Pelham House Resort
Courtesy of Pelham House Resort Should you take your spicy marg by the beach or the pool; the swanky rooftop restaurant or the cool firepit-equipped patio? These are the toughest decisions you’ll have to make at this newly Luxe Dennis Port Hotel, which reopened in 2020 with freshly renovated oceanfront rooms and a slew of fun amenities. And with the opening of two new satellite properties this summer — each with its own unique look but connected to the main resort’s beach bonfires and poolside live music via shuttle — the Cape’s newest hot spot is only getting hotter. 14 Sea St., Dennis Port, MA 02639, pelhamhouseresort.com.
Dennis Cycle Center
The best — and some might say only — way to rent a bike on Cape Cod is from a place right along the rail trail. While there are several options for doing just that, Dennis Cycle Center gets high praise for its wide selection of two-wheelers and accessories — including plenty of options for the littlest cyclers — reasonable rates, and ultra-friendly staffers. Extra props for the expert repair services, for those who need a tune-up on their own summer ride. 249 Great Western Rd., South Dennis, MA 02660, denniscyclecenter.com.
Pain d’Avignon
This may be Hyannis, not Honfleur, but for a few hours at least, you can pretend you’ve teleported to France’s shoreline with a late-morning meal at this boulangerie/bistro, which celebrates its 30th birthday this year. Here, les oeufs are served every which way; crêpes get spiked with Grand Marnier; and the French onion soup is an exemplar of the form. The pristine oysters, though? Those are Wellfleet, naturally. 15 Hinckley Rd., Hyannis, MA 02601, paindavignon.com.
Tree House Brewing Company
Okay, so it’s not technically a bar, but with tickets required for entry (and sometimes selling out), this brewery’s new Sandwich outpost is certainly the most coveted spot around to sip suds at a picnic table overlooking Cape Cod Bay or inside an airy, whitewashed taproom. That’s thanks to Tree House’s IPAs, imperial stouts and porters, and more, which beer aficionados have traveled from far and wide to sample since the brewery opened its first location in western Massachusetts 11 years ago. We’ll let you in on a little secret: They taste even better on vacation. Sandwich, MA treehousebrew.com/visiting-sandwich.
Beach Road
Photo by Elizabeth Cecil President Obama and his family have been known to dine at this hot spot within whistling distance of the Vineyard Haven ferry. One taste of the seafood-forward menu (the blue-swimmer crab app is a favorite), and you’ll see why. Chef Frank Williams honors the handiwork of island fishermen, farmers, and food artisans by transforming it into something sublime; the dining room, meanwhile, oozes nautical charm — a nod to the shipyards and boatbuilders surrounding it — and overlooks Lagoon Pond, the ideal spot to watch the setting sun or rising moon. 79 Beach Rd., Vineyard Haven, MA 02568, beachroadmv.com.
L’Etoile
Photo by Elizabeth Cecil Located in a former whaling captain’s house, this bistro’s bar earns top honors for versatility. Begin with the aptly named “startini” (citrus vodka, Cointreau, lime juice, pomegranate, and prosecco) or another creative cocktail. The singlemalt scotch and bourbon selections are impressive, while wines by the glass cover a lot of terroir in price, varietal, and geography. Then there’s the atmosphere, always lively without being obnoxious: Guests can choose between a seat at the bar, a banquette, or the porch, although the Adirondack chairs on the lawn beckon on balmy nights. 22 North Water St., Edgartown, MA 02539, letoile.net.
The Beach Plum Inn
There’s no shortage of charming inns everywhere on the Vineyard, but none of them has the vantage point of this rustic farmhouse overlooking the absurdly picturesque fishing village of Menemsha. With rooms and cottages available, it embodies the laid-back up-island vibe; the path to the beach, for instance, winds past the chicken coop. Umbrellas, beach towels, and chairs are complimentary, and guests get coveted passes to Lucy Vincent and Squibnocket beaches, but the real reason to stay here is the mind-bending sunsets over Menemsha Bight. 50 Beach Plum Ln., Menemsha, MA 02535, beachpluminn.com.
The Outermost Inn
Owned by James Taylor’s brother Hugh, the Outermost doesn’t accept reservations for brunch, but snagging a coveted table perched atop the famous Aquinnah Cliffs is more than worth the wait. Breakfast favorites like French toast and smoked brisket hash, or lunchier plates such as the excellent veal meatballs, are served in an airy dining room with a constant breeze and stunning views of Vineyard Sound. A walk to the Gay Head Lighthouse is a post-prandial delight. 81 Lighthouse Rd., Aquinnah, MA 02535, outermostinn.com.
Cru
Our favorite time of day to plant ourselves at Cru’s breezy dockside bar is during that sweet spot of around 2 or 3 in the afternoon. After a hot day on the sand, that’s the perfect time to cool off with a Cru-cumber (its famous cucumber martini) and, when hunger strikes — as it always does — the best lobster roll around, served buttery hot or refreshingly cold. One Straight Wharf, Nantucket, MA 02554, crunantucket.com.
Young’s Bicycle Shop
Photo by Elizabeth Cecil Call it the OG of Nantucket bike rentals: For nearly 100 years, this family-owned business has been operating just steps from the ferry terminal, marked by the trademark spinning bike wheel out front. And considering the wide selection of beach cruisers, mountain bikes, and mopeds on offer, it’s no surprise it’s been around so long. Need four wheels for your adventure? Check out the selection of over-sand vehicles for rent. 6 Broad St., Nantucket, MA 02554, youngsbicycleshop.com.
Brant Point Grill
Photo by Elizabeth Cecil We firmly believe that enjoying oysters and clams on the half shell from this elaborate buffet at the White Elephant resort is the only good way to spend a Sunday on island. Decadent desserts (served in miniature sizes for plentiful sampling, natch) and a hefty quarter-pound-lobster-laden bloody mary keep even the busiest of gogetters anchored to their chair for hours to enjoy that one-of-a-kind view of sailboats bobbing on their moorings and ferries gliding in and out of the harbor. White Elephant Hotel, 50 Easton St., Nantucket, MA 02554, whiteelephantnantucket.com/dining/brant-point-grill.
The Nantucket Hotel
Very few hotels these days leave us with a deep feeling of appreciation — that bittersweet sadness we experience upon checking out that we don’t actually live there. Maybe it’s the complimentary antique fire-truck rides for the kids, or the plush robes offered in each room for the adults, or the two heated pools and the spa. Or maybe it’s all of those things combined that make this place feel so special — not to mention the overwhelmingly helpful, attentive staffers who seem like family by the time you sadly make your exit down the grand front stairway to head home. 77 Easton St., Nantucket, MA 02554, thenantuckethotel.com.
Sister Ship
We didn’t expect to fall so deeply in love with everything about Sister Ship (who immediately likes the new kid?), the self-described “relaxed cocktail club” inside the new Faraway hotel. And yet everything from the cozy décor — think turn-of-the-century captain’s quarters meets underground speakeasy — to the Mediterranean-style dishes make this our new favorite spot on island. We’d advise you on what to order, but the kitchen continually changes up the menu with inventive specials. However, they swear that the tender rib-eye for two will remain a menu staple — and thank goodness for that. 29 Centre St., Nantucket, MA 02554, farawayhotels.com/restaurant/sistership.