Best 203 things to do in Osprey, FL

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

A custom chef‑curated feast celebrating bold local flavors and dietary wellness—served right in your home or rental

Paddle Lido Key, then taste your way through downtown Sarasota

Eat your way through Downtown Sarasota with local history and art

Sample Sarasota bites and paired drinks on a guided culinary walk

Fly a private helicopter tour from Sarasota for up to 3 passengers

Fly solo, double, or triple on a parasail flight

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

Paddle between Anna Maria Island and Longboat Key with a guided wildlife-focused route

Paddle Longboat Pass for 4 hours with a map and basic lesson

Paddle Lido Key’s mangrove tunnels with a local naturalist guide

Explore Lido Key’s mangrove tunnels with included gear, map, and a brief lesson

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

Paddle into a Florida Gulf Coast sunset with a guided kayak tour

Paddle a private sunset route with a dedicated guide in Sarasota Bay

Cruise 70 miles to Dry Tortugas to explore Fort Jefferson and snorkel clear waters

Private 2-hour Naples party cruise with music and drinks onboard

Customize a private 4-hour cruise with your own captain and crew

Private 2-hour 21+ party cruise with music and drinks available onboard

Feed fish from a clear-bottom kayak with underwater LED lights in Sarasota

Spend 3 hours cruising Sarasota Bay with a sandbar stop

Private 2-hour sunset cruise to spot dolphins in Sarasota Bay

Rent a tritoon for up to 12 and cruise Sarasota Bay for 4 or 8 hours

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