Winterfest Trolley Tours
Event venue · Pensacola ·

Winterfest Trolley Tours

Event venue · Pensacola ·

Holiday trolley tours, Santa, Grinch, Polar Express, hot cocoa

family fun
performers
train ride
wheelchair accessible
theatrical tours
rainy day plan
photos with santa
pricey
Winterfest Trolley Tours by null
Winterfest Trolley Tours by null
Winterfest Trolley Tours by null
Winterfest Trolley Tours by null
Winterfest Trolley Tours by null
Winterfest Trolley Tours by null
Winterfest Trolley Tours by null
Winterfest Trolley Tours by null
Winterfest Trolley Tours by null
Winterfest Trolley Tours by null
Winterfest Trolley Tours by null
Winterfest Trolley Tours by null
Winterfest Trolley Tours by null
Winterfest Trolley Tours by null
Winterfest Trolley Tours by null
Winterfest Trolley Tours by null
Winterfest Trolley Tours by null
Winterfest Trolley Tours by null
Winterfest Trolley Tours by null
Winterfest Trolley Tours by null

Information

221 Palafox Pl, Pensacola, FL 32502 Get directions

Restroom
Credit card accepted
Debit card accepted
Wheelchair accessible entrance
Wheelchair accessible parking lot

Information

Static Map

221 Palafox Pl, Pensacola, FL 32502 Get directions

+1 850 583 1365
pensacolawinterfest.org
@winterfest_pensacola

Features

•Restroom
•Credit card accepted
•Debit card accepted
•Wheelchair accessible entrance
•Wheelchair accessible parking lot
•Wheelchair accessible restroom

Last updated

Jan 14, 2026

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13 Ways to Celebrate Christmas in Florida

"A downtown holiday festival running on select dates from early November through Christmas Eve featuring free holiday-themed shows at the corner of Palafox Place and Government Street; attendees can reserve photos with Santa or the Grinch and ride themed open-air trolley tours—one based on "The Polar Express" that includes a tap-dancing performance on the courthouse steps, a cup of hot cocoa, and a 20-minute musical journey, and two others inspired by "How the Grinch Stole Christmas" with costumed characters and plentiful photo ops." - Skye Sherman Skye Sherman Skye Sherman is a travel writer based in West Palm Beach, Florida. Aside from traveling, she's also a pilot, scuba diver, bookworm, and fourth-generation Floridian. Her work has appeared in Travel + Leisure, USA Today, Palm Beach Illustrated, Atlas Obscura, and more. Travel + Leisure Editorial Guidelines

https://www.travelandleisure.com/christmas-in-florida-6826391
Winterfest Trolley Tours

Rebecca S.

Google
Amazing, amazing, amazing. They do the best Polar Express trolley trip. Adults and kids will enjoy. Price was good. I would do it again if I am in town. 3, 7 year olds loved it as well as the 75 year old.

Ricki S.

Google
Winterfest is always an absolute blast! While I didn’t get any pictures of the Grinch ride, I have to say—it was INCREDIBLE! Highly, highly recommend it for families who love to laugh and enjoy a great time together. The actors did an outstanding job bringing the experience to life. Such a fun and memorable time for everyone. We also did the train as a family which was fun. Thank you all for making it so special!

Casey C.

Google
Went there and due to rain they canceled the outside show. We had a tap dancing show in a damn parking garage with employees that didn’t really seem to know what was going on. Our family went on the and went to these odd stops around downtown with a Santa that didn’t even have a beard. The train conductor, which didn’t know a single line by heart to the polar express script, got the kids excited for Rudolf to come in the polar express and say hi. Rudolf never showed up. This was a horrible experience, I paid 70 dollars for my family to go and it is something I will never recommend. Next time just cancel the event due to rain and issue refunds. This was unreal.

Alice M.

Google
Before you go please know your child can not sit on Santa’s lap. My 16 month old had to awkwardly sit on the “presents” in front of Santa which honestly are shabby and awkward while Santa did some odd arms out thing behind him. Really unsatisfying. Last years photos were WAY better quality and I felt like they actually took some time with us. This year we waited in line half a hour past our appointment time, which fine I’m sure it gets backed up but then didn’t even have 3 minutes with Santa. It’s like they just clicked the first 25 photos they could and were done, no attempt to take a actual good one. We won’t be back next year unfortunately unless they change the “sit on boxes while Santa creeps behind you” thing. I will attach last years photos and then this years. Definitely disappointed.

Scott M.

Google
Much better than I expected. Grand daughters had great time. Very well done.

Nancy O.

Google
My friend and I visited on the last Sunday night of Winterfest, not quite sure what to expect as neither of us had ever attended. We were delighted with the professional and fun attitude of all the performers, aides, and even the Trolley driver! It was so much fun we are already making plans for next year and plan to bring more of our friends with us and ride all the different Trolley adventures. By the way the hot chocolate was wonderful!

Alicia T

Google
Fun and inspires the Christmas spirit.🎅🤶🦌🌲Stories include A Christmas Carol, A Christmas Story, Peanuts Charlie Brown, Cat in the Hat, nativity, the Grinch and more.

Lee

Google
Great family time. The performers did a wonderful job.