My husband booked us on this sunset cruise. We wanted a lower keyed experience and it was perfect. This tall ship does not serve alcohol or food only water and snacks. The positive side is you get to bring your own alcohol and food if you want. We chose to eat dinner at the Conch Republic seafood house before we boarded. And of course I brought my wine on board. We boarded at 6:15 pm and were greeted by a crew of three. Captain and two mates. They were all awesome full of knowledge answering all our questions while tending to the boat. They are known for their cannon which is fired at other ships veering too close lol. We had a quiet group of 18 souls on board but it was my first time on an actual sail boat so I totally enjoyed it. I highly recommend this as your option if want to avoid the huge boats. read more

See all

My husband and I decided to board for the sunset tour and it did not disappoint!!!! It was our best experience ever (we have been on sunset tours on other vacations). This by far was the best ...it was so relaxing and we were able to interact with steering the ship and putting the sails up..no distracting music or having people trip all over you...this is a date night must or one for a good wholesome family night out with your children that will leave you with a lifetime of terrific memories!! These guys know what they are doing!!!! read more

Schooner Jolly II Rover - Boat Charters Near Me - Key West, Florida

What a fantastic sailing cruise and sunset!!! The Jolly Roger captain and staff made the sailing interactive with ALL guests with cheerful conversations, letting guests help lift the sails, sitting at the helm, and handing out snacks and water!! The cruise was a gentle and smooth sail of the area ending with a great sunset!!!! Highly recommend for an enjoyable couple or family group. read more

We have sailing with these guys since 2016. Every time we are in town, we love to hang with them. This is the best value and sailing tour in Key West! read more

Over priced, Great concept but dry toast experience. Nice crew, no refreshments. Turned out to be only a boat ride read more

We tried not to "over schedule" during our vacation down to the Keys, like we have a tendency to do, especially when there's a 1,001 tempting choices for awesome-sounding activities, but the tempting Groupon, plus the awesome experience of this wonderful day sail were WELL worth it!! Informative hosts, a wonderful, scenic route, and added bonus, not too crowded... Take the opportunity to help "steer" and lift/lower the sails, or just relax and take in the beautiful sights. I was wishing it lasted longer, but really, it was truly perfect. NEXT time, we'll be sure to take their sunset cruise, which I'm sure will be EQUALLY amazing!!! In this amazing place, with soooooooooo many things to do (or NOT do, choice is yours!!) it's hard to decide what activities to do. If you're at all interested in a sail on a BEAUTIFUL ship, on some of the most amazing waters ANYWHERE, don't pass up a wonderful "cruise" on the Jolly II Rover!! read more

See all

If you want a different way to watch the beautiful Key West sunsets, you have to go on a sunset sail on the Jolly Rover II. The whole crew were accommodating and fun to watch and the views you get of the sun going down were picture perfect. A few little surprises on board happen too. Will definitely go again the next time we come back. read more

Schooner Jolly II Rover - Boat Charters Near Me - Key West, Florida

See all

We recommend this business. We enjoyed a fantastic sunset cruise Feb 1, 2023. There are various cruises one can try in Key West. After reading the reviews and observing, we picked this one on the last day of our trip, and glad we did! This sailing schooner is clean and professionally run by captain and crew. It was fun and lighthearted during the cruise, and you learn a little bit about the boat, sailing and key west. They have a couple cannons the crew had fun with. To top it off the sunset was one of the best and had a green flash ending. read more

See all

BSA Florida Seabase Captain Ron and Elijah were great captains. We went for a week with the boy scouts. We went sailing, snorkeling, and fishing. We also went swimming at the mooring, and we swing on a swing into the water. We also saw dolphins and jellyfish. read more

See all

Sail on a traditional schooner with a wonderful crew. Look forward to the canon fire & the rolling thunder! read more

Schooner Jolly II Rover - On the schooner Jolly 2 Rover - Boat Charters Near Me - Key West, Florida

What a great night. We live in Key West and had family in town. The staff was amazing and made the night really special.

The best everything. This was a highlight of my trip to key west. Highly recommend. Much better than all of the other options. read more

Schooner Jolly II Rover - Boat Charters Near Me - Key West, Florida

Great sail tonight on the Jolly Rover! Beautiful ship and amazing crew. Captain Elijah and Crew Chase and Renee could not have been more wonderful. It was a beautiful night and the sail was so enjoyable. I highly recommend this schooner as great way to learn about Key West and see some sights. read more

Lovely sunset cruise with a friendly and fun crew! Captain Bill is welcoming, generous, professional and knowledgeable. Highly recommended! read more

