Ross and I have been extraordinarily blessed to have family and friends visiting us throughout the time we’ve been back in Florida.

For Christmas, his sister Emily and her husband Ryan joined us, and we made the most of Disney’s options outside of the park.

Then my friend Danny visited me while he was in town (on vacation from New Hampshire), and soon my sister will be visiting too!

But since I’ve gotten to visit Winter Park twice now (once with my dad and his wife Karen, and once with my brother Robbie, his girlfriend Ria and Ross), I wanted to write about it.

Winter Park, Florida is a lovely part of Orlando, with charming streets, parks, museums and a railroad running through it all. It’s very upscale, and extremely walkable (a rarity in central Florida!), with restaurants and shops reminding me a bit of Cambridge, Massachusetts. Further explorations farther from the downtown area further confirmed the Cambridge vibe, as we found quirky vintage shops, music, gaming and an amazing ice cream shop. So here are some of the highlights we’ve gotten to experience. We look forward to more on future visits. Special thanks to all of the family who are really the reason we got to this part of Orlando!

The Charles Hosmer Morse Museum of American Art

Of everything I’ve done in this area, the Morse Museum is probably the destination I’d most recommend a trip to see. I’ve always found Tiffany’s work to be beautiful, but it was only in the fall of 2016, when we visited a museum in upstage New York with a Tiffany exhibit, that I realized how insanely gorgeous Tiffany’s stain glass work is. I’m just completely enchanted with it. The museum is a great place to spend a few hours, with audio and booklets to enhance your tour, two videos and the opportunity to step inside a recreated chapel from the World’s Fair and Tiffany’s recreated home, in part. It’s gorgeous and perhaps best of all? It’s free on Friday evenings! Tip: No food and drink are allowed, so leave them out of site or outside; and if you must wear a backpack, you’ll be asked to wear it across your front. 

Bosphorous Turkish Cuisine

Well, if you’re not into good food, you can skip Bosphorous. But this restaurant is really wonderful – it must be good if Karen, a dedicated foodie, was happy to go back when I suggested it as a lunch location! They have a Winter Park location and two Orlando locations, and they have wonderful gluten-free options, but be sure to read the gluten-free menu before you go (or pull it up on your phone) because they don’t have a copy available in the restaurant. I went with lamb shanks and the dark chocolate mousse!

Kelly’s Homemade Ice Cream

When it’s got homemade in the title, it’s time to try some ice cream! Seriously, there’s lots of homemade ice cream out there, but this stuff is very, very good and sometimes exceptionally so. Homemade ice cream is impossibly difficult to find in Orlando. Make a trip for this one. My full review is here. Don’t miss the vintage shop next door!

Mead Botanical Garden

If you need a place for a picnic or to take a walk or what have you, it’s hard to beat a beautiful botanical garden. Orlando has a few options that seem promising, but this one is free, and it’s awesome. Consider some bug spray, wear some sunscreen and go have an adventure.

Cybertron Video Games

Not my thing, but this place is retro and pretty awesome. Ross was in heaven here!

And finally, another place we enjoyed:

Le Macaron French Pastries

This little chain carries tasty macarons and

gelato from France. There’s also a macaron ice cream sandwich option, although the flavors are pre-made so you’ll have limited options. Great for gluten-free folks and gluten eaters alike. I wouldn’t go out of my way for this one necessarily, but if you’re craving gelato or a macaron, it’s a great spot. 

We’ve still got plenty of exploring to do in the greater Orlando area, and our time is running low, so we know we won’t be able to see it all. If you’ve got a recommendation for us or for others, please let us know!