Best 469 things to do in Osprey, FL

Private coastal cruising with flexible routes and sunset options

Cruise Venice’s coast with time for dolphin searching, swimming, and waterfront stops

Cruise coastal waters with time for a sandbar swim, waterfront stops, or an eco-focused outing

Ride through Venice with scripture, music, prayer, and pink flair

Parasail with an 800 ft line and 14 minutes of flight time

Fly parasailing on a private trip for up to 12, with observer spots if space allows

Feed fish and spot marine life beneath LED-lit clear-bottom kayaks

Relax on a 2-hour private cruise through Sarasota and Roberts Bays

Cruise Sarasota Bay and relax at a sandbar

Watch the Sarasota sunset from a private tiki boat

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

Relax on a Sarasota Bay happy hour cruise and watch for dolphins

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

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

Cruise Sarasota’s intracoastal waterways on a 21' Bennington tritoon for up to 10

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

Cruise Sarasota on a 21 ft Chaparral with Bluetooth stereo and swim ladder

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 Sarasota Bay, then taste your way through downtown

Browse local boutiques, enjoy light bites, and uncover Sarasota stories

Sample local flavors while uncovering Sarasota's art, history and circus lore

Sip, shop, and uncover John Ringling's St. Armands legacy

Cruise with Bluetooth audio, a swim ladder, and fishing-ready features