things to do in Osprey, FL

Ride to your own soundtrack with waterproof Bluetooth audio

Head out at sunrise on your choice of two Sea-Doo models

Take to the water on a 2025 Sea-Doo for an evening ride

Try water acrobatics with a jet ski built for tricks

Customize a luxury day on the water for swimming, fishing, sightseeing, or celebrations

Fish inshore with a US Coast Guard licensed captain on a private boat

Cruise Siesta Key by e-bike with a rental timed for sunset

Stretch, unwind, and rejuvenate—right in the comfort of your vacation rental.

Cruise Holmes Beach waters on a 13-passenger tritoon with shade and wrap-around seating

Rent a boat for 4 hours to 7 days, with space for up to 12 passengers

Customize your route with snorkeling, sightseeing, and island stops on a private boat

Customize a private Anna Maria & Long Boat Key boat tour for up to 6 people

Cruise into the Florida sunset with a US Coast Guard licensed captain

Sail for 8 hours and choose Egmont Key, Anna Maria, or Shell Key

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

Cruise Sarasota Bay with a 17-foot deck boat rental

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

Private Gulf Coast cruising tailored to your sandbar, beach, and snorkeling plans

Cruise at sunset with a sandbar stop and a closing toast

Private 2-hour catamaran sail with dolphin spotting

Sail to Shell Key for swimming, snorkeling, and shelling

Private 2-hour sunset sail with bay views and dolphin spotting