Here are some pictures from that trip.
Park Plaza Hotel on Park Avenue. Our balcony suite is just above the street light.
The Wine Room also had some really good "small plates" to mellow out the wine buzz.
Suggested dining options:
Park Plaza Gardens: good food with a lively bar scene. The Sunday brunch with non-stop mimosas is not to be missed, and the restaurant can be accessed through the hotel. In the Cafe , try the Prime Rib French Dip. We did on our night of arrival, and it was excellent.
Croissant Gourmet: a great breakfast stop with French pastries and really good coffee. In addition to pastries you will find hot and cold sandwiches, salads, and specialty quiches.
310 Park South: for lunch there were good soups, salads, sandwiches, plus a superb wine and beer selection. The dinner menu looked good too, but we weren't in Winter Park long enough to eat everything everywhere.
Bosphorous Restaurant: the lamb chops were very tasty and if we had been in Winter Park longer I would have dined there again. I now know the proper pronunciation of raki and it got easier to pronounce after the second or third raki. This establishment also has some pretty tasty Turkish wines.
There are many other restaurants that we would have tried if we had stayed in Winter Park for a few more days.
Winter Park is an excellent long-weekend destination and Amtrak got us there and back for $44 total. The trip is about two hours each way. The Tampa to Winter Park train departs Union Station around 5:45 in the evening and the return from Winter Park leaves around 9:55 in the morning.
Oh yeah, the club car is another perk.