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Key West, FL

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Schooner Jolly II Rover

4.8 (62 reviews)
Open • 9:00 am - 5:00 pm

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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!!!!

Valerie W.

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!!

Lisa G.

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.

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.

Sunset
Kris S.

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.

On the schooner Jolly 2 Rover
Mally W.

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

Shane S.

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

Our view from the sailboat--almost sunset!
Lara W.

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!

Rosie P.

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!

The Jolly II Rover as viewed from Sunset Pier
Adrienne E.

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.

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

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Ask the Community - Schooner Jolly II Rover

Review Highlights - Schooner Jolly II Rover

“The sunset cruise is BYOB (They have a cooler) and they provide a few snacks, but you'll be glued to the beautiful views!”

Mentioned in 19 reviews

Read more highlights

Old Town Trolley Tours Key West

Old Town Trolley Tours Key West

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Manny was our tour guy. AMAZING. TOTALLY THE BEST. it was very hot today in Key West and…read morehe was fabulous The tour was worth every penny.

Not Recommended -- Lack of Respect and Professionalism…read more I cannot recommend this tour company based on the way this tour operator treated people, particularly an older adult. Regardless of the situation, people working in the tourism industry should understand the importance of being courteous, patient, and respectful toward their guests. Unfortunately, that was not my experience. The tour operator was extremely rude and gave what I felt was a completely inappropriate and disrespectful response to a senior citizen. When he received a response in return, his behavior escalated. He became aggressive and appeared ready to get off the bus and confront the person physically. Thankfully, someone younger stepped in and advised him not to get off the bus before the situation could escalate further. What is most disappointing is that this entire situation could have been avoided with something as simple as, "No," or "No, ma'am." There was absolutely no reason for the interaction to become confrontational. Tourism is about hospitality, and respect should be extended to everyone--especially senior citizens. A tour operator represents not only themselves but the company and the destination they are serving. Based on this experience, I would not recommend this tour company.

Tiki Boat Adventures - Epic Sunset Cruises on a floating tiki boat

Tiki Boat Adventures

(12 reviews)

What an AWESOME DAY!!! This was by far one of the best day's…read moreand experiences we've had in our favorite town, Key West!! From the ease of the booking and contact with Captain Morgan as to where to catch the boat to a beautiful day full of sites, fun and laughter. We (the four of us) have been in Key West on many trips and decided with the great weather doing an all day Tiki Boat/Sand Bar trip would be so much fun and it did not disappoint. The highlight of the trip was our Captain. Truly a great guy, friendly, welcoming, great sense of humor and very professional. Of course we gave him a hard time about being "Captain Morgan", which by the way he gets it a lot! We had the best time talking with him and as we all got to know each other we had blast giving each other fun stories and joking around. Morgan told us so much about the waters around the Keys. Took us to several very pretty spots in which we saw more wild life that day then he said he's seen in a while. We saw nurse shark, several dolphin pods and one with a little baby! Sting ray and some barracuda The waters are a beautiful blue like you seen no where else. Captain Morgan took us to see the beautiful mangroves, so many lizards in the trees it was crazy... and just gorgeous. We pulled up on a little beach to check out the views and hang in the water. We brought some drinks, sandwiches and snacks... Such a fun experience to relax on this boat. The tiki theme is so fun, clean boat and great music. Defiantly gives you the island vibe. Highly recommend asking for Captain Morgan, book this company and have a blast. We plan to do this again on our next visit. Great day - Thanks Morgan for making is so!

Okay.....how can you NOT have an awesome time on a "Tiki" boat with a captain whose name is…read more"Morgan?" I kid you not....CAPTAIN MORGAN! He's only been with the company for 4 months---but had all kinds of fun filed facts about Key West. The sun was behind clouds...and it POURED on our way back in....BUT none of that mattered as we had a great captain, fun music, libations :) and friends/family. I would recommend doing this fun, floating tiki party!!!! And try to get Capt Morgan....I am sure everyone would be great....but he's REALLY awesome. Thanks for helping us make forever memories!

