Top picks for Key West Shows & events

Discover 6 Shows & events in Key West on Trip.com, updated November 6, 2026, with experiences lasting from 1 to 2 hours. Find the perfect adventure for your day!

From KRW 99,029 per person, with an average total of KRW 116,129. Choose the option that suits your plan.

With 950 verified reviews, Shows & events Key West boast an average rating of 4.7.

This week's most popular Shows & events: "Key West Sunset Cruise: Dinner, Live Music & Drinks Included", with 622 reviews and a 4.3 rating.

Now on Trip.com: "Key West Signature Sunset Sail with Live Music, Open Bar & Food", a 2-hour adventure in Key West!

The next available day tour departs on November 7, 2026. Book now to secure your spot!

Key West Shows & events usually take about 2 hours — perfect for a relaxed, immersive experience!

25% of Key West Shows & events now offer English-speaking guides

November is the perfect time to visit Key West! Choose from 6 available day tours, including seasonal favorites like Key West Sunset Cruise: Dinner, Live Music & Drinks Included.

Your trip, worry-free! All day tours are run by licensed suppliers with verified reviews, and many include free cancellation before departure.

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6 results for Key West Shows & events

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RecommendedAttractions (13494)Shows & events (6)Boat tours (68)Culture & history (16)Day tours (117)Food & drink (19)Outdoor & sports (29)City sightseeing (20)Nature & wildlife (35)Water activities (58)Travel photography (1)Aerial tours (2)SIM card (36)

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Reviews/Trip Moments

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Reviews: Key West Signature Sunset Sail with Live Music, Open Bar & Food
Guest User2024-08-09
Started amazing but then the weather came in and the Captain made the best decision for the safety of all on board and went back to the harbor and let us stay onboard in the harbor enjoying the music and drinks.
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Guest User2024-08-30
Seen the most amazing sunset ever Never thought that I’d do this but I loved every minute of it and I would do it again anytime time
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Reviews: Key West: Sunset Dinner Cruise with Open Bar & Live Music
Guest User2026-10-11
Such a fun sunset cruise. The food was a buffet and not just appetizers like some others we saw offered. Great music, bartender and crew. We met some fun people and enjoyed having a dining room to sit in while eating. The view was stunning!
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Guest User2024-09-12
There is no better way to start a Key West vacation then by taking a sunset Waters sports dinner cruise. The crew was fun and organized and kept the drinks of rum punch flowing while we enjoyed the fun music of an awesome DJ and of course the most amazing sunset ever. The food was perfect for a dinner Cruz with rice and beans and mahi-mahi and pulled pork and salad and the cinnamon churros filled with cinnamon sugar yumminess, was great happy ending!

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