Sunset Sail Cruise In Key West

We booked at the last minute when we found out the one we had scheduled was in dry dock! I cannot say enough great things about the Jolly Rover! Our crew was fun and knowledgeable! The sunset was amazing! A great time for our group of 6 and we all agreed if your looking for a more peaceful experience of watching the sunset this is the trip for you!

As many times as we have been to the keys, we have never taken the time to do this. We will never go to the keys again without taking this marvelous Sunset cruise!

Had a beautiful sunset cruise with friendly staff

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.

This is the fourth time we have booked this tour. We love it! The ship is magnificent! The crew are helpful and friendly. There is something magical about being on an actual sailing ship. The sails, the waves, the views. The view of the sunset over the water is amazing! And then the canon! So fun! I highly recommend this trip!

The Experience was amazing! The crew was very friendly and informative. We made some wonderful memories.

Wonderful experience! The kids loved the boat, crew and the big cannon blast at the end. It was a smaller group of people and the staff were very friendly and informative. There was no loud music or drunkards, just a beautiful sunset and soft sounds of the boat’s sails. Very calming and beautiful experience!

The Jolly River crew were great and made sure everyone had a fun sunset cruise. The sunset was amazing and cruising around Key West gave you a different view than being at Mallory Square.

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.

We took our sail on May 16th and as luck would have it, for us - we were the only passengers on this sunset cruise. A few other parties had to reschedule due to various reasons but they honored our reservation and our small family of 4 got to help set the sails and even steer the boat! It was both fun to get to do that and relaxing and so peaceful. If you want a party boat, then book a catamaran. If you want a serene experience look no further! We thoroughly enjoyed the entire experience! Bill, and his crew Noah, Atrina(sp?) and Sean were fantastic! We were so happy to find this gem. 100% would return to sail with them again!

Beautiful experience with professional and knowledgeable crew.

Great and friendly crew. Made sure everyone had an enjoyable time and a beautiful view of the sun set. Highly recommend and is great for wildlife spotting. We saw dolphins, tarpon, and sea turtles on during our trip. The owner is also super nice and knowledgeable. Definitely give them a try, you won’t be disappointed.

Relaxing and beautiful sail with a spectacular sunset. Crew was attentive, informative, & professional.

Wonderful people who made a point to get to know each of us. Made us feel right at home! Weather was fantastic and full moon came up giving us a beautiful show! A great trip!!!

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.

Very nice trip gorgeous views, knowledgable and friendly staff.

This was our 2nd sunset sail on the Jolly ll Rover. We loved it both times and will be back. The crew is totally great and the sunsets beautiful.

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.

10/10. Crew was extremely nice and knowledgeable. Sunset was amazing. They let our son pull up one of the sails which was a unique experience. Also the cannon was shot after sunset and it was truly amazing at night. Def worth the $$.

A relaxing sail out to see the sunset. The crew was very friendly and we had a great time. Would again.

Want an alcohol/cramped atmosphere, this isn't it. Want a relaxed sunset cruise with a great captain and crew, do this. We had a great time. The ship was stationed in a great position to view the sunset. They were not rushed. We were one of the first boats out, and the last boat in. The setting was more intimate where you had time to speak to your fellow cruisers, and the number was great.

A relaxing evening on the schooner jolly II Rover. Casual atmosphere. Crew were experienced sailors who answered questions and gave passengers a real taste of sailing and how it must have been during the time of the tall ships. Gorgeous sunset. Would highly recommend.

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.

Very professional captain and crew and beautiful ship. It was a lovely sailing experience and such a great way to view an unobstructed sunset in Key West. Highly recommend!

We had a blast! We went out with eight adults to celebrate a 65th birthday, and had an amazing time. Captain Tom and the entire crew were great. We were lucky to have a beautiful night and fun folks on board. Thanks to all for such a fantastic experience!

We benefited from a smaller group taking the cruise on the same day as us. The crew made the experience totally memorable and it felt like a private tour of the island!

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.

Can’t say enough good things! There was no alcohol or loud music. Just a super friendly crew who truly enjoyed the trip themselves, ocean breezes and fantastic views. Cold water and chips are provided for those who want a snack. There are opportunities to help with the sails or to take the wheel. All in all a very great experience. Firing the “cannon” was great fun, don’t worry, there is plenty of warning to cover your ears. Bill, the owner, was aboard and also very friendly. We would take this cruise again!!

The trip was wonderful. The staff was exceptional. Made it really fun. The owner was also on board and made for great conversation.

Our crew was amazing, courteous and friendly. We had a weather front blow in and our Captain and crew handled it perfectly, never and concern. Definitely a must

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!

Crew was a lot of fun and very knowledgeable. Had good knowledge of the area. Views were amazing! Highly recommend this trip.

We booked a Sunset Cruise on the Jolly II Rover for January 27th. Unfortunately the weather turned very cold for the Keys and the wind was really blowing. They called to say that the Jolly II was not going out, but they could book us on another boat. For several reasons, I specifically wanted to go on the Jolly II versus the other choices. Since we were leaving on January 28th, I explained that I would prefer to cancel the trip and rebook when we came back. The reason that I'm giving them a great review is that they were completely understanding and agreed to refund our payment. I'm truly appreciative of the way they handled the issue and will rebook with them when we return to the Keys.

This was such a wonderful experience. Everything was perfect from the time we boarded till we disembarked. The Jolly Rover ll appeared to be very well maintained and the captain and crew were just great. This was our 50th Anniversary and I will always remember being allowed to steer the ship into the sunset at the end of this perfect day. I can’t recommend this ship and crew enough!

Wonderful cruise, the crew were great and so friendly, we had the best time and highly recommend

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!

The sunset was amazing from the boat, but honestly the trip would be worth it even on a cloudy day! The captain and crew are genuinely kind and fun and very professional. This is our third time doing this sail over the last 15 years and was definitely a highlight of our week here. Not a booze cruise! This is a chill experience and I highly recommend it. As a side note: our 19 yo daughter has cerebral palsy uses a manual wheelchair and that wasn’t a problem at all. They helped get her on and off the boat, so just go for it!

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.

The captain and crew were just really nice. I did a sunset sail, and would recommend the trip to anyone. I have recommended it to family if they go to the area. The crew let me help raise one of the sails, which even as an adult really added to the experience.

This was a great experience. I brought on board my 1.5 year old and 3 year old and the crew let them at the helm, which was a great experience. The crew was especially personal, friendly, and helpful. I give the experience 10/10 and when I’m in key west again, I will take my family again.

Amazing experience…. The crew was great… we loved chatting with Veronica… It was so much better than the regular catamaran cruises..