May 27

May 27 Anniversary Staycation 2026

This year, for our anniversary, we booked ourselves a little downtown staycation. We stayed at the Marriott Orlando Downtown, because it has a lounge and it was cheap. Our goal was mostly to relax, drink coffee, eat a couple of delightful meals, and then end the weekend with massages.

We started the weekend with dinner at Luca Turci in Winter Park on the way to the hotel Friday night.

To start, the chef sent out Parmesan with balsamic glaze, and we shared a Caesar salad. Then I ordered the lasagna, and Christopher had the tagliatelle with mushroom sauce. It was all so delicious.

For dessert, we ordered the tiramisu and then also sent out a glass of pistachio gelato as a little anniversary gift. It was actually a really great combo of flavors, and I might be tempted to try a pistachio latte next time I see one on a menu.

Saturday, we started the day with brunch at The Monroe. We had been to The Monroe for dinner before and enjoyed it, but brunch wasn’t our jam. It wasn’t bad, just not worth the drive and parking if we hadn’t been staying within walking distance.

We had mimosas because it was National Mimosa Day, and started by sharing a coffee flavored cinnamon roll, which we both really liked. I had the biscuits and gravy, which was good and Christopher had the chicken and waffles, which he didn’t like.

Next, we drank coffee around downtown for the day. We started at Qreate Coffee. We each had an iced latte. This coffee was our least favorite of the day, but the vibe was cool in the cafe. It’s smallish, maybe like 6-8 two-top tables.

After Qreater, we took the free downtown bus to the Lake Eola area to see the lake real quick and head to our next coffee stop, Deeply. This was my favorite stop of the day. I thought this was a perfect latte, and the space had a cute minimalist vibe.

On our walk to the next coffee shop, we stopped for a selfie at the Orange County Regional History Center, our wedding venue.

Our third and final coffee shop of the day was Stemma Craft Coffee. This was Christopher’s favorite latte of the day. Such a cutie place with comfy seats and a bright vibe.

It was starting to get rainy looking, so we decided to head back to the hotel and arrived just in time to miss the rain. As soon as we got to our room, it started pouring. We took a little nap before dinner at Kres Chophouse.

We love Kres. This was only our third visit, but we have never had a bad experience, and their steaks are some of our favorites ever.

We each had a cocktail and a filet, then we shared asparagus and potatoes, and creme brulee for dessert. It was perfection. We had a little bit leftover, which we obviously took home, and even leftover, it was delicious.

Sunday morning, we had breakfast in the hotel lounge, just eggs and potatoes and such. There was an omelette station, but the server wasn’t there when we were getting our food, oh well.

On the drive back toward home, we stopped at Bakery 1908 for the first time. We got a few pastries to try and, of course, coffee. The pastries were all super soft, and I loved the lemon filled one.