Key West's Original Watersport Company
Lowest Price Guaranteed 855-378-6386
Key West's Original Watersport Company
Lowest Price Guaranteed 855-378-6386

Sunset Sip & Sail Key West

(11 Reviews)
Sunset Sail
Sunset Sail
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Why Book With Us?

  • LOWEST price in Key West
  • Award Winning Key West Watersport Company
  • Over 33 Years in Key West
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We offer Key West’s Best Watersport trips & tours for the LOWEST price, guaranteed!


2 Hours
201 Williams St Key West FL 33040
Max People : 38
Tour Details

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Departure & Return Location

John F.K. International Airport (Google Map)

Departure Time


Check-in at 5:30

Price Includes

  • Air fares
  • 3 Nights Hotel Accomodation
  • Tour Guide
  • Entrance Fees
  • All transportation in destination location
What to Expect

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Ask A Guest

Tell Us About Your TripThe Key West Sunset Sip & Sail

11 Reviews
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Couple Traveller

What an Amazing Time

Our captain was fantastic. The crew made the experience so much fun with their friendly, funny and carefree island personalities. My husband and I enjoyed to view from the boat. He very much enjoyed the sailing. Drinks and appetizers were good. You can upgrade to top shelf drinks for only $3-5 a drink, but we were happy with was was included. We definitely recommend this! Thank you for a great evening in Key West!

October 24, 2018


Couple Traveller

I have no words to completely describe our experience with sunset as a company. We had a day in key west and wanted to have the most with what we had. After our concierge recommendation, with no investigating of our own, we decided to book a jet ski tour and the sip n sail cruise. Let me tell ya… they were both the most amazing experiences ever.

The sunset sip n sail cruise was just as amazing. Captain Andy, the staff and the band made the cruise, as if the water and the boat weren’t enough. With just a day in Key West, we were so, so pleased with the experience we had. They took the time to make us feel special and welcome. I can not describe to you how great it was to be on board this cruise.

Overall, I would never tell you to even explore other options. There are no other options. This was the best experience we could have had in the day we were there. I can’t wait to go back and wouldn’t even think to look at any other company. Sunset Watersports exceeded our expectations and the staff was even better.

October 17, 2018

Steven from Florida

Group Traveller

So much fun we had to do it TWICE!!

We had a great time that afternoon on our snorkeling adventure. Captain and crew made sure that everyone had fun and took care of our surroundings. The afternoon was full of laughter so much so that we decided to come back later that day for the sip and sail.

This was my favorite trip! The drinks, live music and views were top notch! What a way to end our trip to the Florida keys! Thanks so much for being so welcoming! Sunset Water Sports hang on the those fellas!! They make the trip worth going again.

October 7, 2018


Family Traveller

We were a party of 6 older adults that went on the Sip N Sail sunset cruise on the Sandie Cat. Captain and crew made this trip very enjoyable. It was niceand breezy out and this sailing catamaran was zipping along. The cloud coverage was perfect to illuminate the skyline for one of the most memorable sunset’s we have ever seen.

I think there were only about 18 passengers on this trip, so it was close to being a private tour. We were SO glad that we went with the Sip N Sail trip with Sunset Watersports.

Thanks Sunset and Captain and crew for a very enjoyable cruise.

September 16, 2018


Couple Traveller

The sailing experience and the sunset were spectacular! The crew involved guests who volunteered to help hoist the sail and while always being safety conscious, the Capt. even gave me some time at the helm. Capt. is a real professional as well as very kind and hospitable.

This Cat. has the tallest mast in the harbor and really sails well. The drinks and music were great. To me, the Sunset Sip and Sail is a “don’t miss” when you visit Key West

September 4, 2018