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Sunset Sail Key West

Features Animals
Opens in 15 min: 8:00 a.m. - 10:00 p.m.
Open today: 8:00 a.m. - 10:00 p.m.
Book In Advance
Tours from Sunset Sail Key West tend to sell out - travellers recommend booking in advance!
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Certificate of Excellence
Traveller Overview
  • Excellent94%
  • Very good3%
  • Average1%
  • Poor1%
  • Terrible1%
Travellers talk about
“high tide”(84 reviews)
“conch west”(23 reviews)
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...more
Opens in 15 min
Hours Today: 8:00 a.m. - 10:00 p.m.
See all hours
Suggested duration: 2-3 hours
Contact
202 William St, Key West, FL 33040-6645
Website
+1 305-587-4488
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Ways to Experience Sunset Sail Key West
from US$394.99
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from US$294.99
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from US$79.00
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Reviews (577)
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Show reviews that mention
All reviews high tide conch west general patton private charter beautiful boat wine and cheese highly recommend this experience perfect evening green flash great company captain and crew crackers highlight of our trip an amazing experience great trip laid back these guys
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1 - 10 of 570 reviews
Reviewed yesterday

As an avid sailor I was horrified to see the typical "sunset sails" from the sunset celebration on shore. Huge catamarans literally packed full of people with a single sail up and clearly motoring, with the sail luffing. I'm so glad we didn't end up...More

Date of experience: December 2018
Thank Jason Q
Reviewed 3 days ago

We went on an evening sail on the Schooner, When and If. She is a beautiful wooden boat, the kind you would dream about. Unfortunately, we went out on an evening when a cold front had passed through and the winds were steady at 25-30...More

Review collected in partnership with this attraction
Date of experience: December 2018
Thank Charles J
Reviewed 5 days ago

Captain and crew were knowledgeable about the boat's history and Key West. We had a terrific sail, racing at 9 knots around the Naval Air Station.

Review collected in partnership with this attraction
Date of experience: November 2018
1  Thank frankypat
Reviewed 1 week ago

We find snorkeling in Key West to be hit or miss in winter as the winds and cold fronts pushing thru can stir up the water and reduce visibility. And the crowds on the bigger boats can be less fun. So this trip we booked...More

Date of experience: December 2018
Thank katek01
Reviewed 1 week ago

We did a private sunset sail on the High Tide to celebrate an anniversary last week. I unfortunately didn't catch our captain's name, but both he and Kelly were awesome. We lucked out and had great weather and a great sunset, but either way I...More

Date of experience: November 2018
Thank CJinMD
Reviewed 1 week ago

The sailboat was beautiful. The crew was friendly. One of the guys even fixed my purse strap with a sailors knot and took pictures for us. Good luck on the circumnavigation!

Review collected in partnership with this attraction
Date of experience: November 2018
Thank Go46352748284
Reviewed 2 weeks ago

Great sunset cruise! Friendly crew, cooler full of ice, even saw dolphins. Highly recommend the High Tide.

Review collected in partnership with this attraction
Date of experience: November 2018
Thank Journey10300079904
Reviewed 2 weeks ago

Our sunset sail on the “ When and If” was one of the highlights of our vacation to Key West. The crew were very attentive. A wonderful sail on a very historic boat. Highly recommend!!

Review collected in partnership with this attraction
Date of experience: November 2018
1  Thank Sherpa04213727739
Reviewed 2 weeks ago

We really enjoyed this unique sunset experience. The boat is beautiful and super well maintained. Not too many people on the boat. The team was great: pro and passionate. We recommend, even with kids!

Review collected in partnership with this attraction
Date of experience: November 2018
1  Thank Curiosity61802095802
Reviewed 2 weeks ago

In 6 years, we've been on just about every sailboat in Key West and the "When and If" boat and crew were absolutely the best.

Review collected in partnership with this attraction
Date of experience: November 2018
1  Thank Jane P
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Questions & Answers
Ask a question
chriscK6902HQ
September 6, 2018|
AnswerShow all 3 answers
Response from SethSalzmann | Property representative |
Hi Chris, To answer your questions, Yes we definitely do stay out for the full sunset! We usually like to schedule our sails so that you get 20-30 minutes of the afterglow as we sail back to the harbor. We prefer sailing to... More
0
Votes
Dayc2
June 25, 2018|
AnswerShow all 6 answers
Response from SethSalzmann | Property representative |
Comfortable and relaxed is the only requirement!
0
Votes
amarieb22
November 23, 2017|
AnswerShow all 2 answers
Response from SethSalzmann | Property representative |
If you book through TripAdvisor each private sail for up to six people is shown as (1). It's just so you don't get charged 4 times. You can just book 1 or give us a call to sort it out. Thanks for asking!
0
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