The best way to see a Key West sunset! We have done the sunset cruise with the Jolly II Rover 3 times now, and I can't believe it took me this long to review this amazing trip. If you've been to Key West, then you know how amazing the sunset is! If you've never seen it on the water, then you don't know what you're missing. We watched this beautiful schooner sail by many times at sunset before we took the cruise--it's red sails make it stand out. They are the friendliest, most knowledgeable people who genuinly love what they do & love sharing it with others. It's a great tour around Wisteria and Sunset key and down to the Fort Zachary Taylor beach. We got a great history lesson each time as well--just ask, they love to tell you about Key West & sailing. The sunset cruise is BYOB (They have a cooler) and they provide a few snacks, but you'll be glued to the beautiful views! They even have some small cannons--super fun. If you're in Key West for while, they offer a discount for the 2nd cruise and the 3rd cruise is on them. Skip the tacky booze cruise tours that ruin the harbour and the scene on the water and sail on a schooner! read more

Schooner Jolly II Rover - Our view from the sailboat--almost sunset! - Boat Charters Near Me - Key West, Florida

See all

I highly recommend a sunset sail on this boat! We did a sunset sail on New Year's Eve and had the best time. The weather was perfect and the sunset was beautiful! We got to help put up the sails and drive the boat and learned some interesting stuff about sailing. Captain Ron was a great host and the crew were fun and friendly. We sat and chatted with the boat owner Bill who was an incredible guy. We heard some great stories and history. It was such a relaxing and beautiful trip. Definitely worth the $ and time. You won't regret it. read more

The people running this excursion really take care of their customers! You can tell they are passionate about sailing. They had a groupon offer that we took advantage of. The code did not work but it was not an issue after calling them. You can just make the reservation by phone and then they will accept the groupon upon arrival. During the boat tour, they'll give everybody an opportunity to "drive" the boat, which many people took it as great photo opportunities. They also provide water and several rounds of simple snacks. Good activity if you just want to sit back and relax. read more

We saw the Jolly II Rover sail by when watching a sunset and looked them up the next day. Cool looking schooner. Super friendly crew. Complimentary water and some snacks. They even let guests help raise the sails and will take a picture of you at the wheel. It was a lovely evening watching a beautiful sunset with cool breezes on the water. Oh, and they also shoot at passing ships, which is pretty neat and loud. When we were coming back to dock we saw dolphins swimming alongside. Great experience. read more

Schooner Jolly II Rover - The Jolly II Rover as viewed from Sunset Pier - Boat Charters Near Me - Key West, Florida

Loved every second of this sailing! Our captain was Rio. He and the other crew members were awesome. Very informative and were fully interactive with the guests. They took pictures, joked with us, and explained things about Key West that we'd never heard before. Overall, fantastic experience and well worth the money. $55 per person. The canons fired at other ships was also a lot of fun. For those with hearing sensitivities, this might not be a tour for you or your child. This was the highlight of my trip to the Keys this year! read more

Schooner Jolly II Rover - Boat Charters Near Me - Key West, Florida

Great crew! Very personable, fun and filled with Key West history. With ideal conditions you can't get a better sunset sail experience. read more

Schooner Jolly II Rover - Boat Charters Near Me - Key West, Florida

Had a great time on this sunset cruise! The crew was very friendly and chill, which set the tone that made the other passengers friendly & social as well. Once we were underway everyone was free to mingle and move around. You can BYOB....they even have a cooler to keep it cold for you. If you ever wanted to steer a tall ship, you even can take a turn at the wheel. They have cannons on the ship to fire at other boats (in the pirate way!) and end the evening with "rolling thunder" where the cannon was aimed at the shore & the echo reverberated back. This was one of the biggest highlights of our trip to Key West! We highly recommend for all ages! read more

This was our best excursion for the whole week we were in Key West! We did the sunset cruise and we took out two small kids. Our 6 year old son had a blast trying to find "enemy ships" to shoot the cannon at. He would run up to the Captain to tell him about the newest enemy ship he found and the crew would get the cannon loaded up and ready to fire at just the right time. We were able to bring our own beer to put into their ice chests and they walked around with cheese/crackers/fruit and other snacks that were delicious! The Captain and crew were very friendly and gave us a lot of good information on the history of the area. We were very happy we booked this sunset cruise after looking at several on Yelp. We all had a great time!! The prices were very reasonable as well. read more

The best sail boat in town by far! Sail away with the beat crew in Cayo Wes and experience a true tailored experience sure to blow your pothole outta the water! read more

Great crew, very accommodating. We took the day 2 hour sail. Saw bottlenose dolphins, got to man the helm. Battled another vessel with her cannons. Would sail again. Please tip your crew! read more

Schooner Jolly II Rover - Boat Charters Near Me - Key West, Florida

This was a wonderful excursion. We did the sunset cruise and the "mock" battle in the bay. Very charming and fun. The captain and crew were very nice and accommodating. BYOB. Would definitely recommend. read more

Sunset cruise was awesome and the crew was super great! They were attentive and knowledgable and entertained us with great stories! They are reasonably priced, and allow you to "BYOB". They only sail on Sunday's in the summer because they take Boy Scouts out during the week- so book ahead. Definitely one of the coolest things to do on the island. read more

Schooner Jolly II Rover - The only square sail sailboat on the island - Boat Charters Near Me - Key West, Florida

