United States
Florida (FL)
Florida Keys
Key West
Things to Do in Key West
Sunset Sail Key West
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Sunset Sail Key West

See all things to do
See all things to do
Sunset Sail Key West
5
1,152 reviews
#37 of 342 Boat Tours & Water Sports in Key West
Scuba & Snorkelling • Boat Tours
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8:00 AM - 10:00 PM
Monday
8:00 AM - 10:00 PM
Tuesday
8:00 AM - 10:00 PM
Wednesday
8:00 AM - 10:00 PM
Thursday
8:00 AM - 10:00 PM
Friday
8:00 AM - 10:00 PM
Saturday
8:00 AM - 10:00 PM
Sunday
8:00 AM - 10:00 PM
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About
There's no better way to experience the Florida Keys than right on the water, and there's no better charter to trust with your tour than Sunset Sail Key West. With years of experience and a lifetime of passion, our fleet of locally owned sailboats and personable sailors will show you all the beauty that Key West has to offer. As you join us for a sunset, starlight, or snorkel sail, you'll find that the sparkling waters of the Florida Keys have a way of bringing people together. Our dedicated team is flexible, accommodating, and dedicated to making your sailing experience as smooth and personalized as possible.
Key West, Florida
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Travelers' Choice
2023
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Tours and Tickets by Sunset Sail Key West
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Detailed Reviews: Reviews order informed by descriptiveness of user-identified themes such as cleanliness, atmosphere, general tips and location information.
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5.0
1,153 reviews
Excellent
1,079
Very good
43
Average
11
Poor
9
Terrible
11
animlluvr
Pittsburgh, PA1,566 contributions
Great experience!!
May 2021 • Couples
My husband and I wanted to ride in a schooner on our latest trip to Key West. We booked a day cruise on the When and If Schooner but we were the only ones to book so they rescheduled us on a sunset cruise and honored the fare we paid for the day cruise. The crew was very informative and between the 3 of them had a ton of sailing experience. The ride on a the schooner was very cool! There was a nice breeze making it perfect for sailing. They offered alcoholic and non alcoholic beverages throughout the trip. It was very relaxing and more of an intimate experience versus the large party boats that go out and have music and dancing. We were looking to have a quieter more romantic evening and this was perfect! Highly recommend!
Review of: Sunset Sail on Historic Schooner in Key West
Written May 17, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
NewOrleansNola
Marrero, LA15 contributions
Sailing without a breeze
Jul 2021
It’s pretty tough to try and sail without any wind. But we all know it happens, so we made the best of it for two hours putting around looking for any wind movement we could find. It didn’t happen for us or anybody else out on the water that day. The High Tide is a small, comfortable sailboat with a crew of two and they were really great. These guys went above and beyond to make our little cruise as comfortable as they could. They were friendly and you could tell they loved their work. I would highly recommend the High Tide sailboat and crew for a fun time in Key West. My group of four were treated to a fantastic sunset, smooth ride, calm seas, and the only drawback was no breeze. This was our second booking on the High Tide and we’ll do it again on our next visit to Key West.
Written July 11, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Linda W
Virginia Beach, VA3 contributions
Smooth Sailing
Feb 2020
My husband, sister, brother-in-law and I wanted a personal sunset sail when visiting Key West at the end of February. We got exactly what we were hoping to find with Sunset Sail. We chartered the High Tide that holds up to six guests. We were in extremely capable hands with our very experienced captain and his mate who shared information and entertaining stories about life in Key West. Waters, ice and soft drinks are provided. Bring your own choice of wine/beer/liquor and favorite snacks and you are set for a great evening! Day tours are also available.
Written May 5, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Nicolas R
1 contribution
Absolutely Amazing Sunset Sail on Gen. Patton’s “When and If”
Dec 2021
Absolutely amazing experience! Went with a family group of four people and had the best time. The sunset sail was incredible. The crew were extremely professional, extremely approachable, and made sure that everyone was comfortable, safe, and having a good time. This is a sail boat and we went on a particularly windy day, but the expert captaining by Jack showed in how little sea spray there was. Nonetheless, expect to get at least a little wet and for the boat to rise and fall with the waves. The price is unbeatable, especially because you sail not from downtown Key West but a little north of there and have the seas - and the views and photos - absolutely all to yourselves. No other sail boats or vessels in sight and incredible views of the sunset. We highly, highly recommend the sunset sail!
Written December 18, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
LisaD
Grand Rapids, MI47 contributions
Private sunset sail for 6
Mar 2022 • Couples
Amazing private group sunset sail with our captain, Eric, and first mate Kasey (and trainee Luann)! We booked this trip for our family of 6 and fit comfortably aboard the sailboat (fits up to 12; 6 adults was honestly perfect plus the crew). The sunset was gorgeous and most of our group had never been aboard a sailboat so it was a real treat! The private group booking was no more expensive than doing one of the Key West dinner/drinks sunset sails and for our group we found it to be perfect (no dinner, but water and soft drinks provided plus a cooler with ice, and you can bring your own alcohol and food if you want). We had a perfect evening!
Written March 5, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
O2954WGkristina
Las Vegas, NV1 contribution
The boat was beautiful... Save yourself the $100/pp and read about it online.
Jan 2022
Outside of the boat having a tremendous history, which I'm sure can been found online, the sail was lack luster. We had to bring our own beverages (proprietary wine was offered) and food. Although I am a dog person, there was a dog on the boat running around unleashed barking and jumping into peoples laps. For people with pet allergies, this was quite inconsiderate.

