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Top Key West Sunset Cruises

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  • Islamorada
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  • Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Key West Wind & Wine Sunset Sail

    52

    The Wind & Wine Key West Sunset Sail has been honored with a #1 rating on Trip Advisor three years running....
    Read More

     2 Hours (approx.)
    Best Rate
    $85
    Details
    Best Rate
    $85
    Details
  • Key West Sunset Harbor Cruise

    11

    ...
    Read More

     2 Hours (approx.)
    Best Rate
    $75
    Details
    Best Rate
    $75
    Details
  • Key West Sunset Cruise with Live Island Music

    80

    Come sail along on an ocean breeze and enjoy some of Key West’s best musicians performing live to the backdrop of the setting sun. You’ll...
    Read More

     2 hours  Instant Confirmation
    from
    $63
    Details
    from
    $63
    Details
  • Key West Sunset Dinner Cruise with Tropical Buffet

    92

    Join us for Key West's Best Sunset Dinner Cruise. This 2 Hour trip Includes an amazing tropical food buffet, live music and open well bar....
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     2 hours  Instant Confirmation
    from
    $67.65
    Details
    from
    $67.65
    Details
  • Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Key West Sunset Sail Aboard Schooner

    19

    Enjoy an exquisite 2-hour sunset sailing adventure aboard a stunning modern-built schooner! Take in the sights aboard Schooner America 2.0, the most elegant schooner in Key...
    Read More

     2 hours  Instant Confirmation
    from
    $103.20
    Details
    from
    $103.20
    Details
  • Key West Glass-Bottom Boat Tour with Sunset Option

    85

    See the only living coral barrier reef in the continental United States on this two-hour glass-bottom boat tour from Key West! As you relax on...
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     2 hours  Instant Confirmation
    from
    $49.77
    Details
    from
    $49.77
    Details
  • Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Small-Group Key West Sunset Sail with Wine

    22

    Cruise into the sunset with wines from all around the world, imported and domestic beers as well as hors d'oeuvres. This cruise is great for...
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     2 hours  Instant Confirmation
    from
    $91.38
    Details
    from
    $91.38
    Details
  • Key West Sunset and Cocktail Cruise

    13

    “The Key West Cocktail Cruise is the best thing to happen to Sunsets since cameras and sunglasses!”This is not your average Key West pleasure cruise....
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     2 hours  Instant Confirmation
    from
    $60
    Details
    from
    $60
    Details
  • Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.

    Sunset Sail in Key West with Beverages Included

    38

    Key West is famous for fabulous sunsets and Floridays is famous for our spectacular uncrowded champagne sunset cruise. Our reputation for personal service and attention...
    Read More

     1 hour 30 minutes  Instant Confirmation
    from
    $61.46
    Details
    from
    $61.46
    Details
  • 2-Hour Private Sunset Cruise around Key West

    1

    This is the only 2 hour sunset cruise in Key West that provides a private guided tour around the island.Sit back and relax while your...
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     2 hours  Instant Confirmation
    from
    $200
    Details
    from
    $200
    Details
  • Private Sunset Boat Charter Key West

    1

    Enjoy a private 2 hour sunset cruise in Key West with your family and friends. Sit back and relax while your Captain points out all...
    Read More

     2 hours  Instant Confirmation
    from
    $200
    Details
    from
    $200
    Details
  • 2-Hour Private Sunset Cruise on Tiki Bar Boat in Key West

    1

    Key West is famous for it's sunsets and it doesn't get any better then on a private sunset cruise aboard our custom tiki bar boats....
    Read More

     2 hours  Instant Confirmation
    from
    $456.88
    Details
    from
    $456.88
    Details
  • Private Sunset Cruise Featuring Duck Key

    Duck Key is known for having some of the bluest water in the Keys and we operate the only Sunset Cruise from the beautiful tropical...
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     1 hour 30 minutes  Instant Confirmation
    from
    $345
    Details
    from
    $345
    Details
  • Key West Sunset Booze Cruise with Unlimited Draft Beer and Wine

    3

    Key West Sunset Cruise with Live Music, Unlimited Beer & Wine. Join Sunset Watersports out on the water on our custom 65 foot catamaran for...
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     2 hours  Instant Confirmation
    Details
    Details
  • Key West Wind & Wine Private Charter

    1

    The Wind & Wine Key West Sunset Sail has been honored with a #1 rating on Trip Advisor three years running. See the sunset on...
    Read More

     2.5 Hours (approx.)
    Best Rate
    $2,500
    Details
    Best Rate
    $2,500
    Details

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