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When I wrap up a huge trip like my six week journey through Brazil, I usually like to schedule at least a week of downtown before picking up and jetting off again on my next adventure. Sometimes though, it just doesn’t work that way. Like when I flew back from São Paulo, booked it up to Albany, and had just three days there to recharge and repack before hopping in the car and heading to Boston.

Boston at Night

Why the rush? Well, a few reasons. Primarily, it was the one and only weekend when my blogger crew of , and myself were all available for what we try to make an annual meetup — having travel writters for BFFs can make calendar juggling complicated! I’d been begging, er, inviting them to spend the weekend in my family cottage in Martha’s Vineyard for years, and Boston was the perfect meeting point for the start of our blogging bonanza when we finally made it happen last June.

Perfect not just because of the logistics and location, but because my little sister Olivia was in her second year of calling Beantown home! And to just add one more person and moving part into the mix, my boyfriend Ian was also there — at least for the first 24 hours or so. Ian, who had arrived back to North America just days before as well, took the drivers seat for our roadtrip down to Boston.

Upon arrival, we sprung into action. As I’ve mentioned before, Olivia was working for the Hillary Clinton Campaign — beaming big sister alert — and I couldn’t wait to attend my first event by her, which I promise to share more about later. I ended up pitching in as an underprepared volunteer photographer, and getting to meet Secretary Clinton myself to tell her how proud I’d been to vote absentee for her in the primaries from a tiny island in Thailand!

Honestly, I’ve been trying for about six months to write a blog post about my experience both volunteering with and cheering on the campaign, but it’s been a tough. I really do want to share what was such an exciting and monumental experience followed by one of the greatest shocks and disappointments of my life, but so far I have found myself frozen with grief whenever I get to they keyboard. It’s hard to look back on what were these amazing euphoric memories now that they are shadowed by such incredible sadness. But the story will come, someday. Regardless of how you felt about the outcome of the 2016 election, I’m sure we can all relate to the struggle to process a great sadness.

After the fundraiser, we walked across the street to Legal Seafood and had dinner in front of the harbor with Olivia’s boyfriend, and toasted to Olivia’s incredibly hard work.

Hillary Clinton Fundraiser Boston
Hillary Clinton Fundraiser Boston

The next morning, Ian and Olivia and I went for breakfast at , an adorably kitsch breakfast diner that started the day off on a very colorful note. Then we were off to drop Ian off at departures and pick up both Angie and Kristin at arrivals — can you even believe my luck that all three managed to coordinate their flight times so well!

I did have a minor disaster with parking en route, though. I’d prepaid $50 for forty-eight hours of parking in the lot behind my sister’s apartment — Ouch, right? And that was at a huge discount for pre-booking online! — without realizing that leaving and re-entering the lot was strictly forbidden at that rate. Parking in Boston is seriously insane. But the lovely parking attendant must have read the genuine shock on my face as he explained this, and kindly promised to let me back into the lot again without re-charging me. Hero of the day!

Boston Commons

After dropping the girl’s bags at Olivia’s sweet little apartment on the edge of Boston Commons, we headed out for a stroll and a — my favorite Boston chain! — picnic in the park. We basically just talked a mile a minute stopping ever-so-briefly to snap photos and admire the beauty of my favorite spot in the city.

While the girls and I had discussed a few different options for the afternoon of our one-and-only day in Boston, it was chilly and overcast and we ended up retreating to Olivia’s apartment, which we swiftly converted into a coworking space for a few hours of inbox damage control.

Boston Commons

Boston Commons

Boston Commons

I didn’t feel guilty considering we had a big night out planned. I’ve confessed before that I used to think of Boston as a pretty stuffy and boring city, but Olivia moving there definitely opened my eyes to a trendier and more playful side of Boston.

After an exhaustive search, I’d settled on two venues to share this new view with Kristin and Angie — drinks at followed by dinner at . Both were within easy walking distance of Olivia’s place, and we happily strolled through the chilly start-of-summer night to reach them once she got out of work.

Boston at Night
Liquid Art House Boston

This striking gallery, restaurant and bar felt more New York than Boston, which is high praise coming from this Empire State-er. We ordered a round of pork and leek gyozas and a craft cocktail each, and tucked into our rigorous gossip routine. I was super impressed with everything — the service, the drinks, the creativity of the menu, and of course the amazingly unique setting itself. I’d love to return for dinner someday!

Liquid Art House Boston

Liquid Art House BostonPhoto courtesy of

But on this particular evening, we had reservations at nearby Asian-fusion restaurant Red Lantern. I loved it from the moment we walked in — Liquid Art House was a tough act to follow, but Red Lantern also packs a strong visual punch.

My Southern girls were already ticked by Boston’s crazy strict liquor laws when they were ID’ed at our every stop, and just about fell out of our chairs when we told them the city has no happy hours. That’s right — for liquor to go on sale in The Bay State! Luckily, we weren’t planning to go on a bender; just a few sake cocktails to wash down our dinners. Blackened tuna rice bites and lobster rangoons are just two examples from a menu that impressively blends classic Asian recipes with fresh New England ingredients.

