5 Concerts in Key West Worth Booking

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 on a roomy catamaran with live local music, an open liquor bar, champagne, wine, sangria, premium beer, soft drinks, and hearty hors d’oeuvres. You’ll pass Mallory Square, Fort Zachary Taylor, and Sunset Key before returning to the harbor.

“Dress warmly when in the 60s. Grab a place to sit quickly. Great snacks and drinks. Music selection was broad.”

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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 with crew-served Caribbean buffet, unlimited standard drinks, live music, and views of Mallory Square. Arrive an hour early, and expect shared seating and a possible two-part dinner schedule.

“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’s 65-foot catamaran with live cover music, dancing, unlimited beer, wine, champagne, margaritas, sodas, and seasonal appetizers. You’ll pass sights such as Mallory Square and Fort Zachary Taylor while the captain chooses the best route for sunset views.

“Great time from start to finish. Good band, food and open bar. It was all really fantastic. A must do.”

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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 three-deck Sandie Cat at Sunset Watersports for a two-hour Key West sunset sail. Captain Anna and the crew set the pace while live music, an open well bar, champagne, and light appetizers keep the evening moving. Expect a social boat ride, not a full dinner or adults-only cruise.

“Great cruise. The food is meager so you are not going to make a meal of it. However the drinks were flowing good!!”

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5.Key West: 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 on the upper deck. You will watch the sun set over the Gulf waters, with dinner served in two groups during the cruise.

“What a great time. Great food, friendly staff, comfortable setting backed up by a view of the Gulf of Mexico and the sunset. The entertainment was a Jamaican performer from Kingston. He was awesome on vocals, guitar and synthesizer. He knew how to show the group a good time.”

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