A cultural beacon for Greater Orlando, the picture-perfect city of Winter Park originated as a winter resort for the wealthy in the 1880s.
With its canals, lakes, moss-draped live oaks, and Mediterranean Revival architecture, I will never tire of exploring Winter Park.
You can do this on foot, wandering among cypress trees at lakeside parks, or on the water where the Chain of Lakes is linked by winding canals.
There’s a stylish downtown area, next to Central Park, which has an active station on the SunRail line. From here you can get to Orlando’s Central Business District in a matter of minutes.
This green nexus point is the stage for events like one of the best farmers’ markets in Florida, and a nationally acclaimed art festival.
1. Charles Hosmer Morse Museum of American Art
Set downtown, the Charles Hosmer Morse Museum of American Art is home to one of the world’s most complete collections of pieces by Louis Comfort Tiffany (1848-1944).
On show is a startling array of his leaded glass windows, jewelry paintings, pottery, enamels, furniture, and lampshades.
Many of the items on display were salvaged from Tiffany’s home and studio, Laurelton Hall in Long Island, following a fire in 1957.
Maybe my favorite exhibit of all is the complete interior of the chapel for the 1893 World’s Columbian Exposition in Chicago. This space radiates opulence, with its brilliant mosaics and windows, in a Byzantine-Romanesque style.
2. Park Avenue
Lining the east side of Central Park is a truly elevated Main Street. In the shade of beautiful life oaks there’s a long line of upmarket independent businesses.
Along this brick-paved thoroughfare are boutiques and an international array of restaurants. Most of these eateries have sidewalk tables, under awnings and that oak canopy.
On Park Avenue and its side streets you can shop for luxury home decor, jewelry, designer clothing, cosmetics, fashion accessories, fine art, and more.
The mix of cuisines is equally diverse, whether you’re in the mood for smoothie bowls, New American, Turkish, Italian, French, Thai, Mexican, seafood, or steak.
The district is also bookended by two Winter Park cultural highlights. In the north is The Charles Hosmer Morse Museum of American Art, with its Tiffany masterpieces.
South, Rollins College, counts Fred Rogers among its alumni, and has been visited by presidents from Coolidge to Obama.
3. Central Park
A natural partner to Park Avenue, this leafy space hosts a variety of events and performances throughout the year. One of the recurring events is the Winter Park Farmers’ Market, which I’ll cover in more detail later.
At other times, Central Park is just a pleasant place for a stroll or to relax with a good book or a good friend. There are fountains, tall old oak trees, and abundant flowers, especially in the rose garden in spring.
Railroad tracks cross the park from north to south. Embedded in the greenery, Winter Park Station is served by Amtrak and SunRail commuter trains.
4. Albin Polasek Museum & Sculpture Gardens
In 1950 the Czech American sculptor Albin Polasek 1879-1965 retired to Winter Park. Among his most famous works are The Spirit of Music (1923) in Chicago’s Grant Park, and The Yates Memorial, in Springfield, Illinois (also 1923).
Backing onto Lake Osceola, Polasek’s purpose-built home and studio was opened up as a museum in 1961.
This is the only museum of its kind in Florida, keeping most of its original furnishings. The sculpture gardens are sumptuous, and complemented by the vistas over the water.
There are around 200 works by Polasek on show, as well as pieces from his collection. For an educator’s perspective on his life and work, I’d recommend a guided tour.
5. Rollins Museum of Art
Greater Orlando’s only teaching museum is on the campus of Rollins College. Founded in 1978, the Rollins Museum of Art has more than 5,000 works in its collection.
These holdings are wide-ranging, but have a few focal points, including contemporary art, American painting up to 1950, and European Renaissance art.
When I paid a visit, the museum was in a period of sudden growth. There was a spellbinding display of new acquisitions by the likes of John Singer Sargent, Benjamin West and Thomas Cole.
Some of the museum’s collection is also on show at the college’s Alfond Inn. Proceeds from this refined boutique hotel help fund scholarships.
6. Hannibal Square Heritage Center
Starting in the 1880s, the western half of Winter Park became home to the city’s African-American community. Early residents here worked on the railroads, or filled domestic service jobs in wealthy households.
In 2007, the Crealdé School of Art opened a museum to document this aspect of the Winter Park’s heritage.
The focus here is the Heritage Collection: Photographs and Oral Histories of West Winter Park. This touching display has more than 100 pieces that shine a light on the African-American community.
These are accompanied by a timeline, recording major events from the Emancipation Proclamation up to the election of Barack Obama in 2008.
7. Kraft Azalea Gardens
If you were to ask me how to close out the perfect day in Winter Park, I’d come to this little park at sunset. Just five acres, Kraft Azalea Gardens occupies a nub on the southeast shore of Lake Maitland.
When the sun is low the thick stand of cypresses takes on a magical quality. It’s no shock that this park is a local spot of choice for golden-hour photo shoots.
