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Siesta Key Outdoor Activities

When planning your trip to Siesta Key, there are lots of fun outdoor activities to choose from. If you're seeking to explore the area by water, great opportunities include Siesta Key kayaking, paddleboarding or renting a boat for the day. These activities allow you to see Florida from a different perspective as well as the opportunity to see dolphins, manatees and other sea life up close. If you're feeling a bit more adventurous and you're not afraid of heights, experience the Key and its beauty via a parasail for breathtaking panoramic views. And lastly, if you prefer to stay on land, experience the Siesta Key drum circle or the farmers market, both of which take place every Sunday. Click below for more information on all activities.

Siesta Key Parasailing

If you're an outdoor thrill seeker, then taking a ride on a Siesta Key parasail is for you! Experience panoramic views of the key and its beaches while enjoying the majesty of flight over the clear gulf waters. There's also a good chance that you'll spot a dolphin or manatee while in flight. For your convenience, listed below are popular Siesta Key parasail companies.

Siesta Key Parasailing

Siesta Key Parasail and Jet Ski


1536 Stickney Point Rd, Sarasota, FL 34231 Map

Parasail Siesta


1250 Stickney Point Rd, Siesta Key, FL 34242 Map

Siesta Key Kayaking

Experience natural Florida with a Siesta Key kayaking excursion. If you're seeking that fun outdoor adventure, kayak through hidden lagoons, the Intracoastal waterway and get up and close with Florida's wildlife. Kayaks come in single and double person sizes with the option to "sit in" or "sit on top" and have adjustable seats to fit persons of all sizes. For your convenience, listed below are popular Siesta Key kayak rental companies.

Siesta Key Kayak Rentals

Siesta Paddle Sports


We deliver to your location on Siesta Key.

Kayak Launch at Turtle Beach Park

Siesta Key Bike & Kayak


1224 Old Stickney Point Rd Siesta Key, FL 34242 Map

Siesta Key Bike & Kayak Rentals
If you're seeking to get a great workout while on vacation, consider renting a paddleboard for your outdoor adventure. Unlike kayaks and canoes where the rider propels themselves forward in a seated position, the paddleboard is propelled via the rider in a standing position, hence the name "Stand Up Paddleboarding" or more commonly known as SUP.  Stand Up Paddle boarding gets it origins from the surfboard and officially became recognized as an official sport in 2013. For your convenience, below are popular Siesta Key Paddle Board rental companies.

Siesta Key Paddleboard Rentals

Siesta Paddle Sports


We deliver to your location on Siesta Key.

Gulfside Paddleboards


We are a mobile business and deliver paddleboards anywhere on Siesta Key.

Siesta Key Boat Rentals

If you're seeking to explore the Siesta Key and greater Sarasota area by water, consider renting a boat from Siesta Key Marina or CB's Saltwater Outfitters. They are both conveniently located at the south end of the Siesta Key bridge near the intersection of Midnight Pass and Stickney Point Roads. These businesses offer a variety of boat rental options to choose from including pontoon boats, small boats with sun covers, jet skis and wave runners. Rental options typically include half day or full day. For your convenience, listed below are these popular Siesta Key boat rental businesses.

Siesta Key Boat Rentals

Siesta Key Marina


1265 Old Stickney Point Rd, Sarasota, FL 34242 Map

Siesta Key Marina Boat Rentals

CB's Saltwater Outfitters


1249 Stickey Point Rd, Siesta Key, FL 34242 Map

CB's Saltwater Outfitters - Siesta Key Boat Rentals

Siesta Key Drum Circle

Every Sunday, about an hour before sunset, Siesta Key Beach comes alive with the sounds of beating drums. Since its inception back in 1996, the Siesta Key drum circle has grown into a culture of free-spirited individuals who seek to express themselves through music and dance. All individuals, of any age or musical ability, are welcome to bring their percussion instrument of choice and join in on the fun. The drum circle organizes between the red and green lifeguard stands of Siesta Beach. When attending this fun outdoor event, make sure you arrive early for a good parking spot and bring a chair or blanket to enjoy the sunset and the sounds of the evening.

View an amazing aerial drum circle video produced by Air View Videos.

Siesta Key Helicopter Tours

Experience the beauty of Siesta Key from above in a personalized helicopter tour. Get a bird's eye view of the spectacular beachfront homes and resorts, crystal white sands of Siesta Key and Crescent Beach as well as the bountiful marine wildlife. Tours are typically in 30 or 60 minute lengths.

Tour Siesta Key by helicopter in this video by Florida Suncoast Helicopters.

Siesta Key Helicopter Tours

Florida Suncoast Helicopters


SRQ Airport
1244 Clyde Jones Rd, Sarasota, FL 34243 Map

Siesta Key Sea Plane Tours

Fly over Siesta Key in a sea plane and experience the natural beauty of the area. See beautiful beachfront homes and sea life while you fly like a bird. Choose from a 20, 30 or 60 minute flight in a powered glider that can take off or land in water.

Tour Siesta Key by sea plane in this video by Out and About SW Florida.

Siesta Key Sea Plane Tours

Siesta Key Sea Planes


Multiple pick up locations around Sarasota

Siesta Key Crystal Sands Classic

Originally launched in 2010, the annual Siesta Key Crystal Classic Master Sand Sculpting Competition now draws over 35,000+ attendees each year. This annual Siesta Key beach sand sculpting event, which takes place in early November, attracts top professional sand sculptors from around the country. In a short 24-hour window, the beach is transformed into an outdoor gallery of art as these master sculptors compete to create one-of-a-kind masterpieces which can exceed 10 feet in height. To view some of the unique sand creations that come to life, watch the video below. To view the event schedule or to purchase tickets, please visit their website below.

2018 Siesta Key Crystal Sands Classic

Nov 9, 2018 - Nov 12, 2018


Siesta Key Farmers Market

The Siesta Key Farmer's Market is a local favorite that takes place every Sunday morning from 8am till 1pm in the Davidson Plaza, located in the heart of the Siesta Key Village. At the market, you'll see an array of vendors selling fresh produce, artists selling unique, one-of-a-kind arts and crafts as well as hear the sounds of local musicians. Since parking in the Village is limited, it's likely a good idea to park in the municial lots just east of the village.

Every Sunday, 8am - 1pm

Davisdon Plaza (Siesta Key Village)

5124 Ocean Blvd, Siesta Key, FL 34242 Map