Yankee Freedom Dry Tortugas Ferry

Yankee Freedom Dry Tortugas Ferry

(447 reviews)

We recently took the Yankee Freedom Ferry to Dry Tortugas (8/3/26) and I absolutely loved this…read moreexperience, will 100% be coming back! My sister is on a mission to visit all of the U.S. National Parks, so Dry Tortugas was originally more of a bucket-list stop for her than for me. I honestly didn't expect to love it nearly as much as I did, but it ended up being one of my favorite parts of our trip. By the time we left, I was already thinking about coming back to camp and spend even more time snorkeling! The Yankee Freedom crew made the entire day incredibly easy and enjoyable. From the beginning, they went into so much detail about what to expect. I really appreciated how organized everything was, especially since it's basically an entire day excursion. Breakfast was available on the way out, lunch was provided shortly after we arrived, and snorkeling equipment was included. The bar opening on the ride back to Key West was also a fun way to end the day! After checking out the fort, we had time to explore and snorkel, which was easily one of my favorite parts of the day. The water and scenery were absolutely beautiful. What really stood out to me, though, was the crew. Everyone was so friendly, attentive, and genuinely fun to talk to, especially Matt. We appreciated his recommendations for bars to check out on Duval Street. We actually went to some of the places he recommended later, and they completely lived up to the hype, I had such a great time! He also saved my feet when I apparently decided shoes were optional on a scorching hot wooden dock and started splashing water on my feet for me . It was such a small gesture, but it really summed up how attentive and personable the crew was. I also really appreciated our tour guide, Ali, for answering all my questions. She was so sweet! Thom kept us entertained at the bar on the way home while making my first Rum Runner. Everyone brought something different to the experience, and those little interactions with the crew are honestly a big part of why the day was so memorable. It made the experience feel much more personal than I expected from such a busy excursion. My only "complaint" is that I wish I could have stayed longer! I felt like I could have spent hours more snorkeling and exploring. I went into this trip because visiting the national parks is something my sister loves, and somehow I left already planning my own return trip. Next time, I'd love to camp overnight so I can really take my time exploring and get even more snorkeling in. Between Dry Tortugas itself and the Yankee Freedom crew, this was easily one of the highlights of our Key West trip. If you're debating whether it's worth dedicating an entire day to it, do it. I can't wait to come back!

We made it! In 2022 we were denied our opportunity to visit sure to a tropical storm, what an…read moreawesome day we had today visiting Dry Tortuga National Patk! Every member of the crew is to be commended for their friendliness, helpfulness and all around demeanor. We always felt safe upon the ferry and well informed. The highlight was Hollywood's passion to share his knowledge of the fort. He really brought the times of the fort to life for it. I don't think I can give justice in this review to say how much of a difference it was to have Hollywood guide us on the tour. I know many of the passengers were content with taking a quick tour of the fort before going snorkeling, but they missed out on gaining the experience of why the fort is a national park. Of course, we know we missed out on the long snorkeling experience others had. The food provided was simple offering of fresh bagels as we boarded followed by packaged cereal, fruit, yogurt and coffee/juices. Sack lunch of Jersey Mikes sandwiches, packaged chips and store bought cookies. You also had the opportunity to purchase ice cream sandwiches or drumsticks and other snacks. Barry did an awesome job of making drinks for the afternoon's voyage back to Key West and the price was very reasonable. We highly recommend this activity and would say run not walk to hear Hollywood bring this National Park alive f

Key West Ghost & Mysteries Tour

Key West Ghost & Mysteries Tour

(92 reviews)

5 stars Way Better Than Just Another Bar Crawl! Listen, when…read moremy buddies started yapping about this Key West Ghost & Mysteries Tour, I was like, "Yeah, right ghosts in paradise? Pass the piña colada." I was already half-toasted from Duval Street happy hour, sweating in the humidity, thinking it'd be some cheesy, overpriced gimmick. But man, did it sneak up on me like a whisper in the dark. For what felt like pocket change (didn't even pay friends hooked it up), we wandered the shadowy backstreets of Old Town for 90 minutes, hearing wild true tales of haunted spots: the old firehouse with its dozen restless spirits (including a firefighter named Frank who still haunts the engine room), whispers from shipwrecked sailors on the breeze, and that creepy vibe from places tied to Key West's pirate past and yellow fever epidemics. The guide was a total pro mixing legit history with just enough eerie chills to make your skin prickle without going full horror movie. It's not scary-scary if you're buzzed and laughing with the group; it's more like deliciously mischievous storytelling that makes you glance over your shoulder at every creaky old conch house. What really sold it? Breaking from the usual beach-drink-repeat routine. Sure, Key West is all sun, sand, and rum, but slipping into the island's darker secrets cursed dolls like the infamous Robert, ghostly lights over the water from wrecked ships, and spots where the dead supposedly still linger felt refreshingly different and surprisingly fun. Highly recommend if you love a good story (and maybe a little liquid courage). The guide makes or breaks it, and ours was gold knowledgeable, funny, and just spooky enough to keep things lively. Bonus silly skit (because why not?): Me (whispering dramatically to my friends post-tour): "Guys... did you hear that? Footsteps behind us!" Friend 1: "Dude, that's just your flip-flops echoing." Me: "No, wait shh! It's Frank the firefighter... he wants his hose back!" Friend 2 (laughing): "Or maybe it's Robert the Doll, pissed we didn't say 'please' three times." All of us: "Run!" (We didn't run. We just hit the nearest bar for one more round. Ghosts approved.) Totally worth it. 5/5 even sober, I'd do it again.

