Orlando/Winter Park Anniversary Weekend!

We are around a two hour drive from Orlando. It has become a favorite destination for J and me over the past few years. Do we go to Disney? Nope. There is a whole other part of Orlando outside of the theme park world!

Our favorite areas of Orlando include Winter Park, Audubon Park, and Thornton Park. All of these areas are a stone's throw from Downtown. This post is focused on Winter Park. I'm hoping my tips will entice you to give the other side of Orlando a chance for your next weekend trip.

Picture courtesy of Unlocked Orlando

I attended my first two years of college at Rollins College, a small liberal arts college in Winter Park. I love revisiting the campus. However, my favorite activities in Winter Park are shopping and dining. 

Shopping

Shopping skews on the preppy/resort side as far as clothing is concerned. There is a Lilly Pulitzer (of course). However, there are some other boutiques that carry lots of preppy/resort wear. Here are two of my favorites.

Siegel's Clothing Company - Siegel's has been around for over 30 years. They carry both men and women's clothing. As far as brands, they carry Jude Connolly, Gretchen Scott, Fornash, Southern Tide, Lesley Evers, and many more. I love the selection of fun graphic dresses!

Cerise Boutique - I actually sought out Cerise Boutique, as I learned that they carry Escapada, a resort brand based out of Charleston, SC. They have a great selection and they also carry Jude Connolly. The sales clerk was so helpful. She helped me find every thing in the store in my size!

Dining

When it comes to food, I will completely admit that I'm a snob, especially when we are dining out of town. I will specifically look for restaurants that have James Beard nominated or winning chefs at the helm.  If I had more time, I'd branch out to discover the next great hole in the wall. But when my time is limited, I tend to go with proven winners. 

Photo Courtesy of Ourlando.com

Photo Courtesy of Cask & Larder

Luckily, Winter Park has dining that is right up our alley. Our absolute favorite is The Ravenous Pig. The Pig is a all about local food done in accessibly, but flawlessly. No foam or essence here! It is run by a husband and wife team. They have a new restaurant, Cask & Larder, which is a Southern Public House. We dined there this past weekend for our anniversary. I usually don't order chicken in restaurants (eat it so much at home), but J and I shared a plate of their fried chicken. It was INCREDIBLE!!

Photo Courtesy of Luma on Park

We also tried a "new to us" restaurant called Luma on Park. Style wise, it is the complete opposite of The Pig. Where The Pig and Cask & Larder embrace rustic elegance, Luma is very modern and sleek. Their food is much more "composed". We ordered several small plates to share and each one was flat out phenomenal. At the end of our meal, I was reading the Chef's bio. When I saw he used to work for The French Laundry (and Chef Thomas Keller), the meal totally made sense. Perfection on a plate is what Thomas Keller is all about!

Other favorites include The Briarpatch for breakfast/brunch and great people watching. For sweet treats, I love Croissant Gourmet and le macaron.

Hopefully you'll get a chance to see the other side of Orlando soon!