Best 192 things to do in Osprey, FL

Paddle a 100% clear kayak to mangroves and a secluded beach near Sarasota

Book a private clear-kayak tour with a guide for groups up to 14

Spend 6 hours on the water with a private Siesta Key boat charter

Plan your own 4-hour charter with sandbars, snorkeling, and stops for food and drinks

Cruise Siesta Key waters and watch for dolphins and manatees

Build your own full-day private boat charter from Siesta Key

Watch the sunset from a comfortable boat on a 2-hour Siesta Key tour

Paddle Lido Key’s mangrove tunnels with a guide in 2 hours

Ride a Jet Ski through Phillippi Creek and toward Siesta Key

Cruise Siesta Key on an e-bike scooter hybrid with dual suspension

Experience Siesta Key like never before—from 400 feet above the ocean!

Rent a street-legal 6-passenger golf cart and explore Siesta Key

Cruise Siesta Key’s waterways on a 2024 tiki boat with music, drinks and coastal wildlife views.

Soar above Florida's top-rated beach and spot dolphins during a 12–15 minute parasail flight.

Enjoy a relaxed evening cruise along Siesta Key with music, LED lights and possible dolphin sightings.

Watch playful dolphins and a vibrant Gulf sunset while enjoying complimentary beer and wine.

Enjoy a morning cruise with complimentary drinks while spotting dolphins in Siesta Key.

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

Spot playful dolphins and relax at a scenic sandbar while enjoying complimentary drinks

Ride new Yamaha jet skis across Florida's largest riding area at your own pace

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

Customize your day exploring sandbars, islands, and marine life on a private catamaran.

Rent a 26-foot tritoon with seating and shade for up to 12

Rent a 26' tritoon for a full day with seating for up to 12