things to do in Osprey, FL

Explore Fort Dade ruins, a historic lighthouse, and Gulf Coast wildlife

Bring your crew for a harbor cruise with sunset views, music, and karaoke

Cruise Charlotte Harbor at sunset with food, drinks, and your favorite music

Cruise Charlotte Harbor with music, karaoke, and space to celebrate

Ride Sarasota in style on a Bob Marley Klunker

Set your own pace on a private sandbar day with swimming, snorkeling and lunch

Pedal Sarasota's bayside neighborhoods with museum art and lunch included

Explore Siesta Key's changing underwater snorkeling spots with a captain

Settle in for a captain-led sunset cruise on Sarasota’s waterways

Cruise Sarasota’s historic neighborhoods and bayfront by Comfort Cruiser

Modern jet skis with onboard audio and maintained equipment

Pedal Siesta Key's white quartz shoreline as evening settles in

Choose your own pace on a self-guided ride through Myakka River State Park

Anchor at a sandbar for a private day of swimming and beach time

Take the helm for flexible cruising, fishing, and sandbar stops

Take the helm and explore sandbars and islands at your own pace

Speed, sightseeing, and flexible time on the water

See non-migratory dolphins and unique wildlife while exploring the bays of Manatee and Sarasota.

Experience dolphins, sandbars, and a relaxing sunset cruise in the bays of Anna Maria Island.

Ride an enclosed coach to a pumpkin patch with games, hay rides, and pumpkin picking

Paddle private mangrove tunnels with a guide and look for Sarasota Bay wildlife

Rent a kayak or paddleboard for 4 hours with gear, route map, and lesson

Set sail on an interactive pirate cruise with a treasure hunt

Set sail on an interactive private treasure hunt for your crew