Key West: Sunset Sail Catamaran with Live Music & Drinks

Summary

Key West sunset sail with music, drinks and local color

You’ll step onto a roomy catamaran in Key West for two hours of live music, unlimited margaritas or wine, and fresh appetizers as you drift past Mallory Square and Fort Zachary Taylor. With locals playing music and plenty of space to relax or chat, you’ll catch that famous sunset from the best spot in town — feeling both part of something and quietly your own person for a while.

What’s the experience like?

I didn’t expect to feel so relaxed, honestly. We’d just made it to the dock by Greene Street — I almost tripped over my own flip-flops, but nobody seemed to mind. The crew had this easy way about them, like they’d been doing this forever but still cared if you were having a good time. Once we stepped onto the catamaran (it’s big, 65 feet — you can actually move around), I caught that first whiff of salt air mixed with something fruity from the bar. It was already starting to feel different from those crowded tourist boats I’d seen earlier.

The sun was still high when we pulled away from Mallory Square, but people were already lining up for drinks — margaritas mostly, though one guy went straight for champagne at four in the afternoon. I tried a pinwheel sandwich and some hummus while a local musician started tuning up near the bow. She played something soft at first, then got everyone clapping along. There was this moment when Fort Zachary Taylor drifted past in the distance; someone pointed it out and told us about its history, but honestly I was half-distracted by how the light hit the water — all gold and weirdly calm. My friend tried to say “cheers” in Spanish and got it wrong; nobody cared.

By sunset, everyone had sort of spread out — some on the sundeck with faces turned toward that orange-pink sky, others tucked into shaded corners just talking quietly or laughing about nothing important. The appetizers kept coming around (I probably ate too much fruit), and every so often you’d hear a cork pop or someone singing along off-key. It felt less like an event and more like being invited out by locals who know how to do evenings right here in Key West. The live music really did make it feel personal — not loud or pushy, just part of everything else going on.

I keep thinking about that last bit of sunlight as we headed back in — how everyone went quiet for a minute without anyone telling them to hush. There’s something about watching a Key West sunset from out on the water with strangers who don’t stay strangers long… it sticks with you longer than you expect.

Step-by-step itinerary

Day 1 — Key West Sunset Sail Experience

• Meet at Greene St. and Elizabeth St.
• Board 65-foot luxury catamaran
• Set sail for two-hour sunset cruise
• Enjoy complimentary drinks and appetizers
• Listen to live local music
• View Mallory Square from boat
• See Fort Zachary Taylor at sunset
• Relax on sundeck or shaded lounge

Top questions

Where does the Key West sunset sail depart from?

The departure point is at the corner of Greene St. and Elizabeth St., next to The Conch Republic Seafood Company.

Are drinks included on the Key West sunset sail?

Yes, complimentary margaritas, champagne, beer, wine, soda, and pop are included during the cruise.

Is food provided during the sunset cruise?

Yes, guests enjoy appetizers such as antipasti platters, seasonal fruit, hummus, and pinwheel sandwiches.

How long is the Key West sunset sail?

The cruise lasts approximately two hours.

Is there live music on board?

Yes, local artists perform live music throughout the sunset sail.

Can children join this tour?

Yes, but guests under 18 must have a parent or guardian present at check-in to sign waivers.

Are special dietary requests accommodated?

No, special dietary requests cannot be accommodated for this tour.

What landmarks can be seen during the cruise?

You may see Mallory Square and Fort Zachary Taylor State Park while sailing.

Do I need to bring ID for this tour?

Guests 18 years old and up must bring valid government-issued photo ID; minimum drinking age is 21.

What’s included

Your evening includes boarding at Greene Street near The Conch Republic Seafood Company with two hours on a spacious catamaran featuring unlimited margaritas, champagne, beer or wine plus soft drinks alongside an appetizer spread of antipasti platters, fresh fruit, hummus and sandwiches — all while local musicians play live as you watch Mallory Square slip by under changing skies before returning after sunset.