Braden and I took a little anniversary trip to Boston last week, and it was exactly what we needed. We love to explore new places together, and eat a lot (more like a ton) of good food! I was excited about our trip to Boston, but I was really looking forward to our trip to Cape Cod. After being to both, it really is a toss up. They’re both wonderful in their own ways!

The morning we left for Boston, or initial flight from NYC to Boston was cancelled. Yay! Well, we decided to fly standby and hope for the best. We ended up running through the airport and actually making the flight before our initial cancelled flight. All in all, we got to Boston sooner than we would have originally. Win win! 

Our first day in Boston was spent exploring. We checked in to our hotel (Millennium Bostonian Hotel) that was located right at the heart of the markets, and walked everywhere from there. First stop, cross a lobster roll off the list! We ate lunch at Legal Seafoods and it. was. so. good! Soon after, Braden found his new love, the Cookie Monstah food truck. Yes, a food truck devoted to cookie ice cream sandwiches. Heaven! The rest of the day was spent napping and exploring, and eating some more.

We were exhausted from the 5am wake up and our flights, so we took a nap to get rejuvenated for the game that night. I heard a knock at the door, which turned out to be a little anniversary treat from the hotel. These people think of everything! They sent us a little champagne and dessert sampler, Braden was still sleeping, so I may or may not have eaten most of the desserts myself 🙂 

After we rested up, we headed to Fenway! I love baseball, but I sometimes get a little bored watching games. Not here. Even though it was misting most of the game, we had a blast! I got a Fenway Frank (those things are huge), we danced to Sweet Caroline, and loved every minute!

Day two started in Boston. Breakfast was first priority! Braden got a bagel sandwich from the Quincy Market, and naturally I got Starbucks 🙂 We hit up some shops and explored the markets a little more. After getting our rental car we headed to Harvard. I sadly didn’t take any photos there, and now I’m kicking myself for it! It’s a quaint little town and was much busier than I expected. From Harvard we started our drive to the Cape. We made it to our little B&B, which was so cute, and settled in. 

Our first day in the Cape can be described by three words:  relaxing, walking, and eating. It was raining when we first got to Chatham, so we made our way to a little coffee shop down the street to get a little treat. From there we walked the main street area and popped in and out of shops. The shops there are insanely expensive, so we did a little window shopping instead 🙂 later that afternoon we made our way to The Squire for an early dinner. After that, we went and saw Trainwreck at the tiny little town theater. It was an easy and restful day, for sure.

The next morning we woke up and had little breakfast in our apartment. We hoped in the car and headed to get coffee, from there we went to tour the Lavender fields not too far from us. Slightly disappointing, none of the lavender was in bloom, womp womp. We made our way back to Chatham and took a little walk towards the beach. I couldn’t get over the hydrangeas there! Literally as big as my face! They were everywhere, and I wish I could bring them all home with me! 

That night we went to dinner at a quaint little seafood restaurant that I sadly can’t remember the name of. It was delicious though! We made our second (or third) stop by Buffy’s Ice Cream Parlor, man oh man was it worth it! If you ever make it to Chatham, Buffy’s homemade flavors are a must-try!

Monday morning we made our trip back to Boston. I am so glad we took our trip full circle and finished up the trip back in Boston. This gave us a little more time to explore any places we wanted to see before we left. First stop, Modern Pastry for a cannoli and some sweet treats! We tried the traditional Cannoli and a creme brûlée. It was every bit worth the stop!

After checking into our final hotel, Intercontinental Boston, we dropped off the rental car and walked around the city. Our hotel was on a different end of downtown, which allowed us to explore some of the city we didn’t see on Friday and Saturday. We stopped in a few shops, and may or may not have stopped by the Cookie Monstah food truck again 🙂 we also got lunch from food trucks. I got a little greek salad, Braden had tacos.

Lots of walking happened this last day. We made our way back to the hotel once we started getting a little tired. Once again, nap time ensued. Well, it was more like rest time. I wanted to go for a run, so I made a trip down to the hotel’s gym. This place y’all, the view was insane during my treadmill workout. Afterwards, I gave the steam room a try. Just giving the steam room a visit made me feel like I had paid for a spa treatment, it was wonderful! I headed back up to the room and we got ready for dinner!

We wanted to celebrate our actual anniversary the right way, so we got all fancy and headed to dinner. Boston had just started their restaurant week, so the dinner menu was specially made for that occasion. We had a full 4 course meal and were absolutely stuffed afterwards. I’m talking calamari, clam chowder, delicious entrees, and desserts we couldn’t even eat! Luckily, that key lime pie went home with us and we ate it later that night!

If you haven’t experienced Boston yet, I highly recommend it! When we were planning this trip, I figured the Boston side of the trip would be more Braden’s cup of tea, and Cape Cod would be mine. After visiting both, I’d say that Braden and I equally enjoyed both cities. If we were to go back, we would definitely go back to Boston and explore areas we didn’t have a chance to see! We had a perfect balance of exploring and resting. So, I wouldn’t change a thing! Here’s to the wonderful start of year number three!