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    Up The Keys

    5.0 (11 reviews)
    Open 8:00 am - 10:00 pm

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    Review Highlights - Up The Keys

    Troy is incredibly knowledgeable and brought the history of the islands to life with fascinating stories, fun facts, and great local insight.

    Mentioned in 4 reviews

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    Dolphin Safari Charters - A man captures an incredible shot just inches from a bottlenose dolphin 
 Up-close, wild moments on a Dolphin Safari Charters boat.

    Dolphin Safari Charters

    4.6(94 reviews)
    0.4 mi

    HIGHLIGHT OF OUR TRIP! We have a 2 and 6 y/o and they cannot stop talking about it. The captain…read morestarted by asking what our goals were for the outing. We wanted to 1) see dolphins, 2) snorkel, 3) spend time at a remote sandbar, 4) anything else he recommended. We were able to accomplish all 4, and then some! We had a pod of dolphins swimming around and under our boat, which was amazing. We found a very shallow sandbar and decided to snorkel there, with our kids being young. We saw fish and found a large conch shell that our 6 y/o still talks about days later. We saw the remnants of a lighthouse in the middle of nowhere. And then ended the day watching the sun go down. Just breathtaking. Cannot recommend it enough. There were also a variety of sodas, waters, and snacks available which came in handy with little ones. A nice touch that we were glad to take advantage of while in the middle of the ocean. In summary... yes, it costs more to charter a boat, but the intimate atmosphere with just your family and friends around make it absolutely priceless. I'd pay triple the price to make these memories with my family, and not have 25 strangers in the background of each picture. Splurge once and you will know EXACTLY what I'm talking about.

    Did the three hour dolphin and snorkel ride for $99/person. Originally was supposed to go earlier…read morebut they called me the day before and said the weather would be bad and asked if we could postpone it and I am glad we did because the weather was much sunnier and less windy the next day. James did a great job as our captain. It's nice you can bring your own beverages and they have some snacks on board. We drove around key west stopping at a few points, then rode out to an area to snorkel for a bit where we saw tons of sponges and some little fish, and then head back toward Key West, into the marina, and then back to where we started. Honestly, we didn't see any dolphin until we were on our way back in from snorkeling, and it honestly felt like it was just pure luck that we saw one but thank goodness we did since it was the highlight of the safari. The boat was pretty nice and comfortable. There were 6 total people including Captain James. The front is definitely the best place to see things from, so try to get a seat there if you can, even though it's not under the shaded cover part. It's like $112.36 per person after tax/fees plus there's a big sign on the boat guilt tripping you into tipping at least 20%. It's fine because James did a great job and deserved the 20% tip (although if we didn't bump into that dolphin on the way in, I would've felt a bit ripped off for the price), but basically expect to be out over $130 per person for a three hour boat ride. This can get pretty expensive, especially if you have a family, and I would've felt ripped off if we didn't see a dolphin but luckily we did so it was a cool experience that I definitely recommend when the weather is nice, winds are calm. Their website had higher prices in the description than the $99 that was actually charged so I hope they don't raise their prices because that would get kind of expensive. Especially when I was just in Miami and could rent a 13 person yacht for four hours $1300 so $100/person plus tax and tip is about the most I would be willing to pay for this experience, especially since seeing dolphins isn't guaranteed so you are basically just paying for a 3 hour boat ride.

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    Dolphin Safari Charters - Family enjoying a first-row VIP view, just feet from wild dolphins 
 An unforgettable dolphin watching tour with Dolphin Safari Charters.

    Family enjoying a first-row VIP view, just feet from wild dolphins An unforgettable dolphin watching tour with Dolphin Safari Charters.

    Dolphin Safari Charters - A man and his dog watch dolphins from the bow of a Dolphin Safari Charters boat,
 A private boat charter moment you don't forget.

    A man and his dog watch dolphins from the bow of a Dolphin Safari Charters boat, A private boat charter moment you don't forget.

