TOP 10 Upscale casual dining in Winter Park, Florida

Winter Park Village is a premier lifestyle center situated in the upscale Winter Park community just outside of Orlando, Florida. Visitors can enjoy a leisurely shopping experience surrounded by lush palm trees and charming oak-shaded walkways. After a day of browsing through boutique shops for unique gifts, guests can catch a movie at the on-site theater and savor a gourmet dinner at one of the many restaurants. With a diverse selection of retailers ranging from high-end fashion to beauty salons and spas, Winter Park Village offers something for every shopper. Indulge in a variety of culinary delights and beverages, from casual eateries to upscale dining options. Whether you're looking for a place to relax and unwind or seeking the latest trends, Winter Park Village has everything you need for a memorable shopping experience.

Hillstone Restaurant is a popular dining destination located at 215 South Orlando Avenue in Winter Park, Florida. Known for its upscale yet casual atmosphere, Hillstone offers a diverse menu featuring American cuisine with a focus on fresh seafood, steaks, and salads. The restaurant prides itself on providing exceptional service and a welcoming environment for guests to enjoy a delicious meal. Whether you're looking for a romantic dinner for two or a casual lunch with friends, Hillstone Restaurant is the perfect choice for any occasion.

Hannibal's On The Square is a vibrant and lively establishment located in Winter Park, Florida. Situated at 511 West New England Avenue, this venue offers a unique blend of a bar, restaurant, and night club experience all under one roof. Guests can enjoy delicious food, crafted cocktails, and live music in a stylish and inviting atmosphere. Whether you're looking for a casual meal with friends, a night out on the town, or a place to dance the night away, Hannibal's On The Square has something for everyone. Come and experience the excitement and energy of this popular hotspot in Winter Park.

Fleming's Prime Steakhouse & Wine Bar is a sophisticated and elegant dining establishment located in Winter Park, Florida. Situated at 933 North Orlando Avenue, this restaurant offers a unique blend of high-quality steaks and an extensive selection of fine wines. Guests can enjoy a luxurious dining experience in a warm and inviting atmosphere, perfect for special occasions or casual outings. With its impeccable service and top-notch cuisine, Fleming's Prime Steakhouse & Wine Bar is a must-visit destination for food and wine enthusiasts in the United States.

Blu on the Avenue is a trendy and upscale bar and restaurant located in the heart of Winter Park, Florida. Situated at 326 South Park Avenue, this establishment offers a sophisticated dining experience with a diverse menu featuring delicious food and creative cocktails. Whether you're looking for a casual lunch spot or a lively evening out, Blu on the Avenue has something for everyone. With its stylish decor, friendly staff, and vibrant atmosphere, this is the perfect place to relax and enjoy a night out with friends or a romantic dinner for two. Come see why Blu on the Avenue is a favorite among locals and visitors alike.

Garp & Fuss is a vibrant and welcoming bar and restaurant located at 348 North Park Avenue in Winter Park, Florida. Known for its delicious food and extensive drink menu, Garp & Fuss offers a cozy and inviting atmosphere for guests to enjoy a casual meal or drinks with friends. The menu features a variety of dishes ranging from appetizers to entrees, all made with fresh, locally sourced ingredients. Whether you're looking for a place to grab a quick bite or enjoy a leisurely meal, Garp & Fuss is the perfect spot to relax and unwind. With its prime location in the heart of Winter Park, this institution is a must-visit for locals and visitors alike.

Boca is a vibrant and trendy bar, food, and restaurant located at 358 North Park Avenue in Winter Park, Florida. With its stylish decor and inviting atmosphere, Boca offers a unique dining experience that combines delicious food, craft cocktails, and a lively bar scene. Whether you're looking for a casual meal with friends or a night out on the town, Boca is the perfect destination for a memorable evening in the heart of Winter Park.