How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay

A Couple’s Guide to a Weekend in Boston

It’s rare that SVV and I get to go somewhere for a weekend where it’s just the two of us and we have no agenda. Boston was a treat for that reason alone, in addition to the fact that we made our base right in the heart of the thriving northeastern hub at the Fairmont Copley Plaza.

A Weekend in Boston: Staying at the Fairmont Copley Plaza Hotel

And while we had just shy of 48 hours in Beantown, we know how to make the most of any city escape, no matter how short it may be.

How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay

FRIDAY

It’s a quick and easy flight from Nashville to Boston; we flew out of BNA just after breakfast and touched down in BOS at lunchtime. When we arrived at the Fairmont, our room was all ready to go early so we dropped our bags and freshened up before hitting the pavement.

How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay

In truth, I was exhausted from hosting visiting friends in Tennessee all week and wanted nothing more to nap in that glorious bed, but the city was calling our name and we didn’t want to sleep our way through such a gorgeous spring day.

How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay

One thing I miss from living up north is the abundance of grab-and-go options that are both healthy and affordable. I’m talking, hearty salads, farro bowls, wraps, the like. Nashville simply doesn’t have many fast-casual options, let alone healthy ones, so SVV and I try to get our fill when we travel to big cities like Boston—which is why our first meal was not lobster rolls but rather a quinoa concoction from Dig Inn that left us satisfied and ready to get going.

How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay

How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay
How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay

After that, we couldn’t think of a better way to soak up the sunshine than in Boston Common. Everyone else in town seemed to have the same idea.

How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay

Boston on a sunny day seems a throwback to our days living in Denmark; the second the clouds dissipate and the mercury creeps above 60 degrees, every green space in town is occupied by sun-deprived bodies, the heat drawing them out of their frozen indoor solitary confinement.

How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay

How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay
How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay

How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay

We shopped our way through Back Bay on the walk home to the Fairmont, returned to our rooms to clean up, then headed downstairs for dinner at OAK Long Bar & Kitchen. Everything on the dinner menu looked so tantalizingly good that SVV and I decided to forgo the entrees and instead share a respectable selection of the small plates, as well as a couple cocktails starting with the Kentucky Elixir.

How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay

Merguez lamb meatballs with tomato sauce, gremolata, onion crostini; roasted cauliflower with golden raisins, mint, sherry and almonds; and, of course, mac and cheese with confit pork shoulder, Bechamel cheese blend—we sampled a little bit of everything.

How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay

The meal was mind-blowingly delicious, made only tastier by the fact that we were served by Chakib from Casablanca, who was impressed we’d visited his hometown and steered us through the menu, course by course. After he’d evaluated our cocktail tastes, he was so bold as to suggest new drinks and even have the bartender whip us up something special (good man, that Chakib). We rolled ourselves back up to the fourth floor and vowed never to eat again, a promise we kept for a solid 12 hours until it was time for brunch.

How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay
How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay

SATURDAY

Although I’ve been to all 50 states and well over 120 countries, I’m still one of those travelers who likes to hit all the tourist hotspots and I’ve yet to go to Boston and not walk at least parts of the Freedom Trail.

How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay

Since we had so much walking on the docket for the day, we filled up on a hearty breakfast from OAK because full as I may have been from the previous night, I’m never one to say no to brioche French toast with Irish cream vanilla custard (and if I do then you’ll know the apocalypse is upon us and a zombie has actually overtaken my body).

How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay

How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay
How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay

How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay

On our way out to hit the Freedom Trail, we stopped to get a map with a side of advice from Joe the concierge. The 2.5-mile red brick trail leads from Boston Common to Bunker Hill, and we didn’t necessarily need to go to them all again, so we asked him for his greatest hits list, which he gave us in addition to some of the best photos stops in Boston.

How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay

Copley Plaza is just 10 minutes from the Freedom Trail’s starting point, so we returned to the park and headed east from there, hitting up a handful of the 16 stops like the Massachusetts State House and the Old South Meeting House in addition to Joe’s recommendations before eventually arriving at Faneuil Hall, which was built in 1741 and hosted America’s first ever town meeting.

How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay

How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay
How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay

How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay

Comprising Quincy Market, North Market and South Market, Faneuil Hall Marketplace today is one of the liveliest spots in all of Boston. We ogled the buskers (including one literal pig), inhaled the scent of seafood wafting through the halls, poked through vendors’ stalls and admired the architecture, then continued on our way. When we got down to the waterfront, we found a grassy knoll and finally stopped for a breather.

