D
Tour was great. Had a...
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.
Dinghy Drinking Tour through Key West Waters
+6 photos
At a glance
- Duration
- 3 hours
- Price from
- $85 / person
- Location
- Key West, United States
- Rating
- 4.9 / 5 · 108 reviews
- Languages
- EN
- Group
- Small group, up to 10
- Cancellation
- Free cancellation up to 24 hours before
- Confirmation
- Instant
- Ticket
- Mobile or paper ticket accepted
- Operator
- chester ruder
- Meeting point
- Our meeting place depends on the tides.
Description
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.
Schedule & prices
- Runs
- Every day
- Start times
- 12:00 PM
- Next available
- Mon, Oct 12
- Adult (ages 21+)
- $85
In demand: 20 of the next 28 departures are already sold out.
From the operator’s live schedule on Viator, checked Oct 7.
Tour Options
Itinerary
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.
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.
We often stop at the popular waterfront Hurricane Hole Restaurant and Bar for food and drinks.
What's included
Included
Licensed boat captain
Coolers for the drinks
Not included
Bring your own liquor, beer and sodas if you want to hydrate between stops. We provide ice and coolers.
Traveller Ratings
Reviews collected by Viator and Tripadvisor
4.9
108 reviews
How it compares in Key West
- Starting price $85 is 21% above the typical $70 for tours of similar length in Key West
Excurgo comparison of 346 Viator tours, recalculated daily.
Important Information
- Not recommended for travelers with spinal injuries
- Suitable for all physical fitness levels
- 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.
Cancellation
For a full refund, cancel at least 24 hours before the scheduled departure time.
1+ days before100% refund
0–1 days before0% refund
Frequently asked questions
How long does Dinghy Drinking Tour through Key West Waters take?
Dinghy Drinking Tour through Key West Waters lasts about 3 hours. The itinerary has 4 stops.
How much does Dinghy Drinking Tour through Key West Waters cost?
Prices start at $85 per person for this Key West experience, booked through Viator with the price shown before checkout. There is 1 booking option, so the final price depends on the option you choose.
What days does Dinghy Drinking Tour through Key West Waters run?
According to the operator’s current schedule, it runs every day, starting at 12:00 PM.
Does Dinghy Drinking Tour through Key West Waters sell out?
It can: 20 of the next 28 departures are already sold out, so booking ahead is a good idea.
Can I cancel Dinghy Drinking Tour through Key West Waters for free?
Yes. Cancel at least 1 day before the start for a full refund. Later cancellations are non-refundable.
Where does the tour start?
The meeting point is Our meeting place depends on the tides. Hotel pickup is not part of this experience.
What languages is Dinghy Drinking Tour through Key West Waters offered in?
The experience is available in EN.
Is this a private or a group tour?
It is a small-group experience with a maximum of 10 participants.
Will my booking be confirmed immediately?
Yes, bookings are confirmed instantly.
Is Dinghy Drinking Tour through Key West Waters worth it?
Travellers rate it 4.9 out of 5 across 108 reviews on Viator and Tripadvisor; it is run by chester ruder.
Reviews(108)
Reviews collected by Viator and Tripadvisor
S
Awesome Time!
Chester was awesome! It was a great trip. We had a blast! You will not be disappointed! We will do this again for sure!
Operator response
Thank you! You were a great group.
R
Best thing to do in Key West
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.
Operator response
Thank you! Come back soon
V
Highlight of our trip!
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.
Operator response
Thank you for your great review. We enjoyed the trip too!
B
Unique & Fun Key West Experience
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!
Operator response
Thank you so much. I am so happy you had a great time. Come back again.
E
The best excursion ever
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.
Operator response
thank you Elizabeth!
K
Best day in Key West!
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!
Operator response
Thank you Krista. Looking forward to your next trip
C
Refund
The captain canceled on us 3 days before as he was going out of town. I am still waiting for my refund.
Operator response
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.
A
My kind of boat ride
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.
Operator response
thank you! I hope you come back as a Repeat Offender. Let me know when you call. Chester
J
Fun & Unique Experience!
Super fun and unique way to explore a little piece of Key West. Chester - our Dingy Mate Captain was awesome.
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| Tour | Duration | Rating | Price | |
|---|---|---|---|---|
| Dinghy Drinking Tour through Key West Waters | 3 hours | 4.9 (108) | $85 | |
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from$85
4.9(108) Free cancellation