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Why I Love Boston

As an LGBTQ-friendly destination, Boston is nationally known to be a trailblazer for our community.

by Jimmy Im
The Charles River Esplanade (Photo by Richard Cavalleri)

While strolling along these “memory lanes,” I was impressed with how the places I knew so well managed to preserve the spirit of what makes them unique.

The Charles River Esplanade (Photo by Richard Cavaller)

Nostalgia travel is a real thing.

For nearly a century, research from MIT to Harvard (both in the Boston vicinity) has proven nostalgia improves quality of life and wellbeing and makes you happy. Nostalgia is why people travel to the same place over and over again. It feels good.

This may explain why my recent trip to Boston was emphatically nirvanic. Boston and I have history. I lived in Beantown while attending Emerson College two decades ago, so returning to my former stomping ground was not only moving, I was inspired rediscovering a renowned city that shaped my formative years. Boston’s new tagline as of December 2022 is “Boston never gets old.” It has transformed and gentrified like any major city, and I loved its hard-to-miss progressive attitude that continues to make it one of the most dynamic places in New England.

As an LGBTQ-friendly destination, Boston is nationally known to be a trailblazer for our community. Boston held its first gay pride march in 1971 (a year after New York). The Massachusetts Supreme Judicial Court allowed same-sex couples the right to marry in Massachusetts on November 18, 2003, twelve years before gay marriage became legalized nationwide in 2015. The Advocate named Cambridge the third queerest city in America in 2016, and Boston consistently and proudly scores 100 on the HRC Index. Just last year, Maura Healey was elected the first openly gay governor. Boston is also where I came out, and I was fortunate to live in a city that has long embraced the LGBTQ community.

Boston Public Garden (Photo by Jorge Salcedo)

Boston Public Garden (Photo by Jorge Salcedo)

The incredible attractions, evolving dining scene, wealth of luxury hotels and shops, welcoming LGBTQ community, rich history, and the modern comforts I experienced, make Boston a destination that is always a pleasure to explore.


Getting to Boston is easy for people from New York City, with transportation famously provided through the Chinatown buses ($19) or Amtrak with direct routes under 4 hours. You can even hop on a commercial flight, though airfare is typically high for a 45-minute flight, and the amount of travel time (getting to the airport an hour before, checking in, etc.) is just as long as Amtrak.

For affluent travelers, I discovered the easiest, most convenient and exciting option: a sea plane. You can hop aboard Tailwind Air (flytailwind.com), a commuter scheduled air charter, and the only scheduled seaplane charter in the Northeast. Tailwind Air’s terminal location in Manhattan is on the East River at 23rd St., which is extremely convenient versus the long drives and prices to any airport. Check-in is a breeze (you only need your ID), and you can arrive 20 minutes before departure. Once onboard, the seaplane is spacious, with leather seats that have 36” pitch. It’s a short, 1 hour commute directly to Boston Fan Pier Marina (right in the city). It’s not just convenience that makes Tailwind Air a must; the views are spellbinding, and every seat is a window seat. The seaplane’s cruising altitude maxes at 8,000 feet high. I had magnificent, up-close views of New York City’s skyline, beautiful coastal beaches, and the Connecticut and Massachusetts countryside before we arrived in Boston. The flights are also pet friendly, and Ruby, my 10-lb shih-tzu, sat comfortably in my lap.

Arriving in Boston on Tailwind Air (Photo by Tailwind AIr)

Arriving in Boston on Tailwind Air (Photo by Tailwind AIr)

Once we landed, Ruby and I walked to the famed Boston Commons and Public Garden, known for its campy duck boat tours, as well as its gorgeous landscaping and serenity, which instantly stirred fun memories. On that hot summer day, I wandered Newbury Street and admired the classic low-rise brownstones, high-end salons, art galleries, and luxury brand stores (Rolex, Valentino, Ralph Lauren). I also strolled through the highbrow, scenic Beacon Hill neighborhood known for its cobblestone streets and gaslit streetlamps, and of course the South End, the welcoming “gayborhood” with Victorian row houses mixed in with low-key dive bars.

