Key West: Dinghy Bar Hopping Tour & Mangrove Tunnels

Key west dinghy drinking tour with bar stops & swimming

You’ll float through Key West’s mangrove tunnels by dinghy with a local captain, stopping at waterfront bars where locals hang out. Swim or wade in clear water whenever you want, climb up to rustic docks for snacks and drinks, and share laughs with your group as you explore hidden corners of the island by boat.

Step-by-step itinerary

Dinghy tour with bar stops and swimming

• Board dinghy with licensed captain
• Travel through mangrove tunnels
• See fish and sea creatures
• Swim or wade in clear waters
• Stop at Boathouse dock for drinks
• Visit Stock Rock Cafe for snacks
• Stop at Hurricane Hole Restaurant and Bar

The experience

We clambered into this little dinghy just off the docks in Key West: five of us, plus Captain Mike, who looked like he’d spent half his life on these waters (he probably has). The engine coughed to life and we drifted away from the noise of Duval Street. I could smell sunscreen and salt, and someone’s cheap beer already cracking open. Mike grinned and said, “You’ll want to duck when we hit the mangroves.” He wasn’t kidding: branches scraped my hat right off at one point, but nobody cared. Sunlight kept flickering through the leaves while tiny fish darted below us. It felt like we were sneaking into some secret part of Key West most people miss.

First stop was this old boathouse bar behind a weathered resort: had to climb a short ladder up to the dock (my knees complained but I made it). Inside, faded photos showed what the place looked like decades ago. There were pulleys on the ceiling and locals trading stories over cold beers. The bartender slid over a bowl of peanuts without asking. We tried to say thanks in our best attempt at Conch accent: got a laugh out of her for that one.

Back on the water, someone jumped in for a swim while we floated near Stock Rock Cafe: a real locals’ spot. The water was so clear you could see silvery flashes under the boat. I just dangled my feet in and let the sun bake my shoulders. Honestly, I still think about that feeling sometimes when I’m stuck back at work. We finished up at Hurricane Hole with fried shrimp and another round, everyone a little sunburnt and salty but not really wanting it to end yet. There’s something about drifting between bars by boat that makes you feel like time works differently here.

What’s included

Your day includes a licensed local boat captain guiding your small group by dinghy through Key West’s mangrove tunnels and calm waters, coolers to keep your drinks chilled along the way, flexible stops at two or three waterfront bars depending on your preference, plus plenty of chances to swim or wade whenever you feel like it before heading back ashore.

Before you book

Days and timesMonday, Thursday and FridayDeparts at 12:00

Book up to2h before

AgesAdult (21 and older) · Under 21: can't be included in the booking

GroupUp to 10

Live guideEnglish

Meeting point and pickupNo hotel pickup: you go to the meeting point. Ends back at the starting point.

Cancellation and refundsFree cancellation up to 24 h before the start. After that, no refund.It may be canceled due to bad weather. If that happens, you're offered another date or a refund.

Prices and times updated today

Good to know

Easy physical levelNot for back problems

Operated by chester ruder

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Top questions

What happens if it rains?

It may be canceled due to bad weather. If that happens, you're offered another date or a refund. Free cancellation up to 24 h before the start.

How many people fit in each dinghy?

Each dinghy seats up to 5 people plus your captain.

Can I bring my own drinks on the tour?

Yes, most guests bring their own beer or other beverages. Coolers are provided.

Are there swimming opportunities during the tour?

You can swim or wade in the water at any time during the tour.

What bars do we stop at on this Key West dinghy drinking tour?

The usual stops are Boathouse Bar, Stock Rock Cafe, and Hurricane Hole Restaurant & Bar.

Is pickup included for this tour?

No hotel pickup is included. You will call on the morning of your trip for your meeting location based on tides.

Do I need any boating experience?

No boating experience is needed. An experienced licensed captain leads your dinghy tour.

Is this suitable for travelers with knee or back problems?

If you have knee issues or spinal injuries, some stops may be difficult due to ladders. You can choose to stay in the boat if needed.

What should I wear or bring?

Wear swimwear under your clothes if you plan to get in the water. Bring drinks if you'd like.