A Weekend in Boston – Updated
I’ve been bouncing around the globe this past year. In October, the wind blew me into Boston. I’ve never been to the epicenter of the American Revolution. Everyone I’ve met who has lived or spent significant time in Boston has expressed a deep love for the city. An affordable flight, the call of fall foliage, and an open invitation to visit made me pull the trigger. After just a few days there, I was pleased to discover beautiful skylines, killer music, and scrumptious food. I even made some time to shop around. I returned again June 2019, which leads to a few awesome additions and updates in this travel guide to Bean Town. In honor of the 4th of July, I decided to give it an upgrade!
Where to Shop
I fell in love with quite a few items in one of three Lit Boutique locations. The store carries a healthy variety of retro inspired essentials from brands like BB Dakota, Paige, and Saylor. I tried on several coats and swooned over a few dresses. I didn’t have enough room in my luggage for anything big, but I did pick up a cute little beanie I’ll put to good use. With three locations, you’ll pass one eventually. Do yourself a favor and step inside.
I discovered Covet on Instagram long before I made the trip to Boston. The consignment shop fills its store wall-to-wall with a blend of high-end designer and everyday brands. If you’re hunting for a luxurious winter coat or a new favorite pair of denim, this is your spot. I walked away with a long black shearling vest I’m kind of obsessed with. It’s the perfect winter layering essential. They’re opening up a new location soon on Charles Street, so be sure to follow them.
This is the first boutique along a string I stepped into on Charles Street in Cambridge. December Thieves won best boutique in Boston according to the readers of Boston Magazine. The store carries a collection of emerging designers, everything with a bit of edge. Think one-size linen blouses, red mesh dresses, and cheetah print loafers. I stared for a while at the jewelry collection and adjustable purse straps with bold tiger head pins. This is where you’ll find a statement piece to take home.
This adorable store felt like it was put there to prep for a colorful vacation. I culled through fun woven earrings, brightly patterned dresses, and Ser Verde espadrilles. There is a nice blend of luxe European and American brands here.
I had to wipe a bit of drool from my face here. The employees there were hand picking Marc Jacobs, Chanel, Gucci and Celine dresses and sunglasses for customers like me. I helped myself to a few touches and poses in the mirror. The collection here is truly curated and the experience is personal. I’d like to spend a long afternoon here trying everything on.
This little girly slice of heaven was cutely organized with a kinds of items I felt drawn to, including a Solid & Striped swim suit, Gorjana classic gold hoops, and jumpsuits. They carry well known brands like Citizens of Humanity, Alice & Olivia, and BB Dakota (a personal favorite).
I’m super mad I didn’t return to this boutique for a pair of earrings I loved. Delicate earrings and rings dotted the walls and counters of Soodee. The boutique also carried a large selection of special occasion dresses. The sale rack had some adorable, wearable everyday summer gems on it, too!
Most of my jewelry is vintage. I couldn’t even handle all the goodness in this store. It’s jewelry cases, walls, and counters were jam packed with vintage and modern finds. A literal Sweet Sauce heaven. I also overheard a woman who was having a vintage piece modified by the jewelers. I was incredibly impressed with the knowledge and the selection.
Back toward downtown, I stumbled into an open air bookshop. Actually, it was the backyard of the Brattle Bookshop, which has two floors of used books and third floor of rare and antiquarian books. I found a wide selection of $3-$5 books from Lena Dunham’s book to WWII chronicles. Brattle is one of America’s oldest and largest used book shops.
What to Do
Firstly, I learned it’s Boston Common not CommonS. The park without an S is a central public park in downtown Boston. The rolling hills and nooks of this green space played an important role in nearly every major American war. Today, there’s always something happening. We stumbled upon a family festival, a few historical tours and people from all walks just chilling, feeding the ducks. Take a stroll through here at the least. At the most, bring a picnic and stay for the afternoon and watch the sunset.
If you’re into books, or maps, or both, take a while to meander this historic spot. It’s full of surprises the more you wander. If I had stayed an extra day, I would have posted up here in a corner to knock out some work.
This may very well be my favorite part of the trip. It may have taken the longest, too. It’s all about the view here. Sail boats and yachts dot the horizon as planes float out from the airport to the east of the city. Along the way, you’ll stumble on a range of marinas, restaurants, food trucks, museums and historical reminders of the city’s place in our country’s past.
I’ve loved going to Sofar Sounds shows in Richmond. It wasn’t until this trip that I realized seeing a Sofar show in a new city is a great way to get to know locals and discover new music. Boston has shows every week, and then some. If you aren’t familiar with Sofar here’s a run down: You pick a date and time for a show to attend. You don’t know the location or the bands until the day of the show.
See Boston from a Boat
It was truly a moving experience to get out into the harbor on a boat and appreciate the city and it’s skyline from afar. If you don’t have a friend with a sailboat or whaler, there are plenty of options. I found a really straight forward guide to boating in Boston via Boatsetter, which has maps and links to boats you can rent. For a more athletic take, Boating in Boston rents kayaks, paddle boards, and the like. For sunset tours on sailboats, the famous water taxi and epic adventures on Codzilla, check out Boston Boat Tours.
Where to Eat
My friend who lived in Boston for years had only one recommendation for my visit: have dinner at Eastern Standard. I’m so glad I listened. I linked up with some old friends and indulged in a scrumptious meal that started with raw oysters and ended with one of the bartender’s takes on a Manhattan that I loved. In between were entrees passed around between each other. Each of us shrugged in overwhelming satisfaction at every bite. The vibe was chic and sophisticated.