How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay

How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay
How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay

How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay

Our stomachs were rumbling, so I turned to my trusty on-the-go concierge—the Yelp app, that is—and sought out a lunch spot. The result was State Street Provisions, which lived up to the reviews, and we split a burger and a seared tuna sandwich and guzzled down a couple locally-made brews. We did not, however, make it to a brewery in Boston; that had been on the initial docket until, that is, we found that Sam Adams and several other Massachusetts breweries were actually located in suburbs on the outskirts of town (i.e. too far away given our limited time) rather than in Boston proper.

How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay

But we had to pick and choose carefully on this trip, and we both wanted to make it over to Cambridge, which is in the opposite direction, so a visit to Southie did not happen. Next time we’re in town, however, I plan to make the breweries Harpoon and Trillium top priority. Instead, we hopped in the metro and took the train 10 minutes under the Charles River and over to Harvard Square, which is brimming with shops, cafes, bars and restaurants.

How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay
How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay

How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay

Like Boston Common, the campus was alive with undergrads who seemed to be seeing the sun for the first time after months of hibernation. It’s what my Nashville friends lovingly call National Sundress Day: the first afternoon worthy of shedding those layers of winter clothing and the pallor that accompanies a season of being cooped up indoors.

How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay

We had no agenda other than more meandering, so when we saw a happy hour at the Red House boasting $1 oysters, that became the next stop on our afternoon itinerary. Being in a seafood-deprived state like Tennessee, we get our shellfish fix when we can!

How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay

I had solicited Boston restaurant recommendations from social media and had a list a half-mile long, but in the end, rather than brave the Saturday night dinner crowd outside of the hotel, we decided to go with a reliable choice: OAK Long Kitchen & Bar for a third meal. After all, when you find a good thing, why risk going anywhere that doesn’t measure up? It’s uncommon that I find a hotel restaurant this good, that inventive.

How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay

Rush hour was approaching, so we hopped in a Lyft and high-tailed it back to the hotel after we were done with our Harvard Square exploration. We arrived at the Fairmont just before the happy hour crowd, sidled up to the bar as the sun set the room on fire and made friends with John the bartender. Pro tip: Always befriend the bartender.

“What are you having?” he asked with a twinkle of his eye.

“Whatever’s most dramatic—give me your most photogenic drink,” was my (not highly unusual) response.

Rather than do a double-take, John paused to ponder my request then immediately went to town whipping up four of the prettiest cocktails I’ve ever seen, not to mention the tastiest. The winner was, no doubt, the Smoked Chai Manhattan, which John prepared by charring a piece of oak with a blow torch, captured its essence in a snifter glass, then served the drink up to me in a wisp of smoke.

How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay

How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay

Magical? I’d say so. John is pretty much the Harry Potter of bartenders, and the Smoked Chai Manhattan ranks among my top five favorite drinks of all time, no lie.

How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay
How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay
How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay

How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay

Two cocktails in each, we were hungry and the restaurant was starting to fill up. Rather than waiting for a table, we retreated to our room, cracked open a bottle of wine and ordered in-room dining, which is a limited menu curated from OAK. It seemed like the perfect way to unwind after a long day of walking and an early morning looming on the horizon the following day.

How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay

SUNDAY

Our next destination was my old home, New York City, for a couple days, and our trip there couldn’t have been more convenient. We got up early, grabbed a light but filling breakfast from the Fairmont Gold Lounge, checked out of the hotel then wheeled our bags one block over to the Back Bay Amtrak station. Three hours later, we were stepping off the train in the heart of Manhattan, ready for the next leg of our adventure.

How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay

Boston, you were a dream! Until next time….

How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay

How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay
How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay
How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay

How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay

How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay
How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay

A Weekend in Boston: Staying at the Fairmont Copley Plaza Hotel

How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay
How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay

How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay

How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay
How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay

How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay

This trip was in partnership with Fairmont Hotels & Resorts on behalf of Travel Mindset.

 

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How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay
How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay
How to Spend a Weekend in Boston: Where to Go, What to See, Where to Stay
COMMENTS
  • May 8, 2017

    Absolutely love this piece!

    I haven’t been to this part of America yet, but Boston will surely be on top of the list as far as New England is concerned!

