Best 550 things to do in Siesta Key, FL

Lounge on plush seating and swim from the rear boarding ladder

Rent a 25-foot pontoon for up to 12 people for a full day on the water

Rent a 23-foot pontoon for up to 10 people

Cruise and anchor around Sarasota Bay by deck boat

Rent a 21' deck boat for up to 8 people on Siesta Key

Rent a 23-foot pontoon for up to 10 people

Rent a 21-foot deck boat and cruise the bay with up to 8 people

Ride the waters around Siesta Key with a guide, a sandbar stop, and island views

Choose a bike style that fits your plans for a full day on Siesta Key

Ride Siesta Key and reach the Legacy Trail with an e-bike rental

Cruise Siesta Key with a Class 1 or Class 2 electric bike

Family bike options with kid sizes and child seats

Cruise the Legacy Trail on a comfortable bike with included essentials

Comfortable Jamis hybrid bike rental for Legacy Trail rides

Choose an easygoing or sporty ride for the Legacy Trail

Smooth pedal-assist rides for exploring more of the Legacy Trail

Ride paved trail miles from Sarasota toward Venice

Soar above Siesta Key and spot dolphins on a safe, family-friendly 2.5-hour parasailing cruise

Cruise Sarasota’s Gulf waters on a spacious pontoon with flexible 4- or 8-hour options.

Customize your private cruise with sandbar, beach, dining, and wildlife stops

Set your own pace on a private sandbar day with swimming, snorkeling and lunch

Explore Siesta Key's changing underwater snorkeling spots with a captain

Settle in for a captain-led sunset cruise on Sarasota’s waterways

Explore boat-access-only reaches of Point of Rocks with captain support and snorkeling gear