Last week Marc and I went up to Boston for a quick two-night stay. Our entire time in the city was about 50 hours, so there wasn’t a ton of room for fun! But we still managed to enjoy ourselves.

I lived in Boston for almost four years back in the mid-2000s and while I knew the city extremely well then, so much has changed in the 11 years since I left. It’s always a little strange to walk around a city that was home for so long but now seems like a complete stranger.

Marc kept asking me what it felt like to be back, and I wasn’t entirely sure how to answer. In some ways it felt like a completely different city to which I had no connection, but in others it was like I was taken back in time.

I was 25 when I moved to Boston and almost 29 when I left. Those were some pretty formative years. I like to say Boston is where I grew up professionally. I learned so much about myself while living and working in that city, and in many ways, it shaped who I was as I continued my TV career.

But it also was a time when I was completely alone. Boston is a tough city to crack when you’re an outsider looking to make friends or date. So many of the people who live there are from there and have their own social network seemingly built in. It took me a few years, but I finally made some great friends of my own.

As for the dating aspect, that never quite clicked. Sure, there were several love interests but nothing that ended up being real, and that was tough to take at the time. As we walked around the neighborhoods I used to frequent, I could actually remember the painful moments vividly as we passed the spots where they happened. Like the time I met a totally amazing guy at a bar only to be told at the end of the night that he “kind of” had a girlfriend but that they were breaking up. So, imagine my surprise when I was in a store on Newbury Street the next day and saw him walk in while the girlfriend waited for him outside.

Or, the time I was so excited about a guy who I thought I was going to start dating only to be essentially stood up by him repeatedly over the next few months. As we walked past one of my favorite restaurants (that’s still there) I could see myself sitting at an exact table with girlfriends as we plotted what I would wear for the first date. A date that never happened.

Overall, I absolutely love Boston and my time there. But I was a bit surprised by the types of memories and feelings that kept rushing back. Maybe it’s because Marc was there and for the first time, I was able to experience Boston while with someone else.

Our reason for being in Boston was not necessarily a fun one. Marc and I are dealing with some personal things that needed to be sorted out as we prepare for our future together. One day I hope to explain in more depth, but for now, we’ll keep that to ourselves.

The good news is that we finally received the information we so desperately needed and were able to head back to New York with a plan for moving forward.

Okay, now to the fun stuff! Because the trip was so short we didn’t have much time for anything, but we did have to eat and sleep. So, here is a rundown of where we stayed and dined.

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WHERE WE STAYED

Fairmont Copley Plaza—I have loved this place ever since I lived in Boston and always hoped to one day be a guest. So, I figured why not now! It’s a classic Boston hotel that has been around for over 100 years. It’s located right in Copley Plaza, which is a great central spot. We were able to walk to Back Bay, South End, Beacon Hill, Downtown, and to both the Common and Public Garden.

But the best part? They have a hotel dog! Her name is Carly Copley and she is the most chill black lab you will ever meet. She greets guests at the front door wearing a bow tie and is absolutely adorable. Let’s be honest, she’s the real reason we stayed here!

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WHERE WE ATE & DRANK

Met Back Bay—We arrived in Boston around 3:00 on Tuesday afternoon, too soon for dinner, but too late for lunch. After walking around Back Bay for a bit Marc had just one request, a beer. So, we headed down Newbury Street in search of something with outdoor seating and stumbled upon the Met Back Bay. It was a different restaurant when I lived there, but the outdoor patio was the same, so we gave it a shot.

In order to sit outside you have to order food so we got a couple of appetizers to hold us over until dinner, along with a couple of drinks each. It was a nice place to sit on a beautiful afternoon.

Drink—This bar was recommended by multiple people and we were not led astray at all! Above Drink is the restaurant Sportello (described below) so it was suggested we have a cocktail downstairs and then head upstairs for dinner.

The coolest part about Drink is that there are no cocktail menus. The bar is set up in a long and winding row, so everyone has easy access to the bartenders. This is crucial because all of the cocktails are bespoke. So, you tell your bartender what you’re in the mood for and a few minutes later he or she presents you with a custom drink.

Marc asked for his go-to, something sweet and tropical, and I asked for some version of a spicy margarita with a little hint of fruit and no smokiness. The result was delicious! We were both very happy with the result! We definitely would have had another but we had to get upstairs for our dinner reservation.

Sportello—This Italian spot had a relaxed and laid-back vibe but also served up some serious dishes. And the prices were not extravagant. Since we had some light bites in the late afternoon, we just shared an appetizer and each ordered an entrée. It was more than enough food and also really good.

Stephanie’s on Newbury—Okay, so no one actually recommended this spot! But I had to go there. When I lived in Boston we would come here for brunch all the time. Mainly because they have a huge outdoor patio right on Newbury Street that was great for enjoying the nice weather and people watching.

As soon as I saw that it was still there I immediately dragged Marc over for lunch on Wednesday afternoon. Just as I remembered, the food is good (nothing spectacular) and the outdoor seating is great. We both just had a simple salad, so no complaints!

Citrus and Salt—This was by far our favorite spots and one of the best meals we have had in a while. This was also a recommendation I received on my Instagram stories and I’m so grateful for the heads up!

I tried getting a reservation the day of but they were booked up until late so we decided to just show up and see what we could get. They told us it would be about an hour wait but that we could also eat at the bar. There happened to be two open spots at the bar so we decided to eat there.

First up, the cocktails. In addition to having fun names, they were fabulous! It’s a Mexican restaurant so think various versions of margaritas, mojitos, and tequila-based drinks. I had the Tequila Is Cheaper Than Therapy and it was fabulous.

The food was also amazing. You have to get the guacamole. And try it with the regular chips instead of the tortilla chips for something different. We finished the first order and immediately asked for a second!

Most of the food is meant to share, which is a great excuse to try a bunch of things. We weren’t disappointed with anything and especially loved the Carnitas-Style baby Back Ribs. SO good!

OAK Long Bar and Kitchen—This is the bar in the Fairmont Copley Plaza. We didn’t eat here but did have a cocktail before catching our train back to New York. Much like the hotel itself, it’s all about old school elegance. They have outdoor seating during nice weather, but we stayed inside and enjoyed the comfy couches. It wasn’t anything wildly exciting, but a nice spot to enjoy a glass of bubbly as we celebrated a successful trip.

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