Cancel

    Open app

    Search

    Key Sailing

    4.3 (78 reviews)
    Closed 10:00 am - 5:00 pm
    Updated 2 months ago

    Key Sailing Photos

    You might also consider

    Recommended Reviews - Key Sailing

    Your trust is our priority, so businesses can't pay to alter or remove their reviews. Learn more about reviews.
    Yelp app icon
    Browse more easily on the app
    Review Feed Illustration

    Reviews With Photos

    Key Sailing

    Every year we visit Pensacola and Key Sailing is a must do! This year we did the Paddle Boats and the Pontoon! We had a blast seeing the Dolphins up close and personal and playing at Sand Island. Key Sailing is family owned and operated and they are amazing! Highly recommend and excellent pricing.

    Chicana N.

    On 09/27 we went to Florida and visited KEY SAILING to jet ski and what and amazing time I and my daughter and son in-law had. Great Customer Service I Appreciate Colby so much for going over board to help me .. Thanks to the owners for EXCELLENT CUSTOMER SERVICE FROM THE START UNTIL THE FINISH.. GO CHECK THEM OUT

    In the air
    Madison R.

    It was amazing my friends and I rented paddle boards and we also did parasailing. The staff was amazing and super friendly. We had an amazing time.

    Back left corner platform

    WE ARE LOCAL AND WOULD NOT RECOMMEND RENTING A PONTOON FROM THIS COMPANY BASED ON THIS EXPERIENCE. We have rented sailboats and done parasailing with them with no issues. Reserved/rented "deluxe" pontoon boat for Labor Day. Mechanically the boat functioned. Appearance and safety wise...huge disappointment. See photos. Customer service: check in busy. Launch person was not interested in providing even basic info. Recovery person was welcoming, gave great instructions and was helpful. Due to safety concerns (see pictures) will NOT rent from them again. We understand boats age but to rent with those issues AND not even bother to do basic cleaning is unsafe and unsanitary. Every stowage area with trash.

    Marielle S.

    When we made the decision to vacation in Florida, I knew that I wanted to go on a dolphin sighting expedition. I found Key Sailing on Yelp, David booked it and we were all set. We arrived at Key Sailing a half hour before our sunset trip, as we were told, and we were loaded onto a big boat at exactly 5:45. The good size boat held a lot of people, but didn't feel crowded, water was provided and the whole thing felt very safe. After a few minutes of preliminary instructions, we were on our way. First of all, one of the highlights for me was just getting out on the water and being on the boat. We drove way out into the Gulf for about 45 minutes, so we had a good chance of seeing some dolphins. Our boat "captain" was in constant communication with other boats who had spotted dolphins, so that we had a better chance of seeing some for ourselves. I'm not going to tell you that we saw dolphins majestically jumping out of the water as the sun was setting. As the captain told us- dolphins are wild animals that are going to do what they want to do. However, we did get to see a few groups of dolphins as they were feeding and that was pretty cool. Seeing them can be tricky, because you don't know if you're looking at a wave or a fin, but once you get the hang of it, you have no problem spotting them. I wish I had been able to see more, but I was happy that I saw any and, like I said, I enjoyed being on the boat. On the way back, we were able to see the most beautiful sunset and admire the Florida coast from afar- it was a night to remember. I would absolutely recommend Key Sailing- the trip was great, everyone was professional and it was a lot of fun!

    Janna L.

    ATTENTION.... Do not use Key Sailing for Parasailing! The Rope broke when my daughter and two other kids were on it! They said it happens all of the time! Seriously the scariest thing ever!! Go somewhere else! I'm very thankful they had a safe landing in the ocean and no one got hurt... but the fact that the manager acted like this happens all the time, is a crock!!! 2 years ago, 3 years ago, 14 years ago is all the years we heard when it last happened! WTH... everybody had a different year! The manager was very rude and didn't even want to refund the money. The money wasn't the issue, I just thank God they were lol safe!! But VERY UNPROFESSIONAL AND RUDE! This happened 06/20/2018

    Jessica S.

