things to do in Osprey, FL

Reserve a private caboose for your group’s pumpkin patch train outing

Ride in your own caboose for a festive North Pole outing

Sing along, sip cocoa, and see Sarasota's holiday lights from Dolly the Trolley

Ride a singing trolley to Fiorelli Vineyards for six wines, music and garden time

Explore Venice and Nokomis landmarks with local stories from guide Ronnie

Take in Sarasota’s seasonal light displays from the comfort of a festive trolley

Spend the day immersed in live blues music at GT Bray Park

Ride in first-class comfort to the North Pole for holiday activities and a Santa visit

Settle into air-conditioned coach comfort before a North Pole holiday celebration

Ride open-air coaches to the North Pole for holiday activities and a visit with Santa

Customize a 3-hour beach picnic with setup and cleanup included

Reserve a beach suite setup for six, ready from 10am–4pm

Customize a private 3–6 hour cruise to Egmont or Passage Key with snorkeling and sightseeing led by experienced captains

Set up a 3-hour sunset beach picnic for two

Cruise Anna Maria waters with shade, GPS, and room to relax

A ready-to-use beach setup with chairs, shade, games, and refreshments

Settle into a shaded beach setup with seating, games, and chilled drinks

Settle into a beach setup with shaded cabanas, lounge chairs, games, and chilled water

Settle into a fully prepared beach lounge with shade, games, and refreshments

A ready-to-enjoy beach lounge with cabanas, games, and chilled drinks

Settle into a ready-to-use beach suite for two

Cross Sarasota Bay and paddle secluded mangrove tunnels in a clear-bottom kayak

Private tiki boat evenings with holiday lights, your own playlist, and karaoke

See December's waterfront Christmas lights from your own private tiki boat