Winter Park, Florida: Where to Eat, Drink, Play & Stay

Situated amidst scenic avenues and dynamic cultural landscapes, Winter Park, Florida, represents a community where traditional heritage and contemporary vitality coexist seamlessly. This neighborhood guide explores the myriad treasures to be discovered, catering to both residents enjoying the tranquil daily life and visitors attracted by its welcoming ambiance.

History of Winter Park

Winter Park was founded in 1881 by Loring Chase and Oliver Chapman, who recognized the potential of the area for its abundant lakes and proximity to Orlando. The founders decided to name the town Winter Park due to its favorable weather conditions, particularly during the winter months. Over time, Winter Park evolved into a popular resort destination, attracting wealthy snowbirds from northern states.

Hannibal Square

Hannibal Square, a historically African-American community in Winter Park, played a significant role in the town’s history and development. The neighborhood began as an enclave for laborers working on the railroad and citrus groves, but eventually became a thriving commercial center for the Black community. Today, Hannibal Square is a vibrant hub of culture and diversity, home to numerous restaurants, art galleries, and boutiques.

Key Attractions

Winter Park boasts a variety of attractions that cater to different interests and ages. Here are some must-visit places in the neighborhood:

Lake Killarney

This picturesque lake offers a peaceful retreat for outdoor enthusiasts. It’s a beautiful place to enjoy boating, fishing, and birdwatching while taking in the stunning views of the surrounding natural scenery.

The Charles Hosmer Morse Museum of American Art

For those who appreciate Louis Comfort Tiffany’s fine craftsmanship and intricate designs, the Morse Museum is an unmissable destination. Home to the world’s most comprehensive collection of Tiffany’s work, visitors are enchanted by the stained glass, pottery, and jewelry on display.

The Albin Polasek Museum and Sculpture Gardens

At the Polasek Museum, art transforms into a three-dimensional experience. Sculptures emerge from lush gardens, telling visual stories that engage the senses.

Scenic Boat Tours

Navigate the tranquil waters of the Winter Park Chain of Lakes with a scenic boat tour. It’s the perfect setting to escape the rush of daily life and immerse yourself in the area’s natural elegance.

Winter Park Farmers’ Market

A buzz with local life, the Farmers’ Market is the ideal stop for fresh produce and unique artisanal products. It’s not just shopping; it’s an experience that brings the community together every Saturday morning.

Park Avenue District

Amble down Park Avenue where luxury meets legacy, offering excursions from boutique shopping and gourmet dining to cultural enrichment.

Mead Botanical Garden

With 47 acres of green space, Mead Botanical Garden invites nature lovers to explore its flourishing habitats and winding pathways for a true urban retreat.

Rollins College Campus

Architectural beauty and intellectual vibrancy merge at the Rollins College Campus, where the public can enjoy events and lectures on its idyllic grounds.

The Winter Park History Museum

Journey through Winter Park’s storied past at this intimate museum, showcasing the narrative of this historic neighborhood.

Where to Eat

When it comes to dining in Winter Park, there is no shortage of options to suit every palate and budget.


This rustic Italian eatery boasts fresh ingredients and authentic dishes that leave diners feeling satisfied and delighted.

The Ravenous Pig

A beloved local hotspot, The Ravenous Pig offers a sophisticated yet relaxed atmosphere coupled with creative, farm-to-table cuisine.

Bosphorous Turkish Cuisine

Savor the flavors of Turkey at Bosphorous, where traditional dishes burst with aromatic spices and hearty portions.

Where to Stay

Whether you’re looking for a luxurious getaway or a cozy retreat, Winter Park has options to suit all preferences.

Park Plaza Hotel

Experience old-world charm at the Park Plaza Hotel, with its classic furnishings and convenient location in the heart of downtown Winter Park.

The Alfond Inn

This boutique hotel features elegant rooms and suites, as well as an on-site restaurant and outdoor pool for ultimate relaxation.

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I’m Nicole Mickle, a real estate agent in Orlando, Florida. I’m here to assist you in making the most out of your Florida lifestyle.

In addition, I’m the author behind¬†Florida Homes and Living, a blog dedicated to sharing valuable content about Orlando, interior design, remodeling, and the Florida lifestyle.

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