We will travel by boat to 2 to 3 waterfront bar/restaurants. Along the way we will go through mangrove tunnels and see all sorts of fish and sea life. We can spend as much time as you like in the mangroves, refreshing from our coolers or we can spend more time at the bars on the water. This is a small group tour so we will make it what you want it to be. Wear swim wear under your clothes if you want to get into the calm clear waters.
We stop at the Boathouse when it is open. Behind the resort is an old boathouse where boats were pulled out of the water for repairs. Photos showing the original boathouse are posted and you can see the pulleys on the ceilings. Beer and wine are on the menu and snacks like potato chips and peanuts. We will get there by climbing a small ladder to the wooden dock.
We'll stop at a waterfront locals bar called Stock Rock Cafe and have a drink and snacks if you are hungry.
We often stop at the popular waterfront Hurricane Hole Restaurant and Bar for food and drinks.
Tour was great. Had a fantastic time. Meet up point was unclear and tour guide stated he was not contacted by Viator about our booking. He did accommodate us anyway. Meet up point was 2 miles from were it was stated.
Chester was awesome! It was a great trip. We had a blast! You will not be disappointed! We will do this again for sure!
This is the best tour I have ever taken! So unique and an absolutely hilarious and fun experience. You won’t regret this dinghy ride.
If you're looking for fancy this isn't for you. If you're looking for a fun time with a local character, this is a must! Chester was amazing and we had the best time meandering through the mangroves. We stopped at two bars along the way- the food and drinks at Hurricane Hole were fantastic! It was a perfect way to spend the afternoon. Highly recommend.
We had such an amazing time on our daytime dinghy drinking tour with Captain Chester Ruder! Since it was the off-season, it ended up just being my husband and me, which made it feel like a private experience. The dinghy was perfect for navigating through areas that bigger boats can’t access, and we loved weaving through the mangroves and stopping at two different marinas for food and drinks. Captain Chester was knowledgeable, friendly, and truly down-to-earth—he seemed to know everyone we ran into and made us feel like we were hanging out with a friend rather than on a tour. We always felt safe and comfortable, and the views throughout the day were absolutely incredible. Ending the trip, cooling off at one of his favorite ocean spots was the perfect touch. And as if that wasn’t enough, upon our return, Captain Chester even played and sang us a song on his guitar—a wonderful and memorable way to wrap up the day. This was time and money well spent, and we would absolutely do it again. Highly recommend Captain Chester for a fun and unique Key West experience! P.S. We hope you got your window installed!
We highly recommend this tour !!!! Chester was the best!! I would go on this every time I visit Key West . One of the best exoeriences ever. We met his lovely wife also. She was so nice.
Chester was the absolute best! All I wanted to do was spend a few hours on the water adventure around the island and this excursion did just that! We left with lots of memories, tons of laughs, and a new friend! We will be back and Chester will be the only one we will book with!
The captain canceled on us 3 days before as he was going out of town. I am still waiting for my refund.
This tour is like going boating with a friend. If you are looking for a cookie cutter high volume tour this is not it. Chester will take you places large boats can not go. His knowledge of the area is unmatched and he seems to friends with everyone on the island. Can't recommend enough.
Super fun and unique way to explore a little piece of Key West. Chester - our Dingy Mate Captain was awesome.
Great time, great host. Had a nice trip through the mangroves. Got to see some things you wouldn’t normally see. Definitely recommend.
We had a blast and highly recommend this trip. Chester was an excellent host and we enjoyed hearing about the area. Hope to do this again. Thanks again Chester and Happy Holidays.
If you don’t love having fun and doing something some different in the Keys …..stay away! Chester is awesome and this is a great time off Duval St.
Captn Chester gave us a great day on the water once again. We are repeat offenders and would recommend this tour for a fun day. Saw some fish, sharks, osprey, stopped at a couple bars. He knows everyone and has some great stories to tell. Lots of fun.
Chester was awesome. Had a blast with him. Would definitely recommend to anyone to book him!!!!! The views were spectacular. We even saw a couple of manatees.
Our best day in KW! Captain Chester is so entertaining and knowledgeable. Hang out in the mangroves. Swim. Go to bars. Maybe stop for lunch. It’s great. Just do it!
Was fun , loved the mangrove tunnels. very casual and relaxing way to see local area and some cute waterfront bars and restaurants. Would be fun for groups of couples or groups of friends .
Well...I can't make this s%?+ up! It was fun....but......be prepared. First of all there is no location given until the morning of.....you get a text to call in the morning. Also the app has no approximate location so don't assume it's anywhere near main stuff in Key West...it was a pick up point in middle of a neighborhood. Then.....there were two small dighys.....one had lots of water in it. Then the adventure begins....the boats are teathered together and then you have to have one boat tow the other through mangroves and canal for about 40 mins into more waterway opening. You also have to duck down significantly to get under bridges....on the way back we barely got under the main bridge and the motor even scrapped the top. So we don't actually go to any sanbar bars but 3 bars on the waterway...not exactly what we expected but ok. First bar really nice, beer and wine only. Not fun for those of us that drink liquor. Second bar was the best, great drinks and food, yes liquor. Third bar meh...not very nice, smelled bad and dog crap on the deck. Again beer and wine only. Our Captain was having a lot of fun here and took forever to get out of there. The journey back was an adventure with the mangroves and previously mentioned bridges, but also had to make sure I was blocking branches from hitting my wife in the face......again....lots of water in the boat we were in being towed. Like I said.....I can't make this stuff up. There was some great times and some not so great. But the Captain was a great guy trying to get everyone to have fun.
It was an enjoyable time going through the mangroves and stopping at local bars. He was fun to listen to.
