Winterfest
Book our Trolleys for your next event! In 2022 alone, we transported over 20,000 people using these advanced systems!" 10% discount for active military 20% off the second trolley when you book two trolleys Multiple-day events have major discounted prices available upon request. For multiple trolleys booked on multiple days, prices start at $100 /hr. We provide an app that allows you to track your trolley so anyone in your party can always see where it is. Then your guests can wait inside, out of the elements, until they see the trolley pull up on their phone. We use this system for Pensacon, Fiesta of Five Flags, Winterfest, Greater Gulf Coast Arts Festival, and more. We have used these Geo Trackers on our trolleys for over five years! For single trolley/single-day bookings, the app is available at an additional price. All our trolleys have party lights and a sound system connecting to your device. The Magic of Pensacola Winterfest The snow begins to fall when you enter Plaza Wonderland on Palafox Place. A cup of hot chocolate and the sound of a trolley bell brings back memories of the Polar Express. The conductor calls your name: All aboard for the most beautiful journey you'll take this Christmas season. Take a 25-minute ride aboard our mini-train through Winterfest's lights, snow, and magical scenery!
Winterfest
Events
November 1
Pub & Party Trolley — Hop On, Hop Off
Downtown Pensacola
Downtown Pensacola 321 S. Palafox St. Pensacola, Florida 32501
November 6
Pensacola Winterfest
Downtown Pensacola
Downtown Pensacola 223 South Palafox Place Pensacola, Florida 32502 (850) 583-1365
November 6
Winterfest: The Great Christmas Tree Heist
Downtown Pensacola
Downtown Pensacola 226 East Intendencia St. Downtown Pensacola, Florida 32502
November 6
Winterfest: Grinch’s Merry Match
Downtown Pensacola
Downtown Pensacola 226 East Intendencia St. Pensacola, Florida 32502
November 6
Winterfest: Photos with Santa
Downtown Pensacola
Downtown Pensacola 223 South Palafox Place Pensacola, Florida 32502
November 6
Winterfest: Photos with the Grinch
Downtown Pensacola
Downtown Pensacola 223 South Palafox Place Pensacola, Florida 32502
November 22
Winterfest: Polar Express Tour
Downtown Pensacola
Downtown Pensacola 226 East Intendencia St. Pensacola, Florida 32502
November 29
Elf Parade & Christmas Jubilee
Downtown Pensacola
Downtown Pensacola 116 Zaragoza Pensacola, Florida 32502 (850) 583-1365