Water Activities in Osprey, FL

Paddle the waters between Anna Maria Island and Longboat Key with your own private guide

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

Rent a 22' Bentley pontoon and cruise Sarasota’s Intracoastal waterways

Rent a single or tandem kayak and paddle the Lido Key mangrove tunnels

Get out on the water with free delivery on Siesta Key

Customize a double-decker day on the water with a slide, sound system, and captain

Paddle mangrove tunnels and visit Midnight Pass Beach with a local guide

Customize a private cruise with snorkeling and wildlife searching

Cruise Anna Maria Island waters on a stable 23-foot catamaran

Cast along grass flats and mangrove shorelines for inshore species

Watch the Sarasota sunset from a private tiki boat

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

Toast the sunset on a guided Gulf Coast kayak paddle

Cruise Siesta Key’s shoreline from a beachfront pickup point

Rent a 24' Sea Ray SunDeck to explore Sarasota waterways and sandbars

A private boat charter for your group at sunset

Paddle a tandem kayak from the canals to Tampa Bay

Cruise Anna Maria Island waterways as the sun sets

Paddle Gulf Coast waters at your own pace and explore nearby islands

Search for dolphins, snorkel in shallow waters, and cruise Florida’s coast privately

Cruise Siesta Key’s western coast with time for dolphins, a sandbar stop, and a swim

Explore Tampa Bay reefs and backcountry on a private fishing outing

Cruise Sarasota’s Gulf Coast as the sun sets from a tiki boat

Paddle Lido Key mangrove tunnels with a private guide