What to do and see in Key West, Florida (FL): The Best Concerts & Shows

March 22, 2022 Christa Meece

Does time ever pass in the Florida Keys? Everyone and everything in Key West seems to go at its own pace, right down to the ice melting slooooowly in your margarita glass. Of course, it’s not all limes and leisure – Key West is known as the “Winter White House” because of its appeal to visiting U.S. presidents, and the island has been home to literary greats like Ernest Hemingway and Tennessee Williams. The diving here is phenomenal, as is the kid-friendly Florida Keys Eco-Discovery Center.
Restaurants in Key West

1. Fringe Theater

512 Eaton St, Key West, FL 33045 +1 305-731-0581 [email protected] http://www.fringetheater.org/
Excellent
100%
Good
0%
Satisfactory
0%
Poor
0%
Terrible
0%
Overall Ratings

5.0 based on 2 reviews

Fringe Theater

Fringe Theater is Key West's community-focused theater. We strive to enrich, educate, and entertain our community and those who visit us! Fringe is a 501(C)(3).

2. Waterfront Playhouse

407 Wall Street Mallory Square, Key West, FL 33040 +1 305-294-5015 [email protected] http://www.waterfrontplayhouse.org
Excellent
87%
Good
9%
Satisfactory
2%
Poor
1%
Terrible
1%
Overall Ratings

5.0 based on 259 reviews

Waterfront Playhouse

Named "The Best Professional Theater in Florida" (Florida Monthly Magazine), The Waterfront Playhouse is a not-for-profit, professional theater located on historic Mallory Square in Old Town Key West that attracts locals and tourists alike with a wide range of comedies, dramas, musicals, concerts, and world premieres. Celebrating 81 years of presenting the very best in live theater, check our website for season announcements and events.Join us for an exciting evening of theater in Paradise. When the sun sets, the curtain rises at The Waterfront Playhouse.

Reviewed By 988rebab

The secret of Key West is really the home town comfort behind the crowds and sights and sounds of Duval Street and the bar scene. Its the beaches, the bars, the people and yes, the local theater. If you haven't been to a play at the Waterfront Playhouse, you are missing out on the heartbeat of Key West.

3. Comedy Key West

218 Whitehead St #5, Key West, FL 33040-6595 +1 305-985-7370 [email protected] http://www.comedykeywest.com
Excellent
98%
Good
2%
Satisfactory
0%
Poor
0%
Terrible
0%
Overall Ratings

5.0 based on 52 reviews

Comedy Key West

Comedy Key West is the only comedy club in The Florida Keys. The closest club is in Cuba & they are not as funny as we are. Comedy Key West specializes in bringing national headliners every week. Join us in our intimate downtown Key West club as comedians from Comedy Central, Netflix, NBC, CBS & Comedy Festival Award Winners take the stage. Our headliners are used to playing in venues that hold thousands of guest. Our venue maxes out at 75 guests. Check our updated calendar at comedykeywest.com & swing into see our professional stand-up comedy shows every Thursday, Friday & Saturday.

Reviewed By judys49

We went to Comedy Key West the last night of our girls trip. It was a lot of fun, and we had some good laughs. The food was good too! A must see when you are at KW. We will be back! I even got to get a picture on stage.

4. Truman Waterfront Park

21 E Quay Rd, Key West, FL 33040 https://www.cityofkeywest-fl.gov/egov/apps/document/center.egov?view=detail&id=16481
Excellent
76%
Good
24%
Satisfactory
0%
Poor
0%
Terrible
0%
Overall Ratings

5.0 based on 17 reviews

Truman Waterfront Park

Reviewed By Explorers377 - Horsham, United States

This place is a true hidden gem. We traveled to KW with our 17 month old and this park is a true hidden gem. We visited 3 days in a row! Not only does it have several different playground apparatuses, but the splash pad is awesome as well! The bathrooms were super clean. We loved being next to the coast guard ship and watching people playing with their dogs in the fields. This park was not mentioned in any guide I read beforehand. My husband went running one morning and just stumbled upon it. If I were hotel staff and had people visiting with children, this is one of the top places I would suggest.

5. Red Barn Theatre

319 Duval St Behind the Woman's Club, up the adjacent alleyway, Key West, FL 33040-6685 +1 305-296-9911 [email protected] http://www.redbarntheatre.com/
Excellent
71%
Good
24%
Satisfactory
2%
Poor
2%
Terrible
1%
Overall Ratings

4.5 based on 182 reviews

Red Barn Theatre

Hosts live productions, including plays, cabaret and musicals.

Reviewed By bkingjay - Boston, United States

First time at this venue...saw an incredibly delightful two person play: DANCE LESSON! Dave Bootle and his female costar (Caroline) delivered Oscar performances! Hilariously funny, but also very poignant! You will not be disappointed!

