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2026 Schedule
TICKETS & EXPERIENCES ON SALE NOW

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Explore the Schedule

11 AM - 5 PM

Wednesday

Sep 2, 2026

Friends of Bubba Festival HQ

Key West First Legal Rum

Free

12:30 PM - 2 PM

Wednesday

Sep 2, 2026

A Pirate Looks Back, the Jimmy Buffett Tribute Show

Comedy Key West

$56.88

1 PM - 4:30 PM

Wednesday

Sep 2, 2026

Early Welcome: Island Adventure Sand Bar

Fury Water Adventures

$119.95

5 PM - 8 PM

Wednesday

Sep 2, 2026

Pre-event Official Meetup at the Chart Room

Pier House

Free

9 AM - NOON

Thursday

Sep 3, 2026

Dolphin Watch & Snorkel Combo

Fury Water Adventures

$79.95

9:30 AM - 11 AM

Thursday

Sep 3, 2026

Just a Few Friends Walking Tour

Shrimp Boat Sound

$45.00

11 AM - 6 PM

Thursday

Sep 3, 2026

Friends of Bubba HQ

Key West First Legal Rum

Free

NOON - MIDNIGHT

Thursday

Sep 3, 2026

Chart Room Daily Hangout Headquarters

Pier House

Free

12:30 PM - 2 PM

Thursday

Sep 3, 2026

A Pirate Looks Back, the Jimmy Buffett Tribute Show

Comedy Key West

$56.88

1 PM - 3 PM

Thursday

Sep 3, 2026

Reef & Ritas Snorkeling Trip

Fury Water Adventures

$59.95

1 PM - 6 PM

Thursday

Sep 3, 2026

Truman Waterfront Farmers Market

Truman Waterfront Park

Free

2:15 PM - 2:45 PM

Thursday

Sep 3, 2026

Tales from the Chartroom

Pier House

Free

3 PM - 5 PM

Thursday

Sep 3, 2026

Ultimate Friends Welcome

Pier House

Free

5 PM - 8 PM

Thursday

Sep 3, 2026

Cheeseburger Beach Battle

Southernmost Beach Resort

$15/$35

6:30 PM - 8:30 PM

Thursday

Sep 3, 2026

Commotion on the Ocean Sunset Sail

Fury Water Adventures

$79.95

7 PM - 10:30 PM

Thursday

Sep 3, 2026

“Open Mic / No Mic Night” at Andy's Cabana

Andy's Cabana

Free

8 AM - 10 AM

Friday

Sep 4, 2026

Painting Paradise #1: Shrimp Boat Sound

Shrimp Boat Sound

$20.00

8 AM - 10 AM

Friday

Sep 4, 2026

Plogging the Keys Waterfront Cleanup

Fury Water Adventures

Free

9 AM - 11 AM

Friday

Sep 4, 2026

Island Time Breakfast

Conch Republic Seafood Company

Varies

9 AM - 10:30 AM

Friday

Sep 4, 2026

Just a Few Friends Walking Tour

Shrimp Boat Sound

$45.00

9:30 AM - 2 PM

Friday

Sep 4, 2026

Back Country Escape: Morning Sail, Snorkel & Kayak Excursion

Danger Charters

$105.00

11 AM - 11:30 AM

Friday

Sep 4, 2026

Key West's Favorite Son City Proclamation

Shrimp Boat Sound Studio

Free

11 AM - 6 PM

Friday

Sep 4, 2026

Friends of Bubba Festival HQ

Key West First Legal Rum

Free

11:30 PM - 2 PM

Friday

Sep 4, 2026

Coconut Telegraph Trolley Tour

Pier House

$80.00

NOON - 4 PM

Friday

Sep 4, 2026

Gypsies In The Palace Buffett Tribute Band at Hogs Breath

Hog's Breath Saloon

Free

NOON - MIDNIGHT

Friday

Sep 4, 2026

Chart Room Daily Hangout Headquarters

Pier House

Free

12:30 PM - 2 PM

Friday

Sep 4, 2026

A Pirate Looks Back, the Jimmy Buffett Tribute Show

Comedy Key West

$56.88

1 PM - 3 PM

Friday

Sep 4, 2026

Reef & Ritas Snorkeling Trip

Fury Water Adventures

$59.95

2:30 PM - 4 PM

Friday

Sep 4, 2026

"Shrimp Boat Sound: Echoes From the Edge" Movie Panel

Williams Hall

$15.00

2:30 PM - 4 PM

Friday

Sep 4, 2026

Jimmy Buffett Tribute Show: Ultimate Friends Edition

Comedy Key West

Ultimate Friend VIP Only

3:45 PM - 4:15 PM

Friday

Sep 4, 2026

Tales from the Chartroom ft. Chris Lauber

Pier House

Free

4:15 PM - 5 PM

Friday

Sep 4, 2026

Through the Lens – Photography Exhibit Meet & Greet

Pier House

Free

5:30 PM - 9 PM

Friday

Sep 4, 2026

Duval Street Party ft. the Landshark Band