While strolling along these “memory lanes,” I was impressed with how the places I knew so well managed to preserve the spirit of what makes them unique. I noticed a lot of change (new restaurants, retail, etc), but they perfectly integrated without being intrusive, offering a contemporary boost to each neighborhood.

This includes Four Seasons Boston One Dalton (1 Dalton Street, Tel: 617-377-4888. fourseasons.com/onedalton), a notable (and quite noticeable) 61-floor skyscraper in famed Back Bay (guestrooms go up to the 21st floor). The luxury hotel is in a relatively new area of Boston that is chockfull of high-rise condos and other hotels, but it’s mere steps from the heart of the city and top attractions, such as Newbury Street, Berklee Performance Center, and the Hynes Convention Center. The higher the floor, the better the view, and my Charles Suite on the 21st floor offered commanding aerial views, including Boston’s city center and Charles River, through curved, floor-to-ceiling windows. The suite, upscale with modern furnishings and earthy tones, was well equipped with high tech automatic shades, TOTO Japanese toilet with heated seat, electronic fireplace, separate living and dining area, and a marble bathroom with egg shaped tub with excellent views that included historic Fenway Park.

Four Seasons One Dalton Street Boston (Photo courtesy of Four Seasons)

Four Seasons One Dalton Street Boston (Photo courtesy of Four Seasons)

Four Seasons Boston One Dalton feels more “buttoned-up” from its second property Four Seasons Hotel Boston on Boston Commons, but it’s still so casual you can stroll in wearing shorts and have a leashed dog, like I did with Ruby. The breakfast buffet is quite gourmet (think: coconut yogurt, egg white frittata, avocado toast with confit cherry tomatoes and radish), and my dinner at Trifecta, intimate and contemporary, was impressive (the steak is the scene-stealer). I’d be remiss to not mention the spa, an expansive wellness center on the seventh floor with indoor pool, fitness center, and new wellbeing rituals. My Grounding Ritual massage hit all the right spots, especially after hours of exploring the city on foot (I clocked an average 14,000 steps/6 miles per day), and I was certainly excited with the crystal-infused water, something I hadn’t seen since my visit to a prominent wellness resort in Thailand.

My favorite meal during this trip was at Four Season Hotel Boston (200 Boylston Street, Tel 617-338-4400. fourseasons.com/boston), the original property a block from my former Emerson College dorm. Coterie, an elegant and colorful, brasserie-style lobby restaurant with unobstructed park views, offers a lobster roll that, to this day, I still have withdrawals for. Chunks of fresh and warm lobster volcanoed from a toasty roll soaked in lemon herb butter, which felt more like a sauce. When I return to Boston, my GPS will be set to Coterie.

Fried Chicken With Cheddar-Bourbon Waffles at Buttermilk & Bourbon (Photo courtesy of Buttermilk & Bourbon)

Fried Chicken With Cheddar-Bourbon Waffles at Buttermilk & Bourbon (Photo courtesy of Buttermilk & Bourbon)

As much as Boston is known for dishing out top New England classics like “clam chowda,” the dining scene here is as diverse and competitive as any other global city. Buttermilk & Bourbon (160 Commonwealth Avenue, Tel: 617-266-1122. buttermilkbourbon.com) in the heart of Back Bay and helmed by celebrity chef and author Jason Santos, was a nice surprise with its exciting New Orleans-inspired menu. I loved the restaurant’s design (low ceilings, vibrant art and murals, speakeasy feel), and the outdoor patio was great for people watching. For brunch, I went straight for the signature buttermilk fried chicken thigh with cheddar bourbon waffles, honey butter, sweet and spicy syrup and watermelon chunks to add sweetness. The creamy, buttered jalapeno grits had that “kick” that NOLA is known for, and the hot, house made beignets (a signature NOLA specialty) was just as good, if not better, than the best spots in New Orleans, such as world-famous Café Beignet.

