Overview
Winter Park is a city of 31,000 people (2019) in Florida near Orlando. Winter Park is often seen as a popular tourist destination for those visiting Orlando that want an escape from the typical tourist scene of the Orlando theme parks. There is a quaint, local feel to the suburb even though there are a lot of tourists, especially during the winter months and holidays.
7 sights · 3 things to do · 11 places to eat · 1 bars & cafés · 3 places to stay
Updated from Wikivoyage on 1 October 2026 · Something wrong or missing? Improve it on Wikivoyage
Best things about Winter Park
The Albin Polasek Museum & Sculpture Gardens
Historic home, exquisite art and serene Gardens. Tour the home galleries and sculpture gardens of internationally acclaimed Czech sculptor Albin Polasek. Tour his home in the heart of Winter Park on Lake Osceola. At the …
Charles Hosmer Morse Museum of American Art
Houses the world's most comprehensive collection of the works of Louis Comfort Tiffany, including art glass, leaded-glass windows, lamps, jewelry, pottery, paintings, and the chapel interior he designed for the 1893 Worl…
Rollins Museum of Art
At Rollins College, this gallery features items from Cornell University's renowned permanent collection.
Casa Feliz Historic Home Museum
A former farmhouse in Spanish style, it was built in 1932, moved to 656 N Park Ave in 2000, and added to the National Register of Historic Places on the last day of 2008.
Knowles Memorial Chapel
Historic chapel, built in a Mediterranean Revival style in 1931-32.
Winter Park Historical Museum
Once a freight depot for the railroad, it is now managed by the Winter Park Historical Association, with various artifacts from the city's past.
Plan your trip
Best time to visit & weather
Most comfortable: Oct–Apr. Summer highs reach about 92°F; winter lows dip to about 50°F. Very hot (Jun, Jul, Aug, Sep) — plan outdoor time for mornings. Wettest: Jun and Aug. (climate data from nearby Orlando)
Blue bars: average daily high and low (°F). Purple columns: average monthly rain and melted snow (inches).
Getting there
- From you: to see whether to drive or fly, and how long it takes.
- MCO Orlando International Airport, Orlando — 12 mi away (major hub). Directions
- SFB Orlando Sanford International Airport, Orlando — 14 mi away (major hub). Directions
The main interstate route in the area is I-4 (northeast to southwest), from which there is an exit to Winter Park. Orlando Avenue (north to south) goes through the city itself.
Full “Get in” guide ↓Budget & where to stay
No prices are listed for this place yet. See the Sleep guide ↓ for options.
Sample 2-day itinerary
Day 1
- Morning The Albin Polasek Museum & Sculpture Gardens, Winter Park's Scenic Boat Tour, Charles Hosmer Morse Museum of American Art
- Lunch Tabla
- Afternoon Casa Feliz Historic Home Museum, Winter Park Historical Museum
- Dinner Prato
- Evening Hannibal's
Day 2
- Morning Aloma Bowling Center
- Lunch Boca
- Afternoon Annie Russell Theatre
- Dinner Orchid Thai
Stops are grouped by area so each day needs little backtracking. Check opening hours before you go.
Food for you
Winter Park has a cosmopolitan restaurant scene, and most restaurants in downtown feature cuisines from outside the U.S. Asian and Mediterranean restaurants are a common sight and in the downtown area, all are upscale, with above-average prices.
Cuisine (tap to filter)
What to ask about, for your diet
Diet labels come from each listing's description and cuisine; “likely” means the cuisine usually has good choices, not a promise. Check with the restaurant. Open the food finder
Photos
Map
Every listing with a location. Tap a pin for its Google Maps link.
Understand
Founded as a resort community by northern business magnates in the late 19th and early 20th centuries, fueled by the South Florida Railroad connecting Orlando with northern Florida and beyond. Today Winter Park is home to about 30,000 inhabitants and a popular tourist destination with many festivals. The city is also home to the private liberal arts college, Rollins College.
Its main street, called Park Avenue, is in the middle of town. It includes civic buildings, retail, art galleries, a private liberal arts college (Rollins College), museums, a park, a train station, a golf course country club, a historic cemetery, and a beach and boat launch. Park Ave is prosperous and is the focal point for Winter Park's upscale, "gentrified" downtown, the culmination of which is in Rollins College at the south end. The street's surroundings, including the depot, are immaculate.
