Our Top 5 Live Music Experiences in Key West

1.Key West Sunset Sail with Open Bar, Live Music and Hors D’oeuvres

★★★★★★★★★★4.5 · 3,559 reviews · 2 hours (approx.) · from $79Our pick

Spend about two hours sailing from Key West with an open bar, champagne, sangria, premium beer, cocktails, and chef-prepared hors d’oeuvres. A local musician provides live entertainment as you pass Mallory Square, Fort Zachary Taylor, and Sunset Key. Arrive 30 minutes early and bring a sweater, sunglasses, and photo ID if you plan to drink.

“We had a fantastic time. The crew was awesome and Just George kept us entertained. We were fortunate to have a perfect weather day for the sunset. Highly recommend.”

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2.Key West Sunset Cruise: Dinner, Live Music & Drinks Included

★★★★★★★★★★4.5 · 1,707 reviews · 2 hours (approx.) · from $92

Board a 65-foot yacht at Key West’s historic seaport for a two-hour sunset cruise. Enjoy crew-served Caribbean-style buffet dishes, unlimited well drinks, beer, wine, and soft drinks, then head upstairs for sunset views, live music, and views of Mallory Square and the Florida Keys National Marine Sanctuary. Premium drinks cost extra.

“Very proficient staff. Timely, prompt response to ticket purchase and loading unloading. Food was outstanding.”

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3.Key West Sunset Sail with Live Music, Drinks and Appetizers

★★★★★★★★★★4.5 · 952 reviews · 2 hours (approx.) · from $79

Spend two hours aboard Fury Water Adventures’ 65-foot catamaran with live local music, open drinks, and seasonal appetizers. You’ll pass views of Mallory Square and possibly Fort Zachary Taylor while the captain seeks the best sunset angle. The mood is lively, but shaded seating and three viewing decks give you room to relax.

“Great time well organized fun way to see sunset… good music with Killer Dudes excellent service very fun”

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4.Key West Signature Sunset Sail with Live Music, Open Bar & Food

★★★★★★★★★★4.5 · 314 reviews · 2 hours (approx.) · from $72Best value

Board the Sandie Cat at 201 William Street for a two-hour Key West sunset sail with live music, unlimited well drinks, beer, wine, champagne, and light appetizers. You’ll have three decks for viewing, with Captain Anna among the crew members praised for her friendly command. Check in 30 minutes early and expect a social, family-friendly atmosphere.

“Boat and crew were fantastic and sunset was amazing. We appreciated that the boat turned several times so that all guests could get good views without moving. Huge bonus with multiple dolphin sightings. Drinks were good but food was just sub-par at best. This would have been a 5.0 rating otherwise.”

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5.Sunset Dinner Cruise with Open Bar & Live Music

★★★★★★★★★★4.5 · 228 reviews · 2 hours · from $92

Board The Party Cat at 201 William St. for a two-hour Key West harbor cruise with a tropical buffet, open bar, and live music. You will eat in an air-conditioned dining room, then head upstairs for dancing and sunset views over the Gulf of Mexico. Captain and crew keep the mood lively, with performers such as vocalist and musician Dante appearing on some sailings.

“Awesome food, service, and activity! Highly recommend this sunset dinner cruise in Key West!”

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