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What to do in Winter Park, Florida

What to do in Winter Park, Florida

On our way to Disney World from Jacksonville, we stopped in Winter Park, which is located just outside of Orlando. This is such a gem of a town.

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Winter Park was chartered in 1887 as a place for wealthy families from the northeast to escape harsh winters. It’s large trees, lovely lakes, massive homes, shopping, restaurants, and one of the nation’s top liberal arts colleges continue to make Winter Park a draw today. It is about a half hour from the Orlando Sanford International Airport (If you live in the Grand Rapids area, we took a direct on Allegiant, but you can check out this and other flights for your exact dates here).

What to do in Winter Park, Florida

Along Park Avenue, there are about 5 blocks of shopping… good shopping. As in Pottery Barn, Restoration Hardware, Williams-Sonoma and cute, cute clothing store shopping.

What to do in Winter Park, Florida

Included in these blocks are also many lovely restaurant options. We ate at 310 and had really good food. I had the Mediterranean Salad and my mom ordered the Zucchini Flatbread— sooooo good! We also grabbed some coffee, muffins, and quiche at Barnie’s Coffee Kitchen. Again, the food was very good. The final night we sat on a covered patio overlooking a lush garden and green space at Hamilton’s Kitchen in The Alfond Inn. Again, the food was excellent. Their website boasts the restaurant “offering a distinct Central Florida culinary experience fusing locally sourced ingredients with the rustic, open-table charm of a bygone era”… It’s all true!

What to do in Winter Park, Florida

What to do in Winter Park, Florida

We also took the Scenic Boat Tour. It covered three lakes and all of the mansions one town could possibly hold. Fun fact: the tour guide shared that they have taken almost all (apparently there are one or two left) of the alligators out of one of the lakes. That’s one or two alligators too many for me! But, people were swimming in the lake and jumping from the boathouses. Brave souls.

What to do in Winter Park, Florida

As far as exercise, it is easy to run outside… well, if it isn’t too hot. I ran along the main strip and also around Rollins College down by the lake. It is a quick and easy way to get your bearings.

Speaking of Rollins College… Did you know… Sir Paul McCartney’s son went there? They have also produced Grand Slam tennis champions. And, of course, Rhodes, Fulbright, Goldwater, and Truman Scholars as well. And a Nobel laureate. Tuition is seemingly quite high.

What to do in Winter Park, Florida

Herein comes The Alford Inn (you can book here). First of all, it is gorgeous! Second, it feels elegant. Third, it also houses an Art Gallery. Fourth, you can eat at Hamilton’s Kitchen within its grounds. Finally, all proceeds go to scholarships. I was shocked when I read this. I never would have expected that such a luxuriously operated hotel would donate all proceeds to the college—now that is school pride!

What to do in Winter Park, Florida
Alford Inn Lobby
What to do in Winter Park, Florida
Alford Inn Rooftop Pool

And there you have it… go to Winter Park!

Not headed south until next winter? Here is a pin 🙂

What to do in Winter Park, Florida

One more thing… If you are wondering what to wear.. I wore these shorts from Target quite a bit (and still do at home) paired with a top similar to this from Ann Taylor.