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Orlando Like a Local: Winter Park

The Orlando area has so much to offer beyond the theme parks. The city of Winter Park, just a short drive north of downtown Orlando, is at once historic, chic, and accessible.

With plenty to explore and enjoy, from some of the area’s premier dining and shopping to art, culture, and scenic tours, Winter Park has all the makings of a great Orlando day trip.


Winter Park is home to some of the area’s hottest and best-regarded dining. From upscale restaurants to new takes on traditional dishes, the options abound.

For a memorable meal, it’s hard to go wrong at The Ravenous Pig, a stalwart of the Orlando restaurant scene and one of the Central Florida’s most celebrated restaurants. Offering a creative and ever-changing menu highlighting fresh Florida seafood and seasonal offerings, inspired cocktails, and a delicious selection of craft beers brewed right on premises, “Ravenous,” as locals often call it, is a foodie’s dream.

For a more casual experience, stop by area favorite 4 Rivers Smokehouse for sweet and savory BBQ. Or go elegant and reserve a table at Prato, serving Italian classics made with modern techniques and fresh seasonal ingredients. Nearby, The Wine Room’s selection of hand-crafted wines and artisan cheeses, plus a new tapas-style menu, are sure to please any oenophile.



Take a break from the crowded outlet scene and opt for an easy stroll down Park Avenue. Home to some of the best boutique and specialty store shopping — and people watching — around, this chic destination is thought of as Winter Park’s Rodeo Drive.

From unique gifts at Alex and Ani and hard-to-find editions at Brandywine Books to fashions from Lilly Pulitzer, Lucky Brand and more — plus numerous cafés and restaurants nestled among the unique shops — Park Avenue is the place to see and be seen.


Just up from Park Avenue’s renowned shopping and dining, find yourself at the Morse Museum of American Art. The Mediterranean-style building blends beautifully with its scenic neighborhood. But what’s most beautiful is what’s inside. The museum houses the world’s largest collection of works by Louis Comfort Tiffany, famous for his beautiful art glass, leaded glass “Tiffany” lamps and breathtaking stained-glass windows (as well as being a son of the founder of Tiffany & Company). The museum’s collections also include American art pottery, paintings and decorative art. A hidden Winter Park gem and a must-go for any art lover.


Want to explore Winter Park in a unique way? Climb aboard a Scenic Boat Tour. The guided tour cruises the chain of lakes and manmade canals that peacefully flow through Winter Park. And there’s plenty to see. Look up to witness large cranes swooping down to snag a fish for dinner. Or maybe spy a lazy alligator relaxing on a nearby bank. From navigating quiet paths through lush scenery and past exquisite private homes to sunny open-air lake cruising, this is an invigorating way to get a “behind-the-scenes” view of Winter Park.

Plan these activities and more for your next Orlando vacation

Contact your Personal Concierge today.