Best events in
Key West

Looking for events or things to do in Key West, FL? The island's rhythm is famously tied to the sun, with a daily tradition of gathering at the water's edge to celebrate sunset. Afterward, the energy shifts to the historic downtown, where live music and a celebratory atmosphere fill the streets.

Start an evening at Mallory Square for the nightly Sunset Celebration before exploring the live music scene along Duval Street at spots like Sloppy Joe's.
Experience the local arts culture during the monthly Walk on White, a gallery tour through the White Street Gallery District.
Catch a play at historic venues like the Red Barn Theatre or Waterfront Playhouse for an intimate performance away from the main entertainment drag.

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Lip Sync & Lifeguards - A Fantasy Fest Pool Party

Sat, Oct 17 • 12:00 PM

Blue Flamingo Resort Key West

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LUV2GLOW - LIQUID FREQUENCY - FANTASY FEST 2026 at Rick's Key West

Wed, Oct 21 • 8:00 PM

Rick's Bar

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33rd Annual Homemade Bikini Contest

Wed, Oct 21 • 5:00 PM

Irish Kevin's

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ABC ( Anything But Clothes ) Party

Wed, Oct 21 • 8:00 PM

Southernmost Pint Brewpub - Blast Beer Company Brewery

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2026 Fantasy Fest Parade Viewing Party @ First Flight

Sat, Oct 24 • 6:00 PM

First Flight Island Restaurant & Brewery

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Key West Powerboat Races 2026 - General Admission - Fri

Fri, Nov 6 • 9:00 AM

Sunset Pier

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Key West 11th Annual Casino Night by SOS Foundation

Fri, Nov 13 • 6:30 PM

Casa Marina Key West, Curio Collection by Hilton

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KEY WEST OYSTER FEST: A BENEFIT FOR THE GULF OYSTER

Sat, Nov 14 • 5:00 PM

Half Shell Raw Bar

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Lip Sync & Lifeguards - A Fantasy Fest Pool Party

Sat, Oct 17 • 12:00 PM

Blue Flamingo Resort Key West

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LUV2GLOW - LIQUID FREQUENCY - FANTASY FEST 2026 at Rick's Key West

Wed, Oct 21 • 8:00 PM

Rick's Bar

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33rd Annual Homemade Bikini Contest

Wed, Oct 21 • 5:00 PM

Irish Kevin's

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ABC ( Anything But Clothes ) Party

Wed, Oct 21 • 8:00 PM

Southernmost Pint Brewpub - Blast Beer Company Brewery

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2026 Fantasy Fest Parade Viewing Party @ First Flight

Sat, Oct 24 • 6:00 PM

First Flight Island Restaurant & Brewery

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Key West Powerboat Races 2026 - General Admission - Fri

Fri, Nov 6 • 9:00 AM

Sunset Pier

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Key West 11th Annual Casino Night by SOS Foundation

Fri, Nov 13 • 6:30 PM

Casa Marina Key West, Curio Collection by Hilton

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KEY WEST OYSTER FEST: A BENEFIT FOR THE GULF OYSTER

Sat, Nov 14 • 5:00 PM

Half Shell Raw Bar

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Marketing Breakthrough: 40X Your Holistic Business [$297 Value]

Tomorrow • 10:00 AM PDT

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Online Group Reading - September 27

Tomorrow • 8:00 PM ADT

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Barnes & Noble and Waterstones Virtually Presents: Madeline Miller

Tuesday • 2:00 PM EDT

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Ethically Shady: Navigating the Gray Areas of Interpreting

Sat, Oct 3 • 10:00 AM PDT

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A Norman stitch-up? The story behind the Bayeux Tapestry

Wed, Oct 7 • 7:30 PM GMT+1

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(ONLINE) Women on the Move with Ann Patchett

Tue, Oct 27 • 11:30 AM EDT

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No Title, No Permission, No Problem: Harnessing the Power of Influence

Thu, Nov 5 • 1:00 PM GMT

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Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

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Marketing Breakthrough: 40X Your Holistic Business [$297 Value]

Tomorrow • 10:00 AM PDT

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Online Group Reading - September 27

Tomorrow • 8:00 PM ADT

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Barnes & Noble and Waterstones Virtually Presents: Madeline Miller

Tuesday • 2:00 PM EDT

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Ethically Shady: Navigating the Gray Areas of Interpreting

