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    What to Expect
    Arriving at the sloop, you will be introduced to your Captain and Mate then settle onto the boat for a quick familiarization and safety briefing from the captain while the mate stows anything you may wish to keep in the coolers and prepares the boat for departure.
    A short motor out of the harbor brings the boat to a spot where the captain can turn her into the wind and the mate can hoist the sails - aided by any guests who are feeling particularly enthusiastic! After that, the engines will be shut off so you can enjoy the sights and sounds of Key West in peace and tranquility.
    As you sail in the best direction for the evening according to the wind, the current and the tide, your crew are happy to highlight points of interest along the way and answer any questions for you, as well as take your photo and serve up your drinks and complimentary cheese platter.
    As the sun dips beneath the horizon it's the perfect time to enjoy the colorful view, and shortly after dusk you will make your way leisurely back to the harbor so you can continue your evening in Key West.
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    Reviews (17)
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    All reviews high tide free spirit captain mark sunset sail in key west mel mate boats board crew
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    1 - 5 of 16 reviews
    Reviewed June 1, 2019 via mobile

    Very punctual and on time with everything. Captain and first mates were super professional and helpful. Would definitely go again!

    Date of experience: June 2019
    Thank Allen D
    Reviewed June 1, 2019

    We booked a private sunset cruise with this company after having another cruise with someone else the day before not show up. This second experience was no better - we took a ride share to Stock Island where the boat was located only to show...More

    Date of experience: June 2019
    1  Thank Michelle L
    Reviewed March 22, 2019 via mobile

    What a great sunset sail aboard the “When and If, a schooner commissioned by General Patton for his personal use. The boat is in excellent shape and the crew was amazing and knowledgeable, interacting graciously with all on board, even encouraging the guests to participate...More

    Thank karmaguy
    Reviewed March 15, 2019

    My husband and I booked a private sunset cruise on the Free Spirit, with the expectation of a quiet, romantic cruise. When we arrived we happen to walk past the When and If and noted the crews professional look with matching polo shirts. We arrived...More

    Date of experience: February 2019
    Thank jmmtk
    Reviewed February 4, 2019 via mobile

    I booked my husband and I a private sunset cruise on the High Tide. It was perfect. The crew was friendly and accommodating and we saw the most perfect sunset. Highly recommend this sailboat, company and crew.

    1  Thank ivonnelr62
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    Key Details
    • Sunset Sail Key West
    • Duration: 2h
    • Mobile Ticket Accepted
    • Instant confirmation
    • Languages Offered: English, Spanish
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