48 Hours in Boston: Parkland, Prison & Cannoli – Part One

The Liberty Hotel on Boston's Beacon Hill was a prison until the early 1990s

The Liberty Hotel on Boston’s Beacon Hill was a prison until the early 1990s

Over 48 short hours in late July, I let go of an old dream and (re)discovered my new crush city: Boston, Massachusetts.

I traveled with a girlfriend who makes me laugh, and we walked miles on end each day, ate our weight in carbs, hung out with people we adore, and stayed in a former prison. I’d call that a summer weekend very well spent. When I was 20, I felt sure I’d live in Boston someday, amidst bricks, clapboard and tangles of ivy, my summer weekends spent sailing out on the Charles River or wending my way to the Cape. Instead, the sliding door of life led me westward, and for some odd reason, almost 24 years passed without my so much as setting foot in town.

When I finally returned just a couple of weeks ago, I felt like I was reconnecting with an old crush from my youth. And now that I’m back home in Los Angeles, I regard Boston as a sort of long-distance boyfriend. I can already tell we’re not going to Skype, text or even call every day, but he’ll be there for me when I need a dose of history, greenery, and kick-ass cannoli.

That's Katharine on the left, capturing a selfie of us in Boston's Public Garden

That’s Katharine on the left, capturing a dual-selfie of us in Boston’s Public Garden

My travel companion to Boston was my friend Katharine, one of my favorite people in the world. Over the last 20 some-odd years, Katharine has spent all the time in Boston that I haven’t, visiting with her friend Susan, and later, Susan’s delightful husband, Seth, and the couple’s amazing daughter, Stella. One week before this trip, we’d all been lucky to see each other in L.A, parting ways with a big round of hugs and a breezy, “See you next Friday…on the other side of the country!” (And I agree – we are adorable.)

Katharine was my dream companion for this trip, and not just because of her lovely local friends and her United elite status (which earned me an upgrade to Economy Plus, both coming and going). She knows her way around Boston, she’s whip-smart and funny, loves coffee, food and walking for miles, and is up for exploring almost anything…including the sale racks at Anthropologie.

The Liberty Hotel's Alibi Bar features the iron bars from the prison's original cells

The Liberty Hotel’s Alibi Bar features elements of the original prison cells

Our home base was The Liberty Hotel in Beacon Hill, an elegantly restored  former jail that dates from a time when civic leaders felt criminals would be inspired to a better code of conduct if only prisons looked like cathedrals. The four-star hotel was a working pokey until as late as the 1990s, but is now a very comfortable place to stay, with enough sex appeal to make it a romantic choice for couples while not being off-putting to those of us who are  just friends.

Set across from the Red Line, the Liberty offers views of the Charles River, Beacon Hill, the Public Garden and more

Set across from the Red Line, the Liberty offers views of the Charles River, Beacon Hill, the Public Garden and more

The Liberty’s location is ideal, especially for first-time visitors. It’s right across the street from the Charles/MGH stop on the subway’s Red Line, meaning that when combined with a tunnel ride on the Silver Line bus and a transfer at South Station, it’s a 45-minute door-to-door trip from Logan Airport. Set amidst the drop-dead gorgeous row houses of Beacon Hill, a block from the Charles River and the faux-historic commercial cuteness of Charles Street, the hotel is walking distance from the riverside Esplanade, the West End, the North End and the Waterfront, the downtown Government Center, Boston Common and even Back Bay.

Our room was on the bonafide 13th floor!

Our room was on the bonafide 13th floor!

Our double-queen room was on the 13th floor, marking the only time I’ve ever seen a 13th floor in a hotel. Anyone else know of a hotel with one?


The Liberty uses the (dreamy) Westin Heavenly Beds, as well as a prison-themed version of a do not disturb sign

The room itself was spacious, the beds plush and cozy (if a little short for anyone taller than 5’8″), the marble-paved bathroom huge, with Molton Brown bath products and plenty of surface area for our toiletries, and the fun do-not-disturb sign featured an antique-ish key and a single word: “Solitary.”

The view from our 13th-floor room, to the left and the right

The view from our 13th-floor room, to the left and the right

The room’s two drawbacks? The lack of traditional turndown service you might expect from a nice hotel, and our view of a parking lot, a small slice of the river, and a great deal of the Massachusetts Eye and Ear Infirmary. Rooms on the opposite side of the hall offer gorgeous, sweeping vistas of the Charles River and the Boston Public Garden, though, so be sure to request one of those.

One small corner of the hopping Saturday night scene in the lobby(and a few conspicuously untucked shirts)

One small corner of the hopping Saturday night scene in the lobby (and a few conspicuously untucked shirts)

Surprisingly, the hotel is directly adjacent not only to the Infirmary but also Massachusetts General Hospital, making it a plus for hypochondriacs, allergy sufferers and those who are easily winded by sightseeing. It’s also the site of three of Boston’s most popular bars – Alibi (which features original iron jail-cell bars), the Liberty Bar (which sprawls all around the soaring lobby), and The Yard (a private outdoor courtyard). On Saturday nights, the city’s young/beautiful people get dressed to the nines and descend here en masse, lining up as though it’s Star Wars’ opening weekend all over again. We hadn’t seen so many crisply tailored blazers and bandage dresses since the latest simulcast of the Oscars.


