LIVE MUSIC · KEY WEST

Live Music Shows in Key West: 7 Nights Worth Booking

7 shows  ·  from $72 a seat

This is the shortlist you would send a friend: 7 live music shows worth the money, each with its price, its traveller verdict and the one thing to know before you commit.

Key West Sunset Sail with Open Bar, Live Music and Hors D'oeuvres - Mallory Square from the water
Evening Experiences, Key West Live Music, Live Music, Live Music Cruises, Tour Reviews, USA Live Music

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

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

Key West sunset sail review with open bar, live music, shrimp, wide deck space, practical tips, pricing, weather advice, and honest drawbacks.

“We had a little issue with finding the meeting location but once we found “the pineapple “, it was smooth sailing (pun intended). The crew were awesome. The food and drinks were plentiful and the delightful.”

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Key West Sunset Cruise: Dinner, Live Music & Drinks Included - The buffet: plentiful island-style comfort food
Concerts with Dinner, Evening Experiences, Key West Live Music, Live Music, Live Music Cruises, Tour Reviews, USA Live Music

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

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

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

Review of Key West’s 2-hour sunset dinner cruise with buffet, unlimited standard drinks, live music, and open-water sunset views.

“Love it and it's candid experience!!! We didn't have experience the sunset but the majestic sights are awesome. The dancing bonding was fun. I love the music that was played by the dj. The crews are awesome especially the captain and the dj.”

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Key West Sunset Sail with Live Music, Drinks and Appetizers - A 65-foot catamaran with room to move
Evening Experiences, Key West Live Music, Live Music, Live Music Cruises, Tour Reviews, USA Live Music

Key West Sunset Sail with Live Music, Drinks and Appetizers

Key West Signature Sunset Sail with Live Music, Open Bar & Food - Boarding at 201 William Street
Evening Experiences, Food, Food & Drink, Key West Live Music, Live Music, Live Music Cruises, Tour Reviews, USA Live Music

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

Key West: Sunset Dinner Cruise with Open Bar & Live Music - Cruising the harbor toward the Gulf
Concerts with Dinner, Evening Experiences, Key West Live Music, Live Music, Live Music Cruises, Tour Reviews, USA Live Music

Key West: Sunset Dinner Cruise with Open Bar & Live Music

5.Sunset Dinner Cruise with Open Bar & Live Music

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

Review of Key West’s two-hour sunset dinner cruise, with tropical buffet, open bar, live music, practical tips, price value, and drawbacks.

“Really enjoyable cruise with great buffet food and drinks. The DJ was also excellent and we had a fabulous couple of hours watching the sunset. Definitely recommend!!”

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Key West: 2-Hour Sunset Sail with Live Music - The first views: seaport, waterfront activity, and open water
2-Hour Experiences, Evening Experiences, Key West Live Music, Live Music, Live Music Cruises, Tour Reviews, USA Live Music

Key West: 2-Hour Sunset Sail with Live Music

6.2-Hour Sunset Sail with Live Music

★★★★★★★★★★4.7 · 130 reviews · 2 hours · from $79

Key West sunset sail review with live music, unlimited drinks, appetizers, landmark views, pricing, tips, and practical advice.

“We had a really good time on the Marquesa. Not too crowded, good service and the live music was perfect for the setting. Topped off with possibly the clearest and most amazing sunset over the water.”

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Key West Sunset Buffet Dinner Cruise with Open Bar and Live Music - Cruising Key West as the evening begins
Buffet Experiences, Concerts with Dinner, Evening Experiences, Key West Live Music, Live Music, Live Music Cruises, Tour Reviews, USA Live Music

Key West Sunset Buffet Dinner Cruise with Open Bar and Live Music

7.Key West Sunset Buffet Dinner Cruise with Open Bar and Live Music

★★★★★★★★★★4.5 · 3 reviews · 2 hours (approx.) · from $119

Review of Key West’s sunset buffet cruise with open bar, live music, catamaran views, practical tips, pricing, and honest drawbacks.

“96 guests. Boat was full! There are two dinner seatings, they were crowded and the second seating is right at sunset so you’re down in the dining area , not topside. Did I say crowded? It definitely was. If you like lots of ppl, decent food and don’t care about seeing the sunset….”

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