Image 20Sunset Sail Key West offers an Intimate personalized experience for your party, Sailing daily from Downtown Key West at the Schooner Wharf Bar. 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!

With 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.  Come sail off into the sunset in comfort and style.

HIGH TIDE, Key West’s first charter sailboat is a 33′ Glander sloop built here in the keys in Islamorada.  After undergoing a year and a half restoration She is in “Brand New” condition.  She was designed with classic looks, chartering and sailing lessons in mind.  With her spacious double cockpit and simple sloop rig and shallow draft, HIGH TIDE is one of Key West’s most versatile charter Boats.


Come experience the beauty of a Key West sunset on the turquoise waters of the gulf of Mexico or join us for a half day sail and snorkel on the worlds 3rd largest barrier reef or in the Key West backcountry.

Owned and operated by the one time youngest schooner Capt. on the east coast, Sunset Sail Key West strives to exceed all your expectations and present you with the best and most memorable part of your vacation in the Keys.

We take a maximum of 6 people (including children) on our day and sunset charters.

All trips Include: Ice, Bottled Water, Soft drinks and ample cooler space so you can bring your favorite adult beverage

 Call today to reserve your charter!

We are located at The Key West Bights Historic Seaport @ the Schooner Wharf Bar. For info contact

or call 305-587-4488

_________I’d rather be sailing with Sunset Sail Key West___________

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    Sunset Sail 

    DCIM100GOPRO2 hr sunset sail. Up to 6 Guests (including children) Ice, Soft drinks, Water and gourmet cheese and cracker platter $100.00 per person

    Sit back while the captain and mate raise the sails, shut off the engine and sail off into the sunset!

    Weave in and out of all the larger sunset boats in style as our Captain and crew share their local knowledge and cater to you and yours

    Reservations are required


    Private Sunset Sail


    Reserve the entire vessel for that special evening for your party of up to 6 people (including children). Whether its a special date or a family vacation, a private charter ensures the mood will match your desires. Private charters are recommended for weddings, anniversaries or any special day.  Sunset sails are 2 hours and include our special gourmet cheese and cracker platter, Ice, soft drinks and water.  We allow you to bring any adult beverage of you choice and will be delighted to serve that to you during the cruise               $395.00

    Snorkel Sail 

    PICT0026Custom snorkel sailing trip up to 6 people (including children), snorkel gear, ice, water, soft drinks and snorkel instruction included.

    Snorkel trips are done as Private charters only, price starts at  $395.00


    Day Sail

    photo (9)Morning or Afternoon.  Take a leisurely 1 1/2 hour tour around Key West Harbor and the surrounding area.  A great way to spend part of your day. Up to 6 guests (including children) $250