Events in Key West, Florida

61 upcoming listings — live music, theater, markets, drag, comedy and more, each with a time, a venue and a street address.

What's coming up

• 801 Karaoke with Jeff
  Sun 2 Aug 2026, 4:00 PM — Karaoke
  801 Bourbon Bar · 801 Duval St, Key West, FL 33040 · 21+
• The World Famous 801 Girls
  Thu 6 Aug 2026, 9:00 PM — Drag
  801 Bourbon Bar · 801 Duval St, Key West, FL 33040 · 21+
• The World Famous 801 Girls
  Fri 7 Aug 2026, 9:00 PM — Drag
  801 Bourbon Bar · 801 Duval St, Key West, FL 33040 · 21+
• The World Famous 801 Girls
  Sat 8 Aug 2026, 9:00 PM — Drag
  801 Bourbon Bar · 801 Duval St, Key West, FL 33040 · 21+
• Diva Royale Drag Queen Show Key West, FL - Weekly Drag Queen Shows
  Fri 4 Sep 2026, 7:00 PM — Drag
  Diva Royale - Drag Queen Show · 422 Petronia St, Key West, FL 33040 · 21+
• Illusions The Drag Queen Show Key West - Drag Queen Show - Key West, FL
  Fri 4 Sep 2026, 7:00 PM — Drag
  Illusions the Drag Queen Show Key West · 426 Petronia St, Key West, FL 33040 · 21+
• STEM Saturday
  Sat 5 Sep 2026, 1:00 PM — class
  Key West Branch Library · 700 Fleming St, Key West, FL 33040 · Free
• Illusions The Drag Brunch Key West-Drag Queen Brunch-Key West, FL
  Sat 5 Sep 2026, 1:30 PM — Drag
  Illusions the Drag Queen Brunch Key West · 426 Petronia St Key West, Key West, FL 33040 · 21+
• Beginner's Mahjong
  Mon 14 Sep 2026, 12:30 PM — class
  Key West Branch Library · 700 Fleming St, Key West, FL 33040 · Free · 18+
• Clases Gratis Con Consejeras Certificadas En Lactancia Materna
  Thu 17 Sep 2026, 12:45 PM — class
  Lower Keys Medical Center · 5900 College Road Main Boardroom, Key West, FL 33040
• Breastfeeding and Lactation Education
  Thu 17 Sep 2026, 2:30 PM — class
  Lower Keys Medical Center · 5900 College Road Main Boardroom, Key West, FL 33040
• Cartel Autotronics & Petersons Harley South Beachside Bike & Slingshot Show
  Sat 19 Sep 2026, 10:00 AM — Meetup
  Casa Marina Key West, Curio Collection by Hilton · 1500 Reynolds Street, Key West, FL 33040
• Childbirth Education
  Sat 19 Sep 2026, 10:00 AM — class
  Lower Keys Medical Center · 5900 College Road Main Boardroom, Key West, FL 33040
• Ceramics Painting Class
  Thu 24 Sep 2026, 10:00 AM — class
  Key West Branch Library · 700 Fleming St, Key West, FL 33040 · Free · 18+
• Stroke Support Group
  Wed 30 Sep 2026, 2:00 PM — Support group
  Lower Keys Medical Center · 5900 College Road Main Boardroom, Key West, FL 33040
• Key West Sunset Romance Quest
  Thu 1 Oct 2026, 10:00 AM — Meetup
  Truman Waterfront Park · Southard Street, Key West, FL 33040
• Kooky Key West Scavenger Hunt
  Thu 1 Oct 2026, 11:00 AM — Meetup
  281 Front St · 281 Front Street, Key West, FL 33040
• Random Acts of Kindness Spree in Key West
  Thu 1 Oct 2026, 11:00 AM — Festival
  201 Front St Garage · 201 Front Street, Key West, FL 33040
• Exploring Old Town Key West - Food Tour in Key West | Cozymeal™
  Thu 1 Oct 2026, 11:00 AM — class
  Location provided after booking · Key West, FL 33040
• Brews & Blues
  Fri 2 Oct 2026, 5:00 PM — Live music
  Blue Flamingo Resort Key West · 3820 North Roosevelt Boulevard, Key West, FL 33040
