Dinghy Drinking Tour through Key West Waters
4.9
93 Ratings
Key West
Explore Key West's crystal waters on a dinghy, visit waterfront bars, and swim with sea creatures. Perfect for small groups seeking adventure.
Duration: 3 hours
Cancellation: 1 day learn more
Highlights
  • Key West - 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.
  • Coconut Mallory Resort And Marina By Kees Vacations - 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.
  • Stock Island - We’ll stop at a waterfront locals bar called Stock Rock Cafe and have a drink and snacks if you are hungry.
  • Hurricane Hole - We often stop at the popular waterfront Hurricane Hole Restaurant and Bar for food and drinks.
What's Included
  • Licensed boat captain
  • Coolers for the drinks
What's Not Included
  • Bring your own liquor, beer and sodas if you want to hydrate between stops. We provide ice and coolers.
Additional Information

On this tour, you will see the beautiful crystal clear waters around Key West from a dinghy, a small motor boat that seats up to 5. An experienced licensed boat captain who knows the waters will lead your tour. Dinghies can go through narrow tunnels in the mangrove trees that bigger boats cannot get through. Be ready to duck under branches. We will stop at waterfront bars. 2 or 3 stops depending on your preferences. If your group is larger, we will arrange additional boats. You can get in the water to swim or wade at any time. You will see lots of fish and sea creatures. Most of our guests bring beer, water or other beverages along for the tour. We have coolers to keep them chilled.

  • 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.
Location
Garrison Bight Marina
Eisenhower Drive
Our meeting place depends on the tides.
Cancellation Policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

Customer Ratings
4.9
(93 Ratings)
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Sshaft79
May 11, 2024
A Key West Must!!! - 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!
Review provided by Tripadvisor
Tracey
Dec 30, 2023
Nice way to see some off the beaten track areas, bars and restaurants. - 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 .
Review provided by Tripadvisor
Sal_b
Dec 4, 2023
Good time - It was an enjoyable time going through the mangroves and stopping at local bars. He was fun to listen to.
Review provided by Viator
Mark_r
Oct 28, 2023
Great afternoon with Chester. - 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.
Review provided by Viator
Spowedvm
Oct 27, 2023
A MUST DO FOR RELAXING KEY WEST FUN! - 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!
Review provided by Tripadvisor
Linsmr
Oct 20, 2023
Made the "Must Do" List! - 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!
Review provided by Tripadvisor
Lisabs2375tk
Oct 15, 2023
Best under the radar tour in Key West!!!! - 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!
Review provided by Tripadvisor
Lana
Jul 17, 2023
PARTY! - 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!
Review provided by Tripadvisor
Rvezina
Jul 14, 2023
Dinghy tour with Chester - 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.
Review provided by Tripadvisor
Richie_p
Dec 5, 2023
Can't make this stuff up - 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.
Review provided by Viator
Select Date and Tickets
up to 10 guests
1
Adult
July 2024
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