Shore Leave (11 William E Mullins Way, Tel: 617-530-1775. shoreleaveboston.com) doesn’t promote itself as a gay bar or restaurant, though it was gayer than any actual gay bars and restaurants I visited. In fact, I counted 11 gay pride flags, and the majority of the staff are openly gay.

This subterranean sushi/Asian-fusion restaurant and bar (two floors below street level) in the South End “gayborhood” has a fine balance between whimsical and kitschy (disco ball, strobe lights) and cozy and refined. With karaoke and often live music, the restaurant has a blatant jovial vibe, though the cuisine is serious business. Sushi is fresh caught, and rolls are memorable with thoughtful ingredients, including the signature Shore Leave roll with shrimp tempura that offered a little heat mellowed out by the cool of pineapple. I loved the Wagyu and Crab Clay pot Rice, the chef’s imaginative tribute to a traditional Korean dish I ate growing up, only this dish was presented with elevated ingredients (i.e.,: wagyu vs bulgogi).

For cocktails before or after dinner, head to Delux (100 Chandler Street, Tel: 617-338-5258. thedelux.com), a neighborhood staple known for its eclectic cocktail menu. The bar was one of my favorite low-key, off-the-grid places when I lived in Boston, and it was heartwarming to see how it has since become quite iconic. Closer to Four Seasons One Dalton, grab a nightcap at Dani’s Queer Bar (907 Boylston Street. danisqueerbar.com). The owners are known for their one-off LGBTQ events throughout the city, and the local community is enthusiastic with their new “home.”

I always like to end any trip with a memorable meal, and Alcove (50 Lovejoy Wharf, Tel: 617-248-0050. alcoveboston.com) was quite special. It’s located in another “new” gentrified area that didn’t exist when I lived here. Lovejoy Wharf is an industrial complex right on the waterfront in the West End with views of Charlestown (and access to Charleston Bridge), Boston’s oldest neighborhood known for the USS Constitution Museum and memorial site (Building 22, Charlestown Navy Yard, Tel: 617-426-1812. www.ussconstitutionmuseum.org), and Bunker Hill monument.

Bunker Hill Monument in Boston (Photo by Jorge Salcedo)

Bunker Hill Monument in Boston (Photo by Jorge Salcedo)

The gay owner of Alcove, Tom Schlesinger-Guidelli, has been honored as one of Boston’s leading LGBTQ restaurateurs by the Boston Business Journal and the Greater Boston Chamber of Commerce. Wine enthusiasts will appreciate the selection here, as Alcove has earned Wine Spectator Best Of Wine Lists awards for five consecutive years.

Tom has high standards for hospitality, and I felt the love at Alcove, which celebrates New England based, seasonal dishes (the strawberry gazpacho I had in the summer was rich in flavors and very satisfying). It’s also one of the best patio restaurants I visited thanks to the views and the wonderful breeze, as well as the people watching on Boston’s Harborwalk. It’s a shame I could only make lunch, as Alcove is known to have the most spectacular sunset dinners. It’s a good excuse for me to return, and I’ll check out Tom’s newest restaurant Hook + Line (10 Fan Pier Boulevard. Tel: 617-860-6003. hookandlinebos.com) at the same time.

While in Boston, I loved the new mixed with the old, but what stood out the most was the well-preserved spirit of the city. At times, Boston felt like a city I never knew with wild moments of déjà vu; other times, I was cheering for a city that had become even more spectacular than when I had lived here. That’s the funny thing about nostalgia. It lives in the “reward center” of the brain, so of course I had to love Boston. But even if I didn’t have so many amazing memories, I would continue to visit again and again knowing the incredible attractions, evolving dining scene, wealth of luxury hotels and shops, welcoming LGBTQ community, rich history, and the modern comforts I experienced, make Boston a destination that is always a pleasure to explore.


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