Key West Sunset Sail: Live Music, Open Bar & Appetizers

Summary

Key West sunset cruise with live music open bar & local bites

You’ll board Key West’s newest catamaran for a sunset cruise with live music setting the mood. Sip unlimited drinks from the open bar while sampling local appetizers as you watch the sky shift colors over the water. With friendly guides and an easygoing crowd, you’ll feel part of Key West’s evening rhythm—one of those experiences that lingers long after.

What’s the experience like?

You just sort of step onto the Sandie Cat and everything else drops away. I remember the deck felt warm under my bare feet, and there was this salty breeze that made my hair stick to my cheek in a way that was oddly comforting. The band was already tuning up—some guy in flip-flops strumming something mellow—and people were laughing, not in that forced way but like they’d already had a drink or two. Our guide, I think her name was Jess, handed me a margarita before I even found a seat. She grinned and said, “It’s Key West—no one’s thirsty here.”

I’m not sure what I expected from a sunset sail in Key West, but it wasn’t this feeling of being both part of the crowd and totally at ease. We drifted out past Mallory Square, and someone started passing around plates of jerk chicken sliders (those little Hawaiian rolls are dangerous) and BBQ meatballs. I tried to balance my drink and food while the boat rocked gently—almost lost a slider to the sea but caught it just in time. The sky kept changing colors; orange melting into pink, then purple. At some point, Li from our group tried to order in Spanish and ended up getting two rum runners instead of one—she didn’t complain.

The open bar really does mean open: beer, wine, champagne, whatever you want. I stuck with margaritas because they tasted like vacation. There was this moment when everyone went quiet as the sun touched the water—the kind of hush you don’t plan for but just happens when something feels right. Even the band slowed down for it. It’s weird how quickly two hours go by when you’re watching the horizon disappear behind your glass.

On the way back, people danced (or tried to), someone spilled hummus on their shirt and didn’t care, and Jess told us about growing up here—how locals never get tired of these sunsets. I still think about that view sometimes when I hear certain songs or taste pineapple in a drink. Not every tour sticks with you like that.

Step-by-step itinerary

Day 1 — Key West Sunset Sail with Music and Drinks

• Board the Sandie Cat catamaran
• Enjoy live local music onboard
• Sip unlimited drinks from open bar
• Eat appetizers including jerk chicken sliders
• Watch the famous Key West sunset

Top questions

Is there an open bar on the Key West sunset sail?

Yes, unlimited well mixed drinks, draft beer, margaritas, rum runners, wine, and champagne are included.

What kind of food is served during the sunset cruise?

You’ll get appetizers like Jamaican jerk chicken sliders on Hawaiian rolls, BBQ meatballs, veggie trays, cheese & crackers, pita & hummus.

How long does the Key West sunset sail last?

The cruise lasts approximately 2 hours.

Is live music included on board?

Yes, there is live local music throughout the cruise for entertainment.

Are children allowed on this tour?

Yes; children must be accompanied by an adult.

Is hotel pickup included?

No hotel pickup; guests check in 30 minutes before departure at the dock.

Can infants or small children join?

Yes; infants can ride in prams or strollers and specialized infant seats are available.

Are service animals permitted?

Yes; service animals are allowed on board.

What’s included

Your evening includes boarding Key West’s newest catamaran with three decks for sunset views, unlimited drinks from an open well bar (beer, wine, cocktails), tasty appetizers like jerk chicken sliders and BBQ meatballs plus live local music—all hosted by friendly crew who make sure everyone feels welcome from check-in to docking back at port.