Labor Day Weekend in Key West 2025 – Your Guide to Festivals, Cruises & Sandbar Trips
Labor Day Weekend in Key West is the perfect time to experience the island at its liveliest. From sunrise to sunset, the Conch Republic turns into a tropical playground filled with live music, food and drink festivals, waterfront parties, and unforgettable tours on the water.
Visitors can celebrate Jimmy Buffett’s legacy at the Just A Few Friends Festival, sample craft beers during Key West BrewFest, or cool off with a Labor Day sandbar trip or sunset cruise. Whether you’re looking for laid-back island vibes or non-stop festivities, this complete guide will help you plan the ultimate Labor Day in Key West.
Just a Few Friends – Key West Festival
This multi-day event will feature an exciting lineup of live performances, unique island experiences, and signature gatherings, culminating in the Second Line Memorial Walking Parade and Party in the Park on Sunday. This year’s festival introduces a new way for attendees to enhance their experience with the Latitude Adjustment Hotel Packages and the Ultimate Friend Badge, both offering exclusive perks and premium access to select events. Learn more
Charter a Sandbar Boat for an Epic Labor Day Weekend
Escape the crowds and head out to the sandbars for a Labor Day celebration like no other. Sandbar charter boats take you to shallow, clear waters perfect for swimming, sunbathing, and sipping drinks under the sun. It’s a laid-back, local-style way to enjoy the holiday with your crew.
We’ve got great ideas to spend the day like a local on the water.
Book a sandbar charter or reserve a boat rental for an epic weekend, trips sell fast!
Key West Brewfest
More than 150 beers and micro-brews are on tap at this “tasty” annual event that benefits the charitable efforts of the Key West Sunrise Rotary Club of the Conch Republic. Events from beer dinners, beer brunches, happy hour parties, pool parties, late-night parties, seminars and the Signature Tasting Festival Event are some of the offered activities. Learn more.
Parrots & Margaritas 5K + Flip-Flop Mile
Start your Labor Day weekend island-style with the 2nd Annual Parrots and Margaritas 5K and Flip-Flop Mile—organized by our friends at Mile 0 Events and hosted at the iconic, everyone’s favorite sing-along bar, Irish Kevin’s!
Choose between the full 5K or the easygoing Flip-Flop Mile. The Flip-Flop Mile is just 3/4 of a mile but still full of fun. Skip the sweat and grab the swag—then strut your stuff past Shrimp Boat Sound Recording Studio and head straight to the finish line celebration. Then everyone celebrates the finish with a lively post-race party featuring margaritas, cheeseburger sliders, tropical tunes, and island camaraderie. Learn more.
Cruise Around Key West
Cruise around Key West, island-style, with eco-friendly electric golf carts, Scooter Rentals, or gas-powered Golf Cart rentals. Discover the thrill of our roadworthy rentals, as they get you from one bucket-list spot to the next with a smooth and safe ride, perfect transportation experience for your Labor Day Weekend.
Local Tips for Labor Day Weekend
- Book tours early (Labor Day sells out) – call or text us
- Expect hot temps: plan water-based activities mid-day. See what to pack for your boat day
- Parking is limited: use scooters and golf carts – reserve today
Plan Your Labor Day Weekend Itinerary
- Day 1: Arrival + sunset cruise – book sunset cruises
- Day 2: BrewFest + sandbar charter – reserve a sandbar charter
- Day 3: Festival + live music
- Day 4: Lazy brunch + scooter tour – book your scooter rental
FAQ – Labor Day in Key West 2025
What events happen in Key West over Labor Day Weekend 2025?
Labor Day Weekend (August 29–September 1, 2025) features the Just A Few Friends Festival, Key West BrewFest events, fun runs like the Parrots & Margaritas 5K / Flip-Flop Mile, plus waterfront parties and live music across Old Town.
Do I need reservations for a sandbar charter or sunset cruise on Labor Day?
Yes—boats and tours sell out quickly on holiday weekends. Reserve early for sandbar charters, sunset cruises, boat rentals, and other on-the-water experiences. Same-day walk-ups are limited. So, call, text, or book directly online.
What’s the best way to keep cool during Labor Day Weekend?
Midday heat is real. The best options are sandbar trips, snorkel tours, or late-day sunset cruises. Pack reef-safe sunscreen, plenty of water, rash guards, and a dry bag.
How do I get around Key West on a holiday weekend?
Parking is tight. Most visitors use golf carts, scooters, or eco-friendly electric carts to get around Old Town and hop between events. Book your golf cart or scooter today
Where are the best places to watch sunset on Labor Day Weekend?
Mallory Square is the classic spot, but it gets crowded on holidays. Sunset cruises and local favorites like quieter piers and beachside bars often provide better views and more space. We’ve got a great guide to Key West Sunsets.
Is Key West BrewFest during Labor Day Weekend 2025?
Yes—BrewFest runs over Labor Day with tastings, dinners, pool parties, and the signature festival event. Book early to pair it with watersports like snorkeling, Tiki Boats, or Jet Ski tours.
Are sandbar and eco tours family-friendly? What should we bring?
Yes—kids love the calm, shallow sandbars. We have many trips from private charters, shared charters, and larger group trips.
Bring towels, hats, sunglasses with straps, water bottles, snacks, and reef-safe sunscreen. See our boat rental packing guide.
Can you help use decide on what boat tour to take?
Yes—we’ve got you covered! Give us a call or text. We take the time to understand your group’s needs and match you with the perfect experience, just real local advice and genuine hospitality.
