lagoon 420 catamaran can sleep six with a Master Suite and 2 cabins, each with its own head and shower. Includes daily continental-style breakfast.
Sail Florida Adventures - Key West, Florida Keys, Florida - Monroe County - Sail Florida Adventures offers private day sails and private sunset sails in Key West, Florida. We also specialize in weddings or private sailboat charters for any special occasion. By far the most economical way to get on the water in Key West. Sail Florida Adventures is the only sail company in Key West with a CUA (Commerical Use Authorization) issued by National Park Service.
Schooner Conch Pearl - Key West, Florida Keys, Florida - Monroe County - The schooner Conch Pearl provides private sailing charters and specializes in scuba trips. She is a sailing dive boat. Built in 1988 by Treworgy Yachts in St. Augustine, Florida, Conch Pearl is a 60 foot gaff-rigged Trade Rover schooner, one of only four built of this particular design. As a United States Coast Guard inspected passenger vessel, the Conch Pearl is licensed to carry up to 37 passengers for day sails and 12 passengers for overnights.
Schooner Hindu - Key West, Florida Keys, Florida - Monroe County - Sailing from Key West, Florida for morning, afternoon and sunset charters. The story behind this sleek, 79-foot sailboat rivals the tall tales of any salty dog. The famous William H. Hand Jr. (1875-1946), of Portland, Maine, who pioneered V-bottom power boats, designed the pleasure yacht in 1925 for a wealthy family who commissioned the Hodgdon Brothers in East Boothbay, Maine to build her. Special Thanks to the more than 50 people who contributed significant work to the 2011-2012 restoration of the schooner Hindu.
Schooner Jolly II Rover - Key West, Florida Keys, Florida - Monroe County - Rediscover old world sailing on a classic 80’ Caribbean coastal sailing ship, the same kind used by infamous pirates, rum runners, and those who first sought the freedom and solitude of the Florida Keys hundreds of years ago. Daily Sunset Sails depart Key West’s Historic Seaport nightly. One of the most sought after things to do in Key West, our regularly scheduled sunset sails are perfect for adventurous families or couples seeking a romantic interlude at sea.
Schooner Wolf - Key West, Florida Keys, Florida - Monroe County - The WOLF is a classic 74' topsail schooner built in 1982-1983 in Panama City, Florida by Master builder Willis Ray and Finbar Gittelman, Admiral and First Sea Lord of the Conch Republic. Coast Guard Certified for up to 41 passengers, the Wolf offers day sails, sunset and starlight cruises. Overnight sailboat charters and extended voyages are also available. The WOLF can be chartered by the hour, day or week and is available to travel anywhere, including all of Florida, the Bahamas and Caribbean.
Sebago, The - Key West, Florida Keys, Florida - Monroe County - Key West Sebago offers Key West travel packages for sunset cruises, dolphin charters, snorkeling adventures, weddings, kayaking and parasailing. We are the longest established day charter catamaran operator in the continental US. Enjoy a sunset sail aboard our luxury 41 foot yacht catamaran. Enjoy the highlights of Key West with the Appledore Sunset Cruise on a 65' Schooner. Come and enjoy an authentic Key West adventure on our 86" gaffed rigged historic Schooner.
Stray Cat Sailing Adventures LLC - Key West, Florida Keys, Florida - Monroe County - Stray Cat Sailing Adventures LLC offers Key West private sailing charters. We are a 41' Catamaran and offer private sunset sails, dinner cruises, 1/2 day and full day sails which include snorkeling and kayaking with overnights available including 3 private bedrooms with their own private bathrooms. Food and drink can be included or you may bring your own.
Sunluver Charters - Key West, Florida Keys, Florida - Monroe County - Your dream vacation awaits you on "Sunluver" a luxurious Lagoon 440 Catamaran located in fabulous Key West, Florida. Kick off your flip flops, relax and enjoy the charm of the Key West while living aboard a luxury sailing yacht. See why our guests called it "paradise". Sunluver Charters is independently owned and operated by Captain Bob. Captain Bob holds a USCG 50 ton Master Captains License with a Sailing Endorsement and has been a resident of Key West for over 6 years.
Sunset Sail Key West - Key West, Florida Keys, Florida - Monroe County - Key West’s first charter sailboat is a 33 foot Glander sloop built here in the keys in Islamorada. Sunset Sail Key West offers an Intimate personalized experience for your party, Sailing daily from Downtown Key West at the Schooner Wharf Bar. If you're a small group 6 or fewer you will get to sail in comfort as you will be able to move around the boat, take a turn at the wheel or even help with the sails.
Tortuga Sailing Adventures - Key West, Florida Keys, Florida - Monroe County - Tortuga Sailing Adventures offers private sailing yacht charters and overnight getaways in Key West Florida. We are regarded as the best of the best in Key West luxury sailing charters. Our customized day excursion is all-Inclusive for up to six guests. Grab your friends & family and let's get underway.