Best 550 things to do in Siesta Key, FL

Relax on Sarasota Bay as sunset colors fill the water

Ride Sarasota Bay and Siesta Key waters with safety gear included

Ride side by side on two jet skis in Sarasota Bay

Rent a 22' Bentley pontoon and cruise Sarasota’s Intracoastal waterways

Rent a 24' Sea Ray SunDeck to explore Sarasota waterways and sandbars

Cruise Southwest Florida waterways with room to relax, swim, and sunbathe

Cruise Sarasota on a 21 ft Chaparral with Bluetooth stereo and swim ladder

Rent a 23.5 ft Mako center console for cruising or fishing in Sarasota

Paddle mangroves after sunset with LED-lit views beneath your kayak

Explore the water at your own pace in a clear kayak

Cruise Sarasota Bay with your family or group on a fuel-included pontoon boat

Paddle southwest Florida waterways at your own pace

Explore southwest Florida waterways by kayak with included paddles and life jackets

Ride a 110 hp jet ski with safety instruction, fuel, and life jackets included

Paddle Sarasota-area waterways at your own pace with included gear

Guided sunset jet skiing with room for your group

A custom chef‑curated feast celebrating bold local flavors and dietary wellness—served right in your home or rental

Leisurely 2-hour private cruise from Lido/Longboat Key with coolers and ice onboard

Cruise Florida's Gulf Coast on a private outing with flexible routes and onboard coolers

Customize a Gulf Coast cruise with sandbar swims and waterfront stops

Private coastal cruising with flexible routes and sunset options

Cruise Venice’s coast with time for dolphin searching, swimming, and waterfront stops

Fly a private helicopter tour from Sarasota for up to 3 passengers

Test your trivia skills from the skies over Sarasota