23 Jun 2021
Planning a trip to Key West for Labor Day weekend this year? While much of the country is gearing up for fall and cooler weather, Key West is still warm, sunny, and full of exciting things to see and do. Explore the best historic attractions in Key West, spend a day (or several) out on the water, and experience the lively culture of the Conch Republic on your Labor Day getaway.
Things to do in Key West Labor Day Weekend
Go on an Old Town Trolley Tour
Old Town Trolley Tours are the perfect way to see Key West's top attractions. When you buy tickets to the trolley, you can hop off at your leisure at more than 100 points of interest and hop back on when you're ready for the next attraction. You get unlimited boarding with a day pass, which also includes discounts at some local attractions.
Bar Hopping in Duval Street
The famous Duval Street Key West bars are always lively, and they are especially fun on holiday weekends. You can stroll this entire street popping into bars, restaurants, coffee shops, boutique stores, and more. After snapping a few photos at the Southernmost Point of the Continental US, stop by The Rum Bar for a cocktail. This spot is cozy and serves up delicious frozen drinks in a lively, but laid-back setting.
Then, head north on Duval Street, stopping at spots like the Little Room Jazz Club, Rick's Bar, Sloppy Joes, and Willie T's. And don't forget to grab some food along the way. A few of our favorites are Key West Fish & Chips, Banana Cafe, Paradise Restaurant, or Smokin' Tuna Saloon.
Spend the Weekend on the Water
There's truly no better way to spend your time in Key West than on the water. If you're seeking water adventures in Key West, go on a jet ski tour, sunset sailing excursion, fishing charter, or rent a kayak or stand up paddleboard. You can go out on a dolphin cruise or spend the day visiting Dry Tortugas National Park, an island off the Keys that is home to pristine nature.
For those looking to explore below the water's surface, snorkeling and scuba diving are both hugely popular activities in the area. In fact, Key West is home to the 3rd largest underwater reef in the world!
Key West Events During Labor Day Weekend 2021
Celebrate at Key West Womenfest
September 1-5, 2021
For 5 days, the Key West Womenfest returns to the Southernmost in celebration of all women. This event attracts queer, transgender, and allies to this annual event. Enjoy a variety of activities and events that include live music, parties, tournaments, drag shows, and more.
Cheers at Key West Brewfest
September 2-6, 2021
Calling all beer fans! The Key West Brewfest is back in 2021 for a weekend of beer tastings, paring dinners, brunches, happy hours, pool parties, and more. Breweries from all over the nation come down to Key West for the Brewfest, including Lagunitas, Kona, Dogfishhead, Anchor, Goose Island, Steigl, and more.
Escape to Key West for Labor Day 2021
Search through our inventory of vacation rentals in Old Town, Truman Annex, and more. Our wide selection of Key West rentals can accommodate groups of up to 10 guests.