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You Need to Experience These 9 Events Near Longboat Key

You Need to Experience These 9 Events Near Longboat Key

Sarasota’s beautiful Gulf Coast offers plenty of incredible year-round festivities. We compiled a list of some of the best events near Longboat Key for visitors to get a taste of our favorite celebrations! You’ll find everything from baseball spring training to sand sculpture competitions!

If you’re searching for even more events, attractions, and things to do in the Sarasota area, request our complimentary Destination Guide!

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The Best Longboat Key Events


Spring Training

Pro baseball spring training is one of the most popular spring events near Longboat Key. The Grapefruit League is home to 15 teams that play at a variety of locations along both of Florida’s coasts. Currently, the Baltimore Orioles base their spring practices and exhibition games in Sarasota at Ed Smith Stadium. You can easily purchase tickets for a great price on game days.

Chalk Festival

Visitors and residents can marvel at the sight of artists turning sidewalks into unique masterpieces at the Chalk Festival. This fun three-day event in Sarasota has stunning art, food trucks, live music and more. What a great way to enjoy yourself in the warm Florida sunshine!


Fireworks Spectacular Over Sarasota

The best way to celebrate the Fourth of July in Sarasota is watching fireworks at night over the bay. You can catch excellent views of the show from one of the waterfront parks, watch parties near downtown or one of the fantastic rooftop bars in the city. 

Sarasota Powerboat Grand Prix

The Sarasota Powerboat Grand Prix is one of the most celebrated events near Longboat Key. These boats are super fast and really amazing! The races take place along the shores of Lido Key, where you can enjoy a couple of great beach bars while extending your Fourth of July week festivities!


Giving Hunger The Blues

Live music, delicious local eats, and other Sarasota vendors all come together for a good cause at Giving Hunger The Blues. Proceeds from this annual outdoor music festival near Longboat Key go toward raising money for the Mayor’s Feed The Hungry non-profit program. Enjoy great music, dance and eat all for a good cause!

Siesta Key Crystal Classic International Sand Sculpting Festival

There’s nothing like enjoying the feel of sand between your toes in the fall as you take in an incredible sand sculpting competition. This four-day event takes place on Siesta Key, which is only about a 30-minute drive from Longboat Key. Trust us; you won’t want to miss out on this fun in the sun!

Sarasota Oktoberfest

There are three things you can count on at the Sarasota Oktoberfest: mouthwatering food, live music and big pints of beer! This fun fall celebration takes place in downtown Sarasota and is one of the newest annual events near Longboat Key. During or after the fest, you will find there is a lot to do in our colorful and upbeat downtown. Discover our local eateries, theaters, shopping boutiques, artist enclaves and more.


Sarasota Christmas Boat Parade

The Sarasota Christmas Boat Parade is the best way to kick off the holiday season at the beach! Residents and guests decorate their boats with lights and more, then boat around the bay during this December event near Longboat Key. It is a sight to behold!  A few of the best places to watch the parade are from Marina Jack Restaurant, Bayfront Park, and City Island Park. 

Sarasota Seafood & Music Festival

There’s no better time or place to savor locally-sourced fish, crabs, shrimp and oysters than at the Sarasota Seafood & Music Festival. Feel the rhythm and taste a delectable array of delicious coastal cuisine at this three-day celebration in January. 

Plan Your Longboat Key Getawaythe pool at the All Docked Out property

Our Florida Vacation Connection homes and condos on Longboat Key offer a serene retreat from typical beach crowds. Miles of beach shoreline with few public access points means that you don’t have to share your “private beach” with many others. So, you can kick back, relax and enjoy the beautiful sugar-white sands. We also offer a large selection of rental properties on neighboring Lido Key, where there are plenty of restaurants and shops!

Start planning your Gulf Coast getaway today by booking one of our properties! We look forward to welcoming you to the Florida Vacation Connection family.