Captained Charter On 33ft The Key West's Most Versatile Sailboat!

Cruising Monohull
33 ft
6 Guests

About This Boat

The best way to see the Key West is from the water on a beautiful spacious Sailboat with fantastic Captain! Charter our 33ft Sailing Sloop for up to six (6) guests. Private charters include our gourmet cheese plate, soft drinks/basic mixers, bottled water, Captain and Mate, and of course a cooler full of ice for any adult beverage you bring. Rates as low as $148 per hour (minimum 1.5 hours).


• Private Charter (1.5 Hours): $295 up to 6 passengers

What You Can Expect:

Our Day sails offer a great way to see Key West from the water!  Experience the joy of setting sail and shutting off the engine as we sail you through the colorful waters that surround our beautiful Island.  Sail around Sunset Key and take a look at the Key West's most fantastic National wildlife preserve.  We always have a chance to see dolphins, turtles and countless variety of sea birds. Sit back and relax or take a turn at sailing the boat, this truly is Your trip!

With over 15 years experience sailing and living in the Keys our captains and crew provide you with the local knowledge of  marine life, surrounding islands as well as stories of Key Wests rich and colorful history.

Sunset Sails  

You can also join us on our Sunset Sails! This is a perfect end your day to an island! 

When you sail with us, you sail on a classic sailboat with a max of 6 guests and 2 crew.  We are here to share our love of sailing, so on our 2 hr sunset sail, we hoist the sails and turn off the engine! Our beautiful sloop High Tide is fast and agile allowing us to cover a lot of area and sail around all the bigger boats.

Private Charter 

You will have the vessel as your own, you may bring up to 6 guests, whatever the special day.  On the sloop High Tide. We have had 26 and counting marriage proposals, vow renewals, small weddings, birthdays and countless anniversaries. 

What To Expect Onboard:

High Tide is Key West’s first charter sailboat, sailing out of Key West Harbor since the ’80s and still enjoyed with Sunset Sail Key West. Designed specifically for snorkel trips to the Florida Reef and day sailing Key West water, she is a 33′ 1980 Glander built here in the Florida Keys by the Conch Republic’s First Sea Lord, Admiral Finbar.

Hight Tide’s spacious double cockpit, simple sloop rig and shallow draft provides a breathtaking backdrop for intimate weddings, family gatherings and other special events at Sea. The 33′ custom sloop is the ideal platform to explore and learn about Key West’s “back country” flats and mangrove island bird sanctuaries.

Additional Services:

• Special requests and upgrades are available-  (such as sandwiches, prepared hors d'oeuvres, additional mixers etc...) 

***Captain Seth is a Best of GetMyBoat 2015 award recipient***

If you have any questions, we can answer those through GetMyBoat’s messaging platform before you pay. Just hit, “Request to Book” and send us an inquiry for a custom offer.


  • Type: Cruising Monohull
  • Capacity: 6 People
  • Make Model: 1980 Glander
  • Year: 1980
  • Rental Minimum: 2 hours
  • Length: 33 ft
  • Cancellation: Full Refund 5 Days Prior

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Captained Charter On 33ft The Key West's Most Versatile Sailboat!
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The best way to enjoy a private sailing charter in Key West! The boat is comfortable, it sails very well, the crew is amazing and snorkeling a beautiful coral garden that is a company secret are just some of the amazing things this small company offers. I sail with Sunset Sail Key West every time I'm in Key West!

March 2015

Meet Captain Seth

Captain Seth

From Key West

Member Since Oct 2014

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