Red Lantern Boston

Red Lantern BostonPhoto courtesy of

Red Lantern BostonPhoto courtesy of

Red Lantern Boston
Red Lantern Boston

Red Lantern BostonPhoto courtesy of

After dinner, it was back to Olivia’s for a pajama party. With a ferry reservation to make and a holiday to celebrate the next morning, we wanted to wake up bright-eyed.

Boston at NightPhoto courtesy of

Boston at NightPhoto courtesy of

The holiday in question? National Donut Day, of course! As soon as we caught wind of the impending food-fest, we immediately started searching for the best breakfast baked good Boston had to offer. But Olivia stopped us mid-Google — she already knew the best place in town, which just so happened to be perfectly located on our route to Woods Hole.

was everything I dreamed for and more for such a momentous occasion — after seeing the day’s six offerings, we figured it would be rude not to take one of everything (after all, I’d woken up extra early that morning to finally tick off my goal of going for a run through Boston Commons!)

Blackbird Doughnuts Boston

Blackbird Doughnuts Boston
Blackbird Doughnuts Boston

Blackbird Doughnuts Boston

Blackbird is the only doughnut shop in Boston that bakes on site, and it shows — er, tastes? These gourmet creations were unmistakably made-from-scratch, and fresh out of the oven. If you’re an artisanal donut addict like me, don’t miss this beloved Boston fave!

Blackbird Doughnuts Boston
Blackbird Doughnuts Boston

It was a short but sweet visit and, I figured, the first of many that summer. After all, Boston is a natural transit point for Martha’s Vineyard, where my mom lives in the summer and I bop back and forth to. However Olivia’s work kept her so on-the-go traveling around the northeast I just squeezed in one more blink-and-you’ll-miss-it trip in July, when I stopped in Boston for two nights before catching a flight out to Chicago.

Olivia was deep in the campaign trenches at this point and I was just excited to see her face! Even in the midst of her insane schedule, she cleared a night for drinks at followed by dinner at , both of which I highly recommend in spite of the fact that I do not appear to have a single photo from either (I must have been in the midst of blogger burnout mode.)

The next morning marked Olivia’s last and final scheduled day off for the next four months, when her office would move into seven day workweeks. Who knew a presidential campaign was such a wild ride? (Answer: anyone who watched all seasons of The West Wing.) Exhausted as she was, we made the most of it with a spin class at , brunch on the deck at , and matching manicures, followed by retreating back to Olivia’s for an afternoon slash evening of takeaway and Parks and Recreation reruns. Plus, of course, a non-negotiable stroll through the ever beautiful Boston Commons.

Boston Commons

Boston Commons
Boston Commons

And alas, that was a wrap on the Baackes sister’s stint exploring Boston. Olivia recently moved to Philadelphia, and with her pulling up anchor I can’t foresee any further Boston trips coming up in my immediate future.

That said, I am incredibly grateful for two summers getting to know a different side of a destination I’d always felt pretty “meh” about in the past. Is it my new favorite city in the world? Absolutely not. But I did find an appreciation for it that wasn’t there before. Your favorite little sister kicking around in a place will do that to you. And I’d so glad I got to share the journey with so many special people along the way.

Have you been to Boston? What’s your take?

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34 Comments...
  • My hometown!! Loved the Red Latern shoutout! We will be there in July/August, any chance we cross paths?

    • Meihoukai
      May 12 2017

      Hey Chris! Unfortunately no — as I said at the end of the post, I don’t see any future trips to Boston in my immediate future. Red Lantern is awesome though!

  • Cate
    May 3 2017

    I have always wanted to go to Boston! Looks like such a cool city filled with quality friendship time! Sweet
    Cate recently posted..

  • wow how cool that your sister had that opportunity! Hillary is definitely a role model of mine.

    And I definitely should not have looked at all those donut pictures while I was hungry — yum
    Leah | Nomad’er the Distance recently posted..

    • Meihoukai
      May 12 2017

      Mine as well, Leah. I had photos of her pinned to my bulletin board in college 🙂

  • Erin
    May 3 2017

    I actually ended up in Boston last October for the first time. I had vacation time and was looking for reasonably priced flights from Toronto and i picked Boston and went for a long weekend alone. I stayed at HI Boston which was my first time in a hostel and i enjoyed it! Its so cool seeing your pics in the garden and knowing I was on that same bridge. Also OMG the Lawn on D!!! Such a random awesome place! Do you know of the group Girls Love Travel??? I met up with a bunch of girls while I was in the city and we all ended up at the Lawn together, drinking, dancing and taking pictures on those glowing orb swings 🙂 I went to Harvard and got a tour from a current Harvard Student which was one of my favourite parts of the trip. It was so cool hearing about the Harvard culture and traditions. I also took the train to Salem for a day and went on a walking tour with a real witch. Super eye opening experience and so much fun. It was a weekend I will never forget.

    • Meihoukai
      May 12 2017

      Erin that sounds like an awesome experience! I am a Girls Love Travel member, glad that you found an awesome group there 🙂 Kudos on your spontaneous and fun trip — and trying a hostel for the first time!