• Diva Royale Drag Queen Show Key West, FL - Weekly Drag Queen Shows
  Fri 2 Oct 2026, 7:00 PM — Drag
  Diva Royale - Drag Queen Show · 422 Petronia St, Key West, FL 33040 · 21+
• Illusions The Drag Queen Show Key West - Drag Queen Show - Key West, FL
  Fri 2 Oct 2026, 7:00 PM — Drag
  Illusions the Drag Queen Show Key West · 426 Petronia St, Key West, FL 33040 · 21+
• STEM Saturday
  Sat 3 Oct 2026, 1:00 PM — class
  Key West Branch Library · 700 Fleming St, Key West, FL 33040 · Free
• Illusions The Drag Brunch Key West-Drag Queen Brunch-Key West, FL
  Sat 3 Oct 2026, 1:30 PM — Drag
  Illusions the Drag Queen Brunch Key West · 426 Petronia St Key West, Key West, FL 33040 · 21+
• Beginner's Mahjong
  Mon 5 Oct 2026, 12:30 PM — class
  Key West Branch Library · 700 Fleming St, Key West, FL 33040 · Free · 18+
• Adult Buoy Painting Class
  Thu 8 Oct 2026, 10:00 AM — class
  Key West Branch Library · 700 Fleming St, Key West, FL 33040 · Free · 18+
• Childbirth Education
  Sat 17 Oct 2026, 10:00 AM — class
  Lower Keys Medical Center · 5900 College Road Main Boardroom, Key West, FL 33040
• Lip Sync & Lifeguards - A Fantasy Fest Pool Party
  Sat 17 Oct 2026, 12:00 PM — Festival
  Blue Flamingo Resort Key West · 3820 North Roosevelt Boulevard, Key West, FL 33040
• Golden Hour - A Fantasy Fest Sunset Experience
  Mon 19 Oct 2026, 4:00 PM — Live music
  Galleon Marina · 619 Front Street, Key West, FL 33040
• Sins & Sequins - An Official Fantasy Fest Event
  Wed 21 Oct 2026, 7:00 PM — Festival
  Blue Flamingo Resort Key West · 3820 North Roosevelt Boulevard, Key West, FL 33040
• LUV2GLOW: Liquid Frequency — Fantasy Fest 2026
  Wed 21 Oct 2026, 8:00 PM — Live music
  Rick's Bar · 202 Duval St, Key West, FL 33040 · $36.39 · 21+
• Haunted Mangrove Tours
  Thu 22 Oct 2026, 7:00 PM — Spooky
  Kayak Kings of Key West · 5001 5th Avenue, Key West, FL 33040
• FUNKY GRATEFUL DEAD GET DOWN PARTY (6-piece band) & 4 DJ's AFTER PARTY
  Fri 23 Oct 2026, 6:00 PM — Live music
  Viva Argentinian Steakhouse · 903 Duval Street, Key West, FL 33040
• Nine One Five's Fantasy Fest Parade Viewing Party
  Sat 24 Oct 2026, 6:00 PM — Live music
  Nine One Five · 915 Duval Street #5, Key West, FL 33040
• 2026 Fantasy Fest Parade Viewing Party @ First Flight
  Sat 24 Oct 2026, 6:00 PM — Live music
  First Flight Island Restaurant & Brewery · 301 Whitehead Street, Key West, FL 33040
• Beginner's Mahjong
  Mon 26 Oct 2026, 12:30 PM — class
  Key West Branch Library · 700 Fleming St, Key West, FL 33040 · Free · 18+
• Stroke Support Group
  Tue 27 Oct 2026, 2:00 PM — Support group
  Lower Keys Medical Center · 5900 College Road Main Boardroom, Key West, FL 33040
• Breastfeeding and Lactation Education
  Wed 28 Oct 2026, 2:00 PM — class
  Lower Keys Medical Center · 5900 College Road Main Boardroom, Key West, FL 33040
• Clases Gratis Con Consejeras Certificadas En Lactancia Materna
  Wed 28 Oct 2026, 3:30 PM — class
  Lower Keys Medical Center · 5900 College Road Main Boardroom, Key West, FL 33040
• Ceramics Painting Class
  Thu 29 Oct 2026, 10:00 AM — class
  Key West Branch Library · 700 Fleming St, Key West, FL 33040 · Free · 18+
