Winter Park, FL Road Trips

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. 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.

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. 1 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), ☏ +1 407-647-6294. Tu-Sa 10AM-4PM, Su 1-4PM. 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.”. $12/adult, $10/senior, $10/college student, $7/student. (updated Feb 2024) 2 Mead Botanical Garden, 1300 S Denning Dr, ☏ +1 407 622 6323, [email protected]. 8AM-dusk. 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. free.

Thousands of visitors flock to annual festivals including the Bach Festival, the Sidewalk Art Festival, and the Winter Park Concours d'Elegance. 1 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. (updated Sep 2020) 2 Aloma Bowling Center, 2530 Aloma Avenue, ☏ +1 407 671-8675, [email protected]. 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. (updated Jul 2020) 3 Winter Park's Scenic Boat Tour, 312 E Morse Blvd, ☏ +1 407 644-4056, [email protected]. 10AM–4PM. 18 passengers per boat; a tour throughout the various interconnected lakes of the city. $20/adult, $10/child. (updated Feb 2024)

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. 1 Boca, 358 North Park Ave, ☏ +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. (updated Sep 2021) 2 Bosphorous, 108 S Park Ave, ☏ +1 407 644-8609, [email protected]. 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. (updated Sep 2021) 3 Chez Vincent, 533 W New England Ave, ☏ +1 407 599-2929 (reservations), [email protected]. Award-winning restaurant; French cuisine. (updated Sep 2021) 4 Orchid Thai, 305 N Park Ave, ☏ +1 407 331-1400. Wide variety of styles including many curry, chicken, and seafood options, with widely variable entree prices. (updated Sep 2021) 5 Pannullo's Italian, 216 S Park Ave, ☏ +1 407 629-7270, [email protected]. Recommended dish: ravioli Terricina with Gorgonzola cheese, mushrooms, basil. 6 Power House Cafe, 111 East Lyman Ave, ☏ +1 407 645-3616, [email protected]. Lighter food options; Mediterranean-American cuisine. (updated Sep 2021) 7 Prato, 124 N Park Ave, ☏ +1 407 262-0050. Modern Italian cuisine with outstanding pizza. 8 Tabla, 216 N Park Ave #H, ☏ +1 321 422-0321.

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. 1 Hannibal's, 511 W New England Ave, ☏ +1 407 629-4865, [email protected]. Refers to itself as "the counterpart of Chez Vincent" with its drink and small plate selections. (updated Sep 2021)

1 The Alfond Inn at Rollins College, 300 E New England Ave, ☏ +1 407 998-8090. 112-room hotel with an AAA four-diamond rating, decorated with modern and Spanish architecture. (updated Sep 2020) 2 Park Plaza Hotel, 307 S Park Ave, ☏ +1 407 647-1072, [email protected]. Check-in: 3PM, check-out: noon. Classic hotel, built in 1922. You can arrange for a bellman to bring your luggage from the train station, and there is a valet parking available $20 per day. (updated Sep 2020) 3 Hilton Garden Inn Winter Park, 1275 Lee Rd, ☏ +1 407-755-3733. Check-in: 3PM, check-out: 11AM. A little outside of downtown, to the northwest, with its own restaurant/bar. (updated Sep 2020)

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. 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. 1 Winter Park Railway Station, 148 W Morse Blvd. Cross platform transfer between Sun Rail and Amtrak are only in Winter Park, Orlando Health, and Kissimmee Stations. (updated Sep 2020)

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.