Sat, Oct 3 • 10:00 AM PDT

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A Norman stitch-up? The story behind the Bayeux Tapestry

Wed, Oct 7 • 7:30 PM GMT+1

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(ONLINE) Women on the Move with Ann Patchett

Tue, Oct 27 • 11:30 AM EDT

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No Title, No Permission, No Problem: Harnessing the Power of Influence

Thu, Nov 5 • 1:00 PM GMT

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Washington Crossing the Delaware / The Crossing - Film History Livestream

Sat, Dec 19 • 8:00 PM EST

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Diva Royale Drag Queen Show Key West, FL - Weekly Drag Queen Shows

yesterday • 7:00 PM + 1 more

Diva Royale - Drag Queen Show

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Full Moon Party At Simonton Beach Reggae Vibes

Today • 7:00 PM

Lagerheads Beach Bar & Watersports

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Illusions Drag Brunch West Palm Beach - Drag Queen Brunch - Palm Beach, FL

Today • 1:30 PM + 1 more

2585 S Military Trl

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Diva Royale Drag Queen Show Key West, FL - Weekly Drag Queen Shows

yesterday • 7:00 PM + 1 more

Diva Royale - Drag Queen Show

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Full Moon Party At Simonton Beach Reggae Vibes

Today • 7:00 PM

Lagerheads Beach Bar & Watersports

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Illusions Drag Brunch West Palm Beach - Drag Queen Brunch - Palm Beach, FL

Today • 1:30 PM + 1 more

2585 S Military Trl

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Music events

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Golden Hour - Sunset Experience by Electroniconch

Mon, Oct 19 • 4:00 PM

Galleon Marina

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LUV2GLOW - LIQUID FREQUENCY - FANTASY FEST 2026 at Rick's Key West

Wed, Oct 21 • 8:00 PM

Rick's Bar

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FUNKY GRATEFUL DEAD GET DOWN PARTY (6-piece band) & 4 DJ's AFTER PARTY

Fri, Oct 23 • 6:00 PM

Viva Argentinian Steakhouse

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IAN MAKSIN in KEY WEST: "SONGS of LOVE & PEACE" 2026 Concert Tour

Wed, Nov 11 • 7:30 PM

Congregation B'nai Zion

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Golden Hour - Sunset Experience by Electroniconch

Mon, Oct 19 • 4:00 PM

Galleon Marina

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LUV2GLOW - LIQUID FREQUENCY - FANTASY FEST 2026 at Rick's Key West

Wed, Oct 21 • 8:00 PM

Rick's Bar

Check ticket price on event

FUNKY GRATEFUL DEAD GET DOWN PARTY (6-piece band) & 4 DJ's AFTER PARTY

Fri, Oct 23 • 6:00 PM

Viva Argentinian Steakhouse

Check ticket price on event

IAN MAKSIN in KEY WEST: "SONGS of LOVE & PEACE" 2026 Concert Tour

Wed, Nov 11 • 7:30 PM

Congregation B'nai Zion

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Frequently asked questions about Key West

What's the nightlife scene like in Key West?

The nightlife centers around the lively bars and venues on Duval Street. After the sun sets, crowds head to iconic spots like Sloppy Joe's or the Green Parrot Bar for live music that often continues late into the night.

Are there any free events in Key West?

The nightly Sunset Celebration at Mallory Square is a popular free event. This famous gathering features street performers, musicians, and local artisans, all with a stunning waterfront view as a backdrop. It's a classic Key West experience.

Where can I find art events in Key West?

The White Street Gallery District is the main hub for the local art scene. The monthly "Walk on White" event is a great way to explore multiple galleries and see new work from local artists in a single evening.

What are some popular outdoor events in Key West?

Many of Key West's signature celebrations are held outdoors. Annual street parties like Fantasy Fest and Hemingway Days fill the historic downtown, while venues like the Sunset Green Event Lawn host open-air concerts and other large-scale gatherings.

Which Key West neighborhoods are best for live music events?

Duval Street is the epicenter for live music events in Key West. Historic bars like Sloppy Joe's offer music daily, while slightly off-the-beaten-path venues like the Green Parrot Bar provide a more local atmosphere with acclaimed bands.

Does Key West host any major food and drink festivals?

