High Street Place
This atrium food hall in the Financial District makes a strong case for returning to the office — or, better yet, converting those underused buildings into more housing. But even if you don’t live or work downtown, it’s worth stopping by for one of the city’s best cocktail bars (Daiquiris & Daisies), craveable quick bites like Mike & Patty’s breakfast sandwiches, and globetrotting chef Tiffani Faison’s take on both lobster rolls and pepperoni pizza. 100 High St., Boston, MA 02110, highstreetplace.com.
Grill 23 & Bar
Chris Himmel’s earliest memories involve running around the dining room at Grill 23 & Bar, the stately Back Bay steakhouse that celebrated its 40th anniversary last year. The second-generation owner was five when the restaurant opened; 20 years later, he assumed control of the day-to-day operations, and nowadays is president of the entire Himmel Hospitality Group, which also includes Harvest, Bistro du Midi, and the Banks Fish House. Continue reading ... 161 Berkeley St., Boston, MA 02116, grill23.com.
Boston Chops
Thanks to a few hip newcomers, scrappy Downtown Crossing is having a moment. If you ask us, that’s even more reason to celebrate this luxe steakhouse, which remains a neighborhood favorite after six years. The restaurant is where businessfolk with expense accounts can summon Japanese Wagyu and trophy bottles of Burgundy while the rest of us enjoy modestly priced prime steak frites, melt-in-your-mouth popovers, and excellent cocktails. 52 Temple Place, Boston, MA 02111, bostonchops.com.
Angela's Café
Locals flock to both Eastie locations of this Mexican favorite for crowd-pleasers such as fresh, high-quality guacamole, ceviches, tacos, and burritos. But the best reasons to visit are the rare in-Boston flavors of Puebla, seen in the menu’s rajas poblanas (shredded peppers with sour cream and queso fresco), Adobo-marinated tacos arabes, and dishes sauced with ravishingly complex moles, pipiáns, and tingas. East Boston, angelascafeboston.com.
Prima
Fresh breads and cheeses, jumbo steaks, and big-as-your-face chicken Parm have helped this City Square newcomer carve its own niche among the city’s abundant Italian steakhouses. The elegant design doesn’t hurt, especially the pink-and-red “Rose Room” in the back — book that Valentine’s Day reservation ASAP. 10 City Sq., Boston, MA 02129, primaboston.com.
Comfort Kitchen
The dining scene in Boston’s largest neighborhood didn’t always reflect the area’s diversity — that is, until Comfort Kitchen came along. The restaurant at the intersection of Caribbean, African, Asian, and American soul-food cuisines offers everything from jackfruit sliders and harissa-date chicken bowls from the afternoon café to occasion-worthy plates (think: jerk-roasted duck leg with rice and peas) and Sumac Sour cocktails come dinnertime. 611 Columbia Rd., Dorchester, MA 02125, comfortkitchenbos.com.
Urban Hearth
The four-seat chef’s counter offers a front-row seat to the culinary ballet performed seamlessly by chef Erin Miller and her team, who weave together an adventurous tasting menu from the freshest seasonal ingredients in the tiniest of kitchens. Here, it’s high-end dining sans snobbery — while dishes are plated to tweezered perfection, the vibe is alway sconvivial and warm. 2263 Massachusetts Ave. , Cambridge, MA 02140, urbanhearth.net.
Chocolate Therapy
We’re not exactly advocating eating your feelings…but when the treats come from Chocolate Therapy, it might not be the worst idea in the world. Thirteen years ago, owners Pam and David Griffin left corporate America to try their hand at chocolate-making — and the results speak for themselves. The couple recently relocated their shop to Wayland and keeps the cases stocked with row upon row of bonbons in unique flavor combos (London Fog, Key lime, French toast) that are as beautiful as they are utterly delicious. 63 Andrew Ave., Wayland, MA 01778, thechocolatetherapystore.com.
Table
The bright, San Marzano–based marinara enveloping Table’s generously sized beef, pork, and veal meatballs makes every season feel like tomato season. And that’s not the only reason to celebrate at this restaurant, where every meal feels like a dinner party thanks to the communal seating and family-style platters of food you’ll share with your group. 445 Hanover St., Boston, MA 02113, tableboston.com.
Café Fresh Bagel
A great bagel does three things well: texture, flavor, and shape. And this longtime takeout favorite nails them all. A glossy, crackly crust with a slight chewiness gives way to an interior with plenty of “pull” to it. A hint of sweetness balances any savory toppings you might add (think: lox; chicken salad; or bacon, egg, and cheese), and a perfectly sized middle makes for even toasting and plenty of room for one of nine available flavored cream cheeses. Add a large iced coffee, and every morning is yours for the taking. 896 Highland Ave., Needham, MA 02494, .
Chilacates
Chilacates’ burritos are fresh, authentic, and reliably comforting every single time. The kitchen starts with some seriously generous portions (plenty to save in the fridge for your next meal, trust us.) Then there are the proteins — 12 to choose from, including birria, grilled shrimp, and chorizo, as well as vegetarian options and a breakfast burrito — plus countless sauces and toppings. And unlike most so-called destination burritos out there, with 11 locations, Chilacates is a destination that’s probably pretty easy to get to. Multiple locations, chilacatesmx.com.
Nomad
It may be chaotic in downtown Nantucket on a typical summer day, but inside the apparel and home-goods store Nomad, all is calm. Set in soothing coastal tones, the store offers a place to rest your eyes on a neutral palette of sophisticated home accessories, including throws, pillows, and glassware. Worldly sourced loungewear, jewelry, and sandals, meanwhile, epitomize what we’d call Nantucket barefoot elegance. 17 Centre St., Nantucket, MA 02554, nomadnantucket.com.
Faraway
The main guest house at this chic boutique hotel may date to 1742, but the interior design is firmly planted in the 21st century. Spread out between six buildings, the property features a central swimming pool and perfectly manicured grounds, with sleek common areas that hint at stylish rooms decorated in warm, neutral tones and appointed with five-star amenities. 23 Kelly St., Edgartown, MA 02539, farawaymarthasvineyard.com.
"Cop Slide"
Comedian John Oliver declared this August 2023 viral video “the single best movie of the summer,” and what a groundbreaking work of gonzo filmmaking it was. Seven seconds of an on-duty Boston police officer shooting out of a tube slide like a potato from an exhaust pipe, “Cop Slide” yielded tens of millions of TikTok views, inspired Halloween costumes (and FOIAs), and transformed the City Hall Plaza playground into a tourist attraction. Not your average enforcement beat, but one with way more weeeee!
Wenham Street Cinema
The films are free, the vibe is neighborly, and the seating is bring-your-own at this DIY screening space, which also happens to be a Jamaica Plain home garage. Resident Matt Shuman started casually hosting watch parties here in 2015, but the pandemic necessity for open-air gatherings made his Forest Hills carport an Instagram-official community venue. Now, Wenham Street Cinema’s 2024 season is already underway, with live-music performances, comedy, and movies like Dunkirk and Bring It On programmed through October. 23 Wenham St., Boston, MA instagram.com/wenhamstreetcinema.