Winterfest Trolley Tours
Event venue · Pensacola ·

Winterfest Trolley Tours

Event venue · Pensacola ·

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

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

Information

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221 Palafox Pl, Pensacola, FL 32502 Get directions

+1 850 583 1365
pensacolawinterfest.org
@winterfest_pensacola

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Last updated

Dec 2, 2025

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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

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!

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.

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.

Carolyn F.

Google
Paid 67 for my toddler and my husband and I to go on the grinch Christmas tree heist. The picture had thing one and two in it… they did some type of performance outside the trolley then we rode for like twenty minutes in a hot trolley with Cindy loo who and a cop screaming through a microphone . The trolley wasn’t decorated. No thing 1 or 2. Couldn’t see out of the trolley windows. Very very low budget performance … felt like a money grab. Was very disappointed

Danielle K.

Google
My family and I had a great time at Winterfest last year and this year. I was nervous because it was going to rain, but they moved everything inside and we boarded the trolley from a parking garage to avoid getting wet. I also enjoyed meeting Santa. It is pricey but Santa does spend some quality time talking to your kiddos, and numerous digital photos are taken by a professional photographer and emailed to you immediately after. Overall the whole experience is joyful and well organized. We did have one member of our party back out at the last minute, and no refunds given, but this is clearly stated on their website. This will be part of our family’s Christmas tradition in the years to come!

Danielle G.

Google
Before you had to pay to see Santa or the Grinch it was amazing. Somewhere finally that you could take ur family and enjoy Christmas in Pensacola without being rich. Buy a cup of hot chocolate let kids see Santa, and play in the pretend snow. It was truly great. While I listen to the Christmas carol. But now you have to pay for all of it and not just $5 or $10 it's like $50!!!! It took the happiness right out of it! Season of giving turned into the season of rip-off!!! Kids that are less fortunate can't experience the magic because they can't afford it! That's not cool!

Kathy L.

Google
What a wonderful experience! The trolley tour was amazing with lots of talented actors and singers. So creative! My group spent a good hour or two after our trolley tour at the courthouse area, visited Santa and riding the adorable little train... and drank the best hot cocoa I've ever had. I can see that this will be a new family tradition!