Yes, Key West has several annual culinary events. The Key West Food & Wine Festival offers tastings and dinners each January, and the Key West Lobsterfest celebrates the start of lobster season with a street fair every August.

What makes Key West's annual events unique?

The island's quirky spirit shines through in its annual celebrations. Events like the Conch Republic Independence Celebration in April and the ten-day Fantasy Fest in October showcase the independent and creative character of Key West.

What are some good date night ideas in Key West?

A classic Key West date night can involve watching a play or performance. The historic Waterfront Playhouse and Red Barn Theatre offer intimate settings for live theater, providing a nice alternative to the island's bustling bar scene.

Popular in Key West

Lip Sync & Lifeguards - A Fantasy Fest Pool Party

LUV2GLOW - LIQUID FREQUENCY - FANTASY FEST 2026 at Rick's Key West

33rd Annual Homemade Bikini Contest

ABC ( Anything But Clothes ) Party

2026 Fantasy Fest Parade Viewing Party @ First Flight

Key West Powerboat Races 2026 - General Admission - Fri

Key West 11th Annual Casino Night by SOS Foundation

KEY WEST OYSTER FEST: A BENEFIT FOR THE GULF OYSTER

Lip Sync & Lifeguards - A Fantasy Fest Pool Party

LUV2GLOW - LIQUID FREQUENCY - FANTASY FEST 2026 at Rick's Key West

33rd Annual Homemade Bikini Contest

ABC ( Anything But Clothes ) Party

2026 Fantasy Fest Parade Viewing Party @ First Flight

Key West Powerboat Races 2026 - General Admission - Fri

Key West 11th Annual Casino Night by SOS Foundation

KEY WEST OYSTER FEST: A BENEFIT FOR THE GULF OYSTER

Online Events

Marketing Breakthrough: 40X Your Holistic Business [$297 Value]

Online Group Reading - September 27

Barnes & Noble and Waterstones Virtually Presents: Madeline Miller

Ethically Shady: Navigating the Gray Areas of Interpreting

A Norman stitch-up? The story behind the Bayeux Tapestry

(ONLINE) Women on the Move with Ann Patchett

No Title, No Permission, No Problem: Harnessing the Power of Influence

Washington Crossing the Delaware / The Crossing - Film History Livestream

Marketing Breakthrough: 40X Your Holistic Business [$297 Value]

Online Group Reading - September 27

Barnes & Noble and Waterstones Virtually Presents: Madeline Miller

Ethically Shady: Navigating the Gray Areas of Interpreting

A Norman stitch-up? The story behind the Bayeux Tapestry

(ONLINE) Women on the Move with Ann Patchett

No Title, No Permission, No Problem: Harnessing the Power of Influence

Washington Crossing the Delaware / The Crossing - Film History Livestream

This Weekend

Diva Royale Drag Queen Show Key West, FL - Weekly Drag Queen Shows

Full Moon Party At Simonton Beach Reggae Vibes

Illusions Drag Brunch West Palm Beach - Drag Queen Brunch - Palm Beach, FL

Diva Royale Drag Queen Show Key West, FL - Weekly Drag Queen Shows

Full Moon Party At Simonton Beach Reggae Vibes

Illusions Drag Brunch West Palm Beach - Drag Queen Brunch - Palm Beach, FL

Music events

Golden Hour - Sunset Experience by Electroniconch

LUV2GLOW - LIQUID FREQUENCY - FANTASY FEST 2026 at Rick's Key West

FUNKY GRATEFUL DEAD GET DOWN PARTY (6-piece band) & 4 DJ's AFTER PARTY

IAN MAKSIN in KEY WEST: "SONGS of LOVE & PEACE" 2026 Concert Tour

Golden Hour - Sunset Experience by Electroniconch

LUV2GLOW - LIQUID FREQUENCY - FANTASY FEST 2026 at Rick's Key West

FUNKY GRATEFUL DEAD GET DOWN PARTY (6-piece band) & 4 DJ's AFTER PARTY

IAN MAKSIN in KEY WEST: "SONGS of LOVE & PEACE" 2026 Concert Tour

Points of Interest near Key West

What's the nightlife scene like in Key West?

Are there any free events in Key West?

Where can I find art events in Key West?

What are some popular outdoor events in Key West?

Which Key West neighborhoods are best for live music events?

Does Key West host any major food and drink festivals?

What makes Key West's annual events unique?

What are some good date night ideas in Key West?