Sunset Sail Cruise in Key West
Recommended by 98% of travelers
Badge of Excellence
Key West, USA
- 2 hours (approx.)
- 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.Itinerary
1
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
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Cancellation Policy
You can cancel up to 24 hours in advance of the experience for a full refund.
Traveler Photos
Featured review
Emily_B
We had a wonderful, relaxing time aboard the Jolly Rover. The captain and crew were welcoming, friendly, and fun. The ship was beautiful and it was very interesting to watch the the sailors do their thing.
Reviews
4.9
based on 275 reviews
Emily_B, Apr 2026
We had a wonderful, relaxing time aboard the Jolly Rover. The captain and crew were welcoming, friendly, and fun. The ship was beautiful and it was very interesting to watch the the sailors do their thing.
Bob_B, Mar 2026
A relaxing sail out to see the sunset. The crew was very friendly and we had a great time. Would again.
Curtis_D, Mar 2026
We were looking for a sunset cruise that did not market towards the "booze cruise" crowd, and this was it. You can bring your own snacks or drinks, as the crew does not provide alcohol on board. The crew were all very engaging and took the time to meet all on board and thoroughly explained the itinerary. We could not have been happier, between the beautiful sunset, smooth sailing, and wonderful crew. We would 100% recommend.
steve_l, Mar 2026
this experience was absolutely amazing! i would highly recommend taking this schooner sail boat tour.
Katelyn_M, Mar 2026
Captain Tom and his crew were great! Very informative and a fun time on the water. Worth every penny and can’t wait to do it again.
Kimberly_V, Feb 2026
The trip was wonderful. The staff was exceptional. Made it really fun. The owner was also on board and made for great conversation.
Barbara_G, Feb 2026
Low key sunset cruise. Staff was wonderful
Didn’t want a wild time w drinks so this was perfect. Made memories
ANGEL_M, Feb 2026
Perfect Captain and GIRL POWER CREW! Sweet and attentive to the guests! Highly recommend! Awesomeness beyond believe!
Karsten_A, Jan 2026
This was the best boat tour we’ve been on down here! The crew was super fun and kept us entertained. Capt Harley, Carl, Jeremy and Simone were very friendly and knowledgeable. Carl set off several cannon shots at other boats after some good natured taunting between us. Gorgeous sunset also! Will do this again when we return!
Denise_R, Jan 2026
Great sunset sail with good food, friendly crew, and an overall wonderful experience!
Highly recommend, you will enjoy!
Kent_P, Jan 2026
This crew focuses more on your experience than others I have been with. Others are more "party" boat. This crew was having fun actually sailing and talking with passengers.
Richard_T, Dec 2025
Chatted with the owner for a good portion of the sail...lot of great information. My girlfriend was equally impressed with him and the crew
Thomas_J, Nov 2025
It was awesome and highly recommend. The crew was very fun yet professional. They where knowledgeable and answered every question we had. Its a cruise that didnt need drinks or food to make it ejoyable.
Tara_S, Oct 2025
Really nice boat, beautiful sails. Unfortunately there wasn't a lot of wind that day so we didn't get to see it in full action.
Linda_M, Aug 2025
The ship was a perfect size with about 18 people plus crew. It was smooth sailing and very calming with beautiful views. The crew interacted with all those on board. Some helped lift the sails, children and adults could sit at the helm!!
They even shot off a small cannon at a variety of boats.
Damon_C, Aug 2025
Very good 💯 I love the crew very much love atmosphere the culture good experience Love crew very quiet and pleasant
Chris_C, Jul 2025
It is fun and you get to learn a bit about sailing. No cannons on our trip but was still very cool and peaceful.
Archie_W, Mar 2025
This is a low key beautiful way to experience the beauty of the Keys offshore. The staff were so genuine and kind.
Marc_G, Feb 2025
What a choice! What a perfect sunset sail for a sailor. Want to surprise her to celebrate anything, even just being together, this is it.
LESLIE_C, Feb 2025
Very nice sail with a great crew. Also get to see a cannon being shot off. We had an added bonus of dolphins putting in a show.
Linda_H, Jan 2025
Misunderstood cruise. Thought there were music, snacks and drinks.,it was cold and seats were up
On deck. This trip is for summer. We dudnmt go. Sux people scheduled. We were four and last two didn’t show. We chose not to go under circumstances.
Mark_P, Dec 2024
Great cruise. We had a wonderful time, crew is amazing. Definitely worth the trip and would take it again.
Rossen_N, Nov 2024
Great adventure. Small group fo people, nice plot (pirates), and great experience in Ket West waters. Shots were fired, stories were told. Be a part of Key West history and enjoy the adventure. Chat with the crew. They have lived in the area for a while and can tell you the stories.
janet_w, Aug 2024
We had so much fun when the crew fired their cannons at passing boats! Being on the water a sunset was so pleasant and pretty. The crew were very knowledgable and made it a great experience.
Dixon_B, Jul 2024
Ended up choosing this sunset cruise because it seemed more intimate. It did not disappoint. There were 12 guests on the boat and once we got to sailing it was so quiet and nice out on the ocean. That was until the cannon came out! What great fun it was! We would do it again and again.
Lee_B, Jul 2024
Such a great experience for family or a small group of friends who just want to have a few quiet moments watching the world go to sleep for the evening. Crew is fantastic and engaging and made for a good time.
Robert_B, Jun 2024
Amazing sunset cruise. Everyone from, Bill the owner, Rachel the Captain, Chris the deck hand and all of the deck hands were kind, courteous, informative and made our trip phenomenal! From firing the canons to watching the amazing sunset, we had an amazing experience and will definitely be back!
LINDA_N, May 2024
Wonderful crew, sailing ship and exciting experience! They made us feel comfortable and at home at sea and made my granddaughter's birthday celebration a precious memory. We wanted to stay longer than two hours! What a beautiful experience! We will certainly come back every year.This will be part of our family tradition!
Andrew_F, May 2024
I’ve always wanted to sail, it was an amazing experience to be out there to watch the sun go down. The crew were super friendly and attentive, the captain was great! Really chill and really knowledgeable, pointing out facts about various boats and islands and answering any other questions anyone had. The boat wasn’t super full so it made for an even better experience as you could move around easily. It was fun to watch them shoot off the canon at other passing ships. Choose this over a loud party catamaran you won’t regret it.
Kim_E, May 2024
The sunset cruise was our favorite thing we did in Key West. Captain Rachel and crew were amazing, fun and knowledgeable. We would highly recommend.
From $95.00
per personup to 24 hours before the experience starts (local time)
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Sunset Sail Cruise in Key West
275
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Free Cancellation
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