8 Best Concerts Tours In Key West

Concerts, Cruises & Boat Tours, Drinking Tours, Evening Experiences, Key West, Sunset Sails & Cruises, Tour Reviews

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

/ June 4, 2026

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

Sail Key West at sunset on a large catamaran with an open bar, live local music, and filling hors d’oeuvres. Depart from Elizabeth St.

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

/ June 4, 2026

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

Key West sunset dinner cruise with a tropical buffet, unlimited drinks, and live music on a 65-foot yacht. See sunset from the water.

★ 4.5

“It was a great ride out and back. Captain did an awesome job. Food was good but we didn't care for the music. Sunset was amazing”

1,707 reviews2 hours (approx.)From $92.95by Sunset Watersports

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Concerts, Cruises & Boat Tours, Evening Experiences, Key West, Sunset Sails & Cruises, Tour Reviews

Key West Sunset Sail with Live Music, Drinks and Appetizers

/ June 4, 2026

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

A 2-hour Key West catamaran sunset sail with live music, unlimited drinks, and appetizers—plus views of Mallory Square and more.

★ 4.5

“Great trip!! Well organized, and a perfect amount of time with a beautiful sunset!’ we decided last minute to do it, and it all worked out perfectly”

952 reviews2 hours (approx.)From $79.95by Fury Water Adventures

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Bachelorette Party Cruises, Birthday Party Cruises, Concerts, Cruises & Boat Tours, Drinking Tours, Evening Experiences, Food, Food & Drink, Key West, Party Boat Cruises, Sunset Sails & Cruises, Tour Reviews

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

/ June 4, 2026

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

Sail Key West at sunset on a modern 3-deck catamaran with live music, unlimited open bar, and light appetizers for about 2 hours.

★ 4.5

“It was exactly as expected....drinks and sunset on a big catamaran. Fortunately, it was not super crowded. The staff was great and the boat was clean.”

314 reviews2 hours (approx.)From $72.00by Sunset Watersports

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Concerts, Cruises & Boat Tours, Dining Experiences, Dinner Experiences, Drinking Tours, Evening Experiences, Key West, Sunset Sails & Cruises, Tour Reviews

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

/ June 4, 2026

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

Key West sunset dinner cruise on the Party Cat with open bar, tropical buffet, and live music on the upper deck. 2 hours.

★ 4.5

228 reviews2 hoursFrom $92by Sunset Watersports Key West

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2-Hour Experiences, Birthday Party Cruises, Concerts, Cruises & Boat Tours, Evening Experiences, Key West, Sunset Sails & Cruises, Tour Reviews

Key West: 2-Hour Sunset Sail with Live Music

/ June 4, 2026

6.Key West: 2-Hour Sunset Sail with Live Music

Key West 2-hour sunset catamaran with live music, unlimited drinks and appetizers, plus prime views of Mallory Square and Fort Zachary Taylor.

★ 4.7

130 reviews2 hoursFrom $79by Sebago Watersports

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2-Hour Experiences, Concerts, Guided, Key West, Tour Reviews, Tours

2-Hour Live Music Guided Tour in Key West

/ June 11, 2026

7.2-Hour Live Music Guided Tour in Key West

A 2-hour Key West live music crawl with Maxwell: four venues, drink discounts, venue history, and local music downloads.

★ 5.0

“Went to 3 music venues. One I would have not known to go to and it was fantastic. Max was very knowledgeable of each place and we had a fun time.”

16 reviewsFrom $35.00by Key West Art Walk

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Buffet Experiences, Concerts, Cruises & Boat Tours, Dining Experiences, Dinner Experiences, Drinking Tours, Evening Experiences, Key West, Tour Reviews

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

/ June 19, 2026

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

Key West sunset dinner cruise with tropical buffet, live music, and an open bar on a catamaran with panoramic sundeck views.

★ 4.5

“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….”

3 reviews2 hours (approx.)From $119.99by Attractions4us LLC

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Concerts