Transportation Tours in Sarasota, FL

Ride an air-conditioned trolley at night for musical ghost stories and Sarasota history in October.

Ride an enclosed coach to a pumpkin patch with games, hay rides, and pumpkin picking

Explore Sarasota's historic neighborhoods and cultural landmarks on a 90-minute air-conditioned trolley ride.

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

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

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

Understand Sarasota’s Amish and Mennonite traditions in Pinecraft

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

Take the controls of a locomotive for an hour

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

Join a marshal-protected train ride with a robbery twist

Watch a Civil War battle unfold from aboard a heritage train

Explore Venice and Nokomis landmarks with local stories from guide Ronnie

Ride in your own caboose for a festive North Pole outing

Discover Sarasota a century ago through the stories of its leading women

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