Why You Should Visit Winter Park, Florida

Winter Park
Winter Park

Winter Park is a town you can’t pass up.

It’s also a great town to visit via Central Florida’s SunRail, or as all the cool kids say: via The Train. It’s the simple things.

Catching the SunRail at the DaBerry Station
Catching the SunRail at the DeBarry Station

Winter Park is classy and elegant, retro and very cool.

As you exit the SunRail you’re greeted by the Winter Park Train Station and it’s clean bathrooms. yippee!!

Go potty, grab any brochures that interest you, continue to read this post or stop reading it and give the Mystery Tour of Winter Park a try by clicking here

I recently visited with Aubry (3), my friend Emily and her 4-year-old. Read on to see why you must visit.

We were running a “test tour” of my latest Mystery Tour. If you want to learn more about what a Mystery Tour is check out my page: Mystery Travel.

So now on to the good stuff:

The Frugal Travel Mom: Why You Should Visit Winter Park, Florida

Central Park’s Climbing Tree

All of Central Park is worth seeing, 3 fountains and a really cool peacock statue always make me smile, but there is one tree worth seeing and with kids you have got to let them climb this tree.

The perfect climbing tree.
The perfect climbing tree.
Monkey man!
Monkey man!

Community Playground

Again I roll with kids so playgrounds and park top our list and this playground ranks high on my list because it’s the last of a dying breed of parks: it’s made of all wood. It’s also in the shade and provides picnic tables, benches and an adjacent lake and fitness course.

Swings, wood playground, shade - perfect.
Swings, wood playground, shade – perfect.

A Real Live Sink Hole: Lake Rose

Oh yeah! You know this excites you, I mean, have you ever seen a sinkhole before?

In 1981 this area of Winter Park was swallowed up by a sinkhole taking with it

  • 5 Porches in a repair shop
  • a truck with a camper
  • the Winter Park municipal pool
  • a large part of Denning Drive
  • Ms Mae Rose Williams home

Now that sinkhole is a lake, Lake Rose.

A sinkhole turned lake.
A sinkhole turned lake.


Pottery Barn, the Gap, Williams-Sonoma, Starbucks, Panera, boutique stores, toy store… the list goes on. If you want classy no matter your style, you’ll find it here. Winter Park is a taste above your typical Florida town and it shows best on Park Ave.

Where else would Pottery Barn live in Winter Park? duh!?
Where else would Pottery Barn live in Winter Park? duh!?

Interactive Map Kiosk

This touch screen map kiosk on the north-west corner of Lyman and S Park Ave is a fun way to check out the town. I took a picture of the bathroom map for future reference that day.

Interactive map kiosk
Interactive map kiosk
Map of restrooms in downtown Winter Park
Map of restrooms in downtown Winter Park

Scenic Boat Tour

This is the #1 thing I think you should do in Winter Park. I don’t even wanna show you a picture or tell you, I just say- go; however, the views, the elegant canals, the time on the lake, the history lessons- worth the $12 adults, $6.00 kids.

Tours leave on the hour, every hour from 10am-4pm.

Our tour guide was funny and has a really cool tree behind him.
Our tour guide was funny and has a really cool tree behind him.
Aubry fell asleep, the tour was about an hour and on a cloudy Florida day, perfect.
Aubry fell asleep, the tour was about an hour and on a cloudy Florida day, perfect.
Sneak peak

Visitor’s Center

I’ve become a fan of Visitor’s Centers, you can find coupons and event info as well as get maps and many times get some insider tips.

This one has comfy sofas and air conditioning!

Shady Park

Kind of a hidden park, overshadowed by it’s big sister Central, Shady Park is the place to be on a hot day with kids. A splash pad, and outdoor gaming station and a molecular dog pack some fun into this corner park.

Molecular Dog
Molecular Dog

Rollins College

The oldest college in the state. I didn’t visit, but plan to next time

and yes, there will be a next time!

Thanks Winter Park and to all of you, enjoy!


4 thoughts on “Why You Should Visit Winter Park, Florida

  1. Dear Frugal Travel Mom–

    Great list of things to do in Winter Park. Thanks for sharing. I was only familiar with the boat trip and so was glad to see your other highlights

    Our company, Orange Blossom Tours operates day-trips out of Sebring and so we appreciate getting tips like yours. We regularly visit Winter Park, primarily to attend matinee performances at Winter Park Playhouse. They only do musicals and tickets are very reasonably priced. We saw “Dames at Sea” there a couple of weeks back and everyone in our group, including yours truly, was delighted with the show. Beforehand, we had an excellent lunch at the Cheesecake Factory in Winter Park.

    Once your kids are old enough to enjoy theater, I recommend you take them to WPP. My parents took me to see “Where’s Charlie?” starring Ray Bolger in a Broadway theater when I was 13. Have never forgotten it and have loved going to the theater ever since.

    One more suggestion: the Morse Museum in Winter Park has a fantastic collection of Tiffany glass. Might not be much for the kids (but you never know) but you and your husband might enjoy it.

    Yours in travel–

    Harvey Utech

    Liked by 1 person

    1. Thank you Harvey, I will be sure to check out the Playhouse and a trip with my husband and no children is in the works- so we can enjoy the Morse Museum. Again thank you for your tips and I’m glad you learned a little more about Winter Park; check back often, I hope to highlight a lot of what Central Florida has to offer.
      -The Frugal Travel Mom


  2. Well you all may have noticed that little blonde boy in the pictures, He is mine. He and I accompanied Michelle and her little one on this venture to winter park. I have to say this is an amazing day trip that can easily be done on the cheap with little ones.There is plenty to keep everyone happy and we ended the day with the boat trip, which is a must do activity on this trip! I never knew houses that large existed and that my childhood friend Mr Rodgers lived in winter park. this trip is also a cheap train ride on the Sun rail which just makes the trip that much more fun, you don’t have to worry about parking and the train doubles as an activity for the kiddos. I was also impressed with the cleanliness of the sun rail, very nice trains! Winter park was a fantastic City to walk around and had some awesome parks and the playground on this trip is great, the kids played at the Gigantic wooden playground a while, and it had a good spot to have lunch or a snack. I was blessed to get to accompany Michelle on this trip, its a good start if you are looking to venture out more with your kids. If any of you are the type of mom like I was taking the easy road of “shutting in” and not getting out of the house but dreaming of adventure; I encourage you to grab a buddy and do this trip it is fun and will help build your adventuring confidence! This is a day that you will travel by boat, and train but don’t forget to treat yourself at Starbucks 🙂 it makes for a nice treat at the end of one fun day!

    Liked by 1 person

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