Key West Sunset Cocktail Cruise

From Key West, to Maui, to Tahiti and beyond, the sunset cocktail cruise is a tropical vacation resort staple. Some may even claim that it has been overdone… maybe they want to brush the experience off as “too touristy” or “just for old folks” or “boring”. The way I see it, after years of living right at beachfront Waikiki, along with visits to Key West, remote islands in the Philippines, and a variety of quite nice spots in southern Thailand, this is a lack of wisdom talking. Because the fact is, if only one were able to, it would be perfectly right and proper to cruise out on a beautiful sailboat for a sundowner each and every single evening! In fact, I would like to make it a requirement.

A good sunset cruise is something really special, and it makes for an unforgettable experience. Something about the tropical evening sky brings people together in a shared experience of nature’s grandeur. Sunset over the sea in tropic climes is an event that is celebrated at far-flung spots around the world, from Mallory Square in Key West, to Kalakaua Avenue in Waikiki, out to the beaches of Ko Tao Thailand. It is only that much better when viewed from the water, with no obstructing buildings, traffic noise, or pavement heat to mar the mood. For lovers, wine lovers, and sailors, a Key West Wind and Wine sunset sail is definitely a vacation must-do, and Cool Key West is happy to be able to offer a Key West sunset cocktail cruise that is a truly upscale experience, with a small party on a lovely sailboat, a variety of fine wines and champagne, quality craft beers, and delicious hors d’oeuvres.

You will depart the harbor on a graceful schooner as evening lowers. The gentle breezes and lapping of the blue water calm the heat of the day as the sky begins to color, and you lift your glass with loved ones and new friends to celebrate the good fortune of being in this unique moment. The sun seems to pause as it hangs just over the horizon, and you become conscious of the movement of the boat as it slips almost silently through the light chop stirred by the evening breeze. Just as the red disk touches the water or the lowering clouds flame where they meet the sea, the party goes silent except for the sound of cameras, and couples pull each other close. This moment, though seemingly far less active and exciting than many of the other activities you will engage in during your Key West visit, is one that will stay with you for years.

Now, for those who are in the mood or of the persuasion for something a bit more along the lines of a party cruise, with a bigger crowd, louder music, and stronger drinks, that can be done too. Maybe start the evening with some dancing, or dinner out on the water? Everything is possible with Cool Key West as your sunset cruise hook up. It might even be a good idea to try several cruises and avoid the risk of missing out on anything.

Just go to Cool Key West and click on Key West Sunset Cruises. Everything you need to know is right there, and booking is simple and secure. Do it from your mobile device for the ultimate in convenience. You only live once, so don’t wait – treat yourself to an on-the-water happy hour combined with the famed Key West sunset on a Key West Sunset Cocktail Cruise.

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  • Key West Sunset Champagne Cruise

    Key West Sunset Champagne Cruise

    Watch the famous Key West sunset on a 1.5-hour catamaran cruise. While you enjoy twilight views of the sea as the sun goes down, enjoy...
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     90 minutes (approx.)  Free Cancellation  Instant Confirmation
    Best Rate
    $49.95
    Details
    Best Rate
    $49.95
    Details
  • Key West Sunset Snorkel Sail
    Likely to Sell Out

    Key West Sunset Snorkel Sail

    Enjoy this 3 hour sunset combo trip. We will cruise out to Key West’s best reef location, where you are welcome to jump in and...
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     3 hours  Free Cancellation  Instant Confirmation
    from
    $56.95
    Details
    from
    $56.95
    Details
  • Key West Dolphin Watch Sunset Snorkel Cruise
    Likely to Sell Out

    Key West Dolphin Watch Sunset Snorkel Cruise

    The Cool Key West Dolphin watch triple combo is the best way to watch Dolphins, Snorkel the Key West tropical waters, and see the world...
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     3 hours  Free Cancellation  Instant Confirmation
    from
    $64.95
    Details
    from
    $64.95
    Details
  • Key West Sunset Sail with Champagne, Hors D’oeuvres and Full Bar

    Key West Sunset Sail with Champagne, Hors D’oeuvres and Full Bar

    Admire an exquisitely painted sky during this premium sunset cruise in Key West. Create fantastic memories as you set sail on a modern sailing catamaran...
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     2 hours  Free Cancellation  Instant Confirmation
    Best Rate
    $79.95
    Details
    Best Rate
    $79.95
    Details
  • Sunset Sip & Sail
    Likely to Sell Out

    Sunset Sip & Sail

    Sunset Sip & Sail: Come see the legendary Key West Sunset on a Brand New Catamaran Sail Boat. • Open bar • Live Music •...
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     2 hours  Free Cancellation
    from
    $79.95
    Details
    from
    $79.95
    Details
  • Key West Sunset Harbor Cruise with Premium Drinks, Hors-d’oeuvres and FREE shuttle to location
    Special Offer

    Key West Sunset Harbor Cruise with Premium Drinks, Hors-d’oeuvres and FREE shuttle to location

    Looking for the perfect way to end your day? Join us aboard a 45ft Corinthian powercat, and ride in comfort with this relaxing, catered cruise...
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     2 Hours (approx.)  Hotel pickup offered  Free Cancellation  Instant Confirmation
    $99
    $89
    Details
    $99
    $89
    Details
  • Key West Catamaran Dolphin Watch & Sunset Sail

    Key West Catamaran Dolphin Watch & Sunset Sail

    Set sail from Key West's Historic Seaport for a thrilling dolphin watch and famous Key West sunset sail aboard a luxury catamaran with premium wines...
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     2 hours 30 minutes  Free Cancellation  Instant Confirmation
    Best Rate
    $89.95
    Details
    Best Rate
    $89.95
    Details
  • Key West Sunset Dinner Cruise
    Likely to Sell Out

    Key West Sunset Dinner Cruise

    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  Free Cancellation  Instant Confirmation
    from
    $92.95
    Details
    from
    $92.95
    Details
  • Key West Wind & Wine Sunset Sail
    Likely to Sell Out
    Top10Top 10 Tour Ranked using exclusive Cool Key West data that may include activity quality, traveler reviews, overall popularity, and availability.

    Key West Wind & Wine Sunset Sail

    The Wind & Wine Key West Sunset Sail has been honored with a #1 rating on Cool Key West three years running....
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     2 Hours (approx.)  Free Cancellation  Instant Confirmation
    $109
    $99
    Details
    $109
    $99
    Details
  • Key West Schooner Sunset Sail with Hors D’oeuvres and Full Bar

    Key West Schooner Sunset Sail with Hors D’oeuvres and Full Bar

    Meet for this Key West Sunset Sail at the Key West Historic Harbor. Board a beautiful bugeye schooner, and get acquainted with your captain and...
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     2 hours  Free Cancellation  Instant Confirmation
    Best Rate
    $99.95
    Details
    Best Rate
    $99.95
    Details
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