200 Block Duval Street

Free

6:30 PM - 7:15 PM

Friday

Sep 4, 2026

Bubba Look Alike Contest

200 Block of Duval Street

Free

9 PM - 11 PM

Friday

Sep 4, 2026

Outdoor Movie: Parrot Heads – Jimmy Buffett Documentary

Southernmost Pint Brewpub

Free

9 PM - MIDNIGHT

Friday

Sep 4, 2026

Keep It Going After Party @ Hogs Breath

Hog's Breath Saloon

Free

8 AM - 10 AM

Saturday

Sep 5, 2026

Parrots and Margaritas 5k Run/Walk

Kaya Island Eats

$46.99

8 AM - 8 PM

Saturday

Sep 5, 2026

Through the Lens – Early Buffett Concert Photography Exhibit

Pier House

Free

9 AM - 11 AM

Saturday

Sep 5, 2026

Painting Paradise #2: Louis Back Yard

Louie's Back Yard

$20.00

9:30 AM - NOON

Saturday

Sep 5, 2026

Coconut Telegraph Trolley Tour

Pier House

$80.00

10 AM - 11:30 AM

Saturday

Sep 5, 2026

Just a Few Friends Walking Tour

Shrimp Boat Sound

$45.00

10 AM - 1 PM

Saturday

Sep 5, 2026

Sails Up: Intro to Sailing Experience

Key West Sailing Center

$60.00

10 AM - 11 AM

Saturday

Sep 5, 2026

Private Distillery Tour with Paul Menta

Key West Legal Rum

Ultimate Friend VIP Only

11 AM - 11 PM

Saturday

Sep 5, 2026

Back to the Island Beach Party

801 Bourbon

Free

11 AM - 1 PM

Saturday

Sep 5, 2026

Stories with Friends: Author Showcase & Book Signing

Books & Books @ Studios of KW

Free

11 AM - 6 PM

Saturday

Sep 5, 2026

Friends of Bubba Festival HQ

Key West First Legal Rum

Free

11 AM - NOON

Saturday

Sep 5, 2026

Ultimate Friend's Private Distillery Tour with Paul Menta

Key West Legal Rum

Ultimate Friend VIP Only

11 AM - 12:30 PM

Saturday

Sep 5, 2026

Songs on the Water: Best Friends VIP Harbor Sail ft. Cliff Cody

Fury Water Adventures

Best Friend VIP Only

11 AM - 1 PM

Saturday

Sep 5, 2026

Lunch Like a Local

Hog Fish Bar & Grill

Varies

11:30 AM - 12:30 PM

Saturday

Sep 5, 2026

Paddle Out Tribute

Smather's Beach

Free

NOON - MIDNIGHT

Saturday

Sep 5, 2026

Chart Room Daily Hangout Headquarters

Pier House

Free

12:30 PM - 2 PM

Saturday

Sep 5, 2026

A Pirate Looks Back, the Jimmy Buffett Tribute Show

Comedy Key West

$56.88

1 PM - 5 PM

Saturday

Sep 5, 2026

Margaritaville Beach House Pool Party

Margaritaville Beach House

Free

1:15 PM - 1:45 PM

Saturday

Sep 5, 2026

Tales from the Chartroom

Pier House

Free

2 PM - 5:30 PM

Saturday

Sep 5, 2026

Milagro Margarita Duval Street Bar Stroll

La Concha

$48.00

2 PM - 5:30 PM

Saturday

Sep 5, 2026

Milagro Margarita Historic Seaport Bar Stroll

The Marker Resort

$48.00

4:30 PM - 8:30 PM

Saturday

Sep 5, 2026

Gypsies In The Palace Buffett Tribute Band at Hogs Breath

Hog's Breath Saloon

Free

5 PM - 6 PM

Saturday

Sep 5, 2026

Margaritaville Beach House Trivia Contest

Margaritaville Beach House

Free

6 PM - 8 PM

Saturday

Sep 5, 2026

A Sailor's Sun Sunset Sail on Argo Navis

The Dock @ Sunset Pier

$111.00

6:15 PM - 8:45 PM

Saturday

Sep 5, 2026

Cruisin' Tiki Sunset & Music Cruise

Cruisin' Tikis

$110.00

6:30 PM - 8:30 PM

Saturday

Sep 5, 2026

Wind and Wine Music Sail with Caleb

Danger Charters

$115.00

6:30 PM - 9:30 PM

Saturday

Sep 5, 2026

The Wheeland Brothers + Mike Stack & Friends

Sunset Pier

Free

8 PM - 9:30 PM

Saturday

Sep 5, 2026

Sunset to Stage: Wheeland Brothers Dockside Party

The Dock @ Sunset Pier

$95.00

8:30 PM - 10:30 PM

Saturday

Sep 5, 2026

Friends of Bubba Outdoor Video Lounge

Southernmost Pint Brewpub

Free

9 PM - MIDNIGHT

Saturday

Sep 5, 2026

Keep It Going After Party @ Back Yard EmPOURium

Back Yard EmPOURium

Free