Come between late February and the start of June, and you should catch a glimpse of the egrets that nest in these giants.
8. Mead Botanical Garden
This magnificent botanical garden opened in 1940 in memory of the noted naturalist, Theodore Luqueer Mead (1852-1936).
For one thing, Mead’s friends needed somewhere to house his extensive collection of orchids. More than 80 years later, the Mead Botanical Garden is a joyous oasis concealed within the city.
Winding trails and boardwalks take you across wetlands and upland pine hammocks with some towering trees. There’s a creek, and a pond humming with life, from wading birds to turtles.
One spot I won’t soon forget is the butterfly garden, with a colorful array of flowering plants attracting pollinators.
9. Casa Feliz Historic Home Museum
One man who helped define Winter Park’s residential cityscape was the architect James Gamble Rogers II (1901-1990).
He is most famous for the Florida State Supreme Court Building (1949) in Tallahassee. Yet, for much of the 20th century he worked in Winter Park, building homes in revivalist styles, ranging from Spanish Colonial to French Provincial.
A fine example of his early career can be seen at the Robert Bruce Barbour House, built for a local industrialist in 1932. Also known as Casa Feliz (Happy House), this has a rustic Andalusian style, fronted by a stately loggia.
Some interesting details I enjoyed on my tour—the Spanish terracotta roof tiles,the majolica-tiled courtyards, and the huge hand-cut beams in the living room’s vaulted ceiling.
A well-presented museum exhibit about James Gamble Rogers II had also just opened when I was here.
10. Winter Park Farmers’ Market
Held at Central Park West Meadow, the booming Winter Park Farmers’ Market is up there with the best in Florida. The market happens on Saturdays from 8 AM until 1 PM, and packs a town’s worth of vendors into a relatively tight space.
In addition to seasonal produce, you might find houseplants, herbs, sauces, wines, apple cider, maple syrup, seafood, pickles, cheeses, coffees, fresh bread, pet treats, and a wealth of artisanal crafts.
My one tip is to skip breakfast before coming, because there are some serious food trucks and static vendors. I’ve seen Indian street food, arepas, chicken pot pies, acai bowls, breakfast burritos, ravioli, Belgian waffles, and BBQ here.
11. Scenic Boat Tours
At the city’s lakefront parks, you’ll realize there’s a whole other side to Winter Park waiting to be discovered.
Edged with ferns, palms, oaks, cypresses, and elegant mansions the Chain of Lakes is connected by canals. These meandering waterways were built to convey lumber to a sawmill on the shores of Lake Virginia at the southern end of the chain.
For me, you need to get out onto the water to really get a feel for Winter Park. This can be done via the scenic boat tour, departing daily on the hour from 10 AM to 4PM.
These tours have taken place since the 1930s, and are a gateway to a secret world, brimming with life. The Chain of Lakes is at once wild, with alligators and scores of wading birds, but also opulent.
As well as the grounds of Rollins College, the grounds of numerous sprawling mansions frame the lakes and canals.
12. Winter Park Sidewalk Art Festival
Bringing hundreds of thousands of visitors from all over the country every year, the Winter Park Sidewalk Art Festival is my must-see event here.
Held in Central Park in mid-March, the festival has been a fixture since 1960, and ranks among the best art fairs in the country.
The festival features a wide spectrum of arts and crafts, from paintings to jewelry, but also contemporary mixed-media.
Artists compete for awards in more than 60 categories, with prize money totalling more than $80,0000. The big one is the prestigious Best of Show.
Live music and entertainment are woven into these three days, starting with a kick-off Friday night concert. There’s also a children’s workshop, and a complimentary bike corral throughout the festival.
13. Winter Park Golf Course
In typical Winter Park style, the city’s nine-hole public golf course is couched among live oaks, in a village-like environment.
The holes at Winter Park Golf Course are traced by two churches, grand homes, a cemetery and the passenger railroad tracks.
Dating back to 1914, the course was renovated in the 2010s and is lauded as one of the best public short courses in America. I found this par-35 to be a real test, thanks to the small-ish greens, all guarded by sand traps.
There are new fairways, greens and roughs, and a state-of-the-art irrigation system bringing the second-oldest course in Orlando into the 21st century.
14. Kayaking and Paddleboarding
If you want to navigate Winter Park’s Chain of Lakes in a more active way there are several outfitters and tour companies on hand.
Get Up and Go Kayaking, Otter Paddle Orlando, and Peace of Mind Kayak Tours all offer guided trips in this beautiful environment.
On these adventures you’ll have a little bit more freedom to check out wildlife, or linger in an especially picturesque area. This might be an oak-shaded canal, or a grassy bank with river otters playing.
Sunset paddle tours are available, and you can even head out onto these lakes after dark, on a glow-in-the-dark trip.
You may want ever more independence. In which case, Peace of Mind Kayak offers full or half-day rentals in Winter Park, with drop-offs.