Key West Events 2026-2027
Your guide to live events and things to do in Key West, FL, and nearby areas.
- Updated: November 15, 2026
Events take place across Key West throughout 2026, including major concerts, sports, and live performances happening every week. Browse by date, venue, or category to find what’s happening near you.
- 46 Upcoming Events
- 0 Events This Weekend
- 4 Event Venues
- 8 Event Categories
Browse Events By Category
- All Events 46
- concerts 15
- Live Shows 5
- comedy 26
- festivals 1
Best Events This Week & This Month
Explore featured Key West events including top shows, concerts, sports, and major live experiences across the city.
Key West Events: Today, This Month & Dates
Upcoming Events in Key West
Browse events in 2026 by date and venue, including concerts, shows, sports, and more across the city and nearby areas.Upcoming Confirmed Events 46
- Nov 18, 2026, 8:00 PM Wed — COMEDY, Best Value: Greg Fitzsimmons at Comedy Key West,
218 Whitehead St, Key West, FL 33040, US. From $56, Avg. price ~ $66, 22 tickets remaining! Select Seats - Nov 19, 2026, 8:00 PM Thu — COMEDY, Best Value: Greg Fitzsimmons at Comedy Key West, 218 Whitehead St, Key West, FL 33040, US. From $56, Avg. price ~ $66, 22 tickets remaining! Select Seats
- Nov 19, 2026, 8:00 PM Thu — COUNTRY / FOLK, High Demand, Pay Later Available: Marty Stuart and His Fabulous Superlatives at Key West Theater, 512 Eaton St., Key West, FL 33040, US. From $101, Avg. price ~ $499, Tickets Available: 63. Select Seats
- Nov 20, 2026, 8:00 PM Fri — COMEDY, Best Value: Greg Fitzsimmons at Comedy Key West, 218 Whitehead St, Key West, FL 33040, US. From $56, Avg. price ~ $66, 22 tickets remaining! Select Seats
- Nov 20, 2026, 8:00 PM Fri — COMEDY, High Demand: Dusty Slay at Key West Theater, 512 Eaton St., Key West, FL 33040, US. From $65, Avg. price ~ $403, Tickets Available: 150. Select Seats
- Nov 21, 2026, 8:00 PM Sat — COMEDY, Best Value, Weekend Event: Greg Fitzsimmons at Comedy Key West, 218 Whitehead St, Key West, FL 33040, US. From $56, Avg. price ~ $66, 22 tickets remaining! Select Seats
- Nov 21, 2026, 8:00 PM Sat — COMEDY, High Demand, Weekend Event: Dusty Slay at Key West Theater, 512 Eaton St., Key West, FL 33040, US. From $65, Avg. price ~ $347, Tickets Available: 188. Select Seats
- Nov 22, 2026, 8:00 PM Sun — Concert, High Demand, Weekend Event: The Buena Vista Orchestra at Key West Theater, 512 Eaton St., Key West, FL 33040, US. From $77, Avg. price ~ $296, Tickets Available: 105. Select Seats
- Dec 10, 2026, 8:00 PM Thu — POP / ROCK, Pay Later Available: Shaun Cassidy at Key West Theater, 512 Eaton St., Key West, FL 33040, US. From $120, Avg. price ~ $150, Tickets Available: 138. Select Seats
- Dec 18, 2026, 8:00 PM Fri — COUNTRY / FOLK, Pay Later Available: Mac McAnally at Key West Theater, 512 Eaton St., Key West, FL 33040, US. From $166, Avg. price ~ $219, 23 tickets remaining! Select Seats
- Dec 19, 2026, 8:00 PM Sat — COUNTRY / FOLK, Weekend Event, Pay Later Available: Mac McAnally at Key West Theater, 512 Eaton St., Key West, FL 33040, US. From $163, Avg. price ~ $240, Tickets Available: 31. Select Seats
- Jan 02, 2027, 8:00 PM Sat — ALTERNATIVE, High Demand, Weekend Event: Keller Williams at Key West Theater, 512 Eaton St., Key West, FL 33040, US. From $83, Avg. price ~ $154, Tickets Available: 161. Select Seats
- Jan 12, 2027, 8:00 PM Tue — COUNTRY / FOLK, Pay Later Available: Jim Messina at Key West Theater, 512 Eaton St., Key West, FL 33040, US. From $103, Avg. price ~ $139, Tickets Available: 97. Select Seats
- Jan 13, 2027, 8:00 PM Wed — COMEDY, Best Value: Luis J. Gomez - Comedian at Comedy Key West, 218 Whitehead St, Key West, FL 33040, US. From $58, Avg. price ~ $68, 22 tickets remaining! Select Seats
- Jan 14, 2027, 8:00 PM Thu — COMEDY, Best Value: Luis J. Gomez - Comedian at Comedy Key West, 218 Whitehead St, Key West, FL 33040, US. From $58, Avg. price ~ $68, 22 tickets remaining! Select Seats
- Jan 15, 2027, 8:00 PM Fri — COMEDY, Best Value: Luis J. Gomez - Comedian at Comedy Key West, 218 Whitehead St, Key West, FL 33040, US. From $58, Avg. price ~ $68, 22 tickets remaining! Select Seats
- Jan 16, 2027, 8:00 PM Sat — COMEDY, Best Value, Weekend Event: Luis J. Gomez - Comedian at Comedy Key West, 218 Whitehead St, Key West, FL 33040, US. From $58, Avg. price ~ $68, 22 tickets remaining! Select Seats
- Jan 20, 2027, 7:30 PM Wed — POP / ROCK: Yacht Rock Revue at Coffee Butler Amphitheater, 21 Quay Rd, Key West, FL 33040, US. From $64, Avg. price ~ $131, Tickets Available: 381. Select Seats
- Jan 21, 2027, 8:00 PM Thu — COMEDY: Tom Papa at Key West Theater, 512 Eaton St., Key West, FL 33040, US. From $69, Avg. price ~ $92, Tickets Available: 189. Select Seats
- Jan 22, 2027, 8:00 PM Fri — COMEDY: Tom Papa at Key West Theater, 512 Eaton St., Key West, FL 33040, US. From $67, Avg. price ~ $91, Tickets Available: 191. Select Seats
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Key West Events by Month
Monthly pages help you find upcoming events by season, weekend, and date.
