Often referred to as “Little Europe,” Winter Park gives meaning to the term “living well” and it offers visitors a peak into Florida’s gracious past. Cobblestone streets, pristine lakes and old, and often historic, homes are just part of what make Winter Park a must-see destination for visitors and a coveted neighborhood by locals. Perfectly blended into the tree-lined streets are some of the area’s top museums and galleries, as well as charming chapels with awe-inspiring stained-glass windows and buildings with character that could only exist in a tony town such as this one. While the town may be storied and established, it is anything but sleepy. I’ve built an itinerary to allow visitors the chance to truly experience the city’s character. Lose yourself in the luxury and relaxation of Winter Park.
A Day in Winter Park
Morning: The Glass Knife
8 am: The Glass Knife in Winter Park is a sophisticated and charming bakery and cafe celebrated for its delicious and visually stunning creations. With a menu that blends sweet and savory items, guests can indulge in elegant cakes, delicate pastries, and a variety of unique donuts. The cafe also serves a full breakfast and lunch menu, with standout dishes like the Cheddar Biscuit Sandwich and a selection of freshly brewed Onyx Coffee drinks. Its interior is a beautiful mix of classic elegance and modern design, creating an inviting and comfortable atmosphere for a delightful meal or a quick coffee break.
Late Morning/Early Afternoon: Shop Around
11 am: Shop Around A perfect day should consist of a little shopping and some time outdoors, right? Why not get the best of both worlds by shopping along Park Avenue? With a perfect blend of retailers, such as Lilly Pulitzer, Rifle Paper Co., Tuni, John Craig Clothier, and Monkee’s of Winter Park. Park Avenue holds a little something for everyone.
Late Afternoon: Museums & Culture
2 pm: Winter Park offers a rich cultural scene with a variety of excellent museums, each with a distinct focus. The Rollins Museum of Art, located on the Rollins College campus, features a diverse collection spanning ancient to contemporary works. For art and nature lovers, the Albin Polasek Museum & Sculpture Gardens showcases the work of a Czech sculptor in a serene lakeside setting. The Charles Hosmer Morse Museum of American Art is renowned for its comprehensive collection of works by Louis Comfort Tiffany, including his famous chapel interior. Visitors can also step back in time at the Casa Feliz Historic Home Museum, a beautifully preserved Spanish farm house, and for a dedicated look at Tiffany’s glass creations, the Tiffany Light Museum offers a unique glimpse into his craft.
Evening: Dine Finely
6 pm: AVA MediterrAegean is a modern Greek “Agora” located in Winter Park, offering a multi-sensory dining experience in a refined atmosphere. The name “AVA” is a Greek word for life, water, island, and bird, which the restaurant uses to celebrate splendor, freedom, and joy. The restaurant’s cuisine blends traditional and modern Mediterranean and Cycladic Island flavors, focusing on healthy, balanced eating. The interior design captures the spirit of Cycladic architecture with natural stone and warm details, creating a transportive venue for guests to gather and share life experiences.