Very disappointed, it states clearly on your reservation that you be there 15 minutes prior to sailing time. Our trip was held up for 20 minutes waiting on a wedding party to show up. We were we not offered a partial refund of any kind and to top that off we should have been informed of the type of ceremony that was being held on this cruise. It was very offensive to us and something that we would never be a part of. read more

The staff was wonderful. The captain was personable and informative and the crew was very helpful. The day we went was cloudy, so the sunset was underwhelming, but we were given blankets which was a nice touch. Bring some drinks and snacks if you'd like, but they do have bottled water and they came around with some light snacks. This is a low-key kind of boat ride which is great for those of us who don't want a party boat atmosphere. read more

Had a great time on the sunset cruise. Everyone was very friendly. The crew let us help with the sails and even let us steer. They shot the small cannon at various other boats (it is a pirate ship, after all) and shot the big cannon when we were closer to the dock. We had a wonderful time and enjoyed a great sunset. Would definitely do this again. read more

Such a friendly & courteous crew-Capt Chris, Catherine & Chris. This was a highlight of the trip. Sunset cruise was gorgeous! Saw the Navy Spearhead in action. It gets cool out there so dress in layers. Kids may not enjoy sunset cruise as much-no dolphins. read more

Had an amazing day sail. The captain was awesome, his crew were fabulous and the boat owner was on our trip and he was awesome. The canons were a fun twist on the trip. The boat was awesome. Great conversations, great views, only thing that would have made it better is if we had seen dolphins but they can't control that. Glad we decided to try it. read more

Booked a day cruise and had a great time. Super nice, extremely helpful, and friendly crew. Captain Rio was great! A nice way to spend an afternoon. We had teens and people in their 70s in our group and everyone really enjoyed it. There were younger kids and families too which made shooting the cannons even more fun. The atmosphere is very laid back and casual. You can BYOB which worked great for us. You can pick up beer and wine right at the docks and they have large coolers on board to keep everything cold. They have plenty of bottled water and some light snacks on board, but you can bring your own food too. Highly recommend and agree with all the other 5 star yelp reviews. read more

Awesome sunset sail!!!! You will feel like you are on a real pirates sailboat. Cheese and crackers was a nice touch and BYOB keeps the price down. Each and every member of the crew are so personable and friendly. They let passages help with the sail and get behind the wheel for some great pictures. read more

The Sunset Cruise was just beautiful. This was our second trip on the Jolly II Rover. We had a great view of the Southern Most Point of the United States. We fired multiple cannons at our enemy boats. We enjoyed a fascinating conversation with the owner of the ship. The crew was very friendly and entertaining, Elijah, MaryBret, and Captain Ron made the evening sail a perfect end to the day. read more

We went on a sunset sail for our wedding rehearsal and it was amazing. The crew is awesome and personable, and the owner bill is a quiet man but has an amazing and beautiful ship. Everything went off without a hitch, they even let us steer the boat and help with the sails. The crew went above and beyond my expectations of what I expected. Both sides of our families went and everyone had a blast, one of the best experiences I had in key west. I would suggest the sunset cruse. Bring drinks and some little stuff to munch on. Overall an excellent over the top experience and I would do it again in a heartbeat. read more

Bill, his crew and captain will guide you through history I the open waters for an unbelievable sail! Bring some beverages and relax! read more

Schooner Jolly II Rover - Boat Charters Near Me - Key West, Florida

Me and my wife did the sunset cruise on this beautiful sailboat. She wanted to do this since she was a little kid. Captain Rio and his crew were really cool, Rio was telling stories about the island, history and everything you can think of. One of the crewmembers shot the cannon (blanks ofcourse) at passing competitors/collegues. Very fun. The sunset ofcourse is out of their hands but it was a decent one. Had fun on the 2 hour sail and the wind was pretty good. Also a good thing was that the boat wasnt packed like many of the others were. Great experience for a decent price. read more

Schooner Jolly II Rover - Captain Rio and us - Boat Charters Near Me - Key West, Florida

Great experience! This is a byob sunset sail so be sure to bring along a bottle of wine/champagne (and glasses) or a six pack of beer. We decided last minute to go so we didn't have a chance to get something. My experience would've been different if I actually had booze for the booze cruise. That being said, it wasn't a bunch of drunks on a boat. (At least during our trip.) I wouldn't have known anyone was drinking if the shared cooler wasn't mentioned in the beginning. The ship is really cool and the captain and crew are super friendly. They even let passengers help with the sails and made an effort to connect with everyone on board. And it was a blast "shooting" at passing boats. I'm so glad we decided to do this and would absolutely recommend it to anyone (drinking age or not.) read more

This sunset cruise was more than I expected in a great way. The crew was fantastic and the sailboat was beautiful. The magic moment when the engine shut off and he sails take you for a memorable ride that will stay with you for a long time. I highly recommend this as a must do when down in key west. read more

New to the community and this,by far,was one of the best memorable experiences ever! Such a fabulous crew! They took amazing care of us and even got to steer the boat! Strongly recommend this sunset cruise! Best boat in the Keys for a great time! read more