Winter Park, Florida | Been There, Seen That

Regards for the New Year. Back to posting four days into 2026, maybe with tales of Florida alligator tourism. The change of the year always brings me the same reaction: how did that number get so high? This time around, I wonder how is it that 1976, a good (mostly) year I remember fairly well for a number of reasons, was 50 years ago?

Orlando, Yuriko was surprised to learn, is an actual city. The day after Universal Epic Universe, we drove from our hotel near that park, past Orlando’s sizable downtown, and to the inner suburb of Winter Park. She marveled that the city had a presence besides the sprawl of the theme parks, which are at some distance from the Orlando CBD. Bet she isn’t the only person, upon leaving the theme park zone, with that reaction.

One could devise a pretty good multi-day visit to Orlando, to see its green spaces and historic sites and museums, and take in a few shops and restaurants and some live music, and never pay the Mouse or Comcast a dime. Maybe one day I will do such a visit, but the pull of the theme parks is pervasive. Even my businesses trips of yore (early 2000s) to central Florida tended to gravitate toward the parks. Why would you skip the theme parks? would be the reaction, even — and most importantly — among members of my family. For now, part of a day away from the Theme Park Industrial Complex will have to do.

I’d gotten wind of a tour boat ride on Winter Park’s small lakes that (1) wasn’t expensive and only about a hour long; (2) didn’t require reservations or a damned app or the like to access; and (3) most importantly, was something we could do sitting down, after a day of walking and more walking.

We made it for the noon tour. December 10 was as warm and clear a day in Winter Park as you could ask for, a reminder of why a couple of Victorian businessmen were able to found a town in central Florida and attract wealthy property buyers who aspired to escape the frozen North for a few months.

Our skipper for the tour.

Skipper Bob, let’s call him. He took us from the tour-boat dock on Lake Osceola through a couple of canals to Lake Mizell and Lake Virginia and then back, pointing out some of the posher estates and landmarks along the way, such as the posh boat houses that tend to come with such properties.

Bob also offered up some detail about the history of the area, most of it unfamiliar. I didn’t know, for example, that Fred Rogers was an alumnus of Rollins College, which occupies a sizable chunk of the Lake Virginia shore. I also learned that the college, even in our age of grossly inflated higher-ed tuition, outclasses most others in its high cost.

Out on the lakes, Bob revved up the engine from time to time, spurring the boat forward at a good clip. Wind famously blows long hair into a pleasantly billowing mass at such times, but under the warm sun and blue sky that day, even my shortish hair was picked up by the wind. Felt good.

I liked the passages through the canals. I don’t think I was alone in this.

and offering up some detail about the history of the area, most of it unfamiliar. I didn’t know, for example, that Fred Rogers was an alumnus of Rollins College, which occupies a sizable chunk of the Lake Virginia shore. I also learned that the college, even in our age of grossly inflated higher-ed tuition, outclasses most others in its high cost.

In most of the rest of the country, winter had arrived. In Winter Park, named for the season it is most unlike, you can pass through the tightly packed greenery luxuriating in warm air.

You’re up close to the yards of more modest, but still high-value real estate. Everyone’s got a dock.

The vantage means views of the canopy above.

After the boat tour, we walked a few pleasant blocks along Morse Blvd., away from the lake. This handsome church, First United Methodist, didn’t look open. Too bad.

The city is fond of its peafowl, I understand.

The downtown shopping street in Winter Park is Park Ave. On one side of the street are the likes of Bosphorous Turkish Cuisine, Williams-Sonoma, Ocean Blue Galleries, D’Anne Mica, Fannie Hillman + Associates real estate, Current by John Craig men’s clothing, The Imperial on Park wine bar and Be On Park Fine Jewelry. Life Is Good (registered trademark) products are available on the street.

the shopping side of the street are the likes of Bosphorous Turkish Cuisine, Williams-Sonoma, Ocean Blue Galleries, D'Anne Mica, Fannie Hillman + Associates real estate, Current by John Craig men's clothing, The Imperial on Park wine bar and Be On Park Fine Jewelry. Life Is Good (registered trademark) products are available on the street.

Across the street from the shops is Central Park. The developers were out, I think, to remind New Yorkers of home, but without the likelihood of snow or ice or blizzards like in ’88.