Photo Credit: Airam Dato-on

Winter Park Uncovered: A Local’s Guide to the City

The Encore Resort Blog
March 12, 2024
March 12, 2024

Five miles northeast of Orlando is the picturesque resort community of Winter Park. Walk (or drive) the cobblestone streets where you will find an abundance of local shops, bistros, inns, coffee houses and a fantastic farmers market.

The most famous area in Winter Park is the very busy and charming Park Avenue. This tree-lined street plays host to numerous little restaurants and shops. It’s a fantastic spot to grab a latte, take a walk and do a little sightseeing.

With so many things to see and do in his quaint and friendly town, we thought we’d let you in on our favorites:

Best Dinner in Winter Park

Meatballs served over polenta at Prato restaurant in Winter Park, Orlando, Florida
Ⓒ Prato


Italian cuisine at its most delicious, Prato (Opens in a new tab) blends simplicity and inspiration, from Italy’s rich culinary landscape. Enjoy Italian classics with modern techniques and seasonal ingredients. Guests will love the ambiance of the contemporary design with a rustic feel – not to mention its year-round patio seating.


Turkish hospitality comes alive at Bosphorous (Opens in a new tab) where they handcraft their Anatolian cuisine every day using Halal meats and the freshest vegetables and authentic ingredients – many of which are imported from Turkey. Try their signature hollow bread, Lavas, which is baked to order.

AVA MediterrAegean

This contemporary Mediterranean beauty is wonderfully located in the center of the charming Winter Park. AVA MediterrAegean (Opens in a new tab) is quite the hotspot, so dress up for its shared and family-style eating, which focuses on Cycladic food. Ideal for couples or parties, the menu tempts with a variety of mezze, starters, salads, and raw dishes to kickstart your gastronomic adventure. This modern take on a classic dessert mixes phyllo dough with spiced nuts, which are enriched with walnuts and pistachios in honey, generously seasoned, and served with a dollop of pistachio ice cream.

Best Brunch in Winter Park

240 Rose Cafe

240 Rose Cafe (Opens in a new tab) is located in a historic train depot, has a relaxed ambiance as well as a wonderful brunch menu. They provide a variety of sweet and savory alternatives, including the “Avocado benedict“. They also provide a wide variety of coffee drinks and a daily mimosa special.

The Ravenous Pig

The James Beard-nominated The Ravenous Pig (Opens in a new tab) happens to be one of Orlando’s finest gastropubs. Mixing farmhouse chic with upscale sleek, brunch goers flock to this Park Avenue restaurant for a little patio dining and a lot of gourmet eats.

Ⓒ City of Winter Park


The Briarpatch (Opens in a new tab), Winter Park’s famous restaurant since 1980, serves contemporary American cuisine with a focus on seasonal Florida tastes and fresh local ingredients. Located on Park Avenue, it offers a warm and friendly ambiance for customers to enjoy brunch on the outdoor patio or sandwiches, fresh pastries, and cakes indoors.

Another Broken Egg Cafe

Another Broken Egg Cafe (Opens in a new tab) is a famous chain which provides a wide brunch menu that has something for everyone. From sweet selections like their “Cinnamon Roll French Toast” to savory ones like their “Crab Cake Benedict,” you’ll be able to find a filling lunch. They also serve a selection of breakfast cocktails including unlimited mimosas.

Best Specialty Shops in Winter Park

Ⓒ The Wine Room

The Ancient Olive

Delivering the best in premium extra virgin olive oil and aged balsamic vinegars, The Ancient Olive (Opens in a new tab) is an epicurean adventure for those taste-testers who love to sample and shop. Come hungry and dive into Spanish olives, French mustards, award-winning preserves, dry-cured sausages, nuts, handcrafted pastas, unique cocktail mixers and much more.

The Spice & Tea Exchange

With more than 140 spices, 80+ exclusive hand-mixed blends, 16 naturally-flavored sugars, olive oils, different salts and peppers from around the globe, and countless exotic teas, The Spice & Tea Exchange is your one-stop shop for everything flavorful.

The Wine Room on Park Avenue

The Wine Room (Opens in a new tab) offers a handpicked selection of 156 wines from around the world, accessible for tasting in 1 oz., 2.5 oz., or 5 oz. doses using an innovative Enomatic wine dispensers. Their collection has received The Wine Spectator’s “Best of Award of Excellence” for six years running.

Best Things To Do in Winter Park

Mead Botanical Garden

This 48-acre urban oasis features tall pine trees, hiking trails, a vibrant creek, boardwalk, greenhouse, butterfly garden, and a pond that’s home to turtles, fish and wading birds. At MeadBotanical Garden (Opens in a new tab), you’ll find adventure and tranquility – a world of discovery and experience.

Enzian Theater

A single screen cinema café and home of Eden Bar, the Enzian Theater also hosts the Florida Film Festival. As Central Florida’s only cinema that offers independent, foreign and classic films, Enzian Theater’s (Opens in a new tab)sole purpose is to entertain, inspire, educate and connect the local community through film.

Ⓒ City of Winter Park

Winter Park Boat Tours

Offering scenic, hour-long guided cruises starting on Lake Osceola, Winter Park Boat Tours (Opens in a new tab) takes passengers through three of the seven lakes and two man-made canals on the Winter Park chain. First-time visitors and locals alike love these off-the-beaten-path adventures and the scenic flora and fauna sprawling throughout the tours.

Winter Park Farmer’s Market

Held at an old train depot, the Winter Park Farmers’ Market (Opens in a new tab) takes place Saturdays from 8 a.m. to 1 p.m. and is a popular community gathering place that provides fine produce, plants, baked goods and more.

Charles Hosmer Morse Museum of American Art

The Morse Museum (Opens in a new tab) has the most extensive collection of artworks by the American artist and designer Louis Comfort Tiffany, displaying a wide variety of his work. The museum also has displays of American art pottery, painting, graphics, and decorative art from the late nineteenth and early twentieth centuries. Visitors must schedule appointments to explore the collections.

Albin Polasek Museum & Sculpture Gardens

The Albin Polasek (Opens in a new tab) Museum and Sculpture Gardens is dedicated to American representational sculpture and houses over 200 works by the Czech-born American artist Albin Polasek. It offers guided tours of Polasek’s ancient home and church, as well as an outdoor sculpture garden and gift store.

A Little History of Winter Park

Ⓒ City of Winter Park

Famous for its abundant parks, brick-lined cobblestone streets, museums, spectacular homes, stately trees, vibrant lakes and boutique shops along Park Avenue, Winter Park has, for more than 150 years, been a tourist haven. Northerners would come to the city to get away from the snow and enjoy Winter Park’s beautiful lakes, countless parks, warm temperatures and natural surroundings. Today, it’s a hoppin’ little downtown. If you can’t find something to do, watch, eat, drink or buy in Winter Park, then you weren’t paying attention – because this hub of commerce, culture and entertainment delivers, morning, noon and night.

From a busy day of Winter Park entertainment to an evening of relaxation at Encore Resort at Reunion, just sit back, unwind and breathe. Come home to our guard-gated community which features modern, beautifully decorated 4- to 13-bedroom homes with backyard pools, washer/dryer units, and fully equipped kitchens, plus resort-style amenities like an Aqua Park and free shuttle. This is the perfect way to end your day. Each of our homes offers ample room for you to socialize, relax and unwind after a busy day.

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