things to do in Osprey, FL

Paddle Jim Neville Marine Preserve to water-only Midnight Pass Beach

Experience marine life up close on a comfortable pontoon cruise for all ages.

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

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

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

Paddle Longboat Pass for 4 hours with a map and basic lesson

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

Cruise Sarasota Bay, swim at a sandbar, and relax with water toys and your own drinks

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

Ride a gentle horse along the sand, then cool off with a unique swim in Palma Sola Bay.

Skip traffic and parking on an open-air ride to Bridge Street Pier

Island-hop for 4 hours with snorkeling and water toys, tailored for families

Explore Lido Key’s protected waters and mangrove tunnels at your own pace

Paddle Lido Key’s mangrove tunnels with a local naturalist guide

Cruise Sarasota Bay and Intracoastal waterways aboard a shaded pontoon

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

Soar over Siesta Key’s coastline with an optional Gulf dip

Ride an air-conditioned trolley at night for musical ghost stories and Sarasota history in October.

Kayak Little Sarasota Bay to South Lido’s shaded mangrove tunnels

Paddle Sarasota’s mangrove tunnels on a 2-hour guided kayak tour

Soar over Anna Maria Island with single, tandem, or triple flight options

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

Fly solo, double, or triple on a parasail flight

Paddle a private clear-kayak tour through Robinson Preserve to mangroves and a sandbar