Key West: Sunset Sail with Open Bar, Live Music & Hors D'oeuvres

Summary

Key West sunset cruise with cocktails, live music and fresh bites

You’ll board a modern sailing catamaran in Key West for an evening of open-bar drinks, chef-made hors d’oeuvres, and live music from local musicians as you cruise toward that famous sunset view. With laughter, ocean breezes, and flavors you might not expect at sea, you’ll find yourself pausing to soak in moments you can’t quite photograph.

What’s the experience like?

I almost missed the boat—literally. I’d underestimated how far the Key West Historic Harbor was from my hotel (note to self: next time, leave earlier), so I was a bit out of breath when I reached the catamaran. The crew just grinned and handed me a cold glass of sangria before I could even apologize. There’s something about that first sip—sweet, chilled, a little tangy—that made me instantly relax as we pulled away from the dock. The sky was still pale blue then, not yet hinting at what was coming.

Our guide, Captain Mike (who has this sunburned laugh), introduced the local band tuning up in the corner. I didn’t catch their names—too busy watching pelicans squabble over scraps near the pier—but their music drifted over us as we sailed out. It wasn’t loud or showy; just easy guitar and voices mixing with the slap of water against the hull. Someone passed around shrimp cocktail and these little tart things—I dropped one on my shirt but nobody cared. The air smelled like salt and limes from someone’s drink.

I kept wandering around the deck, sometimes by myself, sometimes chatting with this couple from Tampa who come every year “just for this sunset.” When it finally happened—sky going orange-pink like some painter lost his mind—I tried to take a photo but gave up. You can’t really catch it. There was this hush for a minute, everyone just standing there with glasses half-raised, not talking. I still think about that silence more than anything else.

Step-by-step itinerary

Day 1 — Key West Sunset Sail with Drinks and Snacks

• Meet at Key West Historic Harbor
• Board Marquesa sailing catamaran
• Meet captain and crew
• Set sail and choose a drink
• Enjoy shrimp cocktail and appetizers
• Watch Key West sunset from boat
• Listen to live local music
• Enjoy seasonal mini tart dessert

Top questions

What time should I arrive for the Key West sunset sail?

Please arrive 30 minutes before your scheduled departure time at Key West Historic Harbor.

Is food included on this Key West sunset cruise?

Yes, chef’s hors d’oeuvres are served onboard including shrimp cocktail and other small bites.

Are drinks included during the sunset sail?

The cruise includes an open liquor bar with champagne, sangria, boutique wine, premium beer, cocktails, soft drinks and filtered water.

Is there live music on board?

Yes, local Key West musicians play live music during the cruise.

Are bathrooms available on the catamaran?

Yes, there are dual spacious bathrooms for guest comfort onboard.

Is this sunset sail suitable for all fitness levels?

This activity is suitable for all physical fitness levels.

Can children join the Key West sunset sail?

The minimum age to drink alcohol is 21 years; otherwise all ages are welcome.

What’s included

Your evening includes boarding at Key West Historic Harbor onto a modern catamaran with dual bathrooms for comfort; unlimited open bar featuring champagne, sangria, boutique wines and cocktails; chef’s selection of hors d’oeuvres like shrimp cocktail; plus live performances from local musicians as you watch the sun set over the island waters.