Sunset Sail Cruise in Key West

41 Reviews |
Badge of Excellence This experience is highly rated by travelers and has met our top quality standards.
Badge of Excellence |
Key West, USA

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2 hours (Approx.)
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Sailing on the Rover is an exciting, traditional sailing experience with a Hint of Piracy! Yes - We have cannons! Come sail on Key West's most photographed ship! The Schooner Jolly II Rover is the only squared rigged, topsail schooner in the Historic Seaport! It is Key West's famous "Red Sails in the Sunset" Tall Ship! There is no band playing or loud music. We go sailing! Plenty of room to get up and mingle with other guests. Help raise the sails! Steer the ship! Shoot the cannons! Or just sit back and relax!



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41 reviews

Average 4.95 out of 5 stars based on 41 verified reviews from Cool Destinations and TripAdvisor

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422Beaver, Nov 2022 Verified
First time ever on a sailing ship! Crew was fantastic and the captain was awesome! Loved everything about it.
Ambermarie1187, Oct 2022 Verified
I came on board the Jolly II Rover as a solo sailor for a nice peaceful evening. As a former sailor, I have grown to miss that peace that can only come from a boat under full power of the wind. The rover does not disappoint. We cruised along at 7.5 knots on a breezy fall evening. The crew Gracie and Eric, were truly welcoming and did a fantastic job conversing with guests and handling the sails. Captain Elijah is a real talent, giving us lots of information about the boat and the things around us. The cannon fire on other vessels was an extra special treat and you MUST sign up just to hear the “rolling thunder”! Thank you Jolly II!
H558PRmaryr, Oct 2022 Verified
We had a wonderful time. The crew was experienced and friendly. We would love to sail again! Thank you
RandyandKim, Oct 2022 Verified
I think we got to see it all! As we left the marina, the winds were light and the sky was blue. That meant we were to fly all 7 sails! All sails were hoisted by the time we shot the cannon as we passed Mallory Square. We set course to Cuba (can we sail 90 miles there and back before Sunset?) and enjoyed stories from the captain and crew, and meeting the other passengers. We were watching the sunset begin to paint oranges and red on the western horizon, when part 2 of our adventure began! Unforecast rain clouds were building to the north, between us and the marina, and so was the wind. The crew expertly began reducing sails and made a plan to keep us as dry as possible. Some passengers went down below, but most of us stayed on deck to enjoy an incredible sunset to the west with light rain from the north. As we neared Mallory Square, conditions improved for Part 3, “Rolling Thunder”. You’ll have to come see that for yourselves! The crew was friendly, professional and very entertaining. Jolly II Rover was REAL sailing!,
sharongJ4487PT, Oct 2022 Verified
Awesome sunset sail last night. Crew is fantastic and personable. Captain really knows the best route to enjoy a beautiful sunset. Ship is in excellent shape and a beauty! Highly recommend.
citadel87, Oct 2022 Verified
The sunset sail was phenomenal! The crew was friendly and upbeat! The boat was large enough to find folks to talk with or a quiet spot to enjoy the beautiful weather and sunset. I cannot recommend this experience enough. If you do not book this experience, you are missing out on a wonderful time.
janetv932, Oct 2022 Verified
I looked at a lot of different sunset cruises before choosing the Jolly II Rover and I’m SO HAPPY I chose this one! It was so relaxing and absolutely beautiful evening! The crew is professional, friendly and knowledgeable. I love how it didn’t have a ton of people jam packed like many others we saw. It also wasn’t loud and obnoxious. Such a pleasant and enjoyable evening and my husband loved it too! Just perfect!
Kiliboomer, Oct 2022 Verified
A beautiful evening on a beautiful boat. Clouds and the terrific Crew gave us 3 or more separate SUNSETS with a beautiful finish. Owner Bill, Captain Elisha and Mary Brett and Mark did their usual great job hosting everyone. That is why we take the Jolly II Rover for day sails and sunset sails as frequently as we can. And the progressive discount is a surprise for most guests.
Liquid_Ammonia, Oct 2022 Verified
Lovely sunset cruise with a friendly and fun crew!Captain Bill is welcoming, generous, professional and knowledgeable.Highly recommended!
865LindaB865, Oct 2022 Verified
Wonderful sunset cruise with a very knowledgeable entertaining crew. Highly recommend this tour. It was a very relaxing cruise.

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Product code: C-103151P2

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