Located just seven miles north of the City of Orlando in Orange County, Winter Park’s 30,000 residents enjoy abundant outdoor spaces, a decadent Saturday morning farmer’s market, golf courses, and more museums than you would ever expect to see in such a small area. Created by several wealthy industrialists as their winter haven in the late 19th and 20th centuries, boating, museums, shopping on Park Avenue, and great food make it as delightful today as it was then.
I attended a press trip that included Winter Park. All the opinions herein are my own.
1. Scenic Boat Tour
The Scenic Boat Tour is a must-do and the perfect introduction to Winter Park. It is the oldest, continuously running attraction in the state of Florida since 1938! They operate seven days a week, 364 days a year (not Christmas). Peppered with jokes, facts, and wry asides, Skipper Don Brown’s a treasure trove of information along this gorgeous tour.
The Winter Park chain of lakes is connected by navigable canals created by Charles Mizell of timber fame to ship his product between six lakes (Maitland, Minnehaha, Mizell, Nina, Osceola, Virginia) in the mid-1800s.
The pontoon boats can’t have a roof or cover because the water levels on the lakes can be quite high during the wet season and there isn’t enough clearance for the boats to pass under bridges that dot the canals. Don’t worry, the lake view of all the historic homes make it well worth the trip with people kayaking around the pontoons.
Before you move too far along in our journey, though, it’s time for the first section of the historic shoreline to receive a shout-out. On the right side of the lake once stood the Old Seminole Hotel, the grandest hotel in the state of Florida. In 1886, maybe even the United States. It had 250 hotel rooms and a four-story tall observation tower from which you could see both Lake Osceola and Lake Virginia. Most impressive was its front porch, stretching 600 feet (that’s two football fields). Host to Presidents Grover Cleveland and Benjamin Harrison, many said that Rollins College and the Old Seminole Hotel brought “luxury to the edge of the Florida frontier.”
Sadly, the hotel caught fire in 1902 and burned to the ground.
Along the Scenic Boat Tour route, identify the “Resurrection Fern” and the “Dinky Dock,” an ecologically protected cypress with several homes designed and built by the famous architect, James Gamble Rogers.
2. The Charles Hosmer Morse Museum Of American Art
The Charles Hosmer Morse Museum was created by his granddaughter Jeannette Genius McKean and her husband Hugh McKean who had completed an internship with Louis Comfort Tiffany glass earlier in his life. First housed on the Rollins College campus, the collection outgrew that space, especially after the couple rescued as much as possible from Tiffany’s Laurelton Hall, Long Island, New York home that collapsed during a fire. It was the quick work of Jeannette and Hugh that saved so many panels of this precious work.
Along the tour, you’ll learn how many different mediums Tiffany found to work with. There are his lamps, of course, but also jewelry and furniture, the most astounding windows… explore how the light changes based on your position.
3. Albin Polasek Museum And Sculpture Gardens
Albin Polasek Museum and Sculpture Gardens, with over 400 bronze pieces, visible from the Scenic Boat Tour, remains a popular wedding venue and was donated by the artist’s wife following the death of this incredible Czech American talent in 1962.
However, the story of this museum and its foundation goes further still. When the Capen House was sold, the Polasek offered a safe haven for the original home. The new owners of the land the Capen House stood upon paid for the house to be split in two (called Fred and Ginger after the famous American dance team, Fred Astaire and Ginger Rogers), rolled down the hill, and floated across Lake Osceola to its current location. It took 45 minutes for the first half, according to our skipper, and 15 minutes for the second. Check out the YouTube video from 2010 where a drone covered the event. Movement across the lake starts at 1 minute and 42 seconds.
Also found in Winter Park is the Rollins Museum of Art, the Winter Park History Museum, Casa Feliz Historic Home Museum, and Hannibal Square Heritage Center, with art galleries regularly hosting berry special events. If you’re interested in classes or summer art camp, check out the Crealde School of Art.
4. Kraft Azalea Gardens
While many visitors know to go to Mead Botanical Gardens, one of Winter Park’s best but little-known attractions remains Kraft Azalea Gardens. Popular for weddings, marriage proposals, and birthdays, it’s a magical place.
Located on Lake Maitland’s shores, this 5-acre public garden is free to enter and open year-round from 8 a.m. to sunset, with a boat dock, benches, and eight more acres of park to explore outside the garden. Relax at The Exedra, reminiscent of Golden Gate Park’s Spreckels Temple of Music, wander the great egret rookery, or visit the northernmost Banyan Tree in the state of Florida.
