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Sunset Sail Cruise in Key West

Badge of ExcellenceKey West, USA
Sunset Cruise Sail Key West
  • 2 hours
  • Mobile ticket
  • Offered in: English

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Overview

While most boat tours travel on small private vessels or luxury yachts, this sunset cruise takes travelers around Key West on Jolly II Rover, the only square-rigged, topsail schooner in the area. Board your ship at the historic Seaport at the corner of Elizabeth and Greene streets and sail out to see some of Key West’s best sights, including the Man O War Harbor, Christmas Tree Island, Fort Taylor, and others.
  • A sunset sailing cruise around the island of Key West
  • Sail on a vintage squared rigged, topsail schooner with red sails
  • Views of the Man O War Harbor, Christmas Tree Island, Fort Taylor, and more
  • Includes snacks and on-board coolers of ice with cups and bottled water

What's Included

  • Sunset Sail
  • Snacks
  • Coolers of ice with cups and bottled water
  • Alcoholic Beverages
  • Soda/Pop

Meeting and Pickup

Meeting point

  • 631 Greene St, Key West, FL 33040, USA

    15 minutes before sailing time - In the Historic Seaport at the corner of Elizabeth and Greene streets. At the ticket booth on the dock along side the Conch Republic Seafood Company Restaurant.

End point

This activity ends back at the meeting point.

What To Expect

Schooner Jolly II Rover

2 hours • Admission Ticket Free

Additional Info

  • Confirmation will be received at time of booking
  • Not wheelchair accessible
  • Stroller accessible
  • Service animals allowed
  • Near public transportation
  • Infants must sit on laps
  • Most travelers can participate
  • There is no wheelchair ramp but we will do out best to accommodate wheelchair passengers.
  • This tour/activity will have a maximum of 41 travelers

Cancellation Policy

You can cancel up to 24 hours in advance of the experience for a full refund.

  • For a full refund, you must cancel at least 24 hours before the experience’s start time.
  • If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
  • Any changes made less than 24 hours before the experience’s start time will not be accepted.
  • Cut-off times are based on the experience’s local time.
  • This experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.
  • This experience requires a minimum number of travelers. If it’s canceled because the minimum isn’t met, you’ll be offered a different date/experience or a full refund.

Traveler Photos

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Featured review
James_C
Although we had little to no wind for the sails ,evening weather was beautiful along with the fabulous sunset! Very peaceful enjoyable evening and crew and Captain were magnificent and very knowledgeable! Would definitely do again!