I spent my first dinner here during my most recent trip. Sushi, wings, skinny margs, and more passed our lips. There are two locations in Boston, both are huge and beautiful. Our crew slipped into a cushioned corner booth. The bar was full of Boston’s finest on a Friday night. Poke bowls, Thai Lobster salad, and Impossible Burgers are a few other menu items that caught my eye. I’d say this is a bad ass place to start the night with cocktails or shared appetizers.
This was a random find thanks to Yelp. The two-story bookstore holds a little secret on the first floor: a counter-service restaurant that serves everything from classic breakfast items to quinoa bowls and healthy smoothies. I really loved this concept and left totally satisfied. If I had more time, I would have wandered around and picked up a few books and candles to take home.
There are a lot of restaurants boasting the best seafood in this harbor town. If you’re here for the lobstah, opt for something low-key during the day, especially if you’re planning a walk along the water front. James Hook is a total classic. We ordered lobster rolls and crab cakes to go from the small trailer and took them to enjoy outside. It was a simple, but fresh and filling lunch. The little courtyard outside is perfect for an afternoon in the sunshine.
If I had more room in my suitcase, I’d fill it up with these gourmet nut mixes, chocolates, dried fruits and nut butters. I was drawn into this snack haven by the scent. I was surprised at how far back it went and how large the selection was. Everything is hand-roasted in small batches, so you know the flavor is rich and pure. I’m surfing online to see what I can send to myself home.
This discovery is in the Cambridge area. If you’re into healthy and organic foods, this is a must visit spot. It took me and my friend 30 minutes to even choose what to eat. In the end, I ordered The Lover bowl and a matcha latte with bee pollen. It was a fun and healthy brunch alternative after a night of drinking.
Quincy Market may pull you in to eat, but it felt a bit too hectic there for me to enjoy anything I found. I walked to the Boston Public Market instead, which is an enclosed selection of vendors and restaurants serving up small bites to full meals. I stepped out of there with some freshly roasted pecans and a savory crepe.
Where to Drink
You can enjoy Lord Hobo beer and its concepts a few places in the Boston area. We stopped into the Lord Hobo Beer & Bar in Cambridge for Bloody Marys (hello jalepeno-infused Vodka) and breakfast sandwiches. Outside of the city in Woburn is ground zero and a Mecca for straight chillin, Lord Hobo Brewery. Fine beer and high quality bar food fill up the tables surrounded by good friends here. I tried a few of the beers (gave GF life a pass for the day) and liked the Godmother Stout and Hazy Boomsauce. Everyone is different, though, so get a flight to be sure. Do yourself a favor and balance the booze with an order (or two) of the wings and lobster rolls while you’re there.
This was a surprise find on our way out for an evening. We found a jazz trio remixing classics like “Drunk in Love” and an attentive and knowledgeable bar staff. Dim lights and leather seats elevated the experience. Boston Common Magazine named the bar for having the best “Bespoke Cocktail.” The bartender made my a super special twist on a Negroni, topped with a orange peel twisted into a rose. We were happy here for quite some time.
Boston Seaons Patios at City Hall Plaza
This one is just for the summer months. Margaritas, spiked seltzer, and local beers from dot the happy hour menu here. The dog friendly patio is located in City Hall Plaza, which overlooks one of the most trafficked areas in the city, full of street performers and energy. Be sure to try your hand at the mini putt putt challenges dotted around the patio. You can also grab bites from the adjacent gazebo and periodic appearances by food trucks.
Where to Grab a Cup of Joe
There are several Cafe Neros around town. Head to the one downtown for the atmosphere, perfect for a meeting or to get work done. I found a perch on a second-floor platform overlooking the restaurant. I loved the view and privacy. I snagged a mediterranean salad and simple drip coffee and plugged in my headphones for a few hours of work.
I found Tradesman by simply following Yelp reviews around town. On a Monday, I had several hours of work to crush. I needed somewhere with space, a variety of food options, and good energy. I stopped into a few other coffee shops before I settled into Tradesman. The staff was sharp and attentive. The sunlight poured in all day and lit up the deep wood and brass decor. Meetings swirled around me as I typed away. It was the perfect place to create.
This is one of the larger coffee shops I discovered. I had a hard time finding shops that weren’t packed. It’s just down the road from Boston Common and the waterfront. The cafe has won all kinds of awards and serves up Stumptown Coffee, which is the new holy grail of caffeine beans. I learned that in Portland. I enjoyed a gluten-free cookie, which is a rare find, and caught up on work for several hours here. There’s no wifi, fyi.
If you haven’t learned by now, I kind of live and work in coffee shops. Here’s another discord in Bean Town. It is located right next to the downtown location of Mike’s Pastry, a famous pastry shop. I sat and worked for a few hours here and watched friends meet up and slowly indulge in desserts, hot chocolates, and lattes. It has a distinct Italian ambiance. It’s apparent the decor hasn’t been updated in years, which is just right.
Where to Stay
Located right downtown, The Godfrey’s rooms were big, the bed was one of the more comfortable hotel beds I’ve slept in, and the staff was sweet. Also in the hotel you’ll find George Howell’s Coffee Shop (won best in Boston, too) and Ruka, a sushi bar. We kicked off both nights at the bar downstairs with the bartender, Christian. It was in walking distance to everywhere I needed to go for the weekend, with the expect on of Woburn.
Boston Travel Tip
Flights are pretty cheap to Boston in general. I checked from a few different airports. I use Skip Lagged to keep an eye on the most affordable times to travel. I found round trip tickets for about $200 for both of these trips. I’m seeing $150 for July right now. I’m looking forward to my next visit to escape the southern heat.
