10 Best Things to Do in Winter Park // 2023 Travel Guide

Next door to Orlando is Winter Park, a city founded in the late 1800s, developed as a winter playground by well-to-do northerners who wanted to enjoy the warm climate. The city has preserved its historic character and charm, with brick-lined streets, elegant homes, and majestic trees. Winter Park offers a variety of activities and experiences for visitors, from shopping and dining on the famous Park Avenue, to exploring the many museums and art galleries, to relaxing on a scenic boat tour of the city’s lakes. Whether you are looking for adventure, culture, or tranquility, Winter Park has something for everyone.

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[nikkix]

Excellent video! I'll be driving from Jacksonville to visit Winter Park and Orlando's Icon Park & Universal areas, in the spring with my daughter. Very helpful and informative video.👍

[Studious.Starfish]

I appreciate your video as I will be traveling to this city soon!

[sheilahanna]

AMTRAK rails run their Auto train and another passenger train through Winter Park. Perfect for my commute to Savannah

[robertbabcock]

We have decided Fridays are our days for a Gallivanting Adventures at the senior living community I work at. It’s a hit!!! We are going to Winter Garden first followed by Winter Park on another Friday. Thanks for the inspiration!

[Vocalist]

Nice video. I’d like to add that WP is home to the Bach Festival Society that puts on wonderful concerts in the chapel at Rollins college from October-May.

[Karioka]

Excellent content! I’m moving there soon and this helped me have a better knowledge of my soon to be town area👍

[IndieAnnieJones]

I live in Miami, Florida and I can't thank you enough for all of these little tours that you do. I have gone to several cities in Florida to enjoy what I have in my own backyard practically and it's thanks to all of these videos. I'm also looking for a place that I can possibly retire to so this also is so very helpful😊

[sylvain]

Hi Chad,

Are there any vintage dinner trains near central Florida?

[mphillips]

I want to move to Winter Park, but I'm concerned about the diversity.

[kevindavis]

Chad, I always love your videos, and it was great to see my childhood hometown and former home featured.

I did want to make explicit what is implicit in your discussion of Hannibal Square. The blocks around Hannibal Sq., from Fairbanks to Pennsylvania and roughly New York to Denning, were historically a very vibrant African-American neighborhood from the town’s early days up through the 1990s. (Depugh Nursing Home near Hannibal Square was one of the first state-licensed nursing homes for African Americans anywhere in the US and a model for other communities nationwide, e.g.). However, Black residents are rapidly disappearing from the neighborhood thanks to gentrification. Indeed, the storefronts and restaurants that run right up to the Square itself have allowed predominately White residents and businesses serving the wealthy to move in as rents on Park Avenue became stratospheric. Every time I see a massive contemporary home for sale on a tiny lot I think about the men, women, seniors, families displaced by this.

Thank you for the great videos you do. Even as a FL native I learn new things from your videos all the time.

[charleshamilton]

My maternal grandparents had a home in Winter Park back in the day and traveling from (often frigid) Colorado to see them for school breaks is a wonderful memory. I asked them years later why they didn’t spend the winters in Palm Beach and my grandfather gravely replied the people there were “too loud.” 🤷‍♂️

[winstonsmith]

Winter Park is an awesome place. Great video. Keep up thr good vibes

[crystaljames]

Love your easy-listening videos. I’ve learned so much watching and we are enjoying visiting these communities.
I loved that you mentioned golf. We try to find public golf courses at a reasonable rate in every town that we visit so keep those recommendations coming 😊

[beccaatthebeach]

Went to Jupiter as a child to visit my grandparents - they were in Ocean Trail condos, near the lighthouse! Great video! 🥰🥰