Dinghy Drinking Tour through Key West Waters
Recommended by 97% of travelers
Badge of Excellence
Key West, USA
- 3 hours (approx.)
- Mobile ticket
- Offered in: English
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Overview
Key West is known for its beautiful coastal scenery and its lively bar scene, but there are few opportunities to combine the two. This tour takes you out onto the crystal-clear water, traveling by a small motor boat that glides through mangrove tunnels on its way to two or three waterfront bar and restaurants.
- Small-group tour promises a more personal experience
- Dinghies can go through narrow tunnels in the mangrove trees that bigger boats can't get through
- Great way to explore Key West via its waterways
- Bring your swimwear: There are plenty of swimming opportunities
What's Included
- Coolers for the drinks
- Licensed boat captain
- Alcoholic BeveragesBring your own liquor, beer and sodas if you want to hydrate between stops. We provide ice and coolers.
Meeting and Pickup
Meeting point
- Garrison Bight Marina711 Eisenhower Dr, Key West, FL 33040, USA
Our meeting place depends on the tides.
End point
This activity ends back at the meeting point.Operating hours.12:00 pm
Itinerary
1
Key West
2 hours • Admission Ticket Free
2
Coconut Mallory Resort And Marina By Kees Vacations
30 minutes • Admission Ticket Free
3
Stock Island
20 minutes • Admission Ticket Free
4
Hurricane Hole
30 minutes • Admission Ticket Free
Additional Info
- Confirmation will be received at time of booking
- Not wheelchair accessible
- Not recommended for travelers with back problems
- Most travelers can participate
- You should be able to climb a short ladder and climb in and out of a low boat.
- You must sign a liability waiver and a boat rental agreement.
- You will need to call us the morning of your trip to get the pick up location. It varies according to tides.
- Some stops require climbing a short ladder. If you have knee issues, you might choose to remain in the boat during these stops.
- This tour/activity will have a maximum of 10 travelers
Supplied by
Cancellation Policy
You can cancel up to 24 hours in advance of the experience for a full refund.
Traveler Photos
Reviews
4.9
based on 106 reviews
Renay_H, Jan 2026
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.
Response from Host, Jan 2026
Thank you! Come back soon
Elizabeth_C, Sep 2025
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.
Response from Host, Sep 2025
thank you Elizabeth!
Krista_K, May 2025
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!
Response from Host, May 2025
Thank you Krista. Looking forward to your next trip
Chrissy_S, Mar 2025
The captain canceled on us 3 days before as he was going out of town. I am still waiting for my refund.
Response from Host, Sep 2025
Did you get your refund? Sorry for the late response but I just saw this. Viator or TripAdvisor sends the refunds but I can help if you didn't receive it.
Jessica_S, Feb 2025
Super fun and unique way to explore a little piece of Key West. Chester - our Dingy Mate Captain was awesome.
Brian_T, Dec 2024
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.
Shaun_B, Sep 2024
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.
Richie_P, Dec 2023
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.
Sal_B, Dec 2023
It was an enjoyable time going through the mangroves and stopping at local bars. He was fun to listen to.
Mark_R, Oct 2023
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.
Sheryl_M, Apr 2023
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 !!!
Allen_D, Feb 2023
Capt. Chester was a hoot. But, get ready to duck under a couple of bridges. You gotta be a bit nimble for this ride.
ElainePayne, Feb 2023
Great time and would recommend doing it. Had so much fun and laughs. Chester showed us a great time.
Lawrence_M, Jan 2023
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!
Kevin_S, Jan 2023
Love the low bridges and just the bar hopping on water. Very cool experience can bring your own alcohol which was nice
Douglas_I, Dec 2022
Great fun, Chester did a god job. Would go again. Magroves n bars.
Punctual and friendly, good weather. Thanks
Nicole_S, Dec 2022
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.
Heather_E, Nov 2022
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.
Zane_F, Jul 2022
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
Carla_K, Jul 2022
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
Melissa_H, Jul 2022
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!
Kevin_M, Jun 2022
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
Ingrid_G, May 2022
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!
Don_A, May 2022
Host had great sense of humor! Had beautiful weather and it was an adventure. Had fun time racing a tiki boat😀
April_K, May 2022
Was s great day with little Hiccups that made it a fun adventure. Must do for a great relaxing day. Fun swimming hole and bar stops that were great. Never rushed
Sue_F, May 2022
If you want something truly unique, do this tour. Chester was an amazing guide and showed us parts of Key West we didn’t know existed. This trip is a must do. Saw the back waters, stopped at a local bar, had a great lunch, a few beers. Did a little swimming, beer drinking. A great afternoon.
Quana_C, Apr 2022
We had a blast & meet great people. Enjoy the mangroves a lot, the water was great for a swim, going back 2 one of the bars today
Sarah, Apr 2022
Great time cruising with Captain Chester. Went through mangroves, saw the gulf side and Atlantic side
Mark_R, Apr 2022
We have been to Key West many times and done all sorts of tours but this one was the best by far if you like a little day-drinking combined with a chance to see parts of Key West you won't see on foot.
Beth_C, Mar 2022
Chester our guide was awesome- gave us local knowledge, took us to some fun bars and a great place to jump in the water- I would highly recommend this tour! Total blast!!
From $85.00
per personup to 24 hours before the experience starts (local time)
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Dinghy Drinking Tour through Key West Waters
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