It's a Wicked Good Time: A Weekend in Boston

Joanna Shroyer
Sep 14, 2023
10 min read

Beacon Street through the Boston Public Garden

Heading to Boston is a highlight of my year. We've visited Boston for a weekend three times as a Destination Date. Rather than discuss each weekend separately, I'm going to give you the run down on the things we did and ate and the places we stayed in groups. All opinions are my own; this post is not sponsored in any way.

Each time we visit we fly into Boston Logan International Airport and use Uber to get around inside the city. Be warned, there is A LOT of walking to be done in Boston, so pack comfortable footwear.

Weather: I've been to Boston in January, December, and May. January and December required heavy coats. Think freezing, ha! Pack your gloves, hat, and a rain resistant coat. We've never let a little bit of weather stop up from enjoying ourselves and Boston is no exception. Think layers so you can add and subtract as necessary. We were there in early May, and I always wore long sleeves as well as needed a light jacket sometimes. I really rely on my weather app and pack accordingly. I'll also suggest investing in waterproof boots that won't kill your feet when you walk. I have a pair of Sorel Out N About Wedge Booties that are my go-to for the big city and walking. My feet stay dry and warm, and they are comfortable enough for all day wear.

Where to Stay:

The Liberty Hotel. A Marriott property, the Liberty Hotel is a national historic landmark that was originally the Charles Street Jail. I fell in love with the history and charm of this hotel. The rooms are gorgeously appointed and the beds comfortable. We loved the "Do Not Disturb" sign so much that we asked to bring one home! We only stayed here this

one time because we felt like everything was SO far away from it. If you have the time while you are visiting, think of adding this stop to your list of historic places to visit.

Onyx Boston Downtown (Hilton). I wish I could tell you this hotel was amazing, but it really wasn't spectacular. This is a very loud area of town and what this hotel has going for it most is that it is steps from TD Garden (more on this later). I will admit that we were there at the end of 2021 and the city had not completely recovered from COVID, so it is possible that I didn't get the full experience of staying in the area of town.

Hotel lit up at night — Marriott Custom House

Marriott Vacation Club Pulse at Custom House, Boston. We really enjoyed staying here! The building itself is fascinating as it is the original customs building where visitors were welcomed to the United States. I really liked that the ride share pick up area is not on a main street and it felt walkable to so many places. And, anytime I have a suite, I feel fancy, ha! The only thing we didn't love about this location is that the entire building is on heat or air. We were there during March and were unable to turn on the air in the room. The hotel did, however, provide a fan. I'd like to note that Vacation Clubs have different "rules" than do other Marriott properties, so keep that in mind when you book.

Places to eat:

Prezza. So good we've eaten there twice. Italian like you've never had before. Order the meatballs, Fish Stew, and a dessert sampler. You can thank me later. You seriously cannot go wrong here.

Basile - Fine Italian Kitchen. When I tell you that you've never eaten Italian unless you've eaten it in Boston, you should believe me. This intimate restaurant will make you feel like you've stepped into Italy. It was very dark in this restaurant, so I don't have any pictures of the food. The Pasta Bella Mare was delizioso and I would order it every. single. time. There was not a single dish on the table that wasn't extravagant. Go with the dessert tasting platter and an espresso to finish you off.

Mr. Dooley's Boston. Your classic Irish pub. Stop here before or after supper for live music and a feel for Boston night life: standing room only! We really enjoyed the Guinness Cheese Dip and Super Nachos as a pre-supper snack and, I went with the Dublin Fish and Chips for the main course. I wasn't disappointed. We finished our meal off with the Apple Crisp. Listen to me when I tell you it was on point.

State Street Provisions. I am all about some brunch on Destination Date. Stay out late. Sleep late. Eat Brunch. Repeat. We stepped into State Street Provisions and I was supremely happy. Warm, inviting and a great brunch menu. I went with the breakfast sandwich and coffee; I wasn't disappointed. Justin had the blueberry pancakes. While the pancake was good, the blueberry compote was a pour on. He prefers the blueberries baked in. Our travel partners for this trip ordered an avocado toast that looked amazing if that's your thing. All in all, a solid choice for brunch.

Tradesman Coffee Shop & Lounge . Recommended by a local the night before in Mr. Dooley's; always take the advice of a local. This cozy, eclectically decorated coffee shop was perfection. The pastries looked amazing and the coffee was on point. If I lived in Boston, Tradesman would be on my regular rotation. It shouldn't surprise me that I feel this way as their mission states, "Tradesman is built for comfort in hopes of being a habitual space to charge and recharge between home and the office." Imagine that.

Warren Tavern. Looking for a truly historic location for a meal? Head north to Charlestown, MA to the oldest tavern in Massachusetts. This was a stop on our very first trip to Boston, and I was really happy we made the trip. Be sure to reserve a table as this is in a residential area and is quite popular with the locals. You shouldn't visit Boston without eating at least one Lobster roll so why not have a local favorite in a historical location? I remember it being just as described. Just sitting in the building gives you all the vibes. Just imagine all the talk that went on in here before the Revolutionary War. I have to give Justin credit for choosing a location that was right up my alley. It was definitely out of the way to get to, but the destination was more than worth it!

Theo's Cozy Corner. Located in in the North End, this gem is cash only and well worth the trip. We stopped here for breakfast and were so impressed with the food and service. You'll be squished into a table with barely enough room to move and so close to the people next to you that you're part of their conversation, but that's what makes this place! Justin had the Corned Beef and Hash and I went with the Porto Wine French Toast. It was amazing and the portions were HUGE.

