Six Days, One Island: Just a Few Friends Returns to Key West
Labor Day weekend has quietly become one of the best weeks on the island - six days of music, water and street parties honoring Key West’s favorite son, ending with a second line parade down Duval.
September used to be the quiet month. Locals liked it that way. Then, three years ago, a handful of friends decided the island should have a proper way to remember the songwriter who made it famous, and Labor Day weekend in Key West stopped being quiet.
Just a Few Friends runs Wednesday, September 2 through Monday, September 7, 2026. It has grown every year, and the 2026 edition spans six days and dozens of venues across Old Town.
What It Actually Is
It is not a ticketed festival on a fairground. It is the whole island doing something at once: concerts, snorkel trips, walking tours, bar strolls, a 5K, a paddle-out, film screenings, book signings and pool parties, spread across restaurants, bars, resorts and boats from Stock Island to Sunset Pier.
A large share of the programming is free. The rest is individually ticketed, from a $15 film panel to sunset sails in the $100 range. There are also two VIP tiers, Best Friend and Ultimate Friend, for private receptions and reserved shows.
The charitable side is the real backbone. Souvenir badges serve as the festival credential and a donation at once, with funds managed by the Community Foundation of the Florida Keys. In its first year alone, the festival handed $34,000 to Reef Relief and the Bahama Village Music Program.
How the Week Unfolds
Find the full schedule, festival badges and individual event tickets at Just a Few Friends Key West. Popular ticketed events can sell out, so it is worth making plans early.
Planning Notes From People Who Live Here
Protect Sunday
If you only make one thing, make it the parade and Party in the Park. Both are free, both are outdoors, and the walk from Duval down to Truman Waterfront is the emotional center of the weekend.
Plan Around September Weather
It is September in the Keys. Hot, humid weather and afternoon storms are normal. Plan water activities for mornings and keep the afternoons loose.
Skip the Car
Nearly everything is in Old Town and walkable. Parking during festival weekend is worse than usual, which is saying something.
Book Ticketed Events Early
Small-venue shows tend to go first. Free events generally do not require anything more than showing up, although some may request an RSVP.
Where to Stay
This is a festival built on the premise of a group of friends turning up in one place. Splitting that group across three hotel rooms on three different floors rather defeats the point.
Bahama House
Three bedrooms · Three baths · Private heated pool · Steps from lower Duval
The main house has two bright bedrooms and two full baths, a full kitchen, and a living room with a queen sleeper for extra guests. Behind it sits a private studio cottage with its own bedroom, bath and kitchenette — useful when one couple wants their own door, or when nobody wants to queue for a bathroom on parade morning.
You are walking distance from the parade route at 100 Duval, the Duval Street Party, Southernmost Beach and Truman Waterfront Park. No car, no parking, no cab line at midnight — and your own pool waiting at the end of the day.
Three Weeks Out — Check Dates Now
Labor Day weekend has gone from one of the island’s quietest stretches to one of its busiest, and Old Town homes that sleep a group are among the first to disappear. With the festival opening September 2, remaining inventory is limited.
Check Live Availability
