We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Sunset Sail Key West

Features Animals
Closed Now: 8:00 AM - 10:00 PM
Open today: 8:00 AM - 10:00 PM
Book In Advance
Tours from Sunset Sail Key West tend to sell out - travelers recommend booking in advance!
239
All photos (239)
Full view
Certificate of Excellence
Traveler Overview
  • Excellent94%
  • Very good3%
  • Average1%
  • Poor1%
  • Terrible1%
Travelers talk about
“high tide”(85 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
Closed Now
Hours Today: 8:00 AM - 10:00 PM
See all hours
Suggested duration: 2-3 hours
Contact
202 William St, Key West, FL 33040-6645
Website
+1 305-587-4488
Call
Improve This Listing
Ways to Experience Sunset Sail Key West
from $394.99
More Info
from $294.99
More Info
from $79.00
More Info
Reviews (577)
Filter reviews
570 results
Traveler rating
541
21
2
4
2
Traveler type
Time of year
LanguageEnglish
More languages
541
21
2
4
2
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 captain and crew green flash great company crackers highlight of our trip an amazing experience great trip laid back these guys
FilterEnglish
Updating list...
1 - 10 of 570 reviews
Reviewed 6 days ago

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 1 week 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 1 week 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 2 weeks 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 2 weeks 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 2 weeks 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 3 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 3 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 3 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
View more reviews
Nearby
Nearby HotelsSee all 51 nearby hotels
The Marker Waterfront Resort
1,879 reviews
.04 miles away
The Galleon Resort And Marina
556 reviews
.16 miles away
Cypress House Hotel : Key West
564 reviews
.17 miles away
Hyatt Centric Key West Resort and Spa
2,719 reviews
.22 miles away
Nearby RestaurantsSee all 480 nearby restaurants
Prime Steakhouse
697 reviews
.16 miles away
Fisherman's Cafe
253 reviews
.06 miles away
Cuban Coffee Queen
2,585 reviews
.09 miles away
Kermit's Key West Key Lime Shoppe
2,512 reviews
.08 miles away
Nearby AttractionsSee all 738 nearby attractions
Island Time Charters
47 reviews
.01 miles away
Key West Historic Seaport
613 reviews
.05 miles away
​​​​​​​​​Key West Turtle Museum
44 reviews
.09 miles away
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
Votes