    Our family had the best time on the sunset dolphin cruise. We saw many dolphin, enjoyed the ride, and the crew was knowledgeable and entertaining. Enjoyed the soundtrack for the tour as well. Definitely recommend!

    See all

    Photo of Ed D.
    46
    2
    0

    4 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    10 days ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    9 months ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    9 months ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    1 year ago

    Had a great time parasailing for my son's birthday. Crew was friendly and helpful. Great views, good vibes.

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0
    Photo of Cody W.
    0
    37
    10

    1 year ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    5 years ago

    Helpful 0
    Thanks 0
    Love this 1
    Oh no 0

    5 years ago

    Helpful 0
    Thanks 0
    Love this 1
    Oh no 0

    2 years ago

    Best crew ever for sailings they are amazing, funny, and just great peopleto talk to "Captin Charles, and his first mate John"

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    3 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    5 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    6 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    9 years ago

    Helpful 5
    Thanks 0
    Love this 6
    Oh no 0
    Photo of Erin H.
    88
    10
    0

    4 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    7 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    4 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    15 years ago

    Helpful 10
    Thanks 0
    Love this 4
    Oh no 0
    Photo of Janna L.
    219
    5
    10

    8 years ago

    Helpful 2
    Thanks 0
    Love this 0
    Oh no 1

    8 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0
    Photo of Ileana Y.
    48
    23
    22

    8 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    6 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    9 years ago

    Helpful 1
    Thanks 0
    Love this 0
    Oh no 0
    Photo of Hilary L.
    90
    14
    10

    8 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    7 years ago

    The best experience on the pontoon yesterday! Awesome staff and very accommodating. I will be back!

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    9 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0
    Photo of Marie C.
    10
    78
    254

    10 years ago

    Helpful 2
    Thanks 0
    Love this 1
    Oh no 0

    8 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0
    Photo of Mary A.
    0
    17
    11

    6 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    11 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    5 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    7 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    7 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    7 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    7 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0
    Photo of Les L.
    106
    99
    4

    6 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    7 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    11 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    9 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    8 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    8 years ago

    Helpful 0
    Thanks 0
    Love this 0
    Oh no 0

    Page 1 of 2

    Ask the Community - Key Sailing

    Review Highlights - Key Sailing

    Dolphin cruise is a must if you're on vacation in pensacola the crew was great and we saw plenty of dolphins!

    Mentioned in 9 reviews

    Read more highlights

    You might also consider

    Jolly Sailing & Dolphin Cruise

    Jolly Sailing & Dolphin Cruise

    5.0
    (129 reviews)
    0.1 mi

    We had the absolute BEST time on the Jolly Sailing & Dolphin Cruise!! I serve at a hotel restaurant…read moreon Pensacola Beach, and I can honestly say I will be recommending this to every single guest from here on out--it was THAT good. Mary was our tour guide, and she was truly something special. I wish I remembered the captain's name because he was so kind and welcoming too, but Mary completely made the experience unforgettable. She went out of her way to connect with every single group and person on the boat, and especially the kids. You can tell she genuinely loves what she does, and it shows in every little interaction. My son is 3 and usually stays to himself, but Mary picked him up, let him ring the bell, and everyone cheered for him--it was such a special moment that I'll never forget. As a mom, that meant everything* to me. The whole experience was so fun and interactive--we were waving or dancing every time we passed another boat, laughing nonstop, and just genuinely enjoying every second. The vibe from start to finish was so light, happy, and comfortable. The boat itself was super nice & spacious with comfortable seating, plus you could see everything from every angle, which made it easy to catch every encounter! Pro-Tip: come prepared with your best dolphin puns and your "dolphin call" because they WILL put you to the test This was hands down one of the best experiences we've had on Pensacola Beach. We will definitely be back, and I truly can't recommend it enough!!

