Winnetu Oceanside Resort
The Winnetu takes the prize this year not only for its comfort, charm, and amenities such as poolside cabanas and front-lawn clambakes, but also for its new programming. The resort’s Over-Sand Beach Day package includes a bottle of prosecco, a picnic lunch, and a permitted Jeep waiting to take you on a romp to one of the island’s outer beaches. Signature oyster tours and kayaking expeditions, meanwhile, round out the summer adventures. 31 Dunes Rd., Edgartown, MA 02539, winnetu.com.
Beauport Hotel
The North Shore isn’t exactly tourist-averse, but upscale hotels are still surprisingly hard to come by—which made the Beauport a particularly welcome addition when it debuted in 2016, rendering the site of a Birds Eye frozen-foods plant unrecognizable. Boasting beachfront access and a roof deck with a pool and fire pit, the hotel is a short walk from Gloucester’s downtown. But why would you want to leave when Wellfleet oysters and local craft beer are moments away at the in-house restaurant? 55 Commercial St., Gloucester, MA 01930, beauporthotel.com.
Legal Harborside
For a port city, Boston is surprisingly lean on fantastic waterfront dining. Thankfully, Legal Sea Foods’ Titanic-size flagship offers prime views from lower-level patios and a swinging third-floor rooftop lounge that kisses the space where sky and ocean meet. (A retractable roof and glass walls assist in iffy weather.) Head here to soak up the sun, slurp down oysters, and smell that salty air. 270 Northern Ave. , Boston, MA legalseafoods.com.
Salem
With its prime waterfront location and cute boutiques (hello, J Mode and Roost and Company), Salem has become so much more than ground zero for the witch-tourism industry. The town's many culinary offerings, including new seafood restaurant Sea Level Oyster Bar and a soon-to-open specialty cheese shop, keep gastronomes satisfied. The Peabody Essex Museum, meanwhile, is a must-visit for culture vultures. MA
Rialto
It’s hardly a secret that Jody Adams’s Cambridge institution has mastered high-end Italian fare. But the strength of the vast, separate bar menu—with bites like duck-pâté bruschetta and pan-roasted broccoli, and larger plates like rigatoni Bolognese—might be the biggest secret in Harvard Square. Swing by on Mondays between 5:30 and 7 p.m., when oysters are a buck a shuck. One Bennett St., Cambridge, MA 2138, rialto- restaurant.com.
Shreve, Crump & Low
So a pearl may be nothing more than a grain of sand that managed to irritate an oyster. The finished product is way more likely to soothe than aggravate. Shreve, Crump & Low has one of the largest selections of Mikimoto pearls in New England, including the South Sea collection of creamy white and black pearls studded with diamonds and precious gems. 330 Boylston St., Boston, MA .
Captain Frosty's
Abandon all hope of squeezing into that teeny bikini after a feast at Captain Frosty's, the pocket-size clam shack that's been plying Mayflower and Corporation beachgoers and their overtaxed arteries with fried seafood of every strip—clams, scallops, oysters, shrimp—for more than 30 years. Hungry bathers who are reluctant to watch their love handles grow in real time can don their street clothes and dine at the shack's indoor tables or brick-patio benches. 219 Rte. 6A, Dennis, MA 2638, captainfrosty.com.
L'Espalier
The better the food, the flirtier we feel. And chef Frank McClelland's tasting menu really revs our engines. With choices from white asparagus and oyster salad to decadent poached lobster and a selection of handcrafted cheeses, we guarantee just a few bites will have your date absolutely enamored, too. Impeccable service in the hushed dining room helps seal the deal, ensuring lovebirds a happy ending. 774 Boylston St., Boston, MA 2199, lespalier.com.
The Raw Bar
Mashpee's New Seabury is one of the Cape's toniest communities, brimming with quaint shops, picture-perfect lawns, and crushed-seashell pathways. The Raw Bar, which dispenses cheap beer beneath bare-breasted mermaid memorabilia, is the one place locals and visitors can really let their hair down. And they do—over platters of raw oysters, littlenecks, and heralded lobster rolls. The latter are technically big enough to share, but if you're like us, you'll want to savor every bite of your own. 252 Shore Dr., Mashpee, MA 2649, therawbar.com.
Arnold's Lobster & Clam Bar
Just as hot dogs are a Fenway favorite, it would be silly to skip clams on Cape Cod. And among the dozens of small shacks, Arnold's remains a standout. This quality-conscious spot now has a dining room and screened-in patio—as well as lengthy lines (it's worth the wait, though). Prepare to get messy while scarfing Wellfleet oysters, lobster rolls, and, of course, the famous Arnold's fried clams. 3580 State Hwy. (Rte. 6), Eastham, MA arnoldsrestaurant.com.
Sesuit Harbor Café
Sure, seafood is easy to come by on the Cape. But you're reading this magazine, so you’re looking for the best. Pack your cooler and sunscreen and snag a picnic table at Sesuit Harbor Café: Yes, you’ll wait in a line out the door, sit outside rain or shine, and BYOB, but once those heaping trays of lobster rolls, fried scallops and clams, and Cape Cod Bay oysters are in front of you, you’ll understand. sesuit-harbor-cafe.com.
Polpis Bike Path
Looking for a post-quarantine quad challenge with the best views on the island? Stretching from the Old South Road rotary all the way to ’Sconset, this 9.5-mile paved route is it. Once you’ve cruised past the sky-blue inlets of oyster farms and mile upon mile of emerald-green moors buzzing with songbirds, soothe those achy muscles with an icy drink from the Sconset Market, or refuel with an ice cream (or two). An easy and quick pedal from there to the Sankaty Head Light offers an unforgettable view of the Atlantic. Nantucket, MA
Reelhouse
Outdoor dining is a great way to see the city from every angle — and that's exactly why we love Eastie’s waterfront Reelhouse, which offers uncommonly sweeping skyline views to accompany its specialty spritzes and global cuisine. Plus, it’s just a short walk away from the Tall Ship, its new sibling oyster bar located aboard an actual 245-foot vessel moored at a pier. 6 New St., East Boston, MA 02128, reelhouseboston.com.
Ball and Buck
With deer heads mounted on the wall and a stack of vintage Playboys for sale, Ball and Buck is a refuge for every red-meat-eating, style-conscious male tired of the same soulless shops along Newbury. Yes, you'll find wallets and belts, all made in the U.S. and geared toward a rugged gent with a sense of refinement, but it's the vintage watches, oyster knives, and Ball and Buck special-edition 12-gauge shotguns that set this store apart. If only it had a bar. 144B Newbury St., Boston, MA 02116, ballandbuck.com.