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By Clyde Powell













Key West Florida Sailing Tours and Charters Information


Looks like the the Schooner Western Union is on its way back after undergoing restoration work at a Miami shipyard. Over $100,000 was raised to pay for the work that needed to be done on the aging ship and to get its Coast Guard Certification. The money was raised by the Schooner Western Union Preservation Society. The restoration will continue once it is back in Key West. Donations are welcome to help in this effort to get the ship back in good order. Built in the great tradition of the wrecking vessels that were used in Key West Florida in the 1800's, the 130 ft. Built in 1939 to lay cable for the Western Union cable lines hence its name. National Register of Historic Places. The schooner Western Union has three distinctions. She is: * the last example of a traditional American coasting schooner made in the U.S * the last sailing cable ship on earth. * the last tall ship constructed in Key West.


Have a Sailing Service in Key West and you want to be here e-mail me question (at)  put Key West in the Subject Line.

Any Questions or need help call and ask
Mike Between 9am and 9 pm est. 305-849-1470

 Remember getting there can be half the fun. Meeting and making new friends is an extra plus on any Key West Sailing trip. Ok now all you land lovers it is time to try out your sea legs and jump on board. See what it was like not to long ago before the roar of engines. You can hear the wind in the sails plus the ships hull cutting though the water. You may even get lucky and find a couple dolphins playing in the wake of the ship. Sailing in  Key West

Sailing the waters around Key West

Key West Sailing on Big Catamarans


       Sebago Watersports
Sunset Sails         

      All Day Island Ting       
Gay Sails       

Fury Sailing

Sailing, Music, and Combos 


Aerial view of Key West water and Fury catamaran

Key West Sailing Charters on Schooners, Small Catamarans and Sailboats


Schooner Appledore 

Floridays  Sailing      


Danger Charters Sailing    

Power Boats Sunset Cruises
Life is Good 

Key West sailing at sunset


Charter on the party Cat Key West Sailing

     Sunset Watersports
Sunset Cruises,   Sunset Dinner Cruises,     
 and   Do It All     

There are many different ways you can enjoy sailing in Key West. It just depends on what you are in the mood for. We have many sailboats that will take you on a private sail for the whole day. Visiting small keys so you can relax on the beach, snorkel, fish or kayak. Some have dinner cruises while you relax and watch the Key West sunset. You will find some big wooden schooners that let you relive the days of the wreakers in Key West. By far the most popular are the many catamarans that take you out for a sunset cruise in the Key West Harbor. A great deal for large groups being it is all you can drink of beer and wine some even have cash bars for mixed drinks.
Remember getting there is half the fun.

by Clyde Powell Key West Sailing

Some Video of Sailing in Key West





Check out what Sailing Charters are in Key West. Read reviews from


Key West Sailing Tours and Charters Information

Charter Schooner America 2.0‎
Offering our most premium sailing experience, Schooner America 2.0 is the newest, largest, most elegant vessel designed for Classic Harbor Line. Added to the Classic Harbor Line fleet in 2011, America 2.0 offers the most exceptional day sailing one can find.

Charter Schooner America 2.0

Schooner Jolly II Rover

Schooner Jolly II Rover
Come sail Key West’s most photographed ship – the Jolly II Rover, a square rigged topsail schooner! A Key West sailing adventure aboard the Schooner Jolly Rover takes you back in time on a classic 80’ coastal topsail ship to an era of pirates, rum runners and privateers seeking freedom and solitude.

Schooner Western Union
Schooner Western Union is the official flagship of Key West and the State of Florida. She's one of the oldest working wooden schooners in the United States and on the National Register of Historic Places.


Schooner Western Union

DiggerKat Sailing--Personalized Cruising

DiggerKat Sailing--Personalized Cruising
Personalized Cruising Vacations in Key West and the Bahamas--Design the Sailing Adventure that's just right for you! Experience Key West from the water. Relax to the soft sounds of waves lapping against the boat, watch dolphins play along side the bow, see a myriad of stars at night and design a vacation that's just right for you.
Sunset Sail Key West offers an Intimate personalized experience for your party, we have 2 Beautiful sail boats that each take a maximum of 6 guests Sailing daily from Downtown Key West at the Schooner Wharf Bar and from Stock Island’s Marina Village. If your 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! Our Captains and crew are all keen on giving you a personal sailing experience to remember!

Sunset Sail Key West


Coastal Sailing Adventures
Sail-Training Adventures, Private Sailboat Charters and Weddings at Sea "Fantastic trips in the Florida Keys & Key West " Welcome aboard the Schooner Dream Catcher, designed and built for a spectacular sailing experience in the Florida Keys.

Catamaran Echo
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.

Catamaran Echo

Conch Quest Key West Sailing Charters

Conch Quest Key West Sailing Charters

P.O. Box 776 Key West Florida
Aboard a private four or six hour "Conch Quest" charter, you can sail out to the reef and snorkel (all gear included). If you only have two hours, we can sail around the harbor or enjoy a Key West sunset.

