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.
Union Street Inn
Co-owner Ken Withrow spent 20 years working for famed hotelier Ian Schrager, and the in-town inn he runs with his wife, Deborah, puts that pedigree on full display, from staffers trained to remember your name and wine preference to guest rooms featuring Frette bedding and free, strong WiFi. It’s also the only island B & B to offer made-to-order breakfasts, though individual tables mean you needn’t get chummy with fellow guests. 7 Union St., Nantucket, MA 02554, unioninn.com.
20byNine
Courtesy Photo 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.
Havana Club
Never danced a step in your life? No problem. This Central Square club holds $12 salsa lessons every Friday and Saturday at 9 p.m., plus bachata lessons on Mondays at 8 p.m. You’ll look like a pro by the time the real party begins, with more than 300 dancers burning up the floor from 10 p.m. until 2 a.m. 288 Green St., Cambridge, MA 02139, havanaclubsalsa.com.
The Banshee
Make sure someone on your quiz team checks Twitter before the games begin: Host Mark Daly always provides a few hints for social-media-savvy smarties. His questions run the cultural gamut, from celebrities to geography, sports to current events, and even music, with an audio round worth double points. A monthly tournament offers higher-stakes prizes, while every Wednesday night offers a new chance to win generous gift cards. 934 Dorchester Ave., Dorchester, MA bansheeboston.com.
Porchfest
West African drummers, punksters, Bollywood funksters, and space rockers, all jamming out on porches, patios, and more across Somerville. This outdoor festival just might be the only time all year that you’re going to be happy to hear your neighbor play the guitar. With copies appearing in Jamaica Plain, Roslindale, Arlington, and at the Lawn on D, it’s clear the fun(k) is now infectious. somervilleartscouncil.org/porchfest.
Danger Booth
Photograph courtesy of Zac Wolf When it comes to giving your guests custom photo keepsakes, it's best to think outside the box—or, in this case, the booth. Danger's open-air, freestanding unit (complete with a touchscreen, flash, and printer) can be as civilized or as crazy as you desire, with photo-fun experts on hand to hem a themed fabric backdrop, print out a step-and-repeat, or even hook you up with a designer for one-of-a-kind scenery. Move over, Instagram. thedangerbooth.com.
AE Events
Planning a wedding is like putting together a 1,000-piece puzzle, and the six-person team at AE Events is skilled at making it all fit. Want a seven-course Tuscan feast with live jazz for 400? Done. A 50-person bonfire beach celebration? No problem! From contracts and vendor negotiations to creative extras (taco bar, anyone?), they're steadfast, organized allies. And if your budget is a ball and chain, they'll work with that, too. 546 East Broadway, South Boston, MA 02127, aeevents.com.
Forklift
Mediterranean, Asian, classic American—this Union Square caterer will happily hop from cuisine to cuisine for your wedding spread, incorporating vegan and gluten-free menus with ease. Chefs Dennis Tourse and Jamie Rogers are tight with local farmers, which translates to personalized menus featuring natively sourced ingredients whenever possible. Top requests include avocado beggars' purses and fava-bean crostini with wild mushrooms. 5 Sanborn Ct., Somerville, MA 02143, forkliftcatering.com.
Konditor Meister
Whether it's duplicating Pinterest printouts or dreaming up a wholly original confection, Konditor Meister (German for "master pastry chef") creates wedding-cake wonders. Its tiered masterpieces have delighted couples for three decades with 21 cake-filling combos, from orange-champagne mousse to apple-cinnamon chai. No rubberized icing for your guests, either: KM forgoes fondant in favor of creamier (but equally decorative) rolled white chocolate, keeping both design and flavor front and center. 32 Wood Rd., Braintree, MA 02184, konditormeister.com.
L'élite Bridal & Bridesmaids
This petite third-floor boutique offers a who's who of designers (Amsale, Watters, and Monique Lhuillier) that are sure to please your discerning ladies. Some lines even allow for mix-and-match necklines, styles, and fabrics to ensure pretty little ’maids, all in a row. An added perk: refreshing honesty. If a look doesn't fit, the staff won't force it. 14 Newbury St., Boston, MA 02116, lelite.com.
Ports & Company
Along Route 3, it's the same sad story: shopping plaza after shopping plaza, each offering a slightly different version of the pants you've seen on every one of your coworkers. Break away from the crowd with a stop at this under-the-radar Cohasset storefront, which packs AG jeans, Nicole Miller dresses, cashmere sweaters, and other individualistic pieces onto shelf and rack. 23 S. Main St., Cohasset, MA 02025, portsandcompany.com.
Follain
This pore house founded by Babson College grad Tara Foley has dominated the healthy skin-care market of late—and with good reason. It features environmentally friendly products from more than 30 U.S. brands, like Indie Lee's cleansers and oils and Amber Blue's age-defying serums. Meanwhile, a new collection of men's shaving products rounds out the selection of thoroughly researched, wholesome skin saviors. (Multiple locations.) 65 Charles St., Boston, MA 02114, shopfollain.com.
The MacDowell Company
With decades of experience under their belts, the talented landscape architects and contractors at the MacDowell Company know a few things about exterior design. Whether creating the ultimate backyard oasis or sophisticated stone terraces and courtyards, MacDowell folks shepherd the process from beginning to end, ensuring picture-perfect results at every turn. Go ahead, give 'em a call. Your neighbors will thank you. 21 Center St., Weston, MA 02493, macdowell.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.