7:30 AM - 1:30 PM

Sunday

Sep 6, 2026

Margaritaville Beach House Brunch

Margaritaville Beach House

Varies

8 AM - 8 PM

Sunday

Sep 6, 2026

Through the Lens – Early Buffett Concert Photography Exhibit

Pier House

Free

10 AM - NOON

Sunday

Sep 6, 2026

Bubbles Brunch Sail with Will & Jessica

The Dock @ Sunset Pier

$150.00

11 AM - 4 PM

Sunday

Sep 6, 2026

Friends of Bubba Festival HQ

Key West First Legal Rum

Free

NOON - MIDNIGHT

Sunday

Sep 6, 2026

Chart Room Daily Hangout Headquarters

Pier House

Free

NOON - 1:30 PM

Sunday

Sep 6, 2026

Wheeland Brothers Poolside Acoustic

Ocean Key Resort

Ultimate Friend VIP Only

12:30 PM - 2 PM

Sunday

Sep 6, 2026

A Pirate Looks Back, the Jimmy Buffett Tribute Show

Comedy Key West

$56.88

1 PM - 4 PM

Sunday

Sep 6, 2026

Pool Party at the Marker

The Marker Resort

Free

1 PM - 3 PM

Sunday

Sep 6, 2026

Roger Bartlett

Key West EmPOURium

$20 (early bird)

1 PM - 2:30 PM

Sunday

Sep 6, 2026

Best Friend VIP Show ft. Nadirah Shakoor

Margaritaville Cafe

Best Friend VIP Only

1:15 PM - 1:45 PM

Sunday

Sep 6, 2026

Tales from the Chartroom

Pier House

Free

3 PM - 4:30 PM

Sunday

Sep 6, 2026

Emerald's International Pre-Parade Reception

Emeralds International

Ultimate Friend VIP Only

5 PM - 6 PM

Sunday

Sep 6, 2026

Second Line Memorial Walking Parade

100 Duval Street

Free/Badge perks

6 PM - 10 PM

Sunday

Sep 6, 2026

Party in the Park: Tribute to Bubba

Truman Waterfront Park

Free

6 PM - 10 PM

Sunday

Sep 6, 2026

Key West Artisan Market at the Party in the Park

Truman Waterfront Park

Free

8 AM - 8 PM

Monday

Sep 7, 2026

Through the Lens – Early Buffett Concert Photography Exhibit

Pier House

Free

10 AM - 4:30 PM

Monday

Sep 7, 2026

Tin Cup Sailing Adventure

Danger Charters

$134.00

10 AM - 11:30 AM

Monday

Sep 7, 2026

Just a Few Friends Walking Tour

Shrimp Boat Sound

$45.00

10 AM - NOON

Monday

Sep 7, 2026

Will Kimbrough - Live in the Chart Room

Chart Room

$275.00

11 AM - 3 PM

Monday

Sep 7, 2026

Friends of Bubba Festival HQ

Key West First Legal Rum

Free

NOON - 1:30 PM

Monday

Sep 7, 2026

Pencil Thin Mustache Contest

Chart Room

Free

NOON - MIDNIGHT

Monday

Sep 7, 2026

Chart Room Daily Hangout Headquarters

Pier House

Free

12:30 PM - 2 PM

Monday

Sep 7, 2026

A Pirate Looks Back, the Jimmy Buffett Tribute Show

Comedy Key West

$56.88

1 PM - 4 PM

Monday

Sep 7, 2026

Pool Party at LaConcha

LaConcha

Free

1 PM - 3 PM

Monday

Sep 7, 2026

Reef & Ritas Snorkeling Trip

Fury Water Adventures

$59.95

2 PM - 2:30 PM

Monday

Sep 7, 2026

Tales from the Chartroom

Pier House

Free

3:30 PM - 5 PM

Monday

Sep 7, 2026

Ultimate Friends' Farewell Happy Hour

The Chart Room

Ultimate Friend VIP Only

5 PM - 8:30 PM

Monday

Sep 7, 2026

Island Adventure & Sunset Cruise Combo

Fury Water Adventures

$119.95

5:45 PM - 8:15 PM

Monday

Sep 7, 2026

Island Tiki Sunset & Music Cruise

Cruisin' Tikis

$110.00

6 PM - 8 PM

Monday

Sep 7, 2026

Latitude Adjustment Sunset Sail

The Dock @ Sunset Pier

$111.00

6 PM - 8 PM

Monday

Sep 7, 2026

Come Monday: Cayman & the Mango Men

Sunset Pier

Free

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Your ultimate Key West experience doesn’t stop at the schedule. To help you seamlessly blend our events with the best the island has to offer, we’ve curated a list of trusted local essentials. Explore the historic lanes, map out a day on the water, or secure your island transportation directly below.

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