Hola, Diablo Picante

I can’t really blame the revelers, though, as the sheer array of spaces here are very cool, and the cocktails are downright spectacular. For the sake of research, Katharine and I tried and now applaud the gin-ginger-beer-and-blackberries Blackbird, the margarita-esque Diablo Picante, and the smoky-sweet mezcal-riffic Smoke & Mirrors – so, you’re welcome.

The apple-compote French toast at Clink

The apple-compote French toast at Clink

And we were joined for Sunday brunch by Susan, Seth and Stella in the pithily-named lobby restaurant, Clink, snagging a last-minute table for five and an excellent meal. Standouts were the sumptuous French toast, the quesadilla that comes with a side of scrambled eggs, and the soft-shell crab omelet with veggies and cilantro, as well as the fully manageable noise level.

Aside from feeling like a hopping bar that happens to have an artsy hotel attached to it (or even an artsy hotel that happens to have some medical buildings attached to it), I’d definitely recommend staying at The Liberty. The rooms are comfortable and quiet, the water pressure is stellar and the robes cushy, the staff is kind and accommodating, the food is delicious, and the scene is buzzy. However, you might want to consider it for a special occasion or a getaway where you’re splitting the room cost with a companion, as the lowest priced rooms start at about $360. (For those of you who are Starwood Preferred Guest members, though, be aware that the ongoing Better Tomorrows promotion gives you 40% off every other night of your stay.)

The Rose Kennedy Greenway

The Rose Kennedy Greenway

For our first wander away from the hotel, we set out on foot to pick up the Rose Kennedy Greenway and make our way to the North End. After about a mile’s walk through Beacon Hill, though, we encountered both simultaneously, and chose to simply explore a little of the Greenway to say we’d done it. A long ribbon of public parkland that runs through several Boston neighborhoods, the North End’s grassy expanses feature fluffy perennials, splashy fountains and free summertime concerts. Arrive between golden hour and sunset, and this’ll be downright idyllic, I tell you.

Scenes from Boston's North End

Scenes from Boston’s North End

Rounding our way past the gilt-domed Tunnel Traffic Administration Building (for, as Katharine put it, “all your tunnel and traffic needs”), we picked up The Freedom Trail and delved into the Italian restaurant-and-Paul-Revere-focused North End. This area is full of tourists, so don’t feel alone. It’s fortunately also full of old men chatting (on and off of Vespas), tinsel crowns, narrow backstreets, window-boxes full of geraniums, and hardcore cobbled streets (seriously, wear shoes with sturdy soles). Every other building here is epically historic, including Paul Revere’s House and the Old North Church, home to the steeple of “one if by land, two if by sea” fame.

The three types of cannoli shells at modern Pastry

The three types of cannoli shells at modern Pastry

North End also has the most popular cannoli bakeries in town, but I’d recommend skipping the hordes lined up outside Mike’s Pastry in favor of checking out the sparkly counters and smiling faces at Modern Pastry. I unfortunately found their ricotta filling a little bland without that slightly sour lemon zing that fills my heart with joy, but the chocolate-dipped shell was the perfect balance of crisp and soft. (To find out where I found my favorite cannoli of the weekend, you’ll have to wait for the next installment.)

Lo Conte's Italian Restaurant in the North End

Lo Conte’s Italian Restaurant in the North End

I’m not the world’s biggest fan of Southern Italian food, but when in Rome the North End, I was certainly not going to kick pasta out of bed. Susan had suggested that we dine at Lo Conte’s, a loud, casual neighborhood favorite, where we each enjoyed a glass of Pinot Grigio and split a bowl of absolutely delicious spaghetti carbonara and some mozzarella and tomato with basil, olive oil and a little red onion. Every ingredient of the latter was gorgeous…except the oddly pale, tasteless tomatoes, a near-unforgivable sin in the height of summer. I’d come here again, though, even if just to give that dish a second chance.

On our leisurely stroll/roll home, I held our string-tied box of cannoli like it was a tiara on a velvet pillow, and because we hadn’t seen each other in a few weeks, started to get caught up on what had really been going on in the past month of our lives. Few things will bring friends closer together than a change of scene, because it helps you appreciate your own shared history.


Need more Boston in your life? Well then, stay tuned for…

48 Hours in Boston: Parkland, Prison & Cannoli – Part Two


Our room at The Liberty Hotel and our airfare to/from Boston were sponsored by
The Starwood Preferred Guest Card from American Express,
which earns one Starpoint for every dollar spent on the card and double Starpoints on stays
at participating Starwood Hotels & Resorts, such as The Liberty Hotel.

Please note that all opinions and observations expressed here are my own.

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