City Guide

A Weekend Guide to Boston


Jered surprised me for my 26th birthday with a little weekend getaway to Boston! It was such a relaxing {and cold} trip. It’s also soooo hard for anyone to surprise me…hello control freak, so I don’t know how he manages to pull this stuff off. Plus it’s probably the most stressful thing ever because he knows how serious I am about my planner haha. But nevertheless, I eventually realize that my to-do list can be done later, and that going with the flow is good for the soul

Neither one of us has ever really explored Boston and didn’t know what to expect, especially since living in NYC. But- we LOVED it! It was beautiful, with a ton of history, less cigarette smoke than NYC lolol, less people, and so many cobblestone streets. I always forget just how beautiful New England is. Here’s a little guide for our weekend in Boston. Most of the places we went to were recommendations from Boston friends, locals, and friend’s that have been before.

**This has been updated since our first weekend here! We’ve been back several times, so I’ve added a few more places :).

xx -♡Kait




Flour Bakery & Cafe: Their lunch is simple but so warm!! I went with a soup and salad. The breakfast here is good too. And don’t leave without getting dessert. More on that later, so read on ;).

Tatte Bakery: The best shakshuka in the entire world. I dream about this dish. This is a European style cafe, so you’ll probably find their pastries tend to be less sweet, but still perfect with a cup of coffee!

Coppa: Ahhh so much to say about this place. The meatballs, pizza, and zeppoles are musts! I’ll just leave it at that.

Neptune’s Oyster:  Expect a wait! Pretty much everyone who walked in knew the wait would be 1-3 hours. We got this tip from a friend (thanks, Lex!)–> Go around 11ish, put your name in, and walk around North End. What to order?! Lobster rolls hot and buttered.

Bricco: One of the most delicious pasta dishes I’ve ever had. It’s located in the North End (Little Italy), and definitely authentic/homemade pasta. The smell when you walk inside is unreal . I recommend the Pappardelle al cinghale dish and the shrimp scampi appetizer.

Lolita’s: So cool…has this Ed Hardy/Day of the Dead vibe. This place is all about experience. I recommend getting there a little early if you’re going for dinner. Their margaritas are next level YUM. They give you a complimentary dry ice tequila slush as a palate cleanser and top the meal off with complimentary apple cotton candy with pop rocks. My only regret was not ordering the nachos.

Carmelina’s: Delicious, authentic Italian food. I loved the stuffed pasta shells. The line is often long, so I recommend making reservations well in advance or walking in and adding your name to the waitlist around 4:30-5pm. We chose this place because it was one of the highest rated Italian restaurants in the North End.

Capo: I went here during a girl’s trip to Boston and loved it. The atmosphere, drinks, and food are so good. I also liked that you could order half orders of entrees. There’s a fun little bar area downstairs if ya fancy some post-dinner dancing.

Frenchie: Definitely a gorgeous, photogenic restaurant! They use local and sustainable ingredients. Highly recommend the Nutella crepes or French toast for brunch.


Tatte BakeryTatte Bakery
Flour BakeryFlour Bakery


L.A. Burdick: Grab some hot cocoa and do a little shopping along Newbury St. in Back Bay. Soo rich! I recommend going with the smallest size LOL. I really loved the milk hot chocolate- tasted super rich, so can’t even imagine how rich the dark was! Their hot chocolate mocha is AMAZE.

Curio Coffee: Counter Culture Coffee and Liege waffles. So pretty. So good.

Crema Cafe: Located in Harvard square, this spot has excellent cappuccinos and delicious small bites like tomato soup with homemade bread.

Cafe By Salon: A super cute neighborhood showroom, furniture shop, gallery, AND coffee shop! Great spot to pop in when you’re walking around Beacon Hill. The mugs they use are so unique and it’s very picturesque.


LA BurdicksLA Burdicks
Cafe by SalonCafe by Salon
Cafe by SalonCafe by Salon
Cafe by SalonCafe by Salon


Modern Pastry: I had tons of people recommend Mike’s Pastry for cannolis. But then heard from a blogger friend that locals told her to go to Modern Pastry instead. Well…I was curious and tried both- I mean they were literally a block away from each other, so why not?! Hands down Modern Pastry wins. It was smaller, but more fresh. Everything about it was better. The classic chocolate chip cannoli is great, especially if you’re wanting something a little more authentic.