Climate
As is the case across Orlando, Winter Park's climate is hot and humid during the summer, and variable but on average much cooler during the winter. The Park Ave (outdoor) walk, which isn't too protected from the heat, can be unbearably hot during the peak of summer and it's a relief to go indoors. Added to the fact that parking is difficult in downtown, the best time to visit is during the cooler months outside June-September.
Get in
By car
The main interstate route in the area is I-4 (northeast to southwest), from which there is an exit to Winter Park. Orlando Avenue (north to south) goes through the city itself.
By train
Amtrak runs long-distance trains from New York City on its Silver Meteor and Silver Star routes, both trains continue south to Miami. SunRail commuter trains runs between DeBary and Poinciana in the south via Sanford, Orlando, Kissimmee and points in between on weekdays.
By bus
Get around
Most of Downtown Winter Park is accessible by foot. If you are staying in the attractions area near theme parks and other resorts, it is about a 45-minute to 1-hour drive. The driving time from Winter Park Village to historic downtown Winter Park is about 3 minutes.
See
There are many things to see in Winter Park since it is one of the most classic and picturesque cities in Central Florida. Downtown Winter Park is filled with museums, gardens, bowling alleys, and historical landmarks. Former US President Chester A. Arthur is quoted having said "Winter Park is the most beautiful city in all of Florida." It is a gem of Central Florida and a must-see if you are visiting Florida regardless of where you are from.
- The scenic Olde Winter Park area is punctuated by small, winding brick streets, and a canopy of old southern live oak and camphor trees, draped with Spanish moss.
See The Albin Polasek Museum & Sculpture Gardens
Historic home, exquisite art and serene Gardens. Tour the home galleries and sculpture gardens of internationally acclaimed Czech sculptor Albin Polasek. Tour his home in the heart of Winter Park on Lake Osceola. At the Polasek, the art and gardens illustrate the life and times of this important artist and changing exhibitions celebrate a wide range of “art that tells a story.”.
See Charles Hosmer Morse Museum of American Art
Houses the world's most comprehensive collection of the works of Louis Comfort Tiffany, including art glass, leaded-glass windows, lamps, jewelry, pottery, paintings, and the chapel interior he designed for the 1893 World's Columbian Exposition in Chicago. The holdings also include a major collection of American art pottery and representative collections of late-19th and early-20th-century American paintings, graphics, and decorative arts.
Do
- Thousands of visitors flock to annual festivals including the Bach Festival, the Sidewalk Art Festival, and the Winter Park Concours d'Elegance.
Do Annie Russell Theatre
Built in 1931, it was added the National Register of Historic Places in 1998. The theatre is named after Annie Russell, who lived in Winter Park for 13 years — and taught at Rollins College — before she died. One of the rooms of the theatre is allegedly haunted, and since an incident been closed.
Buy
Many upscale brands have locations in downtown, catering to the crowd that visits from around Orlando.
Eat
Winter Park has a cosmopolitan restaurant scene, and most restaurants in downtown feature cuisines from outside the U.S. Asian and Mediterranean restaurants are a common sight and in the downtown area, all are upscale, with above-average prices.
Eat Boca
Italian-influenced American cuisine with several seafood options, and many wines and cocktails available.
Eat Bosphorous
Turkish cuisine, in the center of downtown, with atmospheric indoor dining and limited outdoor seating. There are a couple additional locations in upscale suburbs of Orlando.
Eat Chez Vincent
Award-winning restaurant; French cuisine.
Eat Orchid Thai
Wide variety of styles including many curry, chicken, and seafood options, with widely variable entree prices.
Eat Pannullo's Italian
Recommended dish: ravioli Terricina with Gorgonzola cheese, mushrooms, basil.
Eat Power House Cafe
Lighter food options; Mediterranean-American cuisine.
Eat Prato
Modern Italian cuisine with outstanding pizza.
Eat Tabla
Diverse range of Indian, Thai, and Chinese cuisine.
Eat Thai Villa
Recommended dish: Tom Yum Gai soup, chili Jam with beef and tofu add peanuts.
Eat The Ravenous Pig
Restaurant, brewery, and general store.
Eat Umi Japanese Restaurant
Japanese cuisine with an emphasis on seafood. Food available to order online.
Drink
Restaurants in downtown have plenty of drinks to offer, and many restaurants have a sizeable bar, so there are not too many standalone bars or pubs here.
Drink Hannibal's
Refers to itself as "the counterpart of Chez Vincent" with its drink and small plate selections.
Sleep
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