Water Activities in Osprey, FL

Paddle with a dedicated guide as the Florida Gulf Coast sun sets

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

Cruise Southwest Florida waterways with room to relax, swim, and sunbathe

Private waterway cruise with time to swim, float and explore a sandbar

Paddle Anna Maria canals or venture into Tampa Bay

Private 6–8 hour Bali 4.2 catamaran charter on Sarasota Bay

Paddle Gulf Coast waters and discover barrier islands with a guide

Set your own course for snorkeling, island stops, sandbars, and dolphin searches

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

Reach offshore reefs for a varied seasonal catch

Cruise Sarasota Bay your way, with time to unwind on a sandbar

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

Paddle Lido Key’s mangrove tunnels with a private guide from Ted Sperling Nature Park

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

Rent a 23.5 ft Mako center console for cruising or fishing in Sarasota

Swim, snorkel, and search for shells on a Little Gasparilla Island sandbar

Explore Sandbars, Islands, and Coastal Wildlife by Private Boat

Enjoy a customizable luxury sail with captain and mate aboard a spacious 42-ft catamaran.

Set your own pace on a self-guided coastal paddle

Design a private day of snorkeling, sandbars and island cruising

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

Private reef fishing for seasonal offshore catches

Sip mimosas on Sarasota Bay while looking for dolphins

Learn to surf in Sarasota with a coach-led lesson