The year-round sun and warmth of Florida makes it the ideal destination any time of year you need a break, and the Labor Day holiday is a great opportunity to take a break and enjoy a long weekend that’s also the unofficial end of summer. Enjoy a vacation full of sand, water, sun, and fun with loved ones before fall arrives. The Sarasota and Bradenton area are mainland Florida destinations that provide the ultimate experience in Florida beach vacations. Not only do they have their own beaches, but they’re also close to several barrier islands that offer a different beach vibe for your Labor Day weekend in Florida.


An escape to beach locations like Bradenton and Sarasota means spending plenty of time on the beach, no matter what time of year you come, but especially during the still-warm weather and waters you’ll find during the Labor Day holiday. You and your loved ones can spend a little extra time out in the sun and in the water, as the sun’s power lessens as fall draws near. Sunbathe, change up your exercise routine with a walk or run on the beach, or take a swim, snorkel, or SCUBA adventure in the waters of the Gulf of Mexico.

Beach Horseback Rides

Saddle up and head out on an adventure this Labor Day. While a trail ride along area hiking trails is the usual experience, you can also take the experience to the water’s edge. There are several companies in the area that provide horseback rides that stroll along the water on the beach. There are even some tours where the horses venture out into the water for an extra splash. Whichever company you choose, advanced reservations are required, and they’ll need details like rider height, weight, and age so they can pair each rider with the horse that best fits their needs.

Boat Tours

A great way to get to know the area you’ve decided to call home for the Labor Day holiday is to get out and explore, both on land and on water. While exploring on land is easy – just hop in your rental car or take a walk, you’ll want to get familiar with the waters of the area too. There are several companies that offer tours of the waters surrounding Bradenton and Sarasota. Guides are full of information about the area’s history and ecology, so you’ll learn some interesting trivia while enjoying time at sea. Keep your camera ready and your eyes peeled for sea life like dolphins, manatees, rays, and more! Book a private tour for you and your loved ones and pack a picnic, including your favorite alcoholic beverages.

Breweries, Distilleries & Wineries

Set aside some “adults only” time and visit the area’s wineries and distilleries. There are several breweries and distilleries that call Bradenton and the surrounding area home, including Naughty Monk Brewery, Darwin Brewing Company, Loaded Cannon Distillery, and more. Wine lovers will want to add a stop at Fiorelli Winery & Vineyard, where the wines are made from grapes grown at the on-site vineyard. Enjoy a tasting or tour or book a special private event. Once you’ve tasted the offerings, choose your favorite wines, beers, or spirits to take back to your rental to pair with your favorite home-cooked meals.

The Keys

Off the coast of Sarasota, Bradenton, and the surrounding area is a group of barrier islands that protect Sarasota Bay from the crashing waves of the Gulf of Mexico. Head to Anna Maria Island, Bradenton Beach, Holmes Beach, Longboat Key, or Siesta Key this Labor Day for an unforgettable day trip. Each island has its own unique flair as well as plenty of Florida fun like parasailing, boat tours, and more without the traffic of the mainland.

The Ringling

Art, history, circus memorabilia, gardens, a historic theater, and more await for you to explore this Labor Day. The property preserves the legacy of John Ringling, one of the five brothers who formed the Ringling Brothers Circus, and his wife Mable. Wander the property and include visits to the State Art Museum of Florida, two circus museums, an education center, the historic Ca’ d’Zan Mansion, Bayfront Gardens, and the historic Asolo Theater where you can see a variety of live performances. The grounds and gardens are always free to visit, and admission to the Museum of Art is free on Mondays, but hours may vary during the holiday.

Celebrate Labor Day in Florida

Enhance your Labor Day retreat to Bradenton and Sarasota with a private vacation rental provided by Anchor Down Vacation Rentals. We offer units as small as one bedroom for a solo excursion, all the way up to eight bedrooms for a Labor Day gathering that includes all your loved ones! After a long day, make a home-cooked meal in your unit’s fully equipped kitchen, and enjoy it in the spacious living/dining areas of your unit, or in a private outdoor space. Relax in a private bedroom or gather your group and watch your favorite movie or TV show.

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