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.

Why the rush? Well, a few reasons. Primarily, it was the one and only weekend when my blogger crew of Kristin, Angie 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 The Friendly Toast, 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 Boloco — 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 Liquid Art House followed by dinner at Red Lantern. 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 Kristin Luna

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 — it’s illegal 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 Kristin Luna

Red Lantern BostonPhoto courtesy of Kristin Luna

Red Lantern Boston
Red Lantern Boston

Red Lantern BostonPhoto courtesy of Kristin Luna

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 Kristin Luna

Boston at NightPhoto courtesy of Kristin Luna

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.

Blackbird Doughnuts 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 The Lawn on D followed by dinner at Sportello, 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 Flywheel Back Bay, brunch on the deck at Stephanie’s on Newbury, 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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