Reviews

5.0
163 reviews
Total review count and overall rating based on Viator and Tripadvisor reviews
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Reviews by Viator travelers.
Showing 1-10 of 163 reviews
Really cool!
Joy_D, Apr 2024
Enjoyed the sail for many reasons - Fun, beautiful, entertaining! The crew made it fun! And the scenery is of course GORGEOUS!!
Awesome sailing experience
Susan_P, Apr 2024
First time in Key West and my son planned this trip for us. It was perfect. Gorgeous weather and our first time on a sailboat. It was amazing. I would highly recommend this excursion for anyone who wants a relaxing sunset experience on the water. Watching the staff shoot the canon was fun too! Crew was awesome!
Great time.
Erin_F, Apr 2024
Lots of fun. I would recommend this trip for families or couples that want to be on a beautiful boat. They let the kiddos have a turn sailing it. What fun.
It’s the perfect romantic...
Kourtney_T, Apr 2024
It’s the perfect romantic date or wedding proposal having the sunset and getting to propose in the captains spot and they helped by taking our picture it was amazing everyone one was super sweet and helpful
Enjoyable evening with a...
Carlyle_H, Mar 2024
Enjoyable evening with a friendly crew. They took time to talk with guests, answer questions and make sure everyone was ok and having a good time. The cannon shooting was fun. Saw some dolphins, no sunset because it was cloudy but a nice ride anyway.
Wonderful experience!
Jan_G, Mar 2024
Great crew. Beautiful sunset. Great view of Key West & surrounding areas.learned a lot about sailing.
We will do this trip again, guaranteed!
Keith_G, Feb 2024
The crew was amazing to watch in action and explained everything about the process. Got to see dolphins too.
Amazing trip. Highly recommend!
Steven_M, Feb 2024
Amazing trip. We have never been on a ship with this many sails. Watching the crew maneuver and coordinate was very interesting. Of course the sunset was also unforgettable!
Sunset magnifico!
James_C, Feb 2024
Although we had little to no wind for the sails ,evening weather was beautiful along with the fabulous sunset! Very peaceful enjoyable evening and crew and Captain were magnificent and very knowledgeable! Would definitely do again!
Anniversary Sunset Cruise
William_P, Jan 2024
Our 40th Anniversary. The crew was absolutely incredible! They were very conscious of our needs, safety, and they knew have to have fun!
Booked a cruise for...
Laura_C, Dec 2023
Booked a cruise for 515pm. From the second after I booked the reservation someone.was calling me saying that the boat was leaving by 4pm. I feel like they consolidated the number of trips this evening and sis not have the 515pm trip. Someone kept.calling me and rushing me and as soon as I finally found parking. I received another phone calls stating we cant wait Any longer and that they were leaving. Horrible.service!
Great sunset ride
Cara_G, Dec 2023
The crew are great and made a difference over other boats we have been on. The boat is nice, ride is smooth. Cannon was a nice touch. Highly recommend.
Worth doing over and over and over again.
Jennifer_S, Oct 2023
From start to finish, each moment was memorable for sure. The crew was amazing. So much fun watching them in action and then mingling with us. So peaceful and quiet. No music and just snacks and water were served. If you wanted to bring something yourself you could. But trust me, that was enough. We were out there to sail, not party. From the firing of the canon to the famous sunset, it could not have been better.
Spectacular sunset views
karlynn_r, Sep 2023
The sunset cruise was great . It was peaceful with no loud music and we weren’t crowded with lots and lots of people. The crew were super nice . I would 100% go on this again .
Nice trip bad info Viator
Joep_P, Sep 2023
It was a great cruise the only problem was that Viator messed it up by telling us it started at 5:15 pm wearers it started 45 minutes later. On the boat they told us that Viator was not able to correct this and that it happened all the time.
Response from Host, Sep 2023
Hello - Thanks for choosing to sail with us. Was a beautiful evening and nice getting a chance to meet you. Thank you very much for this 5 star rating! Very much appreciated! We will work with Viator to correct the starting time error. Hope to see you all onboard with us again. Sincerely, Bill Malone/owner
Perfect Night!!
Susan_D, Sep 2023
This was an incredible voyage! The caption was throughly entertaining and informative and crew delightful. The captain spinned the schooner around multiple times for everyone to get the perfect sunset picture. The owner was aboard too and added depth and knowledge. It was only my 2nd time sailing and our 31st anniversary. Simply fabulous! We will be back!!!
Jolly II Rover Sunset Sail 5/17/23
Meira_D, May 2023
The crew was wonderful and attentive! The sunset sail was so peaceful and relaxing. The cannon was great fun. What a fantastic experience.
Response from Host, May 2023
Hello - Thank you very much for choosing to sail with us and thanks also for this 5 star review! Very much appreciated. Was nice having the five of you join us. We do have a wonderful crew who help make our trips so much fun. We call our trips "Serenity on the Sea! With an occasional blast from our cannon!" The weather has been wonderful and sunset sails just perfect! We are a fortunate group who gets to sailing on a beautiful ship with wonderful passengers. Hope to see you all again. Sincerely, Bill Malone - proud owner of the Tall Ship Schooner Jolly II Rover.
A must-do Key West activity
Alice_C, Apr 2023
We were lucky to have enough of a breeze to shut down the engines completely and enjoy peaceful sailing. Very friendly and capable crew.
Best Sunrise Ever!!
Mary_T, Feb 2023
A wonderful evening on a graceful schooner. Great staff and captain. Beautiful trip! The Jolly Roger even has firing replica cannon!
Response from Host, Feb 2023
Thanks for choosing to sail with us Mary - was very nice having you onboard. And thank you very much for this 5 star review! It was a beautiful evening on the Rover. Our cannon is a replica of a rail gun that would have been on the Spanish Galleon "Atocha". Hope to see you onboard again. Sincerely, Bill Malone - Proud owner of the Tall Ship Schooner Jolly II Rover!
Don’t miss this cruise!
James_E, Jan 2023
Awesome sunset cruise! Amazing crew! Fun time! Would highly recommend! The crew was very knowledgeable and very interactive and engaging! Money well spent!
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From $91.38

up to 24 hours before the experience starts (local time)

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