    Isn’t it nice to have a couples only weekend every now and again? When we eventually make it to NYC, our teen won’t be coming with us as I see New York as a very adult-like type of place with fascinating sights, gorgeous bars, and exciting restaurants.
    p.s. $1 oysters. Mmm. Yes, Please!
    Victoria @The British Berliner recently posted..Have you ever been to Split in Croatia – Bring out the dragons!My Profile

    • May 8, 2017

      Yes, NYC sans kid sounds like the perfect couples retreat—I actually have one such post coming up in the next week or two! =)

  • May 8, 2017

    Kristin your photos are SO beautiful!! If you don’t mind me asking, what lenses do you use? (Especially love the wide-angle shots.)
    Ashley of Ashley Abroad recently posted..Life in Africa: Month 2My Profile

    • May 8, 2017

      Ashley, you’re the sweetest! I take 90% of my photos with my Canon 24-105mm, which I’ve had for seven years now. My secondary lens is a 16-35mm, though I don’t use that one nearly as much as I thought I would (I replaced my 10-20mm with that one a year or two ago).

      Also, it’s a bit hard to find, but I *try* to keep my equipment updated here:

      http://www.camelsandchocolate.com/resources/

  • May 8, 2017

    Once again I would like to point out that the Blog is absolutely fabulous!

  • May 8, 2017

    Awesome place and full with beautiful things. it have so many good things to get fun. Amazing guide you shared to enjoy beauty of that place.

  • May 8, 2017

    I like how you did the 48-hours in Boston and would love other posts like this! Being from the Midwest, I also forget that the east coast has convenient Amtrak stops! I imagine a combined trip to Boston & NYC in our future.
    Leah recently posted..Travel Hacking New OrleansMy Profile

    • May 15, 2017

      Oh, that’s nice to hear, Leah, because I have a Savannah one running today and an NYC one next week. In the past, I’ve steered clear of that but I also realize that sometimes people only have a short amount of time and want a play-by-play post of how best to organize that weekend 😉

      Boston-NYC by train is so easy!

  • May 8, 2017

    So jealous of the great weather you had while there! I was in Boston three weeks ago and it was rainy and meh both days.

    Harpoon has great beer and pretzels – worth a visit for next time!
    Noelle recently posted..7 Easy Ways to Save Money on a CruiseMy Profile

    • May 15, 2017

      We were so strapped for time this visit, we simply had to opt out of have our wishlist. But I hear Harpoon is awesome and it will be the first stop on the next trip 😉

  • May 10, 2017

    Thank you saring amazing beauty of that place. This place is full of peace and beautiful things.

  • May 10, 2017

    Thank you sharing amazing beauty of that place. This place is full of peace and beautiful things.

  • May 11, 2017

    Looks like such a fascinating place, one I would LOVE to visit someday! Useful tips for first time visitors, will be sure to pin this for future travels

    • May 15, 2017

      Thanks, Rehlat! I do hope you get to visit, as well =)

  • May 13, 2017

    I’m drooling over the details in your photos–the hotel looks amazing, as do all the food and cocktails. I love the East Coast. I lived in Connecticut for part of my childhood and definitely remember how charming, cosmopolitan and beautiful those cities can be. I’ve been hoping to plan a family road trip of New England. Looking forward to your NYC post!
    Jenna recently posted..For Your WeekendMy Profile

    • May 15, 2017

      You bet! It’s coming in the next week or two. I find it so much harder to write about places I’ve lived (like NYC) than places I’ve only visited (like Boston) as I know SO much more about those cities. I do love that the NE is well-connected by Amtrak. Wish that were the case for the rest of the country!

  • May 13, 2017

    Your photos are AMAZING! Makes me love Boston more. We are in RI so tend to go up for day trips but I’ve heard great things about the Fairmont in Copley Plaza. I might just need to plan a getaway next time I’m kid-free.

    • May 15, 2017

      Thank you, Tamara! I’d love to see more of RI, as well. I’ve always explored the NE in small, bite-sized chunks.

  • May 15, 2017

    whole heartily thank you for giving out valuable information

  • May 17, 2017

    Haven’t been to Boston in ages! 15 years to be exact! It would be great to return soon and your post is great inspiration. I love a great hotel bar and it seems like the Fairmont delivered. Great photos BTW!
    Jessica M recently posted..Behind the Scenes: Becoming a Travel BloggerMy Profile

    • May 19, 2017

      It does seem like it’s high time for you to return, Jessica! 😉

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