Our second time doing this and we can’t wait to book again on our next trip. Definitely a fun way to see more of Key West than just Duval.
This tour was so much FUN! Chester is laid back, personable and knowledgeable about the area. He allowed us to customize our trip and make it truly our own unique experience. We had a large group and one couple stuck on a delayed flight from the previous day, and when we called him, he moved our meet time back an hour so they didn't have to rush (since we had booked both of the boats and wouldn't interfere with a stranger's schedule). That took so much stress off of us so we could all truly enjoy our experience. Highly recommend. Chester is a cool cat!
We had a great time on this tour! Chester was fun and very informative about the area. We will definitely be doing this again and I will be telling all of my friends traveling to Key West about it!
This is one of the best under-the-radar tours in Key West! Forget the sunset cruise packed with a hundred people and go dinghy drinking with Captain Chester. You'll get to see sights that most locals never get to see, eat the best fresh seafood in the lower keys and day drink. The Captain will tell you as much as you want on local history and color. Say hi to Brandy for us. And remember- if the motor will fit the boat will fit!
Chester was great fun and had a lot of entertaining stories to share. It was very relaxing, good drinks at the bars, and just a great way to end our trip to Key West. Highly recommend!
This is our 2nd trip with Chester and was as fun if not more than the first trip! Went places that you don’t typically visit when in Key West.
Chester's dinghy tour was recommended to us, and so glad it was! We had a blast! It was our favorite part of our KW trip!
Great fun !!! Loved going through the mangroves in the little dingy. Fun stopping at bars for drinks. A different but certainly fun way to spend the day in Key West !!!
Very fun unique thing to do! Chester the guide was great with all the stories. We had a lot of fun going thru the mangroves seeing sharks and seeing some different bars
The absolute highlight of our KW trip!!! Chester was a blast and took us to 2 great stops and a swimming hole. The scenery was amazing. Our group loved this dinghy tour and would absolutely recommend!
Capt. Chester was a hoot. But, get ready to duck under a couple of bridges. You gotta be a bit nimble for this ride.
Had an amazing time with Chester! He knows the local waterways very well and knows all the cool spots to hang out. This is a great trip for anyone looking to have some down to earth fun. Chester is a great host and he makes this trip as fun as possible. Even after the trip was over, we stayed and hung out with Chester in his lovely yard watching his beautiful dog chase wizards (lizards) around. I recommend this trip to anyone who will be visiting Key West, and I am looking forward to doing it again in the future. Thanks Chester!
Great time and would recommend doing it. Had so much fun and laughs. Chester showed us a great time.
Best tour in Key West! Highlight of our trip. Captain was so much fun! Would definitely go again and would recommend for sure!
Great day on the water with Chester. Would definitely do this again. Very educational. Highly recommend this to anyone who likes boats and day drinking!
Love the low bridges and just the bar hopping on water. Very cool experience can bring your own alcohol which was nice
Chester was a fantastic guide and we all loved the excursion. Really quite a great experience, highly recommended and one we’d do again if we came back!
Chester's tour was the group favorite for the week! You'll see the back alley water ways of Key West while you enjoy the local stories and sip your byob beverages. It's the kind of tour where you might have to drive your own boat, our son loved that. If you are at all uptight, you should take a pass on this tour to save you and Chester a headache. He's a super chill, funny guy and it's kind of like choose your own adventure. You can decide to visit bars or mangroves or a combo of both. We stopped at 3 very different bars which were all really fun. This is the kind of 3-4 hour tour you just go with and enjoy the sights and maybe mishaps.....Dinghy Day Drinker Down!!! Nothing else like this tour out there.
By far the best tour in KW. I have been on many. Chester, our tour guide, was amazing, fun and entertaining. We stopped at a few bars along the way through the mangroves. The sites were amazing.
Great fun, Chester did a god job. Would go again. Magroves n bars. Punctual and friendly, good weather. Thanks
My husband and I had an awesome time with Chester. He is well known in KW as a great guy and he was able to show us places we would never have seen otherwise. We were able to find 15-16 huge nurse sharks and a few manatees. It was a fun day on the water! Highly recommend calling Chester direct to get a customized tour.
Excellent. This was a lot of fun. I'm so glad we booked it. Chester does a great job of pointing out different things along the tour and some neat places to stop and have lunch, drink, and even swim. Lots of laughs. I plan on doing this again.
Key West most tourists don't get to see. Chester does great job of explaining the local sights. Have been to Key West many times, but have not experienced these places.
We had an absolute blast floating in the mangroves and bar hopping by dinghy. If you like boats, bars and Key West, this is for you. BTW, the Captain rocks.
Excellent tour! Friendly and enjoyable staff, fun tour through the mangroves to two great bars, and even stopped to swim a bit. If you go on one boat tour in key west, make it this one!
Chester is the man. Not just a boat tour. It’s a beer drinking, bar hopping, sandbar swimming good time. You get more than you pay for. We will return Zane&Brit
Had a great time! Chester was amazing! So relaxing and overall a great time. Would recommend to anyone wanting to get off the beaten path for a while
Fun times with Chester! This is our fifth trip to KW, wanted something different. This was different in the best way. Chester took us down some channels we didn’t know existed. Saw some amazing KW homes. The. Out to the gulf, bar on Stock island, into the Atlantic, and then the mangroves for some gulf swimming. We loved our afternoon and will be sending friends his way!
The whole tour was a blast! Chester was a great tour guide. From hanging out at beach bars to swimming in the mangroves Everything was great
Great trip! We toured and our Captain told us all of the history, very interesting! Bars great! Got in the water in one of the canals, fantastic experience! Thank you! The Texas Three!
Host had great sense of humor! Had beautiful weather and it was an adventure. Had fun time racing a tiki boat😀
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