Sebago Catamarans
305 294 5687
201 William Street Key West, FL 33040
Sailing, snorkeling and champagne sunset cruises, Sebago Watersports has three beautiful custom built catamarans that set sail several times a day. Complimentary beer, wine and soft drinks on every cruise. Half day and full day snorkel adventures.

Sebago Catamarans

Sunny Days Sunset trips

Sunny Days Sunset trips
(305) 296-5556
Come aboard one of our two boats, the Sunny Days and Reef Express. Experience our champagne sunset sails and reef snorkeling trips. We take fewer passengers, and offer personalized attention from our crew. Come join us and leave the crowds to the others.

Blue Ice Sailing Charters
Sail the beautiful waters of Key West aboard our 47' yacht. Enjoy snorkeling on the coral reef, dolphin watch or choose a sunset sail.

Blue Ice Sailing Charters

Key West Sailing Adventure

Key West Sailing Adventure
201 William Street Key West Florida
Why not choose a Key West yacht for your Key West boat and breakfast?
Perhaps our Key West charter or Key West wedding charter.

601 Front St, Key West, FL 33040
Sailing away from the lights and bustle of Key West, these famous sunsets are their most colorful, relaxing, and enjoyable aboard Floridays. We sail for one and a half hours while our wonderful, competent crew goes the distance to make your cruise the most comfortable, peaceful and relaxing possible.


Blu Q

Blu Q
201 William Street Key West Florida
All Male Sailing, Snorkeling, Island Adventures, Kayaking &   All Gay Sunset Cruises. In 1995, I sailed to Key West from Galveston Bay, Texas on my original boat, Brigadoon. For the past 10 years I've logged thousands of miles exploring the beautiful waters surrounding Key West.  Sharing these experiences  is the highlight of each day.  Now, after years of searching for the best boat.

Key West sailing charters and catamaran charters
We are committed to providing the best all inclusive sailing charters and scuba charters available. Our  crewed Key West sailing charters are all inclusive  with your own captain and chef its a luxury vacation adventure in paradise. Our Key West sailing charters offer a luxury catamaran sailing that is much roomier than single-hull sailboats. That's  because the catamarans beam extends the boat's full length  and offers a cockpit that's twice the size with a larger salon.

Key West sailing charters and catamaran charters

Dream Chaser Charters

Dream Chaser Charters
Step aboard our 43ft Yacht Dreamchaser. Enjoy a two-hour sail along with a Four Course Gourmet Dinner out into the Atlantic Ocean and the Gulf waters. Our sunset dinners at sea have been made famous by review in the prestigious

Key West Sailing Club
The Key West Sailing Club is a non-profit organization in beautiful Key West, Florida, dedicated to learning, teaching and enjoying the great sport of sailing. We are a very active club of avid world travelers, competitive racers, and casual day sailors who are all enthusiastic about the art and science of using the wind and the water to get about.

Key West Sailing Club

Double Decker

"Double Decker"
Key West Sailing Charters Florida Keys
Key West, Florida private sailing charters and trips for weddings, sunset dinner cruises, snorkeling, dolphin watching, and eco-tours. Fran Decker invite you to join them on a private sailing trip to cruise the beautiful, tropical seas of Key West, Florida. Enjoy a day on the water, sailing, snorkeling, or viewing the famous Key West Sunset.

Sailing Key West, Danger Charters
During the 2 hour sunset cruise you will enjoy seeing Key West's busy harbor - sailboats of all types, docked cruise ships, birds, dolphins, flying fish, turtles, you name it! If you are lucky, you'll get to see the famous "green flash" at sunset, and yes, it does exist.

Sailing Key West, Danger Charters

Dream Catcher Charters

Dream Catcher Charters
305-745-2114 888-362-3474
Let us take you out for a wonderful time on the waters off of Key West aboard our State of the Art Charter Boats. Perfect for you and your group to roam around the back country or see the open ocean. Offering snorkeling trips, dolphin watching, Safari

Sailing Key West‎.com/
We are committed to providing the best Key West sailing charters and scuba charters available. Our crewed catamaran charters are all inclusive with your own captain and chef is a luxury vacation adventure in paradise. Our charters include unlimited scuba and sport fishing on a modern yacht with your own private spacious cabin, bath & shower facilities. 8 day 7 all inclusive night Key West sailing charters & Key West honeymoon sailing vacations


Sailing Key West

Fury Water Adventures

Fury Water Adventures
(305)294-8899 800-994-8898
Fury Water Adventures is your number one excursion in and on the waters of Key West. Choose from Reef Snorkeling , Sunset Sails, Parasailing or Reef Eco-Tours aboard the Glass Bottom Boat. We also offer the all day Ultimate Adventure!

Have an event or activity you want here e-mail me at
question (at)  put Key West in the Subject Line.


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