Dogwood Cottage
Designed to resemble a Nantucket cottage, this boarding facility boasts attentive round-the-clock care, indoor and outdoor play areas, and your pup’s choice of rooms with beds. And no need to arrange Fido’s travel in addition to your own: Transportation is provided to Melrose, with pickup spots in Beacon Hill and the Back Bay. 20 Tremont St., Melrose, MA 02176, dogwoodcottage.org.
Turner Fisheries
A more self-consciously trendy restaurant than Turner Fisheries might call this a deconstructed buffet: Solicitous staffers bring to your table two apps, an entrée, side, dessert, and adult libation. Your in-laws won't even miss the omelet station. 10 Huntington Ave., Boston, MA 2116, turnersboston.com.
Simco's
There's no seating at this Mattapan institution, so after ordering at the window, be prepared to tear into your thin, footlong dog—slathered with chili, onions, and mustard and wedged into a hot, buttered-then-griddled bun—right there on the street (or, if you have the self-restraint, back in your car). 1509 Blue Hill Ave., Mattapan, MA .
Venison for dinner
At five milligrams less cholesterol per three-ounce serving than white chicken meat, venison satisfies your craving for red meat and your doctor's orders. The bottom line: it's you or Bambi. Guess who we're rooting for?
Galleria Italiana
By day it's a fast-food Italian eatery, but four nights a week Galleria Italiana is transformed into a trattoria, complete with background opera music and an Abruzzi-inspired menu. Try the risotto with spinach and four cheeses or the pasta with tiny mussels from New Zealand. 177 Tremont St., Boston, MA .
Teuscher
Ever wonder why the church once outlawed chocolate as too sensual? Airlifted weekly from the little chocolate gnomes in Zurich, delectable with the finest cream, butter, and milk chocolate, these are the kind of chocolates you eat so slowly that they melt in your hand long before they get to your mouth. 230 Newbury St., Boston, MA .
Baker's Best
Fabulous chicken (the piccata is especially wonderful), great veggie pizzas and calzones, and some of the best Caesar salad we've ever had. They'll even cater your weekend party, or—chicken soup to shank bone—your Passover Seder. 27 Lincoln St., Newton Highlands, MA .
The Rooftop Pool at the Colonnade Hotel
If summer finds you in the city instead of on the Vineyard, console yourself with a noon swim at the Colonnade's rooftop pool, then have lunch and work on your tan. For $20 you get use of the pool, towels, and a changing room, plus a light salad or sandwich. Bring your own sunscreen. 120 Huntington Ave., Boston, MA .
Brick Cellar at Atria
Estonian beer, caipirinhas with a citrus twist—this swanky underground bar is not your typical Vineyard watering hole. The drinks are fun, the atmosphereis cozy and intimate, and the food (including 10 different burgers) is tasty. Don't miss the photo booth on your way out. 137 Main St., Edgartown, MA atriamv.com.
Interlocks
The stylists at Interlocks don't just cut your hair. They teach you how to maintain the style, and which products to use to keep your tresses looking salon-perfect long after you've left the chair. And with an adjacent full spa, this is a one-stop shop for hair, nail, and body needs. 58 Merrimac St., Newburyport, MA interlockssalon.com.
Oro
There's no better way to start a Sunday than at Oro, just a stone's throw from the water in Scituate Harbor. Your morning coffee will go perfectly with the Nutella-stuffed French toast and brûleed bananas, but if a bloody mary is more your speed, try it with the Waldorf chicken-salad sliders and fries. 162 Front St., Scituate, MA restaurantoro.com.
Tresses & the Day Spa
Still feeling stressed from nearly missing the ferry? Have a knot in your neck that needs professional untying? Get yourself to Tresses, where the firm yet gentle hands of well-trained masseurs will work out whatever ails you. Don't be surprised if it becomes the highlight of your island stay 117 Pleasant St., Nantucket, MA nantucketspa.com.
Appetito
The Sunday brunch buffet at Appetito is to die for, with scrumptious eggs benedict, fluffy muffins, and perfectly seasoned homefries. Alas, eating any of it is out of the question: Everyone's checking out the tautness of your abs and the number of fat grams piled on your plate. Stick, good sirs, to the fruit. 1 Appleton St., Boston, MA .
Constitution Marina
Dock your boat, park your dinghy at no extra charge, fish for striped bass around the corner, and best of all, swim in Constitution Marina's new outdoor pool. One added perk that makes this the best deal in town—free parking for boat-owners. 28 Constitution Road, Charlestown, MA .
Continental Café
Garlic soup at the Continental Café (the Portuguese half), 445 Somerville St., Somerville. This pungent broth, supporting croutons and a perfectly poached egg, is strong enough to clear your sinuses but subtle enough so that it won't leave your close friends gasping. 445 Sommerville Ave., Somerville, MA .