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    Stand Up Paddleboard Key West

    4.8 (64 reviews)
    Closed 10:00 am - 7:30 pm

    Stand Up Paddleboard Key West Photos

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    Gerry B.

    Our guide Cassie was awesome. Half of our group had paddle board experience and half hadn't. Cassie gave us a great tour, no pressure at all to the newbies, and it didn't seem like anyone was waiting around. We held starfish and baby (non stinging) jelly fish, saw aneomone, bait fish, a few barracuda, and mangrove crabs. And the crab in the picture. Would definitely recommend.

    Getting ready for our 2hr paddle board trip. Beautiful day in key west and just introduced to our tour guide Sam.
    Marcus L.

    Amazing paddle boarding trip. Sam was an amazing guide that made it super relaxing while educating us on the importance of the mangrove ecosystem. Sam was the perfect guide as he led the tour at our speed.

    The sunset tour!
    Dawn B.

    My husband and I have toured with SUP Key West for three years straight. It's educational. It's active. It's fun. It's memorable. We have had three different guides in our three visits over three years and we learned something new every time. They have great staff, I'm beginning to believe the just have great hires who are passionate. We recommend this business to any friends visiting the area. They made us huge fans of paddleboarding and the mangrove forests. It is our must-do activity every time we visit the area.

    Mangrove photo opp
    Amanda T.

    Decided on SUP for a paddleboarding tour with two of my friends. Great decision! They went above and beyond! They picked us up for free from our hotel and brought us to the launch site. Brook was our guide and she rocked! Cold water, informative tour through mangroves and channels, and lots of fun and wild life. I highly recommend the sunset tour from 6-8pm.

    Beginner SUP-ers!!!

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    9 years ago

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    9 years ago

    Kassy was awesome! Funny and very knowledgeable about the marine life and Key West area. Her dog Sunny was a joy to watch.

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    Page 1 of 2

    Ask the Community - Stand Up Paddleboard Key West

    Review Highlights - Stand Up Paddleboard Key West

    The paddle boarding starts with a lesson teaching you how to stand on the board and paddle properly.

    Mentioned in 9 reviews

    Read more highlights

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    Old Town Trolley Tours Key West

    Old Town Trolley Tours Key West

    3.7
    (187 reviews)
    2.8 km
    Takes reservations
    Private events

    So I normally write long and detailed reviews, but this one will just be a quick one so I can…read morereview my recent 2026 vacation while the memories are still fresh! I bought my ticket for the Old Town Trolley Tours Key West as part of the Norwegian cruise line excursions list and therefore, paid more than I would have normally for something like this. I have been to Key West a few times before and had seen many of the important sites on the island on my own but my friends were doing this trolley tour so I did as well. And I still learned a lot! Manny, our tour guide, was born and raised on Key West and therefore, had a great perspective on everything. I think he is the reason why I recommend this tour. Like many others have said, the trolley itself isn't too comfortable but it is sturdy, and you can get on and off as much as you want. As we were on a moving vehicle, I didn't get the best pictures so you probably won't either. Look up the trolley schedule and plan your get on/get off stops well. And try to get a local tour guide if you can!

    We had tickets for the 07.18.26 trolleys. For $50 per person, it was definitely not worth it for…read moreus. It might be a solid tour of Key West, but we were wanting to get the tour while using the hop on and off part of it. We waited approx 15 minutes for a trolley at stop 11. There were 2 trolleys. I wondered why they weren't spaced out apart. But ok. We took it to stop 1 and did some touring and shopping. When we were ready to go, there are several trolleys at the stop, but no drivers. We waited a good 20 minutes before we left. They explained that they're only doing trolleys every 30 minutes now that the cruise ship had left port instead of 15 minutes. With how many trolleys we're going, why wasn't there a trolley leaving every 5 or 10 minutes? So then we got off at stop 5 to see what we wanted to see. By the time we were done, there were no more trolleys. UPDATING THIS REVIEW TO 3 stars. Because of the comment from the business, I did request a refund and I did receive it today. Thank you. ** Updated review to 3 stars. Per the business comment, I did put in for a refund. I did receive it today. I appreciate that. Thank you. ** I was very dissatisfied. Fix the timing. I have used 1 other system like this in Boston and it worked great! Trolleys coming and going all the time. I will not use this again in Key West or anywhere else this company is operating. Again, probably great if you're just going to do the tour. If you're going to use the hop on and off, start right when they start operating. I'm giving 2 stars because the tour people e has seemed to be knowledgeable.

    Photos
    Old Town Trolley Tours Key West
    Old Town Trolley Tours Key West
    Old Town Trolley Tours Key West

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    Tiki Boat Adventures

    Tiki Boat Adventures

    4.4
    (12 reviews)
    1.1 km

    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!

    Photos
    Sandbar Sunset Combo trips May 1 to Aug 31 at 4:30
    Sandbar Sunset Combo trips May 1 to Aug 31 at 4:30
    Tiki Boat at sandbar
    Tiki Boat at sandbar
    Girls on tiki boat

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    Girls on tiki boat
    Yankee Freedom Dry Tortugas Ferry

    Yankee Freedom Dry Tortugas Ferry

    4.4
    (441 reviews)
    2.1 km
    Takes reservations
    Private events

    great crew, food and total experience! Great snorkeling and educational tour of the fortread more

    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!

    Photos
    Yankee Freedom Dry Tortugas Ferry
    Yankee Freedom Dry Tortugas Ferry
    Yankee Freedom Dry Tortugas Ferry

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    Key West Ghost & Mysteries Tour

    Key West Ghost & Mysteries Tour

    4.3
    (92 reviews)
    2.5 km

    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.

    Photos
    Ted telling a scary story in front of an infamous funeral home.
    Ted telling a scary story in front of an infamous funeral home.
    Key West Ghost & Mysteries Tour
    Home place of Robert the Doll

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    Home place of Robert the Doll
    Key West Extreme Adventures

    Key West Extreme Adventures

    4.9
    (69 reviews)
    2.9 km

    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

    Photos
    Key west
    Key west
    Key West Extreme Adventures
    Key West Extreme Adventures

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    Stand Up Paddleboard Key West - paddleboarding - Updated August 2026

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