August 07, 2025

This Labor Day Weekend, Key West comes alive with two unique celebrations you won’t want to miss. The Key West BrewFest returns for its 15th year, featuring over 60 breweries pouring more than 225 craft beers, along with pool parties, food pairings, and the Signature Tasting event on the beach. At the same time, Just A Few Friends offers a heartfelt tribute to Key West’s favorite son, Jimmy Buffett, with four days of events including concerts, a Second Line Parade, cocktail crawls, rum tastings, pool parties, and more. And yes, there will be Cheeseburgers in Paradise! Whether you’re here for craft brews, live music, or the laid-back island vibe that encompasses the spirit of Jimmy Buffett, there’s plenty happening in paradise. Photo credit: Just A Few Friends Key West.

brewfest

Key West Brewfest

Now in its 15th year, Brewfest is a true Labor Day tradition in Key West, blending craft beer culture with island-style fun. With 60+ breweries, 225+ beers, pool parties, pairing dinners, and a signature beachfront tasting, it’s one of the most anticipated weekends of the year. All proceeds benefit local scholarships through the Key West Sunrise Rotary Foundation.

Key West Brewfest Info: https://keywestbrewfest.beer

just a few friends

Just A Few Friends

Four days of music, memories, and island storytelling honoring Key West's favorite son, Jimmy Buffett. There will be concerts, a parade, book signings, walking tours, panel discussions, pool parties, and more.

Festival Highlights:

Live performances by Nadirah Shakoor, Will Kimbrough, Roger Bartlett, and more
Second Line Memorial Parade and Party in the Park on Sunday, August 31
Margarita strolls, brunches, happy hours, and culinary experiences
Sunset sails, tiki cruises, and beach parties
Book signings, film screenings, and Buffett-inspired panels
Exclusive meetups, contests, afterparties, and more

All proceeds support Reef Relief, Bahama Village Music Program, and the Key West High School Marching Band.

Just A Few Friends Info: justafewfriendskeywest.com

Here's What's Happening at Our Resorts

The Marker Key West Harbor Resort and our sister property, Southernmost Beach Resort, are proud sponsors of Key West Brewfest and Just A Few Friends.

brewfestbeer

Southernmost Beach Resort Events

Pool Floatie Chug & Race
Thursday, August 28 | 1:00 to 4:00 PM | Shores Pool

Race across the pool on an inflatable float while chugging beer. Yes, it’s exactly as fun as it sounds. Free event – Register Here

Grilled Cheese & Beer Pairing + Trivia
Thursday, August 28 | 6:00 PM | Dewey Deck

A five-course pairing of gourmet grilled cheese sandwiches and craft beers, followed by island-themed trivia. Limited seating — this one sells out fast. $69.84 per person (includes tax, fees & gratuity) Get Tickets

Pool Party + Belly Flop Contest with Islamorada Brewing
Friday, August 29 | 1:00–4:00 PM | Pineapple Pool

Kick back with music, games, cold beer, and the return of the fan-favorite belly flop contest.
Free event - Register Here

cheeseburger battle

Cheeseburger Beach Battle & Tribute Concert
Friday, August 29 | 5:00–8:00 PM | Southernmost Beach

Sample tropical cheeseburgers from 8+ local restaurants and vote for your favorite while Margaritas in Paradise performs live (5:30 PM). Tasting and voting take place from 5:00 to 7:00 PM. Limited to 300 tasting tickets.
*This event sells out fast.
$20 General Admission | $35 with Burger Tasting
Get Tickets

Brewfest Signature Tasting
Saturday, August 30 | 3:00–8:00 PM | Southernmost Beach Resort

The flagship tasting event with 60+ breweries and 225+ beers. VIP Admission includes early entry, access to a VIP lounge with specialty pours and light bites, and extended tasting time. General Admission opens at 5:00 PM.
VIP: $100 | GA: $50
Get Tickets

margaritasinparadise

The Marker Key West Harbor Resort

Margaritas in Paradise LIVE Concert + 3 Daughters Brewing’s “Drink & Draw” Pool Party
Sunday, August 31 | 2:00–5:00 PM | The Marker Key West Harbor Resort

This is where Brewfest and Just A Few Friends come together. Enjoy a poolside concert by Margaritas in Paradise and take part in an interactive “Drink & Draw” session with 3 Daughters Brewing. Music, beer, art, and fun. Event Info

Plan Your Ultimate Key West Labor Day Getaway, book now.

“Wrinkles will only go where the smiles have been.” – Jimmy Buffett

This Labor Day, we're celebrating craft beer, the unmistakable spirit of Jimmy Buffett, and those laid-back island moments that only Key West can truly deliver. As Jimmy himself famously said, "It's five o'clock somewhere," and it's always five o'clock here. #lovethemarker

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