36 Hours in Boston

March 21, 2016

36 Hours in Boston I A guide on where to eat and what to doA little post on 36 hours in Boston this past weekend!

The past few weeks I have been settled into New York and not traveling. It’s been such a nice respite and allowed me to prioritize working out, seeing friends and getting lots of things done that had been sitting on my to do lists.

That being said, I had started to get a bit of the travel bug. I was counting down to heading to Colorado this week but that was all the travel I had planned between January and May. And then very serendipitously, Westin Hotels & Resorts reached out asking if I’d like to help them celebrate World Sleep Day (March 18th) by experiencing their Sleep Well program at one of their properties. I had been hoping to get back to Boston this year so it seemed like the perfect destination for a quick, two-night stay.

36 Hours in Boston I A guide on where to eat and what to do

Taylor and I took the train up and had a great 36 hours in Boston at The Westin Copley Place. The best part? Thanks to the Westin we majorly relaxed. We slept like queens in the hotel’s Heavenly beds, indulged in a very delicious breakfast in bed from their Sleep Well Menu, took an afternoon nap in our Heavenly robes, had calming teas before bed and learned that their hotels are all working to have guests maximize their “Westin Weekends.” Which translates into late Sunday check outs, extended breakfast hours all weekend and additional perks. It was the perfectly restorative weekend. (This hotel is also right across from the Amtrak Back Bay station and located in central Boston so we were so pleased with how easily we could get around.)

36 Hours in Boston I A guide on where to eat and what to do

36 Hours in Boston I A guide on where to eat and what to do

That being said, we maximized our short trip by seeking out loads of fun and food while in town. So if you’re interested in visiting Boston soon for a quick but productive trip, here’s how to prioritize your 36 hours.

36 Hours in Boston I A guide on where to eat and what to do


Neptune Oyster

Don’t come here hungry because your wait will be substantial. But man is it worth it. Taylor and I both commented that on multiple occasions. We had a late lunch of indulgent, hot and buttered lobster rolls with fries and rosé. It was by far the most delicious lobster roll I have ever had. It was washed down with the perfectly chilled wine we ordered to accompany our lobster + fries. Pretty much as close to New England heaven as you can get! Put this joint at the top of your list.

36 Hours in Boston I A guide on where to eat and what to do

Mike’s Pastry

Home of the famous cannolis in Boston’s North End. You can pick them up to go while you await your table at Neptune’s as they are just a couple of winding blocks away from each other. I recommend the chocolate chip cannoli and the rainbow sprinkle adorned champagne cookies. This place is packed but the lines move quickly. Be warned it is cash only!

36 Hours in Boston I A guide on where to eat and what to doAlden & Harlow

This was our first meal in Boston and we ventured over to Harvard territory aka Cambridge (where I had never been) in order to dine on interesting ingredient combinations like savory monkey bread with pesto, steak with horseradish labne, and octopus with insane roasted tomato calabrese. Washed down with hand crafted old fashioneds, we both left so perfectly stuffed and raving about the meal. (Of note this place is known for their “secret burger” but it was sold out already by 7pm. The locals next to us told us the steak we settled for is actually better so not to sweat it over said secret burger. Just a tip!)

Stephanie’s on Newbury

This brunch institution is seemingly known by every Bostonian. We popped in for a quick breakfast before we caught our train home. It supposedly gets very busy but you can make a reservation so you may want to do so. Taylor and I decided the best order is the fluffy, light and oh-so decadent Belgian waffle with strawberries and whipped cream; add a side of bacon. Heaven!

36 Hours in Boston I A guide on where to eat and what to do


Isabella Stewart Gardner Museum

Several people recommended this museum to Taylor and I and it was our one cultural pursuit of the trip. Go for the art and stay for the beautiful and peaceful atrium. You’ll take in some Matisse and John Singer Sargent gems and the whole museum can be seen in under an hour making it a very reasonable stop on your quick weekend stay in Boston.

36 Hours in Boston I A guide on where to eat and what to doExplore Beacon Hill

The Beacon Hill neighborhood is full of charm. The small side alleys, brick homes with colorful doors and winding cobblestone streets make it extremely Instagram worthy and will lead to musings about what life living in Boston would be like. It was literally so charming that I failed to take a single photo there on my camera (rather was snapping left + right #whoops).

Boston Public Garden

You can easily walk from the Westin Copley Place to the Boston Public Garden which is such a lovely respite in the busy city. I recommend taking in Newbury Street on your way over and then when you decide to exit the park, head to the neighboring original Cheers for a beer in the bar that’s not short on character by any measure.

36 Hours in Boston I A guide on where to eat and what to do

I am already plotting my return to this great and historic city. Any recommendations on what to check out on my next trip? Hope you had a great weekend yourself!

Shop What I Packed for the Quick Trip:

Many thanks to Westin for partnering on this post and providing such a memorable stay.

comments +

  1. Sounds like such an amazing trip! Sometime’s a weekend trip is all we need to recharge our batteries and get away for a couple days. All those food places you visited sounds delicious, I want a lobster roll ASAP!

    xoxo Nicole


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