Winter Park walking tour: Move beyond the theme parks to find some of Central Florida’s best shopping and dining


City of Winter Park, Florida official seal.Introduction

The city of Winter Park, FL is home to an extraordinary collection of shops, restaurants, cultural venues, and even a top-tier college. In many ways Winter Park represents the best of what Central Florida has to offer visitors and residents alike. You won’t find any flashy “tourist traps” here. Instead, you’ll find a spectacular variety of small businesses offering top-of-the-line services in a small town atmosphere. If all you know of Orlando is the theme parks, you owe it to yourself and your family to visit. Disney and Universal are reasons to come to Orlando, and Winter Park is the reason to stay.

My exploration of Winter Park begins with showcasing two of my favorite businesses. Then I will provide some guidance for a Winter Park walking tour.

By the way, you can click on any image in this post to view it full-screen. You can also view and share many of these images on the OI Facebook page.


The Wine Room

The Wine Room on Park Ave might actually be the most well-known of Winter Parks restaurants and wine bars, as it was featured a few years ago on a Samantha Brown special. And although it may no longer be accurate to call it a “hidden” gem, it is still at the top of the list when I want to brag about local Orlando venues.

The Wine Room in Winter Park, Florida.
The Wine Room in Winter Park, Florida.
The Wine Room in Winter Park, Florida: Pick a wine, any wine.
Pick a wine, any wine.

The idea here is very simple and yet very appealing. You put a certain amount of money down on a custom charge card–say, $50–and then you use that card to sample wine by the glass using devices like the one above. The result is a sublimely entertaining wine tasting experience that is equally satisfying to the novice and the aficionado.

The Wine Room in Winter Park, Florida: Where to begin... and then to end?
Where to begin... and then to end?

If wine just isn’t your thing, they also have a selection of beer and champagne. Add to that a menu of cheeses, flatbreads, salads and sandwiches, and you have the makings of a wonderful evening. Or afternoon.

Official website:


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Sassafras Sweet Shoppe

Sassafras is a perfect example of a boutique that is uncommon in today’s world of suburban strip malls, and yet surprisingly common in the city of Winter Park.

Sassafras Sweet Shoppe in Winter Park, Florida.
Sassafras Sweet Shoppe in Winter Park, Florida.

On their Facebook page, the shop describes itself as featuring:

Candy from the 1800’s to today. We offer lollipops, vintage candy, gummies, hard candy, chewing gum, chocolates, sugar free candy, rock candy, jelly beans, licorice and more. Snacks offered include popcorn in a variety of flavors, caramel apples, cotton candy, cookies, popcorn balls, ice cream and soda pop!

Sassafras Sweet Shoppe in Winter Park, Florida: A sampling of the selection.
A sampling of the selection.
Sassafras Sweet Shoppe in Winter Park, Florida: Nothing wrong with this picture.
Nothing wrong with this picture.

In a place like this it is easy to feel the love that must go into opening up such a whimsical boutique.

Official website:


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Winter Park walking tour

The vast majority of Winter Park’s activity occurs on or near Park Ave. This makes a walking tour of the the area very easy, as you just need to find parking anywhere in the area, make your way to Park Ave, and then begin your browsing. Below you will find an embedded Google map of the area. I have many businesses marked, and you’ll find photos and additional information as you scroll down through the post. However, you may want to open my custom-made Google map in a separate window since there is so much information on it. If you’d like to do that, use this link: OI Winter Park walking tour map.

By the way, I did my best to include as many venues as I could. If you already have a favorite and I missed it, please let me know!

Here are the photos and venue information:

Winter Park Historical Museum in Winter Park, Florida.
Winter Park Historical Museum.


Bosphorous Turkish Cuisine in Winter Park, Florida.
Bosphorous Turkish Cuisine.


Croissant Gourmet Bakery in Winter Park, Florida.
Croissant Gourmet Bakery.


Briarpatch Restaurant in Winter Park, Florida.
Briarpatch Restaurant.


Earth Inspired Living in Winter Park, Florida.
Earth Inspired Living.


Orchid Thai Cuisine in Winter Park, Florida.
Orchid Thai Cuisine.


Tug Boat & the Bird in Winter Park, Florida.
Tug Boat & the Bird.

Circa 1926 Restaurant in Winter Park, Florida.
Circa 1926 Restaurant.


Morse Museum of American Art in Winter Park, Florida.
Morse Museum of American Art.


The Paper Shop in Winter Park, Florida.
The Paper Shop.


The Cheese Shop on Park in Winter Park, Florida.
The Cheese Shop on Park.

http://www.thecheeseshoponpark.comUrbanspoonYelp — Facebook — Twitter

Eola Wine Company in Winter Park, Florida.
Eola Wine Company.


Peterbrooke Chocolatier in Winter Park, Florida.
Peterbrooke Chocolatier.


Violet Clover in Winter Park, Florida.
Violet Clover.


Cigarz on the Avenue in Winter Park, Florida.
Cigarz on the Avenue.




Just in case you need it, here’s the link again for my map: OI Winter Park walking tour. Also, the City of Winter Park publishes a number of maps that might be useful for you, including one for bike paths and a parking guide. You can download them from the official City of Winter Park website.

If you are in the neighborhood of Winter Park but you’re in the mood for a little more attitude, you might want to swing into PR’s Taco Place.

Last but not least, Winter Park also hosts several festivals. Check out my review of the 2011 Winter Park Sidewalk Art Festival.

Enjoy my complete Winter Park photo gallery with more than 100 images below.


Winter Park walking tour – photo gallery

Taylor Strickland Taylor Strickland is the Owner & Editor at Orlando Informer, the internationally awarded independent resource for guests visiting Orlando. In this position, he leads the website's overall direction and day-to-day operations, working with a team of writers, editors, developers, and producers.

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