Events by Show & Venue
Browse Key West events by show and venue. Explore performance schedules, event counts, and upcoming dates across the city.
Greg Fitzsimmons
218 Whitehead St, Key West, FL 33040
Upcoming Events: 14
Nov 18, 2026 8:00 PM
Marty Stuart and His Fabulous Superlatives
512 Eaton St., Key West, FL 33040
Upcoming Events: 18
Nov 19, 2026 8:00 PM
Dusty Slay
512 Eaton St., Key West, FL 33040
Upcoming Events: 48
Nov 20, 2026 8:00 PM
The Buena Vista Orchestra
512 Eaton St., Key West, FL 33040
Upcoming Events: 17
Nov 22, 2026 8:00 PM
Shaun Cassidy
512 Eaton St., Key West, FL 33040
Upcoming Events: 24
Dec 10, 2026 8:00 PM
Mac McAnally
512 Eaton St., Key West, FL 33040
Upcoming Events: 4
Dec 18, 2026 8:00 PM
Keller Williams
512 Eaton St., Key West, FL 33040
Upcoming Events: 7
Jan 02, 2027 8:00 PM
Jim Messina
512 Eaton St., Key West, FL 33040
Upcoming Events: 10
Jan 12, 2027 8:00 PM
Luis J. Gomez - Comedian
218 Whitehead St, Key West, FL 33040
Upcoming Events: 11
Jan 13, 2027 8:00 PM
Yacht Rock Revue
21 Quay Rd, Key West, FL 33040
Upcoming Events: 18
Jan 20, 2027 7:30 PM
Tom Papa
512 Eaton St., Key West, FL 33040
Upcoming Events: 6
Jan 21, 2027 8:00 PM
Bumpin' Uglies
512 Eaton St., Key West, FL 33040
Upcoming Events: 28
Jan 24, 2027 8:00 PM
The Jayhawks
512 Eaton St., Key West, FL 33040
Upcoming Events: 13
Jan 25, 2027 8:00 PM
Mile 0 Fest Key West
35 E Quay Road, Key West, FL 33040
Upcoming Events: 1
Jan 26, 2027 Time TBA
Pete Yorn
512 Eaton St., Key West, FL 33040
Upcoming Events: 13
Feb 06, 2027 8:00 PM
From long-running shows to packed venues, this list breaks down what’s playing across Key West. Check schedules, event counts, and upcoming dates by show and location.
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Frequently Asked Questions
Quick answers about tickets, prices, and game day details.
What events are happening in Key West right now?
A little bit of everything — concerts, shows, sports, comedy. Key West rarely sits still. Check the schedule above to see what’s happening today, this week, or whenever you finally make plans.
How often is the event schedule updated?
Pretty often — like, more than your group chat actually commits to plans. New events get added as soon as dates and venues are confirmed.
Can I browse events by date or venue?
Yep. Filter by date, venue, or category and skip the endless scrolling. Your future self will appreciate it.
Are events held year-round in Key West?
Yeah — Key West doesn’t really take a season off. There’s always something going on, even when the weather’s doing its thing.
Where do events take place in Key West?
Everywhere — arenas, theaters, stadiums, clubs, and venues across Key West, FL. Big stages, small stages, and everything in between.
Do new events get added regularly?
All the time. If a tour drops or a game gets scheduled, it usually shows up here faster than you hear about it from friends.
Browse Events by Category
Find concerts, sports, theatre, comedy, and more in Key West and nearby areas
About American Arenas®
American Arenas® is a live-events platform that connects event schedules, venues, and ticket options through trusted marketplace partners. Listings are updated regularly as new events and dates are confirmed, helping users discover what’s happening and explore available ticket options across concerts, sports, shows, and more.