If you want a great captain that puts you on fish with great knowledge of the area go with Captain…read moreMike... We had a great trip on March 21, 2026.

Why 5 stars? Because a private paddleboarding adventure is pretty awesome, it turns out…read more --- --- --- This was such a cool experience! My wife and I have been on group paddleboard tours and we've been paddleboarding where you're just sent out on your own for a certain amount of time, but we've never had a guided tour like this. It was cool because we'd never been to Key West, while our guide knew the lay of the land like it was her own backyard. She gave us a path and a purpose, which I really liked. When we go out on our own, we tend to just aimlessly wander, but that definitely did not happen here! Not only did we have a path, but we were educated about different things along the way, and just about life in Key West, in general. Because I'm a terrible person, I don't remember our guide's name, but she was awesome! The only issue I had was getting our trip booked. I actually purchased the Yelp deal, which saved us some money, but I didn't want to end up booking online because I'd already paid for the Yelp deal. I kept calling them over and over again, but never heard back from anyone after leaving messages. Finally, the morning we planned on arriving, we called and someone actually answered the phone. He was woken up by the call being forwarded to his phone and sounded frazzled. He said he'd been working at a bar until the early hours of the morning and that his partner was supposed to have answered the phone. Regardless of that weirrdness, he quickly called around and got us a guide before calling me back to let me know when to show up - which was ASAP. It definitely wasn't the most conventional way to book an appointment, but we made it and really enjoyed it!

Such a unique Key West experience that I won't soon forget!…read more I've been paddle boarding numerous times but never on an organized tour. After reading a bit more info on this biz's site, we decided to take an afternoon tour which started at 1:30. SUP Key West also offers morning and sunset tours, but this ended up being perfect timing for us - we could sleep in and let brunch digest before hitting the water. Now, for the tour. Our guides name was Brian, the owner of SUP Key West. Booking online was a breeze and $45 per person. Once we arrived, we met the other two in our group, grabbed some life jackets (optional to wear but must be on the board) and took to the water. I love being active but wouldn't consider myself "outdoorsy." That being said, I don't know too much about the mangroves or the ecosystem surrounding the Keys so this whole experience was really eyeopening. While we drifted through the mangroves, Brian talked about how they were formed, gave more info on the birds we spotted and pointed out the sea life, even picking up and passing around sea cucumbers, jellyfish, sea stars and algae. To top it all off? We saw a nurse shark! His enthusiasm for the environment was contagious and had me eager to learn more. About halfway through, he asked if we had immediate plans and since we didn't, we took the long way home so the tour actually lasted a little over two hours. It wasn't a huge workout until the very end when we were battling some winter wind. By the end of it, I was exhausted. Brian brought along a cooler of water which was nice in case you need some hydration along the way. All in all, a different activity to do while in Key West. This was my boyfriend's first time paddle boarding and left a great impression so hopefully I can get him on the water a little bit closer to home next time. Whether a local or a tourist, I'd say it's definitely worth taking part in.

A day out with Captain Derek on his gorgeous boat is worth every penny! If you want a truly…read morememorable and exciting highlight for your trip to Key West, I highly recommend Boundless charters! We had the best day on his boat last year that we booked it first thing this year! Another sensational adventure for our whole family!

Accompanied the flotilla to Cuba and boat parade in Havana Harbor. Incredibly organized every…read moreaspect from the departure to the return. Great communications and response. Staff was committed to the comfort and pleasure of the cruisers. The Cuba experience was a once in a lifetime thrill. Thanks to all.

OMG is all I can say. If want the charter of a lifetime this is it. The sandbar experience,…read morewildlife dolphins. Amazing!!

Great time on the water with Captain Alie! This is a very personal trip, not a crowded boat at all…read more She is very knowledgeable about the water in KW, which made us all feel safe. There is no set destination, the captain visits s bunch of spots depending on the time of day and weather conditions, so every trip is unique and customized. Boating with this charter is a true local experience. I highly recommend going with this charter over one of the larger companies.