If you're going to do a ghost tour--for the love of God, do it in Key West. Forget the cheesy ghost…read morewalks in cities that have to invent half their legends. This is Key West, where the humidity alone feels haunted, and half the locals already look like they've made peace with the afterlife. The Key West Ghosts & Mysteries Tour is the best of the bunch. You're not just shuffling along behind someone in a cape muttering about "orbs"--this is real-deal weird history. The streets themselves creak with old shipwreck stories, curses, and that doll (yes, that doll, Robert the Doll) who stares into your soul like he's still holding grudges from the 1900s. By the end of it, you're not sure if you're spooked by the stories or by the fact that people actually survived Key West before air conditioning. Pro tip: do it in the winter. In July, you'll be sweating so hard you'll mistake heat stroke for paranormal activity. In December, the air's crisp, the island's alive, and a walk through Old Town's lantern-lit streets feels like slipping between worlds. It's equal parts creepy, funny, and fascinating--a Key West cocktail mixed with history, ghosts, and just enough rum-soaked madness to keep you guessing.

Key West Food Tours - Old church built by slaves. Now a private home.

Key West Food Tours

(217 reviews)

We took this tour and had a wonderful time. We were guided to five restaurants and tried delicious…read morefood and drinks. The Cuban sandwich and key lime pie were to die for. We went to a cuban cigar making shop and some other shops we wouldn't have found on our own. Angie was an amazing tour guide. She was very knowledgeable about Key West. She kept us together, she kept us on the shady side of the street & followed traffic rules to keep us safe. I highly recommend this tour and suggest you ask for Angie.

Key West Food Tours was a great experience with a variety food and drink samplings and walking tour…read moreof a few KW neighborhoods, with a bit of history mixed-in. Kyle, our guide for the day, was great and talked about Key West's past and present and local customs, including its major industries throughout the years (cigars, rum, ship wrecking [which to me sounds similar to Ransomware today] and more), the common use of Bahaman light blue believed to ward off evil spirts and also birds (not evil but can make a mess), and tour of Gato and Old Town, parts of town that you'd normally not know about as a tourist. He also made sure everyone was hydrated and had multiple chances to cool off as it was a humid, sunny afternoon. The food stops included El Siboney for Cuban pork, beans and rice, bread and plantains, The Rum Bar for an iced rum drink, Mangoes for conch fritters and tomato based conch chowder, Kaya for mahi mahi and, to finish it off, Cuban Coffee Queen for Cuban espresso and key lime pie. We met people from all over including Spokane, WA, Minneapolis, MN, and other parts of Florida.

Key West Extreme Adventures - Snack time!

Key West Extreme Adventures

(69 reviews)

Captain Matt and Tanner were great. Super informative about the wildlife, environment and kept the…read moremood light with jokes. Kids on board were able to feed a shark if they wanted to. They got us back to shore before heavy rains started. Would highly recommend!

As a filmmaker and photographer, I've documented a lot of different environments, but my experience…read morewith Key West Extreme Adventures was something special. This is a family-run business and you can feel that local, small-town pride from the moment you step on the boat. What impressed me most wasn't just the wildlife--though seeing bottle-nosed dolphins and sharks in their natural habitat was incredible--it was the professional camaraderie. Even though there are other tour companies out there, the captains are in constant communication, sharing sightings and even helping each other out with gear or debris in the water. It's rare to see that kind of collective stewardship in a competitive industry. The tour is also deeply educational. The guide did a fantastic job dispelling myths about sharks and explaining the biology of the animals (like the dermal denticles on their skin) with a level of respect that shows they aren't just using nature for a paycheck--they are actively protecting it. If you want an authentic, respectful, and insightful look at the Florida Keys' ecosystem, this tour is a must. I captured a large portion of our tour--including the sharks and dolphins--starting at the 2:26 mark in my vlog here: https://www.youtube.com/watch?v=og6BrVsB2QM

Schooner Jolly II Rover - boatcharters - Updated October 2026

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