The Top Spots in Winter Park Part II

Beautiful cobble stone streets and delicious eats. Discover the local hotspots and hidden gems of Winter Park.

For over a century, tourists and locals have flocked to Winter Park for its charming neighborhoods, rich history, and lush green scenery. Immersed with art and entertainment, the culture of this city is captivating to all ages. Enjoy nature filled walks along Lake Maitland, find one-of-a-kind gifts within Hannibal Square or Winter Park Village, and learn about the acclaimed architects and artists that called Winter Park home. 


  • Before you go, visit to find events and happenings.
  • Make sure to pack sunscreen, as you will want to spend a majority of your day taking in Winter Park’s majestic lakes and parks.
  • Winter Park is 8.7 square miles in land. Bringing a bike will allow you to avoid any parking hassles. 
  • Many Winter Park shops are closed on Sunday. Check store hours before visiting.
  • Kraft Azalea Gardens is a great place to bird watch. Bring binoculars and cameras to capture a variety of different species. 

Missed Part 1? Read it here.


Kraft Azalea Gardens

Known for its gigantic cypress trees and relaxing setting, Kraft Azalea Gardens leaves any of its visitors feeling tranquil and at ease. Stretching 5.22 acres along the shore of Lake Maitland, Kraft Azalea Garden is open to the public but can be reserved for wedding ceremonies with no more than 20 people.

Polasek Museum

After retiring to Winter Park, FL in 1949, Czech-born sculptor, Albin Polasek, requested to turn his personal gallery of sculptures into a public museum. Today, locals and tourists visit the museum to take in beautiful art while strolling through the historic home and gardens of Albin Polasek. 

Casa Feliz

One of Winter Park’s oldest and most prized landmarks, Casa Feliz, is a historic Spanish Farmhouse and museum designed by acclaimed architect, James Gamble Rogers II. Staying true to its name, “Happy House,” Casa Feliz hosts hundreds of celebrations each year including annual events, parties, and weddings.


Winter Park Farmers’ Market

Every Saturday morning from 7 a.m. to 1 p.m. at the old train depot, you’ll find rows of fresh produce, flowers, plants, and some of the most delicious baked goods in town, for sale at the Winter Park Farmers’ Market. Pick up groceries for the week while trying a number of fresh juices and homemade dips.

Hannibal Square

Arguably some of the best home décor and gift shopping in the city can be found in a quaint little village just two blocks west of Park Avenue, called Hannibal Square. Home to the wildly popular stationery shop, Rifle Paper Co., and the trendy home furnishings store, Gilded Home, Hannibal Square has something for everyone.

Winter Park Village

Located on 17-92 in between Lee rd. and Fairbanks, Winter Park Village hosts a variety of retailers from chain stores to independent boutiques. Shop fashion favorites at the popular women’s apparel store, White House Black Market, or find hidden treasures like vintage jewelry and antiques at Adjectives Market. Men can browse for apparel at Jos. A Bank, and the whole family can unleash their inner rockstar while demoing some of the latest musical equipment at Guitar Center. 


Fiddlers Green

For almost 20 years award winning Irish pub, Fiddlers Green, has been serving up authentic Irish cuisine along with a variety of different spirits and beers. Feast on a piled high corned beef sandwich for dinner, and savor their famous bread and butter pudding for dessert. After your meal, check out live music while sipping on an Irish ale. 

The Wine Room

All wine lovers will rejoice after choosing between 156 hand-selected wines to sample from state-of-the-art dispensing machines, at The Wine Room on Park Avenue. Each wine has a description of the origin and flavor so that you can sample styles you already love, or excite your pallet with a new taste.

Winter Park Fish Co.

Winter Park Fish Co. provides a laidback dining ambiance that is modeled after fish houses in the Florida Keys. With their promise to abide only by sustainable seafood practices, each piece of fish is filleted in house daily and served fresh. Customer favorites are the Applewood Smoked Bacon Wrapped Trout or the Classic Fish Tacos.

Want more Winter Park? Read part 1 of the blog here. 

Categories: Local Love