  • Marni
    May 3 2017

    I LOVED Boston!! It’s exciting to see a different take on it, as my experiences were very different (although I did pass by Legal Seafood, I didn’t eat there as it felt like a weird choice after visiting the aquarium). I hope to return some day soon – it’s a great historical city and the perfect destination to explore by foot.
    Marni recently posted..

    • Meihoukai
      May 12 2017

      Ah, I LOVE the Boston Aquarium. So fun! Glad you had a good time 🙂

  • I’ve never been to Boston or to the East Coast, but I have a feeling that I would love it, as I prefer American towns that are more European-like.

    I hear, Boston is one of them lol!

    ‘Love the photograhy and how great for blogger girlfriends to get-together for a bit of a knees-up and a natter!
    Victoria @The British Berliner recently posted..

    • Meihoukai
      May 12 2017

      Yes! We are hoping to recreate another one this summer 🙂

  • I love this!! Although I’m originally a New Yorker, I lived in Boston for 7 years before moving to Germany to work for adidas HQ. It’s such a beautiful & quaint city, and I miss having the ocean so close by as we are now land-locked in Nuremberg.

    It looks like you were able to hit up some great spots in the city! It also helps to have the sis as your personal guide.

    Great post as always!
    michelle

    • Meihoukai
      May 12 2017

      Indeed it does — looking forward to exploring her new home of Philadelphia next!

  • Dominique
    May 4 2017

    Boston looks like such a wonderful place! I’ve read so much about it, and it’s on my wishlist for such a long time – I can’t believe I haven’t been there yet!
    Dominique recently posted..

    • Meihoukai
      May 12 2017

      Ha, frankly, it’s never been at the top of mine — yet I’ve gone so many times! Looks like it will probably be a while again until my next visit now, though.

  • Elizabeth Howell
    May 4 2017

    I lived there briefly and boloco was my go-to work lunch – the bangkok thai burrito with tofu, delish!
    Elizabeth Howell recently posted..

    • Meihoukai
      May 12 2017

      YUM I’m obsessed with Boloco. Love that they have the mini sizes too — perfect for when you aren’t starving but just need a snack.

  • Ijana Loss
    May 4 2017

    I’ve been to Boston one time and it didn’t wow me, but I’m always willing to give places a second chance. I think it’s awesome that you and Olivia have such a good relationship! Plus it’s kinda cool that she seems to move to new cities all the time, and then you get to visit them all 😀

    • Meihoukai
      May 12 2017

      We are indeed very lucky… we definitely had a pretty tumultuous relationship growing up so I think we earned this one, lol. Her job does bring her all over! Can’t wait to explore Philly next!

  • Megan
    May 4 2017

    The West Wing is one of my all-time favorite shows 🙂

    • Meihoukai
      May 12 2017

      Confession: I’ve only seen a few episodes! But it’s majorly on my to-watch list right now!

  • Rachel Clarke
    May 4 2017

    I’ve never been to Boston, but after reading this I’d certainly love to go!! I think the whole world was shocked by the American election – I know I was…

    Parking in all major cities is such a nightmare haha, thank god for the nice security man! 🙂
    Rachel Clarke recently posted..

    • Meihoukai
      May 12 2017

      Yeah… still reeling from those results. And ugh, parking. Boston is the most frustrating city I have EVER been to for parking.

  • Francesca Beckett
    May 4 2017

    My heart goes out to your sister! I’ve worked on an election campaign before, but we won by a landslide and it was the best feeling. I can’t even imagine the opposite – especially under the circumstances… Hey -at least there are delicious doughnuts to comfort eat though. Right?
    Francesca Beckett recently posted..

    • Meihoukai
      May 12 2017

      It was certainly one of the greatest shocks and disappointments of my life, and so I can only imagine how she feels. So impressed that she is right back out there fighting again for another progressive candidate. I guess you just have to put one foot in front of the other.

  • Chris
    May 4 2017

    Mmmmmm, Donuts… (or should that be Doughnuts?)

    I love Boston and in truth New England as a whole.

    So compact, easy to get around and you don’t have far to head to gorgeous seaside towns, hills or gorgeous woodlands!

    • Meihoukai
      May 12 2017

      I heart New England too — so excited to explore Maine this summer!

  • becky hutner
    May 5 2017

    OLIVIA IS A BADASS

  • I love everything about this! And I hope Liv gets to work for the Democratic candidate for 2020; she’s such a bad ass!
    Kristin @ Camels & Chocolate recently posted..

    • Meihoukai
      May 12 2017

      I hope so too… can’t wait to see who will run!

  • Rhiannon
    May 6 2017

    I’m from Australia, and I’ve wanted to travel the east coast of USA for such a long time! I finally made it to New York a few years ago, after dreaming about visiting my whole life! Boston is definitely on my bucket list, looks like such a great city! 😀
    Rhiannon recently posted..

    • Meihoukai
      May 12 2017

      Ah, did you love New York? Greatest city in the world, in my humble opinion 🙂 There’s actually a bit of a rivalry between New Yorkers and Bostonians — you know what side I’m on!