6. The Studios of Key West

533 Eaton Street, Key West, FL 33040-6801 +1 305-296-0458 [email protected] http://www.tskw.org
Excellent
81%
Good
13%
Satisfactory
3%
Poor
0%
Terrible
3%
Overall Ratings

4.5 based on 91 reviews

The Studios of Key West

The Studios of Key West provides a collaborative & supportive environment for creative experience. We offer studio space, lectures, workshops, residencies, partnership projects & nurture the creation of work. Our mission is to build audiences & support the advancement of established & emerging creative people in the Florida Keys. Our purpose is to remind us of our own creativity, empower artists to show us the world in new ways, use the arts to build friendships & establish Key West as a beacon of cultural activity. The Studios was founded with the vision of bringing world class artists to the island, connecting them with local audiences & artists, & offering space to explore their creativity. We’ve hosted Pulitzer prize winners, world renowned artists & musicians, & introduced students to different ways of seeing & working. Our little stage bristles with talent, & every month hundreds of people visit The Studios to take in new experiences & catch up with old friends.

Reviewed By roberttraceyb - Key West, United States

The Studios of Key West has become a true artistic center worthy of high praise. It's something you might find in a large city, and yet it's in the middle of a quaint, small town. Great art, great classes, a fabulous bookstore, and top-quality theater productions. It should definitely be one your list to check in advance for events.

7. The Cabaret At La Te Da

1125 Duval St, Key West, FL 33040-3156 +1 305-296-6706 [email protected] http://www.lateda.com/
Excellent
76%
Good
16%
Satisfactory
5%
Poor
2%
Terrible
1%
Overall Ratings

4.5 based on 600 reviews

The Cabaret At La Te Da

Reviewed By Hateworking - Lawrenceville, United States

What a performer! I didn't want the show to end. Loved the story telling and humor and the acts! Icons like Bette, Cher, Marilyn! I am so glad we went. I hadn't planned well so my husband and I just showed up in hope's there were seats still available! Very reasonably priced, two drink minimum which is the norm for most shows/comedy clubs we have attended near where we live and honestly I wish I had looked into even staying at the hotel! The bars, outside of the hotel and whole package looked wonderful! I wish I could had stayed and caught another show but our time in KW was so short. Next time! Thank you for one of the highlights to our trip!

8. Key West Theater

512 Eaton St, Key West, FL 33040-6881 +1 305-985-0433 [email protected] http://www.thekeywesttheater.com
Excellent
67%
Good
26%
Satisfactory
0%
Poor
5%
Terrible
2%
Overall Ratings

4.5 based on 42 reviews

Key West Theater

The Key West Theater is a newly renovated performing arts center that is home to the Key West Theater & Community Stage, Rams Head Promotions, Grateful Guitar, Back Stage Listening Room and the Key West Theater Recording Studio. Originally built in 1848 as the 1st Baptist Church of Key West, the building has a rich history as a church, dance club and concert venue prior to being transformed into a fully working performing arts center. We provide top tier music, concerts, comedy & variety specials and locally produced Key West events.We are committed to making performing arts relevant in the lives of more people by providing space and demonstrating that the arts engages, inspires and unites communities.

Reviewed By Walsh13k - Saratoga Springs, United States

A great entertainment venue to see one of your favorite singers/comedians/artists. Tables are arranged that so every seat is very good. Service is excellent. Great performers (Tom Papa was fantastic). Prices are reasonable. Order a drink and prepare to be entertained!

9. Key West Symphony

Key West, FL 33041 +1 305-292-1774 [email protected] http://www.keywestsymphony.com/
Excellent
60%
Good
20%
Satisfactory
0%
Poor
0%
Terrible
20%
Overall Ratings

4.0 based on 5 reviews

Key West Symphony

Professional symphonic musicians from across the United States are recruited for each concert performed by this orchestra.

10. Key West Burlesque Theater

600 White St Upstairs Theater at Kelly's Caribbean Bar, Key West, FL 33040-7153 +1 305-619-2275 [email protected] http://www.keywestburlesque.com
Excellent
46%
Good
23%
Satisfactory
15%
Poor
8%
Terrible
8%
Overall Ratings

4.0 based on 13 reviews

The Premier Entertainment Theatre Troupe in Key West Florida. An ever-changing hilarious lineup of amazing song, dance, and burlesque performers! Shows are in entertaining mix of Comedic Satire-Goofy Schtick- Comedy and Show Girl Glamour- Original Burlesque Musicals and Variety Shows! Special Guests from all over the USA- Festival Extravaganza in February- Produced by Marky Pierson Directed by Tatah Dujour- Established 2006-

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