Best 203 things to do in Osprey, FL

Sightsee local waterways on a private charter with flexible 2–8 hour options

Customize your 2-hour private TriToon cruise with a captain included

Customize a 4.5-hour private sandbar charter with a captain

Rent a 20' deck boat with Bluetooth stereo for up to 10 passengers

Rent a 21' deck boat for up to 10 and cruise the Intracoastal Waterway or Gulf

Cruise the Intracoastal Waterway on a 22' pontoon, up to 12 passengers

Rent a 26' Panga for fishing or diving, up to 6 passengers

Rent a single or double kayak for 4 or 8 hours

Rent a 20' deck boat for up to 10 passengers on the Intracoastal Waterway or Gulf

Rent a 22’ deckboat for up to 10 and cruise the Intracoastal Waterway or Gulf

Rent a 22’ pontoon for up to 12 on the Intracoastal Waterway

Rent a 22’ pontoon for up to 12 on the Intracoastal Waterway

Rent a 22’ pontoon for up to 12 on the Intracoastal Waterway

Cruise for 4 hours with a licensed captain on a private, customizable trip

Private 1 hr 45 min sunset cruise for up to 6 with a licensed captain

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

Soar up to 1,200 feet and enjoy panoramic views on an exhilarating parasail ride.

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

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

Launch from Turtle Beach and paddle to Midnight Pass

Paddle the mangrove tunnels of Ted Sperling Park with a local guide

Paddle Lido Key mangrove tunnels with a private guide

Paddle Lido Key’s mangrove tunnels from Ted Sperling Park

Paddle Midnight Pass on a private Siesta Key kayak or paddleboard tour