Located in Orange County, north of Orlando, Florida, Winter Park has always been considered a winter resort.  With more than 28,000 residents, Winter Park is best known for the elegant homes, glistening lakes, museums and shopping. This is a nature lover’s destination boasting over 70 parks. While Winter Park offers a variety of options to keep you entertained, Orlando’s attractions are just minutes away.

Named Lakeview in 1851, the city was re-named Osceola in 1870. In 1881, Loring Chase,  a Chicago businessman, visited the tiny town surrounded by pine forests and lakes.  Chase soon realized that the area could provide refuge to wealthy Northerners seeking an escape from harsh winters.

Winter Park, Florida

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The railroad that ran from Orlando to Jacksonville helped to simplify his plan. Making the perfect Eastern bend into Winter Park, the tracks served as a convenient transport from the cold North. The railroads also brought the laborers and craftsmen who were in high demand.

With the establishment of Rollins College in 1885, the areas growth continued.  Rollins is now the oldest college in the state of Florida. Rollins College was constructed along the shore of Lake Virginia, and residential homes began popping up to the south along the lakeshores and new streets.

This quaint little town soon earned a reputation as an art and literary colony.  The economy slowed with the bitter freezes in 1820, which affected the citrus trade. A Florida Land Boom occurred in the early 20th century when wealthy Northern businessmen once again invested in the area, but collapsed in the late 1920’s. The city of Winter Park was incorporated in 1925 before the collapse.

The period after WWll saw intensity in economic development. Since 1950 the region has seen the development of the Kennedy Space Center, Disney World, and the evolution of Orlando into a banking service center. Many of Winter Park’s original historic buildings were lost because of this growth.

Winter Park is now thriving. It is literally bursting with diverse restaurants and shops, and offers an abundance of educational and cultural opportunities for local residents and international tourist.

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Our Favorite Things to Do in Winter Park,Florida

Our mini guide below will help you find some of our favorite things to do during your stay in Winter Park Florida

Casual Dining Options

For those looking for a more relaxed and lively atmosphere, opt for one of Winter Park’s more causal restaurants and cafes, offering a variety of great food at reasonable prices right in the neighborhood. Some of our favorite casual dining options are listed below.
 

Winter Park Fish Company

This is a counter-serve eatery with communal seating inside and a partly covered patio outside. The interior is bare-bones almost resembling a shack yet the food is anything but. There are mouth-watering fried seafood baskets and a market fresh fish menu. Winter Park Fish Company has a commitment to sustainability and “fish friendly” practices. Be forewarned, however, their menu items like the conch fritters and crab cake sandwich cause lines. Our advice is to go early or expect a wait.

If you like fish, visit them at: 761 Orange Ave Winter Park, Florida

(407) 622-6112
 

Prato

A stylish Italian eatery, Prato celebrates Italian cuisine from Italy’s rich culinary landscape. The food, which is made from scratch, never disappoints. Their meatballs have quite the reputation. Prato has been a local favorite since opening their doors in 2011, so reservations are recommended.

Dine at the Prato at: 124 N Park Ave (Morse and Park Ave) Winter Park, Florida

Call for reservations: (407) 262-0050
 

The Ravenous Pig

Recently relocated to this new address on W Fairbanks Avenue, this restaurant offers a constantly evolving menu of New American cuisine with choices ranging from pub food to more complex options. You’ll also find Prohibition-inspired cocktails, a nice array of microbrews (some of which are brewed onsite), and a thoughtful wine list. The food is consistently fabulous making The Ravenous Pig a foodie’s dream.

Recently relocated, The Ravenous Pis can be found at: 565 W Fairbanks Avenue Winter Park, Florida

Call for reservations: (407) 628-233
 

Fine Dining

In search of high quality food, décor, and service? Then a Winter Park fine dining experience is in your future. Below are some of our favorite upscale restaurants in Winter Park, suitable for a special occasion, a romantic night out, or a relaxing sensory experience with an award winning chef… Bon appetite!
 

Luma

Luma offers a progressive menu which changes daily. The atmosphere is inviting and the service is exceptional. Luma also features one of the most extensive wine lists in the area. From the small plates like sweet potato soup with maple crème fraiche and pistachio oil to main dishes like Long Island Duck confit with a tamarind glaze to desserts like lemon verbena panna cotta or malted chocolate cremeux (we had to list two, they sounded so amazing!) Luma is considered the gold standard in Central Florida.

Luma is located at: 290 S Park Ave Winter Park, Florida

Call for reservations: (407) 599-4111
 

Hamilton’s

Nestled inside the Alford Inn, Hamilton’s fuses locally sourced ingredients with traditional Southern fare. Showing its Southern charm, meals are served in an upscale community setting. Named after the 9th President of Rollins College, Hamilton Holt, the restaurant pays homage to one man’s pursuit of innovation and philanthropy, not only through its unique brand of hospitality, but through their support of student scholarships to Rollins.

Hamilton’s serves brunch and dinner, and also has special lounge menu. You can visit them at: 300 E New England Ave Winter Park, Florida

(407) 998-8090
 

Chez Vincent

Chez Vincent offers a traditional, romantic French dining experience in an indoor-outdoor setting that is both comfortable and elegant. This upscale dining room also serves lunch and a wonderful Sunday brunch. It’s the food is authentically French; from the Fruits de Mer to the Les Viandes the plates are exquisite, especially when paired with a lovely bottle of French wine.

