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 always eventually realize that my to-do list can be done later, and to allow life to catch me off guard from time to time.

Neither one of us has ever really explored Boston and didn’t know what to expect, especially since living in NYC. But- I 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.

xx -♡Kait


Back BayBack Bay
Tatte BakeryTatte Bakery


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.

Tatte Bakery: The best shakshuka I have ever had. I still dream about that dish. This is a European style cafe, so you’ll probably find their pastries tend to be less sweet, but also perfect with a cup of coffee!

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 insane. 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.


Bricco- North EndBricco- North End
Neptune's Oyster- North EndNeptune's Oyster- North End


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.


Union Square Market at Boston Public MarketUnion Square Market at Boston Public Market
Crema Coffee- Harvard SquareCrema Coffee- Harvard Square


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, and of course, I had to to try. HOLY HEAVEN. 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 Market- BEST!Modern Market- BEST!
Flour Bakery- Sticky BunFlour Bakery- Sticky Bun
Flour BakeryFlour Bakery

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- ShoppingNewbury Street- Shopping

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.


Quincy Market- North EndQuincy Market- North End
Back BayBack Bay
North End, Boston's Little ItalyNorth End, Boston's Little Italy
Marlborough StreetMarlborough Street

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!


The Public GardenThe Public 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!

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


Acorn Street, Beacon HillAcorn Street, Beacon Hill
Beacon HillBeacon Hill
Back Bay- Marlborough StreetBack Bay- Marlborough Street
North EndNorth End

Where we Stayed

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.

Charlesmark in Back Bay Charlesmark in Back Bay

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