There was little to no engagement from the staff to the sailors.

I do tend to take a sunset cruise where ever I go on vacation; Caribbean (20yrs), Amsterdam, Paris, Africa, China, Thailand, Russia and more...

Save yourself the $100/pp and read about it online.
Written January 24, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
willys1945
Illinois476 contributions
Best 2 Hours spent in Key West
Jan 2021
Rarely does a crew member make a sunset cruise so enjoyable. Captain Kayla was absolutely delightful, skillful at her job, shared immense knowledge the vessel and surrounding area and what it is like to sail the When and If to Boston and back. The When and If is a great boat with tremendous history. There was tons of room for the 15 guests. I wish I could post photos.
Written January 23, 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
BostonArmywife
Boston8 contributions
A perfect sailing adventure
Feb 2023 • Couples
We took a 2 hour day sail on the When and If and it was the highlight of our vacation this year. The captain and her crew were great, sharing the history of the schooner and details about the local area, all while skillfully handling this beautiful boat and serving us drinks. History lovers will appreciate the stories of her past, how she came to be built, her owners, and the tragedy that ultimately led her to where she is today. We were fortunate to have perfect weather with bright sun and a light breeze but I think this could be a lot of fun in stronger wind too. We felt the pricing was very reasonable compared to some of the others in Key West and a great value. I can't recommend this adventure enough and can't wait to do it again, whether in Key West or Salem.
Written February 2, 2023
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Shannon P
1 contribution
I was lied to
Feb 2022
I was worried I would arrive late to my sailing so I contacted the office. I spoke to a very kind gentlemen that reassured me they could wait a few extra minutes and to come on. I was happy to see that my GPS was wrong and I was only going to be 6 minutes late to the dock. When it was 5:00, I contacted the office again and he was very kind once again. He told me he would be passing my number on to the crew so they could contact me directly. Almost as soon as I hung out my phone range, I missed the call because I was turning into the marina. I called the number back 1 minute later. It was someone from the vessel, I believe his name was Jeff. I told him I was arriving but that it would take me a few minutes to walk to the dock and if I was creating a burden I didn’t want to hold them up. He said that “everyone was checked in and they had all had their safety spill.” I said, okay. Just go ahead without me and thankyou for the call. I then proceeded to put my car in park and walk to the dock anyway. I had intended to leave a cash tip for the crew. I knew I had taken a spot from the boat, and I didn’t want them to miss out on tips. However, when I arrived at the dock I encountered a very sweet, but very frustrated couple. They had also been left. The were just a few minutes late as well. I was angered by the situation at this point. The person who called me from the boat literally told me EVERYONE was on board! That was a lie. Had I known that he was missing other passengers, I would have easily made it to the boat by asking for an extra 2 minutes to walk there. I contacted the office immediately and explained my frustration. The office staff talked in circles. They told me no refund would be issued and said no one had lied to me. I am appalled by how this business treated me and how they spoke so ugly to the sweet couple with me.
Written February 20, 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
Rick H
Anderson, SC5 contributions
Afternoon Sail
Sep 2020 • Couples
What a wonderful afternoon! We sail and wanted to go out and experience sailing beautiful Key West. The crew customized the sail to fit our desires and created a very memorable vacation adventure. From initial contact through docking at the end of the sail, we were treated spectacularly with the utmost professionalism! Thank you for a very memorable afternoon.
Written September 6, 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.
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