• Key West Sunset Romance Quest
  Sun 1 Nov 2026, 10:00 AM — Meetup
  Truman Waterfront Park · Southard Street, Key West, FL 33040
• Kooky Key West Scavenger Hunt
  Sun 1 Nov 2026, 11:00 AM — Meetup
  281 Front St · 281 Front Street, Key West, FL 33040
• Random Acts of Kindness Spree in Key West
  Sun 1 Nov 2026, 11:00 AM — Festival
  201 Front St Garage · 201 Front Street, Key West, FL 33040
• Mangoes Drag Brunch Royale — Halloween Edition
  Sun 1 Nov 2026, 11:30 AM — Drag
  Mangoes Restaurant · 700 Duval St, Key West, FL 33040 · $55.20
• Illusions The Drag Brunch Key West-Drag Queen Brunch-Key West, FL
  Sun 1 Nov 2026, 1:30 PM — Drag
  Illusions the Drag Queen Brunch Key West · 426 Petronia St Key West, Key West, FL 33040 · 21+
• Exploring Old Town Key West - Food Tour in Key West | Cozymeal™
  Mon 2 Nov 2026, 11:00 AM — class
  Location provided after booking · Key West, FL 33040
• Diva Royale Drag Queen Show Key West, FL - Weekly Drag Queen Shows
  Fri 6 Nov 2026, 7:00 PM — Drag
  Diva Royale - Drag Queen Show · 422 Petronia St, Key West, FL 33040 · 21+
• Illusions The Drag Queen Show Key West - Drag Queen Show - Key West, FL
  Fri 6 Nov 2026, 7:00 PM — Drag
  Illusions the Drag Queen Show Key West · 426 Petronia St, Key West, FL 33040 · 21+
• STEM Saturday
  Sat 7 Nov 2026, 1:00 PM — class
  Key West Branch Library · 700 Fleming St, Key West, FL 33040 · Free
• Key West Powerboat Races 2026 - VIP Tent - SUNDAY
  Sun 8 Nov 2026, 9:00 AM — Meetup
  Sunset Pier · 0 Duval Street, Key West, FL 33040
• Key West Powerboat Races 2026 - General Admission - Sun
  Sun 8 Nov 2026, 9:00 AM — Meetup
  Sunset Pier · 0 Duval Street, Key West, FL 33040
• ZaneCrawl • Key West • 11/13-11/15
  Fri 13 Nov 2026, 12:00 PM — Comedy
  Key West · Key West, Key West, FL 33040
• Sea Turtle Shell-ebration with Save-A-Turtle
  Sat 14 Nov 2026, 6:00 PM — Meetup
  Key West Aquarium · 1 Whitehead St, Key West, FL 33040 · $13.45
• Ceramics Painting Class
  Thu 19 Nov 2026, 10:00 AM — class
  Key West Branch Library · 700 Fleming St, Key West, FL 33040 · Free · 18+
• Clases Gratis Con Consejeras Certificadas En Lactancia Materna
  Thu 19 Nov 2026, 12:45 PM — class
  Lower Keys Medical Center · 5900 College Road Main Boardroom, Key West, FL 33040
• Breastfeeding and Lactation Education
  Thu 19 Nov 2026, 2:30 PM — class
  Lower Keys Medical Center · 5900 College Road Main Boardroom, Key West, FL 33040
• Childbirth Education
  Sat 21 Nov 2026, 10:00 AM — class
  Lower Keys Medical Center · 5900 College Road Main Boardroom, Key West, FL 33040
• Stroke Support Group
  Mon 23 Nov 2026, 2:00 PM — Support group
  Lower Keys Medical Center · 5900 College Road Main Boardroom, Key West, FL 33040
• STEM Saturday
  Sat 5 Dec 2026, 1:00 PM — class
  Key West Branch Library · 700 Fleming St, Key West, FL 33040 · Free
• Mangoes Drag Brunch Royale — Christmas Show
  Sun 20 Dec 2026, 11:30 AM — Drag
  Mangoes Restaurant · 700 Duval St, Key West, FL 33040 · $55.20
• Key West Songwriters Getaways!®
  Tue 27 Apr 2027, 10:00 AM — Meetup
  Duval Street · Duval Street, Key West, FL 33040

Listings are seeded from venue and organiser calendars. See them on the map.