Shepard
A stock of syrups, infusions, and other mixology gimmicks is unnecessary when your way with the classics is so sound. Such is the case at Shepard, where bar manager Nic Mansur mixes one mean Manhattan, among other elegant, restrained cocktails. Factor in the Francophile wine list and eclectic array of apéritifs, and you’ll want to spend the entire evening at the bar, away from the dining room din. One Shepard St., Cambridge, MA 02138, shepardcooks.com.
Giulia
This lovable Porter Square trattoria specializes in subtlety, right down to its dim lighting, intimate ambiance, and exposed-brick walls. The straightforward dishes—delicate house-made gelato and hand-rolled pastas with simple sauces, almost all available with a dusting of shaved truffles—are best accompanied by one of the restaurant’s dozens of regional wines. 1682 Massachusetts Ave., Cambridge, MA 02138, giuliarestaurant.com.
Armando’s
The DiPaolo family’s metal-deck magicians continue to churn out crisp yet pliable New York–style pies, all blanketed with house-made red sauce. Grab a cold can of grape soda, bask under the plastic glow of Little League placards along the wall, and raise a greasy slice to a half century of West Cambridge history. 163 Huron Ave., Cambridge, MA 02138, .
Chatham Bars Inn
Sweeping oceanfront views and luxe accommodations (did someone say spa butler and private beach?) are par for the course at this classic resort. But the Chatham Bars Inn is always a step ahead. Produce is sourced from its 8-acre farm. The spa overlooks Japanese rock gardens. Tired of boating and swimming? Pay a visit to the lush croquet court. And if you ever need to leave the resort, just borrow a house Lexus with unlimited miles. 297 Shore Rd., Chatham, MA 02633, chathambarsinn.com.
White Elephant
Leave your car on the Cape. Nantucket’s iconic harborfront resort, and its well-appointed rooms, are no more than 10 minutes from anyplace you’d want to go: Young’s for bikes, the Juice Bar for ice cream, the beach and ferry, too. And if you’re looking for the best on-island massage, you don’t even have to leave the building. 50 Easton St., Nantucket, MA 02554, whiteelephanthotel.com.
20byNine
Martha’s Vineyard is known for many things, from crispy fried clams to breathtaking beaches. But top-notch craft-cocktail bars wasn’t one of them—that is, until 20byNine came along. You can’t go wrong with a Manhattan, which comes close to the classic drink’s platonic ideal. After just one, you might be bold enough to cozy up to your bartender and ask for that day’s “smash,” a rotating off-menu creation. 16 Kennebec Ave., Oak Bluffs, MA 02557, 20bynine.com.
Ace Wheelworks
Sure, you can buy a decent bike anywhere, but the friendly folks at Wheelworks make the hunt stress-free. Once you've made your pick—be it a fixed-up second-hander or a brand-new designer bike—cycle easy knowing that anytime you need expert servicing, the team will take care of it. On warmer days, staffers line up the refurbished rides outside the store for easy browsing. 145 Elm St., Somerville, MA 02144, wheelworks.com.
Elisabeth Accardi, Upon a Star Events
With the friendliest vibe in the business, Accardi pinpoints your vision (and budget), creating kid-friendly bashes with unforgettable touches—ice-blue marshmallow fondue, retro toy stations, DIY designer-bag crafts. Employing former babysitters as her high-energy helpers, the Andover mom and former stage actress specializes in birthdays and bar/bat mitzvahs, but can make magic wherever you need to keep a group of kids entertained. uponastar.net.
The Kirkland Tap and Trotter
This mellow gastropub goes beyond carnival fare with nourishing plates like house-made spaghetti with meat sauce, or fish and chips, all accompanied by fresh, organic veggies. The space is so big that yowling tots won't raise brows, and servers happily accommodate the smaller set (in other words, modifications aren't frowned upon). 425 Washington St., Somerville, MA 02143, kirklandtapandtrotter.com.
Eyestarr
Not to be confused with those glue-on falsies of yore, lash extensions are painstakingly applied, one by one, to your own lashes. Sound extravagant? Perhaps, but skilled lash masters like Andrea Starr, of Eyestarr, have begun taking extensions from special-occasion accessory to daily must-have. Starr's work is both meticulous and natural-looking. From her bright, sunny shop on Newbury Street, a boldface clientele emerges batting a thousand. 291 Newbury St., Boston, MA 02115, eyestarr.com.
The Druid
Within the enormous spectrum of Irish-ish spots in Boston, what ultimately sets the Druid apart is its unwavering commitment to the basics (a perfectly poured Guinness, traditional live music sessions, an affable barkeep), plus some surprises, including a seasonal braised oxtail soup, Pretty Things Meadowlark IPA on draft, and trivia nights that pay cash prizes. 1357 Cambridge St., Cambridge, MA 02139, druidpub.com.
The Sinclair
With top-notch bookings (courtesy of promoters Bowery Boston) and the city's best-designed concert experience, the Sinclair is the House of Blues, only more intimate; the Paradise, without poles obstructing the sightlines; the Middle East downstairs, with a balcony and style. And no other venue can sustain this level of buzz, with surprises like Converse's weeklong run headlined by Passion Pit, Slayer, the Replacements, and Chance the Rapper this past spring. 52 Church St., Cambridge, MA 02138, sinclaircambridge.com.
Children's Beach
As its name implies, Children’s is a pint-size beach perfect for the entire family and delightful in its proximity to the cobblestone streets of the historical downtown. Lifeguarded — and with restrooms! — the shoreline comes complete with a grassy park, a playground, a bandstand, and the Surf, a kid-friendly restaurant where your crew can eat grilled cheese and hot dogs to their heart’s content while watching the ferries come in and out of the harbor. We can almost guarantee everyone will fall asleep on the ride home. 15 Harbor Way, Nantucket, MA 02554, nantucket-ma.gov.
Catalano Architects
Classic, timeless, and inspiring are words that come to mind when you see a house designed by Tom Catalano. Committed to designing spaces that are both functional and enduring, his firm’s number one goal is to create homes that suit their inhabitants’ lifestyles. Equally as important is honoring the integrity of the structure and seamlessly integrating it with its surroundings — which imbues even newly designed abodes with a sense of permanence. 125 Pearl St., Boston, MA 02110, catalanoarchitects.com.
Glossier
Shopping for cosmetics is a tactile experience; how else can you know whether the lip gloss or foundation you’re buying actually works for your face? That’s why we’re so glad this cult-favorite beauty brand recently landed in Boston. Brimming with testers of all the must-haves — from the miracle-working brow pomade to the heavenly gel-cream blush known as Cloud Paint — the pink-hued shop is designed for experimentation and delight. 120 Newbury St., Boston, MA 02116, glossier.com.