Chez Vincent is a little taste of French gourmet in Winter Park, n’est pas? 533 W. New England Ave Winter Park, Florida

(407) 599-292
 

Locally Owned Restaurants

Winter Springs may be a small city but it is big on flavor. You won’t find the latest food trends in Winter Springs but what you will find is locally-owned, authentic, cuisine celebrating the different cultures that make up the tapestry of the city. Whether you are in the mood for fine dining or a casual family-style experience, rest assured that the city of Winter Springs will deliver (literally in some cases!). Here are some of your favorite food choices in Winter Springs:
 

Stefano’s Trattoria

If you like homestyle, authentic Italian food then look no further! This is a family-friendly, casual atmosphere serving up large portions of some of the best Italian food in the area. Voted the best Italian food in al of Central Florida, Stefano’s was started by local restauranteur Stefano LaCommare who originally hails from Sicily. The food here bursts with flavor and the staff will treat you like a member of the family. This is a five-star experience without the five-star price tag.

1425 Tuskawilla Road Winter Springs, Florida

(407) 659-0101

Corfu Greek Restaurant

Serving up old world Greek dishes that are made from scratch, this family-owned eatery feature some of the best tasting Greek food in the Orlando area; don’t let the strip mall location fool you. Lunch and dinner are the main focus here with a breakfast option only served Thursday – Sunday. Portions are always generous and prices always reasonable. Try popular appetizers like the Spanakopita, Tzatziki or Hummus to the Charbroiled Octopus, Whole Fried Calamari and Fried Smelts. The menu at Corfu has no shortage of authentic and flavorful options. The lunch menu includes the classic Greek gyro sandwiches as well as a treat for vegetarians with their own souvlaki. They have great choices for the kids as well with chicken tenders with fries and penne pasta with red sauce. And there is a nice selection of Greek wine and beer to wash it all down.

124 W State Rd 434 Winter Springs, Florida

(407) 542-1814
 

Casey’s Grill

Casey’s is classic American bar food in a casual environment. Think wings, great burgers and cold beer! In addition to the wings and burgers there is lots of standard fare to be found on their menu including salads and sandwiches. Entrees range from fish and chips to catch of the day. Generous portions, drink specials and lots of tvs for all of your game day watching!

1335 Tuskawilla Rd Winter Springs, Florida

407-696-0533
 

Nightlife

If its nightlife you are after then Winter Springs has plenty to offer. Whether you are a wine connoisseur, appreciate a good craft beer or want to kick up your heels on the dance floor, there’s enough variety to keep you busy. This list of must-visit hot spots will help you plan your nightlife adventure!
 

Red Cypress Brewery

At Red Cypress, the beers are proudly Florida born and brewed. Opening its doors in 2015, the owners of Red Cypress have a passion for craft beer and a passion for adapting the West Coast beer culture to the Sunshine state. Brew masters use locally sourced ingredients like orange peel and name their brews in homage to the legends and tales of Florida. Devil’s Chair, anyone?

Although they don’t serve food, they do allow you to bring in food from the nearby restaurants or food trucks. Not sure what to drink? Try a flight. We hear the Hollow Earth Bourbon Barrel Stout is legendary. Be sure to grab a growler or two to take home!

855 E. State Rd 434 Winter Springs, Florida

(407) 532-0341
 

Spill Wine and Beer

Looking for a great neighborhood bar with a quaint feel? Spill Wine and Beer fits the bill. Offering a small wine list and a nice selection of beer, it’s a relaxing atmosphere to wind down, listen to live music and enjoy an appetizer… Who doesn’t love a nice wine and cheese pairing?! There is seating both indoors and out, with a nice fire pit for chilly evenings. Spill is known for its friendly and welcoming atmosphere, so expect to meet a lot of regulars here.

1196 Tree Swallow Dr #1314 Winter Springs, Florida

407- 278 – 8219
 

Buchanan’s

Buchanan’s is a great place to go for a game of pool or a refreshing cocktail. The newest entry in the live music scene, Buchanan’s has a large dance floor and also hosts Corn Hole, giant Jenga, and Beer Pong competitions. There is also a separate indoor smoker’s lounge, keeping the main room smoke-free.

290 E State Road 434 Winter Springs, Florida

(407) 542-7919

Splash Around

Boasting beautiful weather, water everywhere, and more than 70 parks, Winter Park is brimming with outdoor adventures. Winter Park offers a multitude of activities to keep everyone entertained outside. From scenic boat rides to paddleboard adventures, you can’t help but enjoy the great outdoors here.
 

Scenic Boat Tours

Get ready to travel the Winter Park water chain, through three of Winter Park’s seven lakes and two narrow man-made canals. An 18 passenger vessel transports you to an experience that includes gorgeous vistas, towering cypress trees, and a myriad of tropical flowers. Be sure not to blink so you don’t miss the large cranes swooping down for an afternoon meal, or an alligator taking a lazy nap on the nearby banks. Tours last an hour and are narrated by an experienced guide.

Tour the waterways at: 312 E Morse Blvd Winter Park, Florida
(407) 644-4056
 

Maui B’s Paddleboard

Maui B’s has been in Winter Park since 2007. It’s the original paddle board company in Central Florida, bringing the sport directly from Maui. They offer paddle board lessons, tours, rentals, and on-board yoga/fitness classes. Don’t be surprised if a manatee swims by and plants a front flipper on your board. Maui B’s highly experienced and patient instructors ensure a great experience for any age and every fitness level.

Hang 10 at: 116 S Semoran Blvd Winter Park, Florida
(800) 671-9905

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