Boston is one of those cities that feels grounded in history but still moves with a certain ease. The streets are a mix of old brick, brownstones, and pockets of glassy new buildings, and everything feels a little more compact and walkable than you expect. It’s a city you can settle into quickly—part coastal, part academic, and just enough energy to keep things interesting without ever feeling overwhelming.
Most days start best on foot. Walking through neighborhoods like Back Bay or Beacon Hill, you get a sense of how much character the city holds—tree-lined streets, historic homes, and little details that make you slow down. A stroll along the Charles River Esplanade is an easy way to ease into the day, especially in the morning when everything feels quieter.
Boston also carries its history in a way that feels present, not just preserved. Following the Freedom Trail takes you through some of the city’s most important sites, but even without a plan, you’ll find pieces of it everywhere. Stops like Faneuil Hall and the surrounding areas blend that historical weight with a more modern, active atmosphere.
Food here leans classic but done well. Seafood is the obvious move, especially around the North End, where you’ll also find some of the city’s best Italian spots. The neighborhood is lively, a little crowded, and exactly where you want to end up for a long dinner that turns into walking around after.
As the day shifts into evening, Boston slows down in a way that feels intentional. The waterfront and Seaport areas bring a slightly more modern energy, with rooftop bars and restaurants that overlook the harbor. It’s a nice contrast to the more historic parts of the city and gives you a different perspective without ever feeling disconnected. If you have time, getting just outside the city is worth it. Places like Cambridge, home to Harvard University and Massachusetts Institute of Technology, feel like an extension of Boston but with their own rhythm. It’s quieter, a little more academic, and easy to spend an afternoon wandering.
To Eat:
- Townsman – A more refined, slightly under-the-radar spot that feels polished without being overly formal. The menu leans seasonal and ingredient-driven, with dishes that feel thoughtful but not complicated. Good for a slower dinner when you want something elevated but still relaxed.
- Bin 26 Enoteca – Cozy, wine-focused, and perfect for a casual night that turns into a few more glasses than planned. The food is simple Italian—small plates, pasta, and things that pair well with wine. It’s an easy, no-pressure kind of place.
- Audubon Boston – Laid-back, slightly local-feeling, and a good mix of food and drinks. It’s the kind of place that works for brunch, dinner, or just stopping in without a plan. Feels easy in the best way.
- The Barking Crab – Right on the water and very much a “Boston in the summer” kind of spot. It’s casual, a little chaotic, and perfect for seafood and drinks with a view. Come here more for the setting than anything else.
- Coppersmith – Big, industrial space with a rooftop and a fun, social atmosphere. It’s lively without feeling overdone, and a good option for groups or a more casual night out. Works well for both food and drinks.
- Neptune Oyster – Small, always packed, and one of the best seafood spots in the city. The lobster roll is what everyone comes for, but everything here is done really well. Be ready to wait—it’s part of the experience.
- Contessa – Rooftop, polished, and very much a scene. It’s Italian, but the real draw is the setting—views over the city and a crowd that leans dressed up. Great for a later dinner that turns into drinks.
- SRV – Venetian-style small plates in a warm, modern space. It feels elevated but still approachable, with great pastas and a strong wine list. Good for a relaxed but really solid dinner.
- O Ya – One of the best sushi experiences in the city. It’s more of a splurge and definitely a full night out, but everything is incredibly thoughtful and well executed. Worth it if you want something special.
- Mamma Maria – Classic North End Italian in a more refined setting. It’s quieter and more intimate than the typical spots in the neighborhood, which makes it great for a longer dinner. Feels timeless.
- Row 34 – A go-to for oysters and seafood, with a slightly more modern, lively feel. It’s busy in a good way, and works just as well for a casual dinner as it does for drinks and a few plates. Easy, reliable, and always good.
- Saltie Girl – Small, stylish, and very seafood-forward. The tinned fish selection is a standout, and the whole place feels a little more curated than your typical seafood spot. Great for something different.
- Toro – Lively Spanish tapas spot that’s perfect for groups. The energy is high, the plates are meant for sharing, and it’s one of those places that gets louder as the night goes on. Fun, social, and a little chaotic.
- Pammy’s – Worth crossing into Cambridge for. It’s cozy, a little romantic, and known for its pastas and thoughtful dishes. Feels like a neighborhood spot, but one you plan your night around.
- Uni – Sleek, Japanese-inspired, and a bit more under-the-radar. It’s great for a later dinner, especially if you’re looking for something that feels a little different from the usual Boston spots. Cool without trying too hard.
Coffee & Bakeries:
- Tatte Bakery & Café – One of the best coffee and breakfast spots in the city. It’s bright, consistently good, and perfect for starting the day without overthinking it. Come for coffee and pastries, but you’ll probably end up staying longer.
- Pressed – Casual, quick, and great when you want something lighter. Think smoothies, bowls, and easy lunch options that don’t feel heavy. A good reset spot in between bigger meals.
- Flour Bakery + Cafe – One of the most iconic bakeries in the city for a reason. Everything is consistently good, but the sticky buns are what people talk about. It’s the kind of place you end up going back to more than once without planning to.