Flour Bakery & Cafe: Their sticky buns supposedly beat Bobby Flay’s, so of course, I had to to try. HOLY. Just get it, even if it’s just to try a bite. The sticky bun is like a honey bun mixed with a cinnamon bun mixed with pecan pie. Also beware—this is not to be confused with their sticky bread pudding.

Fomu Ice Cream: Plant-based ice cream and treats. Rich and delicious with unique flavor options like Maple Sweet Potato Pie Ice Cream with chunks of marshmallow.

Honeycomb Creamery: Locally sourced homemade ice cream. They have both dairy and non-dairy options. The seasonal flavors here are EVERYTHING. It’s located between Harvard Square and Porters Square, along Massachusetts Ave.


Mike's PastryMike's Pastry
Modern Pastry- so much more freshModern Pastry- so much more fresh
Flour BakeryFlour Bakery
Union Square DonutsUnion Square Donuts

Things to Do

Newbury Street: We loved this area! All the shops are in stunning brick townhomes. There’s a Chanel, Anthropologie, restaurants, Pressed Freeze, L.A. Burdicks, and lots of other shops. Perfect location and right in Back Bay.


Newbury Street ShopsNewbury Street Shops
Boston Public Market in North EndBoston Public Market in North End

Fenway Park: It was really cool getting to learn about the history behind Fenway Park. Jered loves baseball and played in college, so he probably liked this more than me.

Isabella Gardner Museum: Highly highly recommend! The courtyard is lavishing. It houses an art collection of world importance, including paintings, sculpture, and other decorative arts.

Quincy Market: Definitely a touristy spot, but fun to walk through and right in the North End area. There’s cute booths, lots of food options, and Reginas Pizza (which tons of people recommended!).

North End: Boston’s Little Italy. We spent a lot of time here trying out restaurants, strolling through the Boston Public Market, and taking pictures. Loved this part of Boston.

Greenway Carousel: Great place for kids, adults, and Instagrammers. But seriously…it’s a really cute carousel and makes for some stinkin’ cute pics. Located near North End.


North EndNorth End

Boston Public Market: One of the best donuts I’ve ever had was from Union Square Donuts. Amazing. There’s coffee, flowers, seasonal teas, fresh fruits/vegetables, and goods from local purveyors. They also had an apple cider bar with slushies and you could order different flavors- hot, cold, or sparkling.

Public Garden: A mini Central Park. Go across the bridge and walk through the other park. You’ll meet the friendliest group of squirrels that’ll eat right out of your hand!


Public GardenPublic Garden
Walking through North EndWalking through North End
Public GardenPublic Garden

Beacon Hill: If you walk to the North End, you’ll most likely pass through Beacon Hill. We walked here from the Back Bay and saw so much along the way- also made the walk to North End pass by fast! You’ll see beautiful streets like Chestnut St, Charles St, and Lime St.  The most photogenic? Acorn Street. It’s all cobblestone with lovely row homes. If you visit when it’s cold, chances are there will be way less people, perfect for pics!

Back Bay Area: SOOO beautiful! Highly recommend strolling through Marlborough Street and looking at all the gorgeous homes.

Harvard Square: Lots of coffee shops, cute flower shops, the dreamiest Anthropologie…and the obvious- Harvard University.


Acorn StreetAcorn Street
Bay Area-Marlborough StreetBay Area-Marlborough Street
Back BayBack Bay
Beacon HillBeacon Hill
Beacon HillBeacon Hill
Harvard SquareHarvard Square
Harvard SquareHarvard Square

Where to Stay

Fairmont Copley: I stayed here with girlfriends the second time I was in Boston (been 3x so far!), and this was by far my favorite hotel to stay in! It felt like you stepped into a fairytale. The location, the hotel, the restaurant, decor…everything…it was perfect! There were cute leopard print donuts from a local bakeshop waiting on us when we arrived and the staff was very friendly. We also stayed during the holiday season, which made it even prettier.


fairmont-copley- boston
fairmont-copley- boston-kait
fairmont-copley- boston
fairmont-copley- boston
fairmont-copley- boston
fairmont-copley- boston
fairmont-copley- boston
fairmont-copley- boston

Charlesmark Hotel: Jered chose this hotel for us based on location! It was absolutely perfect. It used to be a townhome. The rooms were nothing special, but they had a cute restaurant/bar area downstairs and provided bagels from a local shop for breakfast. It was quaint and had everything we needed, especially since we’re rarely in the room.


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