Winter Park is Orlando’s Chic Upscale Suburb

Our journey today takes us to the city of Winter Park which is located just a few miles northeast of Orlando, Florida.  Winter Park was originally founded as a winter resort community for wealthy northerners in the late 19th century.  The area has continued to maintain its wealthy reputation.  Winter Park is one of the wealthiest cities in the Orlando area.

Park Avenue, better known as Park Ave to the locals, serves as the main street for the city of Winter Park.  Park Ave and areas within a few blocks of this main street have many retail shops, art galleries, museums, a park, a train station, a golf course and country club, a historic cemetery, lakes, and Rollins College-a private liberal arts college.  The shops and restaurants here in downtown Winter Park are upscale to meet the tastes of the city’s well-to-do residents.

As we arrived in Winter Park we noticed the elegance of the city.  The streets are paved with dark red bricks.  The landscape is breathtaking as fully grown Oak trees appear to be hundreds of years old and have spanish moss hanging down from the branches.  The tree-lined streets are filled with beautifully manicured large homes.  We began walking down a couple of side streets next to the golf course and saw squirrels playing in the surrounding trees and could hear birds singing and chirping.  Across the street we noticed “Casa Feliz” (Happy House).  We learned that it is a restored historic Spanish home that was designed by James Gamble Rogers II, a famous architect. The home overlooks the Winter Park Golf Course.

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We continued our walk south on Park Avenue and stopped for a visit to the Charles Hosmer Morse Museum of American Art.  This place has an extensive collection of art work and pottery. More information can be found here Morse Museum

As we left we arrived at Central Park and watched the arrival of the Amtrak Train (shown below).

Central Park is a wide open area complete with beautiful shade trees, park benches, statues, a flower garden, and an artistic fountain.  Park Avenue and all of the upscale shops and restaurants are located adjacent to Central Park.  We sat for a while and took in the sights and sounds of the scene.  It is so relaxing and peaceful in the park on this Saturday afternoon.  Afterwards we decided to stroll along Park Avenue and do some shopping.  Here you will find many independent boutique shops along with familiar names including Williams-Sonoma, Alex and Ani, Talbots, and Gap. There are also a few fine jewelry stores located along Park Avenue.  One of the most popular places we found on Park Avenue is The Wine Room.  Here you buy a prepaid card, receive a wine glass and then sample more than 100 different wines or you can purchase from thousands of available bottles. Cheeses and tapas are available too.  The Wine Room is a great place to sit back, relax, and socialize.

Walking east a few block is another row of shops and restaurants in an area known as Hannibal Square. The design of the buildings with their balcony railings is designed to give that New Orleans vibe.  This area is quieter than Park Avenue and has many excellent restaurants.  It’s the hidden gem of Winter Park because it is not as popular as Park Avenue but offers some beautiful views and great restaurants.  We decided to have a late lunch in Hannibal Square at Armando’s.  We sat outside by the sidewalk and enjoyed the area while dining.  Armando’s is an excellent Italian restaurant that offers Brunch, Lunch, and Dinner and our server Michael was excellent.

After dinner we finished the evening by doing some more strolling back on Park Avenue before getting a cup of coffee, sitting at a table outside, and watching the locals walk by.  The atmosphere here has such a warm hometown feel to it.  Park Avenue really transitions from daytime where you will find a more relaxed atmosphere with people wearing casual attire.  Then as nighttime arrives you will find many locals coming out to have dinner at the upscale fine dining restaurants and they are dressed very nice.

As we stroll back through Winter Park we walked through some of the hidden walkways located along and behind the main shops.  There are even more intimate restaurants and shops to visit.  We discovered a little french pastry shop named Le Macaron.  The lady working there gave us a sample of a Salted Caramel Macaroon that was so delicious.  Other dessert shops include Kilwins and Peterbrooke Chocolatier.  We love desserts!

Today was a wonderful day.  With the stress of a hectic week it was wonderful to relax with the locals along Park Avenue in Winter Park.  The shopping, dining, museums, and park provided an enjoyable day for us.  We hope that if you visit Orlando, Florida that you will find time to visit Winter Park and discover the beauty this city has to offer.

Below are some more pictures of our journey to Winter Park, Florida.

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