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

Wednesday • 7:30 PM

Congregation B'nai Zion

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Key West 11th Annual Casino Night by SOS Foundation

Friday • 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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Sea Turtle Shell-ebration with Save-A-Turtle in the Florida Keys!

Sat, Nov 14 • 6:00 PM

Key West Aquarium

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Sunday Recognition Brunch - Key West Oyster Fest 2026

Sun, Nov 15 • 9:00 AM

Half Shell Raw Bar

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Autumn Pairings: An Evening at the Mansion

Wed, Nov 18 • 6:00 PM

George's | Café • Bar • Spritz

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Agave Tequila Tasting Class

Wed, Dec 2 • 5:30 PM

526 Angela St

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Great Gatsby NYE 2026

Thu, Dec 31 • 8:00 PM

First Flight Island Restaurant & Brewery

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

Wednesday • 7:30 PM

Congregation B'nai Zion

Check ticket price on event

Key West 11th Annual Casino Night by SOS Foundation

Friday • 6:30 PM

Casa Marina Key West, Curio Collection by Hilton

Check ticket price on event

KEY WEST OYSTER FEST: A BENEFIT FOR THE GULF OYSTER

Sat, Nov 14 • 5:00 PM

Half Shell Raw Bar

Check ticket price on event

Sea Turtle Shell-ebration with Save-A-Turtle in the Florida Keys!

Sat, Nov 14 • 6:00 PM

Key West Aquarium

Check ticket price on event

Sunday Recognition Brunch - Key West Oyster Fest 2026

Sun, Nov 15 • 9:00 AM

Half Shell Raw Bar

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Autumn Pairings: An Evening at the Mansion

Wed, Nov 18 • 6:00 PM

George's | Café • Bar • Spritz

Check ticket price on event

Agave Tequila Tasting Class

Wed, Dec 2 • 5:30 PM

526 Angela St

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Great Gatsby NYE 2026

Thu, Dec 31 • 8:00 PM

First Flight Island Restaurant & Brewery

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Managing Your Emotions - Prof Ethan Kross

Tuesday • 7:00 PM GMT

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This Little World: a New History of Tudor and Stuart England

Wednesday • 7:30 PM GMT

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Lean Global Connection 2026

Thursday • 2:00 PM UTC

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Physicians Financial Wellness Conference 2026

Sat, Nov 14 • 1:00 PM EST

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HBR Book Webinar: Unspeakable

Mon, Nov 23 • 1:00 PM GMT

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How to Choose a (New) Career Fast

Thu, Dec 3 • 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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PLAYFUL ARCHITECTURE: Drawing in Colour and Monochrome

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Managing Your Emotions - Prof Ethan Kross

Tuesday • 7:00 PM GMT

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This Little World: a New History of Tudor and Stuart England

Wednesday • 7:30 PM GMT

Check ticket price on event

Lean Global Connection 2026

Thursday • 2:00 PM UTC

Check ticket price on event

Physicians Financial Wellness Conference 2026

Sat, Nov 14 • 1:00 PM EST

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HBR Book Webinar: Unspeakable

Mon, Nov 23 • 1:00 PM GMT

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How to Choose a (New) Career Fast

Thu, Dec 3 • 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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PLAYFUL ARCHITECTURE: Drawing in Colour and Monochrome

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Hunk-O-Mania Male Revue Strippers Show - #1 Male Strip Club in Key West, FL

Today • 8:00 PM

Hunk-O-Mania

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Muscle Men Male Strippers Revue & Male Strip Club Shows Key West FL

Today • 8:00 PM

Muscle Men Male Strippers Key West

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Kooky Key West Scavenger Hunt

Tomorrow • 11:00 AM + 1 more

281 Front St

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

Tomorrow • 1:30 PM

2585 S Military Trl

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Hunk-O-Mania Male Revue Strippers Show - #1 Male Strip Club in Key West, FL

Today • 8:00 PM

Hunk-O-Mania

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Muscle Men Male Strippers Revue & Male Strip Club Shows Key West FL