    We booked this tour through Viator a few days in advance. The team communicated ahead of time that…read morethe departure time could change or even be canceled due to weather. Our tour ended up being moved to an earlier time the day before. I did receive a couple of different text messages about the start time, which caused a little confusion on my end, but the crew communicated well and kindly waited for us before departing. The address synced perfectly with the gps to the exact departure location. Parking was free and available immediately by the dock area, but notes this will likely not be the case during peak tourist season. The tour itself was lovely. We had beautiful weather, and the crew was attentive and knowledgeable, sharing interesting history and stories about the bay throughout the ride. We saw dolphins and were able to capture plenty of videos and photos. This would be an especially beautiful tour to take in the evening to enjoy the sunset.

    Photos
    Miss Mary making sure EVERY one feels included.
    Miss Mary making sure EVERY one feels included.
    Captain Mike
    Captain Mike
    Jolly Sailing Dolphin watching

    See all

    Jolly Sailing Dolphin watching
    Premier Dolphin Cruise

    Premier Dolphin Cruise

    3.9
    (31 reviews)
    0.1 mi

    (May 22, 2024) I highly recommend this 2 hours dolphin and…read morebay cruise excursion. If you're staying on Pensacola Beach, it's a super easy drive and park situation. Park near Felix's restaurant and enter downstairs under Felix's. There is a little ramp that takes you to the bay side where you catch the boat. No signs mark the area, but you will see others waiting in the area. These are most likely your fellow boaters. They suggest you arrive 45 minutes prior to departure. Our tour was scheduled for 10:00 AM; we arrived at 9:20 AM. The wait is easy with the beautiful scenery are lovely breeze. There are tables and chairs to sit at while waiting. The boat came out of the bay to get us, so don't be surprised if you don't see a boat when you first arrive. You will walk in the sand for a short distance before taking the pier to get onto the boat. A gentleman will take your last name that you made the reservations under, so you don't need tickets to show the reservation. The guys can help you on the boat if needed. The boat is a double decker. The lower area is shaded with large 3-3-1/2' port type widows which are open for a great breeze and maximum viewing. The captain will briefly go over safety instructions and what to do in case of an emergency. This is standard procedure on any chartered vessel. Don't be late! We had a group of 4 board at the last minute so all the instructions they missed had to be restated. Very annoying and rude, so don't be THAT person/group. You must stay seated while leaving the pier, but after you leave, you are free to roam the vessel. All seats are around the perimeter of the boat and each side of the boat has 7 windows. There's plenty of room for viewing. The captain does a great job of turning the boat so everyone gets to see the dolphins no matter which side you are seated. They sell canned sodas, bottles water and chips; no alcohol. There are plenty of grab bars to steady yourself once the boat gets going. It was a very smooth ride. Even when fishing boats went by us and created wake, we didn't feel much at all. I don't think anyone would have trouble with sea sickness. There is plenty of room for strollers, adult walkers, etc. No restrictions on purses. Several people had diaper bags for the kids and backpacks. There is a restroom onboard. We saw several pods of dolphin. It was a so neat how they come very close to the boat. Dylan/Dillion, of the boat hands, was so good at engaging with our group. Though he is young (born in 2001), he has been in Pensacola all his life and is very knowledgeable about the dolphins and the history of Pensacola. He was a pleasure to meet. After the dolphin viewing we took a cruise around the entire bay. We saw Ft. Pickens, the haunted lighthouse, million dollar homes, the military base area and so much more. I wasn't expecting the cruise to be as much fun as the dolphin viewing. They played reggae music while we cruised. I'm so glad we decided to do this tour! We were returned to the same area we left originally. For only $30 (plus taxes/fees and not including cancellation insurance you can add), this was a great deal! The vessel staff work for tips, so please remember to take care of them.

    Great Experience. Little confusing finding the dock where we board. Had a great time. Saw plenty of…read moredolphins. Crew were super laid back and chil. I would recommend.

