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.
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 from Orlando on weekdays.
- Winter Park railway station, 148 W Morse Blvd. 2020-09-11
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.
- The Albin Polasek Museum & Sculpture Gardens, 633 Osceola Avenue, Winter Park (just east of downtown Winter Park, on the north side of Osceola Ave on Lake Osceola), 28.596741°, -81.34352°, +1 407-647-6294. Tu–Sa 10AM-4PM, Su 1–4PM, M closed. 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.”. Adults $12, seniors (60+) $10, college students with ID $10, students (K-12) $7, members & children 4 & under are free 2022-08-06
- Mead Botanical Garden, 1300 S Denning Dr, 28.583966°, -81.358835°, +1 407 622 6323. A 47.6-acre (19.3-ha) park that encompasses several ecosystems. It has an amphitheater, butterfly garden, discovery barn and a recreation center. Many structures are more than 100 years old. 2020-09-13
- Charles Hosmer Morse Museum of American Art, 445 N Park Ave, 28.6009°, -81.3514°, +1 407-645-5311. Tu-Sa 9:30AM-4PM; Su 1-4PM; open until 8PM Fridays Nov-Apr. 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. Adult $6; senior (60+) $5; student $1; children free (under 12); free for everyone 4PM-8PM Fridays Nov-Apr 2019-03-02
- Cornell Fine Arts Museum, 1000 Holt Ave, 28.5923°, -81.3486°, +1 407 646-2526. Tu 10AM-7PM; W-F 10AM-4PM, Sa Su noon-5PM. At Rollins College, this gallery features items from Cornell University's renowned permanent collection. Free 2019-03-02
- Casa Feliz Historic Home Museum (Robert Bruce Barbour House), 656 N Park Ave, 28.6027°, -81.3511°, +1 407 628-0230. 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. 2020-09-11
- Knowles Memorial Chapel, 1000 Holt Ave, +1 407 646-2115. Historic chapel, built in a Mediterranean Revival style in 1931-32. 2020-09-11
- Winter Park Historical Museum, 200 W New England Ave, +1 407-647-2330. 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. 2020-09-13
Do
- Thousands of visitors flock to annual festivals including the Bach Festival, the Sidewalk Art Festival, and the Winter Park Concours d'Elegance.
- Annie Russell Theatre, 1000 Holt Ave. 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. 2020-09-13
- Aloma Bowling Center, 2530 Aloma Avenue, 28.6012°, -81.318°, +1 407 671-8675, alomabowl@alomabowlingcenters.com. M noon–midnight, Tu–Th 10AM–midnight, F noon–midnight, Sa 10AM–midnight, Su 10AM–10PM. One of the three locations across the Orlando area. There are league competitions on some nights. 2020-07-20
- Winter Park's Scenic Boat Tour, 312 E Morse Blvd, 28.5978°, -81.347°, +1 407 644-4056, ron@scenicboattours.com. 10AM–4PM daily. 18 passengers per boat; a tour throughout the various interconnected lakes of the city. $16 per adult, $8 per child (including tax) 2020-07-20
Buy
Many upscale brands have locations in downtown, catering to the crowd that visits from around Orlando.
- Farmers' Market, 28.5977°, -81.3528°. Sa 8AM–1PM. Open 51 Saturdays a year, the exception being March's third Saturday. The goods in the market include plants and farm produce. 2021-09-26
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.
- Boca, 358 North Park Ave, 28.6004°, -81.3509°, +1 407 636-7022. M–Th 11AM–10PM, F 11AM–11PM, Sa 10AM–11PM, Su 10AM–10PM. Italian-influenced American cuisine with several seafood options, and many wines and cocktails available. 2021-09-25
- Bosphorous, 108 S Park Ave, 28.5974°, -81.351°, +1 407 644-8609, WinterPark@bosphorousrestaurant.com. 11AM–10PM. 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. 2021-09-26
- Chez Vincent, 533 W New England Ave, 28.5959°, -81.3564°, +1 407 599-2929 (reservations), chez@cfl.rr.com. Award-winning restaurant; French cuisine. 2021-09-26
- Orchid Thai, 305 N Park Ave, 28.5998°, -81.3511°, +1 407 331-1400. Wide variety of styles including many curry, chicken, and seafood options, with widely variable entree prices. 2021-09-25
- Pannullo's Italian, 216 S Park Ave, 28.5964°, -81.3509°, +1 407 629-7270, pannullosrest@aol.com. Recommended dish: ravioli Terricina with Gorgonzola cheese, mushrooms, basil.
- Power House Cafe, 111 East Lyman Ave, 28.595°, -81.3507°, +1 407 645-3616, chris@powerhousecafe.com. Lighter food options; Mediterranean-American cuisine. 2021-09-26
- Prato, 124 N Park Ave, 28.5982°, -81.351°, +1 407 262-0050. Modern Italian cuisine with outstanding pizza.
- Tabla, 216 N Park Ave #H, 28.5992°, -81.351°, +1 321 422-0321. Diverse range of Indian, Thai, and Chinese cuisine. 2021-09-25
- Thai Villa, 7355 Aloma Ave, +1 407 677-8957, thaivillaorlando@yahoo.com. Recommended dish: Tom Yum Gai soup, chili Jam with beef and tofu add peanuts.
- The Ravenous Pig, 565 W Fairbanks Ave, 28.5933°, -81.356°, +1 407 628-2333. Restaurant, brewery, and general store. 2021-09-25
- Umi Japanese Restaurant, 525 S Park Ave, 28.5937°, -81.3508°, +1 407 960-3993, umiwinterpark@gmail.com. Japanese cuisine with an emphasis on seafood. Food available to order online. 2021-09-25
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.
- Hannibal's, 511 W New England Ave, 28.5959°, -81.3563°, +1 407 629-4865, Chez@HannibalsLounge.com. Refers to itself as "the counterpart of Chez Vincent" with its drink and small plate selections. 2021-09-26
Sleep
- The Alfond Inn at Rollins College, 300 E New England Ave, 28.595687°, -81.347536°, +1 407 998-8090. 112-room hotel with an AAA four-diamond rating, decorated with modern and Spanish architecture. 2020-09-13
- Park Plaza Hotel, 307 S Park Ave, 28.5957°, -81.3513°, +1 407 647-1072, frontdesk@box2110.temp.domains. Check-in: 3PM, check-out: noon. You can arrange for a bellman to bring your luggage from the train station, and there is a valet parking available $15 per day. 2020-09-13
- Hilton Garden Inn Winter Park, 1275 Lee Rd, 28.6063°, -81.3664°, +1 407-755-3733. Check-in: 3PM, check-out: 11AM. A little outside of downtown, to the northwest, with its own restaurant/bar. 2020-09-13