things to do in Osprey, FL

Uncover Venice's sinister history on an after-dark walk with a spirit guide

Taste your way through Venice’s architecture and history on foot

Fish offshore with gear, bait, and a licensed captain included

Chart your ideal day on Venice waterways with a licensed captain

Set sail with live Jimmy Buffett tribute music aboard River Skipper II

A convenient street-legal way to explore Nokomis

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

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

See Sarasota’s Art Deco, Mediterranean Revival, and Mid-Century Modern architecture by van

Join an interactive circus-themed whodunnit on a rolling Sarasota trolley

Ride a 13-mile historic railroad excursion in open-air or air-conditioned cars.

Understand Sarasota’s Amish and Mennonite traditions in Pinecraft

Cruise to Egmont Key for shelling, snorkeling, and beach time on a private boat

Cruise Sarasota Bay on a private dolphin eco tour aboard the Anna Maria Explorer

Cruise Anna Maria Sound at sunset on a 2-hour dolphin-watching boat ride

Ride a Sarasota metaphysical trolley tour with sound healing and mini tarot readings

Sing 70s & 80s hits on a trolley with a bar stop at 99 Bottles

Visit the gift shop and model railroad display in Parrish

Take the controls of a locomotive for an hour

Join a marshal-protected train ride with a robbery twist

Ride an open-air train to the pumpkin patch for games, hay rides, and pumpkin picking

Assigned First-Class Seats for a Pumpkin Patch Rail Trip