Winter Weekend Getaway: 48 Hours in Boston

In the Northeast winter isn’t just a season, it’s a lifestyle. But, just because it’s cold doesn’t mean you can’t travel. So if you find yourself in the pride of New England lace up your boots, throw on your best Patriots knitted cap, and get to visiting these great destinations.

Day 1:

11 AM: Head directly to brunch at Lulu’s Allston, do not pass go or collect $200.

On most weekends, you’ll find me in one of two places, at home avoiding people, or at a bottomless brunch. I strongly suggest arriving early at Lulu’s Allston because, within 20 minutes of being seated, the place was absolutely packed and brimming with folks eager to get their morning drink on. Though technically not bottomless, the Mimosa Bottle special is an acceptable second option. It comes with cute cups of three seasonal juices and a bottle of bubbly on ice.

My go-to brunch entrée is always eggs benedict and Lulu’s does a funky rendition called “White Trash Hash” served with tater tots, topped with braised short rib and poached eggs. Given its name I expected it to be a little messy and trashy but it more than delivered in flavor despite its very clean presentation.

1 PM: Hang out in Chinatown and walk off those mimosas before checking into the Doubletree Hotel in Downtown Boston.

Quick question, isn’t it slightly offensive to refer to areas that are predominantly inhabited by Asians solely as Chinatown? What about all the other Asian countries that are represented in the area? Is it more PC to call it Little Asia? Anyways, I digress…

Just steps away from the heart of Chinatown you’ll find the Doubletree. If you’re not good with directions, just use your nose and follow the scent of the warm chocolate chip walnut cookies they offer you as much and as often as you’d like during your stay. For a hotel located in the heart of the city, the room was surprisingly spacious, clean and comfortable.

3:30 PM: Harpoon Brewery

Let me start off by saying I don’t drink beer. However, even for a non-beer drinker like me, Harpoon Brewery was a must visit. It was a blistery seven degrees outside when I arrived but there was still a long line out the door. If you buy a tour ticket for just $5 you can skip ahead and get inside a little faster while you wait for your tour to begin.

Harpoon Brewery gives you a true beer hall experience. Taps on taps on taps and snacks on snacks on snacks. I ordered a pretzel with the classic IPA cheese and garlic butter.

As for the tour, the best part the last 10 minutes. It’s a free for all of all the Harpoon brews you can drink! As a non-beer drinker, it was cool to get a feel for all the different varieties that exist without the pressure to like them all. I was even able to try the last batch of their Clown Shoes Special Release. By far my favorite brew was the Harpoon Craft Cider. The ingredients are so straightforward. Fermented apples. It was crisp and delicious and for a moment I was transported to slightly warmer fall days where all I needed was a cardigan to stay warm and look cute.

6:30 PM: Get Bougie at The Beehive

Yelp, Google Reviews, Zagat, and any hipster Bostonian will tell you that The Beehive is the trendy place to bee (pun totally intended). Our hostess was a little shady when we arrived without a reservation, so she told us our only option was to sit at the upstairs bar. Luckily a nice bartender told us that there also was the option to sit at the downstairs bar which was right next to the live stage (and probably one of the best views in the house). Live jazz music, creative drinks, and a chill ambiance. This place definitely gave me “too bougie for their own good” vibes, but the food was filling and delicious. The Beehive is for sure the type of place you take your white friends to.

9 PM: Cheers, where everybody should know your name but doesn’t.

A tourist trap but a good one at that, Cheers on Beacon Hill is the original inspiration for the setting of the TV show with the same name. They didn’t know my name, nor did they ever ask but it’s okay because the giant TV’s they have are perfect for watching the Patriots crush it in the Playoffs. Any drink you order comes in a souvenir mug you can purchase if you’d like.

Day 2

11 AM: Brunch Round 2

For a fast, affordable, and delicious meal on Boylston Street, stop by Towne Stove and Spirits. The menu is standard, the portions are large, and the food is flavorful. Consider getting the Chicken and Waffles with Grits and Bacon. BONUS TIP: If you park in the Prudential Center parking garage, you can get your ticket validated and avoid $45 parking.

1 PM: Stroll the Streets of Boston

Step out into the cold for a quick second then step back into the warmth of the Prudential Center. Make your first stop the Tesla store where you can hop in and check out the latest models and not feel like a poor plebian for a few minutes.

Next stop Sephora. I have been to many Sephora’s in my life, I’ve even been to the Champs-Elysees flagship store in Paris, but the Sephora at the Prudential Center is top notch. Immediately when you walk in, there are these high-tech stations for optimal prep and primping but most importantly this Sephora has WOMEN OF COLOR ON STAFF! I counted four as I walked around which is honestly a new record for me.

The Prudential Center is more high-end stores, so if your wallet is tight it’s a perfect time to pretend you’re rich and window shop until you drop. If you’re feeling more adventurous you might even find a sugar daddy. When I went into the Gucci store, I saw a man grab a girl by her waist and call her “sweetie” and it definitely wasn’t in the loving grandfather way. Get it how you live it girl. Get. That. Money.

Once you’re done looking at things you can’t afford, step out onto the streets again and head east on Boylston and you’ll pass the Boston Public Library on your way towards the Boston Commons Frog Pond where you can ice skate while checking out some of the historic buildings in the city.

5:30 PM: A+ views at the Top of the Hub

Get yourself an early reservation 52 floors above the Back Bay at Top of the Hub. An early reservation gets you prime seating and 360-degree views of the Boston skyline, plus with shorter winter days, you can watch the sunset and see a beautiful night skyline while eating top-notch cuisine. I highly recommend the Portuguese Style Chicken. It was my most memorable meal of the trip.

8 PM:  Game of Thrones Pop Up Bar at Precinct Kitchen and Bar

Get an authentic Boston Southie experience at J.J. Foley’s.

When I was initially planning this trip, it seemed like every Boston based publication recommended the Game of Thrones pop up bar. I can’t even say this place had potential because they really did the bare minimum. I can’t even give them an E for Effort because there was none. There were a few House Flags, a poorly executed throne, and some hay???  After about 5 minutes of uncontrollable laughter, I left without getting drinks and made my way south.

To end the trip on a good note, I made my last stop J.J. Foley’s Cafe in Boston’s South End. A truly authentic Irish pub experience (accents included!) this bar truly made my inner bearded Irishman come out. Although not a traditional Irish menu item, the Loaded Nachos were super tasty and filling.

Got an Extra Day?

Consider checking out the John F. Kennedy Presidential Library and Museum. Dig deep into the life, history, and legacy of one of the most influential Presidents in our nation’s history. Also, I love a good conspiracy theory, so I feel like maybe clues are hidden in the museum or something (although that’s probably not likely).

What is your favorite spot in Boston? Let me know in the comments below.