Bill and his team were great! My family and I had fun. Bill was very knowledgeable, friendly, and…read morefunny. We saw two nurse sharks, lots of sponges, some crabs, and fish. Going down the mangrove creek was fun! This was doable for beginners.

We had an excellent morning kayaking with Chris, our guide. He is so very knowledgable about the…read morebirds, the mangroves, the sea, and all the creatures! We were able to glide through mangroves, saw black tipped reef sharks, and heard so much about the area. Chris is a wealth of information! He helps rescue birds so we learned all about his experiences. My husband and I highly recommend this tour!!!!

Lovely sail along the Key West Coast! We had a wonderful time and had great service (super friendly…read morecrew) from Milo, Chelsea, Dan, Brad (or Brian...sorry). Anyway they were great! We will definitely go again!

We went on the stargazing sail last night (3/12/26) and it was just really so great!…read more We have lived, six months each year, on Key West for 10 years, and never heard of it until last week & we thoroughly enjoyed it, very glad we went! Often feel silly being pseudo residents (elsewhere in FL otherwise), doing touristy things, but we are always willing to try something new, especially if it involves boating! The crew was wonderful, and Astronomer Kevin is an incredibly smart man, who put on a great presentation. Literally perfect sailing conditions, comfortable boat & all around super experience. Will recommend this to our many, many guests and local friends. Kudos to your staff!

Don't let the fact that she has less than 10 reviews fool you. Captain Victoria has been giving…read moretours in the Keys for more than 35 years. In fact, we just went a couple of weeks ago, my second time with her - after my first trip with you 21 years ago!! And it was way better than the first! She was recommended to me by my colleague who worked as the Environmental Horticulture agent in Monroe County, so he got around and knew folks. He was completely correct that Captain Vicki (as she was known then) was on top of her game. I went with two HS friends and it capped off a very memorable road trip. Fast forward to Sunday morning (July 10), when I'm wondering how in the world I'm going to figure out a snorkeling trip for my kid on our one day in Key West and we're up late (around 9:30 am). So of course, I check Yelp to figure out of all the brochures I have from the kiosks, which company do I have the best shot with. Imagine my surprise when I saw Dancing Dolphins. I REMEMBERED that aspect of her tour. So I took a chance, dropped her a message off her site - and not more than 5 minutes later, I had a phone call. Miracle of Miracles, she had the morning free. 45 minutes later, we met her First Mate, Erin, on the dock and away we went! We really didn't have an idea of what we wanted to do beyond snorkel, so Capt Vicki filled in the rest. She isn't kidding when she says that the Dolphins know her call sign. Three minutes after she put it out there, we had mother and baby come to say hello - we were very concerned when they were under the boat as we were moving. They didn't stay long, Vicki seemed to think they took a break from fishing, but it was way cool that they were so close to the boat. The snorkeling was marvelous! Thankfully, I had invested in a pair of prescription goggles, so I fulfilled a bucket list item to snorkel the reef and be able to see. I couldn't believe how many lobster were hiding. And to see this cobalt blue welk making a meal of one was just fascinating. There were the typical angel fish and wrasses, sea urchins and coral (though you could see how Florida's reefs have taken a beating). It was so way cool to see a 5 foot ray come whizzing by! Another special point for Erin and Vicki is that they work with people with mobility issues. So they had an idea of how to get Grandma (81 years young) into the water once she decided to go for it. Erin did an outstanding job of accompanying her so she wasn't afraid and felt secure. And Erin also provided all the pictures we would want, all included in the cost of the charter. We were out for four hours, the perfect time. We'll definitely be back. Count yourself lucky if you can score a charter with these gals. They work primarily on word of mouth, so like I said, don't let the small number of reviews fool you. They're the best kept secret in the lower Keys! Not everyone can afford a charter, but if you have four to six people, it's so worth it to book them as a charter for the personal touch.

What an adventure...what a mystical day with the oh so knowledgeable Captain Victoria…read more.. She IS the Dolphin Whisperer I will treasure the memories made that day! I went with my oldest friend and her 94yr.old Dad We did the full day excursion