    Dolphin Safari Charters

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    Sunset Watersports - snorkel the reef in key west

    Sunset Watersports

    3.7(205 reviews)
    2.6 mi
    Eco-friendly
    Locally owned & operated

    The 2-hour sunset cruise was an absolutely amazing experience with stunning views and a relaxing…read moreatmosphere from start to finish. The food was fresh and delicious, and the open bar offered a great selection of drinks to enjoy while watching the sun go down. The crew was exceptionally friendly, professional, and made sure everyone felt comfortable and well taken care of. The price was very reasonable, especially considering the quality of service and overall experience. I'd highly recommend this cruise to anyone looking for a perfect way to spend an evening on the water! my special thanks to Emily, Danny and Captain Jon, You guys are amazing!!!

    We used this company for parasailing and jetskiiing and had a great time! I booked online less than…read morea week in advance and their prices for both activities were among the lowest of all the companies I looked at. The kicker is when I signed up for jet skiiing, they offered me 20% off the early bird parasailing at Smathers Beach. It had to be on the same day so we did parasailing in the morning and jetskiing in the evening. Early bird wasn't that early as it was scheduled for 10am. We arrived around 9:15am as it said to arrive 45 minutes early. This was not necessary and the address shown was near where the shack was on the beach (there are 2) so they pointed us to the right one. The wait was lovely on the sand and rocky jetty that goes out. Our parasailing experience was great as there was only one other party with us on the boat. We were all up in the air for the same amount of time and I felt like it wasn't too short. The view was nice and it wasn't too cold that early in the morning. We did jetskiing at 4pm and the directions for parking were great! It was in the back of a nice hotel and after a short safety demo, they asked us who wanted to go fast so they could order the group. After one short run, they reordered us for the optimum ride. Being second in line, we cruised around at top speed (the jet skis are governed) and did donuts while we waited for people to catch up. It was awesome! We traveled 25 miles (I tracked it on my running app) and went all around the island, hitting key spots. After we got back, we were allowed to use the nice pool at the hotel they operate out of, which was a nice touch!

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    Sunset Watersports - Kayak tour in key west

    Kayak tour in key west

    Sunset Watersports
    Sunset Watersports - Paddleboard tour in key west

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    Paddleboard tour in key west

    Ghost Key West

    Ghost Key West

    4.6(7 reviews)
    1.7 mi

    During the Sloan's Key West Ghost Hunt in the city, we learned about Robert the Doll who was…read morebrought to the island as a gift to some kid and that kid basically was mesmerized by said doll. Who knew dolls could be so big? Anywho, it was interesting enough for us to visit said doll and sign up for the 2nd tour bearing the Sloan name. This one was conducted at East Martello Museum, an old Civil War fort which surprisingly dates back to the 1860's. Our tour was conducted by local author David Sloan. He literally wrote the book on Robert the Doll, which you can buy on this tour and around the city. He also wrote other Key West ghostly tales like Haunted Key West, Ghosts of Key West and The Key West Key Lime Pie Cookbook ("limes have to die for this delicious pie" may or may not be words used in that book). David is a masterfully engaging storyteller who explains the history of Robert as well as the ol' Civil War Fort known now as the East Martello Museum, which sits at the entrance to the Key West Airport. Equipped with one Dowsing Rod and an EMF Reader that lights up when spirit energy is nearby, we wandered around the fort, into dark hallways, trying to bring out some spirits. People occasionally got hits (red and orange) but mine stayed green so spirits must be avoiding me like the gals did in high-school. The tour ends with everyone sitting around a glass case containing Robert the Doll. He's the main attraction. Great storytelling by David as some sounds are heard on the thingy that plays sounds (I forget the name). There were tales of people taking pictures of the doll or disrespecting the doll having horrible things happen to them. It was believable enough for us NOT to take pictures or whip it out and taunt the doll. I did take a picture of the poster of Robert the Doll though. The only thing bad that happened was my Windows PC rebooted on me without asking! Ugh! There's an extra add-on to stay afterwards to explore the fort on your own. We did not participate, but a few on our tour did. I haven't heard from them since! Should you go? Yes! It was interesting and informative and captivating. You can tell David has a passion for telling this tale and the stories of the fort and all things spooky. He's as Key West as a chicken crossing the road.

    The guy that did our tour was amazing! So much fun, looking forward to going back again! Enjoyed…read morehearing all about Robert the Doll and seeing him!

    Photos
    Ghost Key West  - Cool art during the tour

    Cool art during the tour

    Ghost Key West
    Ghost Key West

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    Up The Keys - historicaltours - Updated May 2026

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