Best 465 things to do in Siesta Key, FL

Paddle mangroves after sunset with LED-lit views beneath your 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

Cruise Siesta Key’s western coast with time for dolphins, a sandbar stop, and a swim

Spend 4.5 hours cruising, snorkeling stops, and sandbar time off Siesta Key

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

Cruise Siesta Key’s western coast with your private group

Cruise Siesta Key’s western coast on a private 2-hour daytime or sunset boat ride

Plan a private coastal cruise with your own food and drinks

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

Customize a private cruise along Florida's western coast

Private coastal cruising with flexible routes and sunset options

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

Cruise coastal waters with time for a sandbar swim, waterfront stops, or an eco-focused outing

Paddle Lido Key, then taste your way through downtown Sarasota

Shop boutiques and enjoy bubbles and light bites in Sarasota’s historic districts

Eat your way through Downtown Sarasota with local history and art

Browse boutiques while exploring John Ringling’s legacy over tastings and sparkling wine