Best results for Water Activities in Osprey, FL

Tailored private cruises for sunsets, wildlife, and celebrations

Fish Anna Maria waters with a fourth-generation local captain

Paddle a tandem kayak from the canals to Tampa Bay

Paddle Anna Maria canals or venture into Tampa Bay

Customize a 4-hour private cruise with snorkeling, paddleboarding, dolphin watching, and more.

Customize your day exploring sandbars, islands, and marine life on a private catamaran.

Scan Sarasota's coastal waters for dolphin sightings by jet ski

Rent a kayak or paddleboard and explore Turtle Beach waterways with a provided map

Rent a pedal kayak and explore Sarasota Bay with all gear and safety equipment included.

Take in Sarasota Bay views, local history and waterfront wildlife from the water

Cruise Sarasota Bay on a 112' Westport with a private crew

Cruise, swim, and unwind aboard a private Yellowfin charter

Fish Gulf waters with a licensed captain, mate, and fully equipped boat

Cruise Sarasota Bay and relax at anchor aboard a crewed 112-foot Westport

Cruise, swim, and relax aboard a crewed 112-foot Westport yacht

Sip mimosas on Sarasota Bay while looking for dolphins

Celebrate your bride-to-be with music, Gulf views, and a private party cruise

Sail the Gulf with music, a celebratory toast, and a private party atmosphere

Celebrate the bride with music, Gulf views, and time to toast together

Cruise with up to 13 friends on a spacious pontoon equipped for sandbar hopping

Cruise Anna Maria Island by captained tritoon with room for up to 6

Private sandbar cruise to Jewfish Key for swimming, snorkeling, and shelling

Cruise to Egmont Key for shelling, snorkeling, and a Florida state park stop

Cruise local sandbars and look for dolphins from Bradenton Beach Marina