Today • 8:00 PM

Muscle Men Male Strippers Key West

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Kooky Key West Scavenger Hunt

Tomorrow • 11:00 AM + 1 more

281 Front St

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

Tomorrow • 1:30 PM

2585 S Military Trl

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ZaneCrawl • Key West • 11/13-11/15

Friday • 12:00 PM

Key West

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KEY WEST OYSTER FEST: A BENEFIT FOR THE GULF OYSTER

Sat, Nov 14 • 5:00 PM

Half Shell Raw Bar

Check ticket price on event

Autumn Pairings: An Evening at the Mansion

Wed, Nov 18 • 6:00 PM

George's | Café • Bar • Spritz

Check ticket price on event

Mangoes Drag Brunch Royale Christmas Show

Sun, Dec 20 • 11:30 AM

Mangoes Restaurant

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ZaneCrawl • Key West • 11/13-11/15

Friday • 12:00 PM

Key West

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KEY WEST OYSTER FEST: A BENEFIT FOR THE GULF OYSTER

Sat, Nov 14 • 5:00 PM

Half Shell Raw Bar

Check ticket price on event

Autumn Pairings: An Evening at the Mansion

Wed, Nov 18 • 6:00 PM

George's | Café • Bar • Spritz

Check ticket price on event

Mangoes Drag Brunch Royale Christmas Show

Sun, Dec 20 • 11:30 AM

Mangoes Restaurant

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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

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

Key West 11th Annual Casino Night by SOS Foundation

KEY WEST OYSTER FEST: A BENEFIT FOR THE GULF OYSTER

Sea Turtle Shell-ebration with Save-A-Turtle in the Florida Keys!

Sunday Recognition Brunch - Key West Oyster Fest 2026

Autumn Pairings: An Evening at the Mansion

Agave Tequila Tasting Class

Great Gatsby NYE 2026

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

Key West 11th Annual Casino Night by SOS Foundation

KEY WEST OYSTER FEST: A BENEFIT FOR THE GULF OYSTER

Sea Turtle Shell-ebration with Save-A-Turtle in the Florida Keys!

Sunday Recognition Brunch - Key West Oyster Fest 2026

Autumn Pairings: An Evening at the Mansion

Agave Tequila Tasting Class

Great Gatsby NYE 2026

Online Events

Managing Your Emotions - Prof Ethan Kross

This Little World: a New History of Tudor and Stuart England

Lean Global Connection 2026

Physicians Financial Wellness Conference 2026

HBR Book Webinar: Unspeakable

How to Choose a (New) Career Fast

Washington Crossing the Delaware / The Crossing - Film History Livestream

PLAYFUL ARCHITECTURE: Drawing in Colour and Monochrome

Managing Your Emotions - Prof Ethan Kross

This Little World: a New History of Tudor and Stuart England

Lean Global Connection 2026

Physicians Financial Wellness Conference 2026

HBR Book Webinar: Unspeakable

How to Choose a (New) Career Fast

Washington Crossing the Delaware / The Crossing - Film History Livestream

PLAYFUL ARCHITECTURE: Drawing in Colour and Monochrome

This Weekend

Hunk-O-Mania Male Revue Strippers Show - #1 Male Strip Club in Key West, FL

Muscle Men Male Strippers Revue & Male Strip Club Shows Key West FL

Kooky Key West Scavenger Hunt

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

Hunk-O-Mania Male Revue Strippers Show - #1 Male Strip Club in Key West, FL

Muscle Men Male Strippers Revue & Male Strip Club Shows Key West FL

Kooky Key West Scavenger Hunt

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

Food & Drink events

ZaneCrawl • Key West • 11/13-11/15

KEY WEST OYSTER FEST: A BENEFIT FOR THE GULF OYSTER

Autumn Pairings: An Evening at the Mansion

Mangoes Drag Brunch Royale Christmas Show

ZaneCrawl • Key West • 11/13-11/15

KEY WEST OYSTER FEST: A BENEFIT FOR THE GULF OYSTER

Autumn Pairings: An Evening at the Mansion

Mangoes Drag Brunch Royale Christmas Show

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?