Winter Park the Hidden Gem of Orlando, FL

When you think of Orlando, Florida the first thing that comes to mind is Disney World, Universal Studios, and the beach. I have been to Orlando a thousand times since I was a kid. I never thought about anything outside of the theme parks. On my recent trip to Orlando, I wanted to see what else the city had to offer.

I started researching and I decided I wanted to stay away from the theme parks. I picked a hotel in the heart of downtown. I recently attended a blogging conference, “Blogger Xchange”, and the travel bloggers talked about photo shoots when you travel. I decided to have a photo shoot in Orlando. I searched Airbnb experiences and found the Tattooed Bride. I booked a photo shoot with her and she stated meet me in Winter Park, Florida. My initial thought was, “where in the hell is Winter Park, Florida”. As many times as I have been to Orlando I have never heard of Winter Park.

Photo shoot day comes and I take a 20 minute Lyft ride to Winter Park. My first thought was this is a quaint little town. I met Amy aka Tattooed Bride at the farmers market. Amy and her husband own a tattoo shop in Winter Park and Amy is a photographer. We got to know each during my two hour photo shoot. Amy took me on a tour of some of the most beautiful areas of Winter Park.

Winter Park is absolutely stunning. Beautiful historic buildings, brick streets, Spanish moss and weeping willow trees, lakes, cute cafes and bars. Its so quiet there.

After my photo shoot I decided to stay a little longer and explore. I walked up and down streets and was just amazed at how quiet it was. Very different vibe from the city. I never felt like I was in danger which is a plus. Winter Park is a place I would to relax and get away from the world.

  • Beautiful Buildings - Winter Park, Florida
  • Local Restaurant - Winter Park, Florida
  • Quite Streets of Winter Park, Florida
  • Winter Park, Florida
  • Park in Winter Park, Florida
  • African American Museum - Winter Park, Florida
  • Heritage Center Winter Park, Florida
  • African American Museum Winter Park, FL

Fun Fact: Mr. Rogers (Mr. Rogers Neighborhood) attended Rollins College in Winter Park, Florida

I stopped by the Winter Park History Museum where I met the director Susan Skolfield. She showed me around the museum. The exhibit at the time was historical hotels of Winter Park. She explained that exhibits are displayed for two years and then they are changed. It was pretty cool to see how hotels were built and decorated in the 1900s to now. Mrs. Skolfield told me about the African American museum in Winter Park, but unfortunately it was not open during my time there.

  • Winter Park Historical Museum
  • Winter Park Hotel Exhibit
  • Winter Park Historical Hotel Exhibit
  • Winter Park Historical Hotel Exhibit
  • Winter Park Historical Hotel Exhibit - Paint by Numbers
  • Winter Park Historical Hotel Exhibit
  • Winter Park Historical Hotel Exhibit
  • Winter Park Historical Hotel Exhibit
  • Winter Park Historical Hotel Exhibit
  • Winter Park Historical Hotel Exhibit
  • Winter Park Historical Hotel Exhibit - Park Plaza
  • Winter Park Historical Hotel Exhibit
  • Winter Park Historical Hotel Exhibit
  • Winter Park Historical Hotel Exhibit - Vintage Better Homes and Gardens
  • Winter Park Historical Hotel Exhibit
  • Winter Park Historical Hotel Exhibit - Chess Game
  • Winter Park Historical Hotel Exhibit - Kids Area
  • Winter Park Historical Hotel Exhibit
  • Winter Park Historical Hotel Exhibit - Front Desk

I really wish I could’ve spent more time in Winter Park. It’s a beautiful hidden city. If you are traveling to Orlando, take some time to visit Winter Park, Florida.

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​Meals and Miles was created by Monique and Leon Tillman. This site was developed to share our trips, food, and tips with the world.  We want people to see and know that you do not have to be rich to travel and eat well. We hope to inspire individuals and couples to try new adventures and foods. Seek adventures you never thought of and live on the wild side while enjoying each other. LIVE A LITTLE MORE, EXPAND YOUR BOUNDARIES AND HAVE BLAST! ​ The idea for Meals and Miles came one summer evening in July of 2014, while riding in the car to Washington D.C.  Monique always wanted to start a blog, but never knew what to blog about. We were laughing at some of the adjectives our friends use to describe us and our love for traveling. So we thought, "Why not show others how to have fun with their spouse? Why not blog about our trips? Why not show people the things we do?" We thought of names for our site the whole weekend. And during one of our random laugh sessions, as Leon was talking crazy, meals and miles came up and it stuck! ​ We have traveled to a total of 31 of 50 states, 11 Island, and 5 countries! ​ On this site we will post our trips, photos, and reviews for various destinations, restaurants, and accommodations. Please leave vacation reviews and comments in the designated areas.  Now owner, Monique Tillman is an official Independent Travel Agent with InteleTravel.com. She can book anything from hotel accommodations, airline tickets, vacation packages, car rental, tours, excursion, etc. Although Meals and Miles is our brand, trips will be booked under Monique Tillman as an Independent Agent for Inteletravel. Meals and Miles site will promote vacation deals, but please be clear ALL vacations will be booked under Monique Tillman as Independent Agent with Inteletravel.com.

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