5. Saturday Morning Farmers Market
Advertised as the “Number one produce and plant market in Central Florida,” Winter Park’s Farmers Market contains the city’s central park and lives up to the hype with a lovely, festive gathering place with vendors and shoppers reveling in the fresh, colorful produce, assortment of plants, baked goods, artisanal crafts, and other offerings. The City of Winter Park Sidewalk Art Festival is held in this same location each year. Details can be found here.
The train station stops nearby. They are still serviced by Amtrak.
6. Winter Park Shopping
Rifle Paper Company
Winter Park’s Park Avenue provides ten tree-canopied blocks where you can wander around the 140 specialty shops, cafés, boutiques, and coffee shops. If you love stationery, you’ll want to stop at Rifle Paper Company.
Interested in gourmet chocolate? Peterbrooke Chocolatier’s assortment of chocolate delicacies will tantalize your taste buds.
The Impeccable Pig
Need to find a chic outfit or trendy accessories? Check out The Impeccable Pig.
The Wine Room On Park Avenue
If you’re looking for a decadent restaurant experience with a special wine, cheese, and charcuterie (or to take as a gift to those at home), you’ll want to check out The Wine Room.
Winter Park Restaurants
As with most wealthy towns, Winter Park’s restaurants provide an embarrassment of riches. The sheer abundance of food found from The Glass Knife to the surprisingly good “college food” at Rollins College to the James Beard nominated chefs James and Julie Petrakis of The Ravenous Pig with special attention to great locations for vegans and husbands in need of “daycare,” there’s something for everyone in Winter Park.
The Glass Knife Cakes And Café
Executive Chef Kristy Carlucci and General Manager Bianca Hinksman recommend reservations at The Glass Knife if you’d like to eat on the porch on a typically busy day.
Displays of season-specific items atop the glass display cases filled with decadent croissants, pastries, and cakes. Menus for brunch and beverages hang above rows of freshly made doughnuts.
Look closely at the long, butcher block table beneath the rectangular chandelier base and dropped pendant lights that line the entire 12-seat table. Therein lie several eponymous glass knives in multiple colors. The imperfections make them stunning.
Two places to eat on Rollins College’s Campus, the Boat House and the Student Cafeteria, Skillman Dining Hall, bring you to campus but you’ll stay to walk around and see why it highly ranks each year on the “Most Beautiful College Campus” list.
The college’s cafeteria is spacious, light, and inviting with some of the best views on campus across an Olympic size pool over Lake Virginia.
Dave’s Boathouse, a Star-K Kosher certified facility offers a dark wood finish large bar area as you enter from the lakeside with cozy dining and large tables to fit your party size.
If you’d like to stay on campus, check out The Alfond Inn.
Ethos Vegan Kitchen
Enter Ethos’ fun, festive atmosphere to a wide display of artwork, from the playful to the profound, you can choose to be seated or place a takeaway order behind the hostess station. You’ll be impressed with the “common” names in this vegan restaurant from sausage rolls and “chickun” or pork. Even bay cakes, their rendition of crab cakes, move quickly across the restaurant as happy plant-based diners eat their fill.
Fiddler’s Green Irish Pub And Eatery
Wives, take notice. Fiddler’s Green Irish Pub on Fairbanks Avenue declares itself:
“Winter Park’s oldest husband daycare center. If you need time for yourself, leave your husband with us. Packages, 1, 2, 3 pints available.”
It’s listed right under the Jameson sign, so it must be true.
Their bill of fare contains only two pages but is jam-packed with flavor and fun with plenty of Irish dishes and American favorites. Try the Irish egg rolls, boxty potato pancakes, shepherd’s pie, Irish stew, or the favored corned beef and cabbage.
The Ravenous Pig
James Beard nominated chefs James and Julie Petrakis have spent 16 years refining the customer experience at The Ravenous Pig. If you’re ready for a Florida twist, try the s’mores French toast (a thick, dark, brioche served with maple syrup, burnished marshmallow, and a dark chocolate mousse), pimento cheese fries, or fried chicken cordon bleu.
For a real treat, order the longboard of charcuterie that crosses the entire five-seat round-top table. Our server introduced us:
“Here we have soppressata, Saville Road cheddar, tête de cochon, and the lomo, the Toscano, and the camembert accompanied by a spicy IPA mustard as well as date jam, lamash, and salted walnuts.”
It’s impressive — a wine and cheese connoisseur’s dream.
Downtown Winter Park is close enough to downtown Orlando to make it an excellent day trip.
For more information on traveling to Florida, check out these articles: