Key West: Tiki Bar Sunset Cruise with BYOB & Harbor Views

Summary

Key West harbor cruise with tiki bar boat, sunset views, and local stories

You’ll step onto a floating tiki bar in Key West Harbor, toast new friends as your captain shares stories about shrimp fleets and sunsets, watch for that elusive green flash (no promises), and drift home past historic docks as night falls—maybe feeling lighter than you expected.

What’s the experience like?

I’ll be honest — I booked this Key West tiki bar sunset cruise mostly because it sounded funny. Floating around on a thatched-roof bar with strangers? Why not. But once we stepped onto that little boat (it really is shaped like a bar, stools and all), I felt this weird mix of excitement and calm, like something good was about to happen. Our captain, Mike, handed out cups and pointed at the ice chest — “Whatever you brought, we’ll keep it cold.” The sun was still high but you could already smell salt in the air and hear music drifting from shore. Someone tried to connect their playlist to the bluetooth stereo but gave up after three tries — nobody minded.

We cruised slowly past places I’d only read about: Sigsbee Key, Wisteria Island, even Sunset Pier where people waved at us like we were celebrities or maybe just ridiculous. Mike kept up this steady stream of stories about old shrimp boats and why Mallory Square gets so crowded at sunset (he says it’s for the jugglers; I think it’s for the light). There was this moment when we rounded Fleming Key — everything got quiet except for the soft slap of water against the hull and someone’s laugh echoing off the roof. I sipped my drink (BYOB is genius) and tried to catch that “green flash” everyone talks about as the sun hit the horizon. Didn’t see it. Still kind of magical.

On the way back through Key West Harbor, Mike pointed out what used to be a turtle plant — now just an old building with faded paint — and told us how shrimpers would dock here after weeks at sea. The air smelled different then, he said. I don’t know if that’s true but it stuck with me. We finished whatever snacks we’d brought and watched as lights started flickering on along the docks. It felt like we’d been gone longer than two hours somehow, in a good way.

Step-by-step itinerary

Day 1 — Key West Tiki Bar Sunset Cruise

• Board custom Tiki Bar Boat
• Cruise past Sigsbee Key and islands
• Pass by Sunset Pier
• Sail past Mallory Square Sunset Celebration
• Find vantage point for Green Flash
• Enjoy cocktails and snacks near Fleming Key
• View historic Shrimp Fleet and Turtle Plant

Top questions

How long does the Key West tiki bar sunset cruise last?

The cruise lasts approximately 2 hours from departure to return.

Is there a bathroom on board the tiki bar boat?

Yes, there is a walk-in bathroom available on board.

Can I bring my own drinks on this sunset cruise?

Yes, it's BYOB—bring your favorite adult beverages and snacks.

Does the tour include pickup from my hotel?

No hotel pickup is included; you'll meet at the dock before departure.

What does the tour provide besides the boat ride?

The tour provides a USCG certified captain/guide, bottled water, ice, cups, blender, bluetooth stereo system, and life vests.

Is this sunset cruise suitable for kids or infants?

Infants are allowed but must sit on an adult's lap throughout the tour.

Are there any fitness requirements for joining?

The tour is suitable for all physical fitness levels.

Will I see wildlife during the harbor cruise?

Your captain will point out local wildlife along with landmarks as you cruise by various keys.

What’s included

Your evening includes a two-hour harbor cruise aboard a custom tiki bar boat with shaded seating and padded stools; guidance from a USCG certified captain; bottled water; plenty of ice; cups; use of blender; bluetooth stereo; life vests—and you just bring your favorite drinks or snacks along for the ride before returning to Garrison Bight marina.