Blackbird Doughnuts. Artisanal doughnuts with a rotational menu that are handmade every day. There are seven locations throughout the city to choose from. We enjoy choosing local fare when we are traveling and this was perfect for a mid afternoon snack and coffee. Check out their offerings and stop in!

Mike's Pastry & Modern Pastry. If you read up on Boston, you'll find that there is a cannoli "war" going on between these two bakeries. Naturally, we had to try them both out and decide on a favorite. There might be a line, especially, at peak times, but trust me when I say they move quickly. The workers here are aware that they offer something the public wants and help to move things along. In order to do a proper tasting, you'll have to order the same thing at both bakeries. We ordered cannoli and lobster tails. I think Justin ordered a cheesecake at one of the locations. My advice, pick one and share, ha! In our case, it ended up a draw for the cannoli. I liked the pastry cream at Modern and the shell at Mike's. No one wins the lobster tail war but Carlos Bakery (iykyk). Neither of their shells or pastry cream could compete IMO. With all that said, it's a MUST DO on your first trip to Boston.

Mike's Pastry. Think pastry market. No tables no fancy lights. You'll stand in a Q-line that can be out the door and onto the sidewalk and be ushered to the next available server. Make your selection and they will box it up with bakers twine and send you on your way. The experience here is in the pastry itself, not in the location. Specializing in cannoli, you can get just about any kind you can think of!

Modern Pastry. Beautifully filled, lit, and curated bakery cases line the entrance as you enter. I genuinely want every single thing by the time I reach the counter. The line moves quickly and and may even be out the door. Get your pastries and beverages to-go or grab a table. Every time we have been here it has been SLAMMED, so we've always taken our food to-go. The atmosphere is electric and busy. I think you could get any kind of cake, cookie, macaroon, or cannoli your heart desires here. Modern is an experience.

Things to do:

Boston Tea Party Ships & Museum. Join the reenactment of the Boston Tea Party and learn about an important part of American History. Yes, it could be considered cheesy by some, but we really enjoyed it. Check out a replica boat and throw some "tea" overboard. I think this would be an especially fun way for kids to experience history. We walked up and purchased tickets on the spot; however, we weren't visiting during peak season. Consider planning your trip and purchasing tickets ahead of time; tours run every half hour. After your tour, you'll be ushered into the gift shop and Tea Room. Take the time to do the tea sampler! I really enjoyed "tasting" history.

Boston Public Garden & Common. Situated across the street from one another, these public parks are not to be missed. The Public Garden is America's oldest botanical garden! When we were here in May, the tulips were in full bloom, truly a gorgeous sight. The Public Garden is perfect for meandering and listening to street musicians. There is a large lagoon where the Swan boats run seasonally, statues, and fountains to see. Enjoy a stroll! The Common is America's oldest public park and is wide open spaces with a playground and seasonal ice skating.

Freedom Trail. Pick it up and put it down whenever you are ready as the trail is clearly marked with red brick throughout the city. The Freedom Trail is 2.5 miles long and free to use. There are paid walking tours you can schedule or use the free audio linked at the beginning of the paragraph to hear the history at your leisure. Want to see the Freedom Trail mapped out for you? It's here. Thank you to the National Park Service for doing all the hard work and providing these resources.

Boston Public Library. The architecture here is mesmerizing; I was in awe of the building. Tourists are common in the library so don't be nervous about going in. You know how in the movies the study room in grand libraries are full of students? That's EXACTLY how this library was. I was overwhelmed by the idea that I could be walking among our country's next great -fill in the blank-. Be sure to check it out.

ree — Emmanuel Episcopal Church of Boston

Newbury Street. Wander down Newbury Street for upscale shopping and architecture gazing. Be sure to check out the Emmanuel Episcopal Church of Boston and stroll into The Newbury Boston. Funny story about this hotel We were last in Boston in January. It was FREEZING. We had strolled around the Boston Common and needed to use the restroom. There are not a lot of public restrooms (and in my experience they aren't well kept) and it's customary to purchase food items when entering an eatery to use the facilities (which we weren't interested in). Next best option? A nice hotel. The Newbury is a gorgeous boutique hotel attached to the Tiffany's. SCORE. My friend and I headed downstairs to use the ladies room while the guys waited outside. When we got back to them, they inquired as to what took so long . . . well. When we got to down to the bathroom and got ready to handle our business, there was a collective sigh as our freezing bottoms encountered the heated seat. Without discussion we decided to just sit for a bit. Moral of this story? Visit the Newbury Boston before you head down the street.

Harvard. Just across the river from Boston is one of the most iconic universities in the country. We took a jaunt over there on our last trip to look around. Honestly? I wasn't impressed. I mean, the buildings are old and interesting, but the campus is not pretty at all. Maybe I need to visit again in spring. Should you make the trip be sure to snap your picture at Harvard Square and stop in at the Harvard Co-op to do some shopping. As a bonus when coming from Boston, you'll likely drive right by MIT and can say you've seen it ;). The most exciting thing about checking out Harvard for me? Finding the Blue Bottle Coffee.

Bruins. A little known fact: I LOVE professional hockey. The Bruins play at TD Garden which is a gorgeous venue that also hosts the Celtics and concerts. Be sure to check out the event line up before your visit. You never know what you might catch! Back to the Bruins. If you've never taken in a hockey game, it's a must do. Show up early, be sure to hit the pro shop, bring a coat -it's freezing in there-, and have a great time. Hockey is quick moving and exciting to watch. I know you won't be disappointed.

Faneuil Hall Marketplace. Shopping, dining, and entertainment with a backdrop rich in history. What could be more exciting? This is a great place to grab lunch during your wanderings through Boston.

Rose Kennedy Greenway. This beautiful park is worth the stop to take pictures at the gorgeous swings. Take a load off and swing a while.