Private Key West Sunset Sail

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based on 45 reviews
  • Duration:2 hours (approx.)
  • Location: Key West, Florida
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2 Hr. Private charter sailing from downtown Key West onboard Key West's First sailing charter boat, the pretty green sloop "High Tide"
USCG Certified for up to 12 passengers, the Sloop High Tide and Sunset Sail Key West make for the perfect Key West sunset sail
Peaceful, private and exclusive!
Your captain and mate will take you out to watch the sunset from your own private classic sailing vessel, with soft drinks, bottled water and coolers stocked with ice provided for any adult beverages you choose to bring.
Reserve ahead, there is after all, only one High Tide sunset sail per day!
Price is for up to 6 guests, 12 guests max!.


WHAT'S INCLUDED

WHAT TO EXPECT

ADDITIONAL INFO

CANCELLATION POLICY

Posted By : MBGChicago
Had a lovely time out on the water off the historic Key West port, aboard the 33 foot High Tide. Harley and Casey were wonderful hosts, and were very knowledgable about the local waters. We were provided with plenty of ice, water, and soft drinks during our sunset sail, and thoroughly enjoyed our time under sail. The cheese platter was a nice little nosh while taking in the scenery. Thanks again for all your skill and hospitality!
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Posted On : 2024-05-06 21:36:42 full ratings


Posted By : jameyandjaime
We took our grandmother on a sunset sailing for her 85th Birthday. We were on High Tide with Harley and Casey. They made the trip so wonderful. We all had an amazing time. And that was due to them. They made sure we saw the sunset perfectly. Truly a wonderful experience. We would highly recommend this sailing to anyone!
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Posted On : 2024-04-14 15:32:02 full ratings


Posted By : xcone
I wanted a sail that was just that, a sail, not a booze cruise or snorkel or sunset sail. They gave me exactly what I was looking for. We spent 4 hours cruising in 12 to 15 knot winds on a beautiful day. The crew, Logan and Hannah were an absolute delight and allowed me to help work and sail the boat a Glander 33. The website wasn’t very clear about what they provided in terms of snacks and liquids but that wasn’t the fault of the crew. The only recommendation I have is that it is time for a new set of sails.
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Posted On : 2023-11-08 23:02:50 full ratings


Posted By : Grimwol
Before I start this I want to personally thank the Captain and Mate for taking our reservation at last minute and making my wife's birthday memorable!

We started our evening out under smooth waters of the Florida Keys and passed Mallory Square, the captain told us lots of stories about the history of the area and pointed out landmarks and we had a great time talking! A short time later we got to see the Navy Seals training from a helicopter on our way out to sea so that was a treat to say the least. We kept going out and was lulled into silence with the stunning sunset over the stunning water. It looked like it was out of a fairy tale. When the sun went down and we turned to go home we were met with another stunning view. The moon had risen was full over the waters overlooking Key West. It was so beautiful it could make you cry. I think this is the first time I was sad that something was over. This is most assuredly something that I would want to do again!
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Posted On : 2023-09-30 05:10:16 full ratings


Posted By : yvonnes311
Great private sunset cruise on High Tide sailboat. They kept us out of the rain and it was fun to see where the rain was falling all around us while we stayed dry. We ordered the cheese tray and brought wine. I was impressed with the cheese tray, expensive cheeses plus prosciutto and salami. They supplied water, sodas and seltzer. We would have paid a similar price for our family to do the large party public sunset sail -50 plus people on the boat. This was much nicer for us. Joe and Mark were our captains. Great guides!
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Posted On : 2023-08-20 09:44:40 full ratings


Posted By : ericlN7829KB
When we found out we had an all woman crew we were excited. Jade (Captain) & Tabitha (mate) made our memorial cruise, peaceful and fun for our family. We couldn't have asked for a better send off for our friend.
Thanks Eric and Michael
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Posted On : 2023-07-26 21:39:24 full ratings


Posted By : sarahbD8167IM
What an experience! Logan was a wonderful captain! Tabitha made sure we were having a great time. The boat was beautiful and held our group of 10 comfortably. The conversation was wonderful. There is no better way to see the beautiful Key West sunset. Highly recommend this private sail!
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Posted On : 2023-07-03 17:06:35 full ratings


Posted By : szymons475
I recently proposed to my girlfriend on the sunset sail and it couldn’t have been a better experience. The Captain Dan and his mate Tabitha took really good care of us and made the moment truly special. There is no better way in Key West to watch the sunset and I would definitely recommend the trip.
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Posted On : 2023-04-21 12:42:50 full ratings


Posted By : stevehU6526BF
Captain Dan and First Mate Puck (too many Jeff’s in Key West, so he christened himself Puck) were friendly, fun, and first rate sailors. Spectacular sunset sail. Definitely a five star experience. Six stars, if the scale allowed!

Steve and Nancy H
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Posted On : 2023-04-14 19:03:29 full ratings


Posted By : laurenandjimbooker
I got a private sunset sail for my hubbys birthday. The boat was beautiful and the crew were friendly and fun. I highly recommend using this company.
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Posted On : 2022-07-17 12:04:53 full ratings