    Photos
    Dolphin watch
    Dolphin watch
    Blue Angels Cruise
    Blue Angels Cruise
    Dolphin Watch

    See all

    Dolphin Watch
    Condor Sailing Adventures

    Condor Sailing Adventures

    5.0
    (69 reviews)
    0.1 mi

    I cannot say enough wonderful things about Captain Kirk and his incredible Condor 40 trimaran,…read more*Dare II*! We took our three girls (ages 3 to 8) on a dolphin tour with Condor Sailing Adventures, and it was easily one of the highlights of our trip and one of the best family experiences we've had. I'll admit, as parents, we were a little nervous when we saw the "don't get seasick" disclaimer. I mean... seasickness isn't exactly something you choose. But Captain Kirk and *Dare II* put those worries to rest immediately. This boat is basically the Ferrari of the ocean. It's unbelievably smooth and stable. Even our youngest stayed happy the entire time, laughing, pointing out dolphins, and having zero tummy troubles. I've never experienced anything quite like the way *Dare II* glides across the water. Captain Kirk was fantastic--knowledgeable, patient, and genuinely wonderful with kids. He made the whole experience feel personal, relaxed, and fun while making sure everyone felt safe and comfortable. We saw so many dolphins up close, and the small group size made it feel special instead of crowded and touristy. And then came the surprise that absolutely made our girls' day. At the end of the tour, Captain Kirk let each of them take a turn at the helm and "drive" this Ferrari of a boat (with his close supervision, of course). Their faces lit up like it was Christmas morning. Watching them steer *Dare II* was the perfect ending to an already magical day. If you're looking for a truly special, family-friendly experience in the Pensacola/Gulf Breeze area, this is it. Captain Kirk and *Dare II* are in a league of their own, and we're already talking about when we can come back.

    Dare II Experience! We sailed past boatloads of tourists and enjoyed our own personal captain…read morewithout charter prices. Captain Kirk let each of us take our turn at the tiller, chased and watched some dolphins, provided drinks and snacks, and shared some of his experiences as a professional racer on a unique 40-foot Condor racing trimaran. Racing before the wind, relaxing in adjustable recliners, sitting up on the pontoons watching the water speed by underneath and enjoying the sun & salt spray made for an unforgettable day! Are you ready to take the Dare II?

    Photos
    Pontoon riding.
    Pontoon riding.
    Supermoon rising
    Supermoon rising
    Condor Sailing Adventures

    See all

    Hot Spots Charters

    Hot Spots Charters

    4.1
    (47 reviews)
    0.1 mi

    2nd time out with them! Great outfit and ask for Capt Tyler. Awesome birthday trip for our boys!…read moreWil be back.

    I really hate to write this review because I've chartered a few times with Hot Spots over the past…read morefew years but today, I encountered one of the rudest guys and was really blown away by his attitude. I had a 6 hour private charter scheduled for me and my son for the 28th of this month. We come down for the PG World Series each year and close out our ball games with a fishing trip so as a mom, I plan ahead and booked this trip about a month or so ago. Because of all the rain forecasted, we decided to cancel this charter and take a trip to Tamarindo in July. I called to cancel the charter today, 9 days in advance and the guy laughed numerous times and said "that's 10 days away, but ok." I let him know I was well aware of the timeline and that we didn't want to take a chance on the rain. The possibility of storms was part of the reason but I also decided to just take a trip to Tamarindo and fish instead. The trip to Costa rica is 5 days and only $1700 more and we get a 10 hour fishing day so I thought it would be a cool experience for my son since he's already gone out with Hot Spots several times, this would be a little different. This review is based solely on the poor & rude service of the kid I spoke to today. I have had great experiences in the past but they were with Cash & Jason.

    Photos
    Hot Spots Charters
    "The only way to out fish a woman is to leave her at the dock!" Captain Dan
    "The only way to out fish a woman is to leave her at the dock!" Captain Dan
    Jean and Jack caught these guys simultaneously.

    See all

    Jean and Jack caught these guys simultaneously.

    Key Sailing - boating - Updated July 2026

    Loading...
    Loading...
    Loading...