- Bricco Panetteria – Tucked down a small alley in the North End and feels like something you’d stumble on in Italy. It’s tiny, no-frills, and all about really good bread and simple pastries. A true hidden gem.
- Bova’s Bakery – A Boston institution that’s been around forever—and open 24/7. It’s classic Italian pastries, cookies, and late-night energy all in one. Feels like part of the city’s fabric.
- Bakey – A newer favorite known for its warm, gooey babka and pastries. It’s a little more modern and casual, but the quality is there. Perfect for a quick stop that still feels special.
- Sofra Bakery & Cafe – Worth crossing into Cambridge for. The pastries and dishes lean Middle Eastern–inspired, which makes it feel completely different from the typical Boston café. One of those spots people go out of their way for.
To Drink:
- The Wig Shop – A hidden, speakeasy-style spot tucked behind a salon—very much a “you have to know about it” place. The cocktails are creative but still approachable, and the whole experience feels a little playful. Great for starting the night somewhere that feels different.
- Offsuit – Small, intimate, and one of the best cocktail bars in the city right now. The menu leans minimalist and thoughtful, with subtle twists on classics. It’s the kind of place where you go for one drink and stay for three.
- Backbar – One of the most creative cocktail programs in the area. The menu changes often and leans playful, with drinks that feel unexpected but really well executed. Worth heading just outside the city for.
- Brick & Mortar – A hidden upstairs bar that feels slightly under the radar. It’s dark, cozy, and known for really well-balanced cocktails. Perfect for a low-key, late-night vibe.
- The Beehive – More of a full atmosphere than just a bar. Think live music, dim lighting, and a slightly eclectic crowd. It’s a great place to start the night and let it turn into something longer.
- Wink & Nod – A speakeasy-style spot with rotating themes and a creative cocktail menu. It leans a little more experimental, which keeps things interesting. Good if you want something less predictable.
- Citrus & Salt – Bright, fun, and more social than serious. The cocktails lean tequila and mezcal, and the whole place has a lively, almost vacation-like energy. Great for groups or a more upbeat night.
- OAK Long Bar + Kitchen – A classic, polished hotel bar inside the Fairmont. It’s elegant without feeling stiff, and perfect for a pre-dinner drink or something a little more refined. Feels timeless in the best way.
- Eastern Standard – A Boston institution that’s recently made a comeback. It’s buzzy, classic, and works for everything from dinner to late-night drinks. One of those places that always feels like something is happening.
- The Silhouette Lounge – A true dive bar and a complete contrast to the rest of this list. It’s cash-only, no-frills, and very local. Go here when you want something unpolished and real.
- Oak Long Bar + Kitchen
- Alden + Harlow– More food-driven, but the bar scene here is just as good. It’s lively, a little crowded, and great for cocktails that turn into dinner (or the other way around). A solid all-around night spot.
- A4cade – A4cade – A hidden arcade bar tucked behind Roxy’s Grilled Cheese. It’s playful, a little chaotic, and a fun change of pace from more polished cocktail spots. Good for groups or a late-night stop.
- Cafe Fixe – More low-key and neighborhood-feeling, but great for a relaxed drink. It leans wine and simple cocktails, with an easy, unfussy vibe. Good for slowing things down.
- Burro Bar – Casual, lively, and tequila-forward. It’s more about margaritas and a fun atmosphere than serious cocktails. Easy, social, and always a good time.
To-Do & See:
- Walk the Freedom Trail
- see: the Massachusetts State House, Bunker Hill Monument, Paul Revere’s House, and the site of the Boston Massacre (+ many more!)
- Catch a Red Sox game at Fenway
- Walkthrough the Boston City Garden or play frisbee at the Boston Commons
- Visit the Isabella Stewart Gardner Museum
- See the Boston Tea Party ships
- Grab a cannoli in Boston’s North End (I recommend Bova’s Bakery!)
- Get a brewery tour at Downeast Cider House
- Shop along Newbury Street
- Check out the most Instagrammed spot in Boston: Acorn Street, in the cute neighborhood of Beacon Hill
This fall I was asked a pretty urgent and rad request — the guys at Jos. A. Bank brewed up this idea and proposed to steal me for a weekend and drop me into a new city for 37 and 1/2 hours. The catch? I was to get around the city without a car, only wearing Jos. A. Bank’s TravelTech line with 37.5 Technology — I was up for this challenge! A few days before the trip, it was announced that the city was going to be Boston – and I was so excited! I’ve been to Boston a few times visiting two good buddies – hey Joe & Alex! – and really love the city. I was a bit familiar with the city but beyond excited at the chance to explore this New England city even deeper… and this time with a ticking clock!
Boston is a city that doesn’t try too hard—and that’s exactly what makes it work. It’s easy to navigate, full of character, and gives you just enough of everything without feeling like you need to rush. The mix of history, water, and everyday energy makes it somewhere you can keep coming back to and experience a little differently each time.
Stay Risky.
– John
Photography by Menelik Puryear
1 comment
Love the one you posted from Boston. You look great as always