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Most visiting Florida think of sandy beaches, busy coastal cities, or a vacation with Mickey Mouse in Orlando. Pristine lakes and old-fashioned charm don’t typically come to mind. So when we heard about “Winter Park”… well …we had to explore this winter haven in the state of endless summer! Not to be confused with Winter Park in Colorado for skiing.

Part of Orlando Kissimmee Florida, Winter Park is just minutes outside of busy Orlando with a completely different, owith historic vibe, a live-oak canopied chic downtown and great old-Florida feel!

Winter Park was founded as a resort community by New England business magnates in the late 19th and early 20th centuries. Its main street, called Park Avenue, strolls elegantly through the middle of town, drapped with beauitufl mossy trees. Park Ave connects upscale art galleries and boutiques, to the private liberal arts college (Rollins College), and museums, a pretty green park with peacocks, a train station, nearby golf course country club, historic cemetery, and a beach and boat launch.

A little Winter Park history:

Chester A. Arthur reported that Winter Park was “the prettiest place I have seen in Florida” as 21st president of the United States, in 1885.

In 1904, Charles Hosmer Morse became the biggest landowner in Winter Park. His patronage continued in the 1920s, when he purchased a 200-acre parcel, where he kept peacocks – now the city seal and mascot.

Mister Rogers went school in Winter Park at Rollins College, 1951 where he acquired his degree in music. A beautiufl statue of “everyone’s favorite neighbor” and his TV show characters is the centerpiece of the liberal arts college campus.

Winter Park is one of the wealthiest communities central in Florida, home to many old-money families, million and billionaires living along the waterfront of the chain of lakes.

1972, Henry Swanson, an agricultural agent and “resident layman expert on Central Florida water,” publicly warned mayors of sinkhole danger here from overdevelopment and excessive groundwater use. Swanson predicted thatWinter Park would be especially at risk. In May 1981, a massive sinkhole opened near Winter Park’s Denning Drive and Fairbanks Avenue.

Winter Park Sidewalk Art Festival is one of the nation’s oldest, largest juried outdoor art festivals

Fun things to do:
Definitely take the Scenic Boat Tour 10 – 4 on the hour. First come/first serve. $20pp.
At 312 E Morse Blvd, at Dinky Dock Park, just outside of downtown.

Rent a Kayak or Paddleboard to explore the lakes from Dinky Dock Park. Explore the Venetian Canal which connects Lake Osceola to Lake Maitland, the longest canal. This then connects to Lake Maitland and on up to Howell Creek Fern Canal – and Lake Osceola. From here you can glimpse beautiful Albin Polasek Museum and Sculpture Garden from the lake, a popular park and event weddign venue. Fort Maitland Park connect through more canals to Lake Maitland and Lake Minnehaha. The possibilities are endless to paddle by pretty homes on peaceful waterways.

Charles Hosmer Morse Museum of American Art is a fantastic Tiffany glass, lamp, jewelry and art display – the largest collection in the world including Tiffany’s incredible chapel reconstructed here.

Kraft Azalea Gardens is a wonderful short Bike Ride from downtown Winter Park, esepcially spectauclar when in bloom.

Rollins Museum of Art – part of Rollins College – has an amazing art collection. Also visit the Mister Rogers statue in the heart of Rollins’ campus.

Where to Dine & Drink, Sip & Savor in Winter Park
AVA MediterrAegean is a very chic location and delicious high end cuisine, make a res, sit back and enjoy the the theatrical dinner presentation!

Prato is in the heart of town on Park Ave, with a great bar, delicious Italian food, flatbreads, burgers, pasta, Italian. Servers are great, and when teh patio doors are open tot he sidewalks its a sublime bistro atmosphere with locals luncing, sipping and gissiping.

The Ravenous Pig is a 10-minute walk from downtown Park Ave, but worth it. Excellent food, best kale salad, crab and corn beignets, delicious oxtail pasta, wonderful creative cuisne in a humble but convivial spot.

The Wine Room on Park Avenue has a happy hour, and you can tap your wine from the vast selection of vineyards with a card tasting system. Good flatbreads here too.

Lots of great happy hours in Winter Park all along Park Ave Monday- Friday

Fabulous shopping along Park Ave, so many high-end ladies and men’s clothiers, from traditional to fashion forward like Tuni and Savannah Taylor dress shop!

Where to stay in Winter Park
The Langford Hotel served as a gateway to “Old Florida” as a grand old hotel. Now the refurbished 2014 Alfond Hotel, which funds local scholarships to Rollins, is full of $30 million in artwork. Great place to stay, beautiful rooms, gracious bars and living spaces, a short walk from Park Ave.

Park Plaza Hotel on Park Plaza has a prime location and gracious balconies with hanging plants over the main street. Rooms are dated, but the prices and location are right.