Sunset Sail Cruise in Key West
Recommended by 98% of travelers
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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
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 295 reviews
Sort by: Most insightful
Great experience. Sunset was awesome and boat was great. Crew was absolutely top notch! Highly recommend this excursion.
We truly enjoyed our sunset sail. It was calm, quiet, and incredibly relaxing — exactly what we were hoping for. The crew was kind, polite, and made the experience feel welcoming from start to finish.
While I personally wasn’t a fan of the comments about the captain’s adult personal life, everything else about the trip was wonderful. The views were breathtaking, and the atmosphere was perfect. We still had an amazing time and would happily recommend this experience.
This cruise was fantastic! It was a relaxing, non party atmosphere but not at all boring! Great crew!
Amazing experience! Very interactive, we hoisted the sails and steered the ship! They even fired a cannon. Highly recommend this experience, so much fun and an amazing sunset.
The Experience was amazing! The crew was very friendly and informative. We made some wonderful memories.
Amazing, down-to-earth crew, captain, and owner of the ship! Seems they really care about what they do: giving people an authentic sailing experience. What we loved most about this tour is it let nature speak for itself. We witnessed an unforgettable sunset, saw some dolphins, and shot a cannon. Not a party boat. Great for the whole family or a memorable moment with a loved one.
Crew members were very engaging. They got younger passengers to participate in the raising of sails and steering the boat. Assisting everyone as needed getting aboard without calling attention to the effort necessary due to passenger’s health or fitness level. Provided water and snacks. Made the entire experience very pleasant. Great trip for a quiet sunset for couples and family without the rowdiness of a booze cruise. No loud music or party atmosphere.
Relaxing and beautiful sail with a spectacular sunset. Crew was attentive, informative, & professional.
Me and my party loved this experience to sail on a real scooter sail boat. Space is limited to a small group. The crew was fun and interactive giving the passengers the oppertunity to hoist the sails and even Captain the boat at the helm. Heart warming was watching a young man with Downs Syndrome at the helm. This young man came aboard with his pirate hat on ready for an adventure and the crew made sure he did. Thank you all for a wonderful sunset sail! We will do it again with your incentives for return guests.
Lovely sunset sail. Not a noisy party boat but a peaceful sail as the sun set over Key West. Highly recommend!!
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.
A relaxing sail out to see the sunset. The crew was very friendly and we had a great time. Would again.
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.
this experience was absolutely amazing! i would highly recommend taking this schooner sail boat tour.
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.
The trip was wonderful. The staff was exceptional. Made it really fun. The owner was also on board and made for great conversation.
Low key sunset cruise. Staff was wonderful
Didn’t want a wild time w drinks so this was perfect. Made memories
Perfect Captain and GIRL POWER CREW! Sweet and attentive to the guests! Highly recommend! Awesomeness beyond believe!
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!
Great sunset sail with good food, friendly crew, and an overall wonderful experience!
Highly recommend, you will enjoy!
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.
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
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.
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.
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.
Very good 💯 I love the crew very much love atmosphere the culture good experience Love crew very quiet and pleasant
It is fun and you get to learn a bit about sailing. No cannons on our trip but was still very cool and peaceful.
This is a low key beautiful way to experience the beauty of the Keys offshore. The staff were so genuine and kind.
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.
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.
From $95.00
per personup to 24 hours before the experience starts (local time)
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Sunset Sail Cruise in Key West
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