STAY

Fly into Providence, Rhode Island, and meet a driver at the airport. Transfer to one of our recommended hotels in Newport, either The Vanderbilt, an early 20th-century mansion recently renovated by Auberge Resorts Collection and located in the heart of town, or Castle Hill Inn, perched right on the coast about 15 minutes from the city center by car. The former has a dark contemporary-eclectic décor, and the latter is brighter, with a classic-modern style.

DINE

The Mooring Seafood Kitchen & Bar has a bright harborside dining room that can be opened or closed to the docks, as well as cozier wood-beamed spaces off the water. Oyster fans should take advantage of the impressive raw bar. At Castle Hill Inn, Aurelia restaurant serves seafood-oriented tasting menus in a formal setting.

EXPLORE

Newport is best known for its “cottages,” the opulent summer homes of many of America’s wealthiest New Englanders in the Gilded Age. The grandest is the Breakers, a Renaissance Revival palace with an interior ornate enough to dazzle a Medici. Consider taking a behind-the-scenes guided tour. Sailing enthusiasts will surely enjoy an outing with America’s Cup Charters, which offers private and public excursions aboard former America’s Cup racing yachts (the Andrew Harper Travel Office can help make arrangements). Fans of classic cars can visit two separate automobile museums: the small but highly worthwhile Audrain Auto Museum in downtown Newport, which has rotating temporary shows, and the larger Newport Car Museum about 15 minutes north of the center, which has a strong permanent collection encompassing a range of periods and styles. You might also consider an outing with Newport Classic Car Company. And it’s simply a pleasure to stroll the center of Newport, where much of the 18th- and 19th-century architecture remains preserved. Spring Street, not far from The Vanderbilt, has a wealth of appealing boutiques and galleries. The Touro Synagogue National Historic Site, the oldest synagogue in the United States, is also a short stroll from The Vanderbilt. It hosts both tours and prayer services.

EN ROUTE

If you’re traveling between mid-June and mid-September, transfer 30 minutes to the Rhode Island Fast Ferry launching from North Kingstown’s Quonset Point. Alternatively, Seastreak offers year-round service to Martha’s Vineyard from the New Bedford ferry terminal, about 45 minutes from Newport.

STAY

Arrive in Oak Bluffs or Vineyard Haven, depending on your ferry, and transfer to either the Harbor View Hotel, a resort on the edge of Edgartown overlooking the sea, or The Charlotte Inn, a gracious converted mansion with highly attentive service on a quiet street in the center of town. The Charlotte Inn is hardly the only well-preserved historic mansion in Edgartown; elegant examples fill the center, standing as a testament to the wealth generated from whaling in the past.

DINE

Right on the harbor in Edgartown, Atlantic Fish & Chop House serves straightforward but enticing fare. Menu highlights include a bone marrow and cod brandade starter topped with Asiago cheese gratin, a satisfying swordfish steak accompanied by a lemon beurre blanc, and wild striped bass crusted with pumpkin seeds and served with a charred-tomato vinaigrette. Gourmands might also enjoy a BYOB boat tour of Cottage City Oysters, which includes oysters plucked right from the water and shucked on board.

EXPLORE

Perhaps take a private walking tour of Edgartown and/or do a private half-day exploration of the island’s high points with Edgartown Tour Company. The Aquinnah Cliffs are especially scenic, and Menemsha looks like the archetypal New England fishing village (both draw crowds in high season). Martha’s Vineyard also offers a variety of fine beaches and a web of hiking trails, as well as numerous pleasure cruise options.

EN ROUTE

From mid-May to the end of October, it’s possible to take the Hy-Line Cruises ferry from Oak Bluffs on Martha’s Vineyard to Hyannis.

STAY

Rent a car at the dock and drive about 30 minutes to the long-recommended Wequassett Resort and Golf Club. Take the rest of the day to relax in your accommodation (ideally with a sea-view patio or terrace), by the beach or at the pool.

DINE

A block off Chatham’s Main Street, Impudent Oyster’s bright dining room has white tablecloths, but it still feels appealingly casual, especially with its lively bar in the back. Opt for unfussy seafood dishes like superb classic clam chowder or the decadent Nantucket scallop sandwich with crumbled bacon, melted Monterey jack and tartar sauce on a soft baguette.

EXPLORE

Wequassett itself offers myriad activities, including tennis clinics, award-winning golf and a variety of spa treatments, plus children can take advantage of its extensive kids’ club. A beach extends away from the main pool, but for more of a castaway feel, a motor launch shuttles guests to and from the more remote Outer Beach (umbrellas, chairs and water provided). Other water-based activities include seal-watching tours, sailing, fishing and kayaking. The resort also serves as a fine central base for excursions. Extending north and south from Wequassett is the Cape Cod National Seashore, encompassing many enviable beaches and beautiful hiking trails amid dunes, forests and salt marshes. Historic Chatham, with its many shops and restaurants, is a short drive south, as is the Chatham Municipal Airport. From there, Stick’n Rudder Aero Tours offers highly recommended scenic biplane flights.

STAY

Wequassett can arrange for a private yacht transfer directly from the resort’s pier to Nantucket. Choose between White Elephant Harborside Hotel, a stylish waterfront complex; The Wauwinet, a lavishly restored landmark hotel; or the Inn at White Elephant, an inviting 20-room hotel featuring a contemporary décor.

DINE

Aside from the restaurants located in our recommended hotels, the charming, atmospheric American Seasons serves excellent food just a short walk from the center of town. The menu features French- and Italian-inspired cuisine made with local ingredients, such as chitarra pasta with fresh tomatoes, or a chicken liver foie gras parfait. Seafood is the obvious choice, but the roast duck with rutabaga and spiced quince is superb. Service is excellent, and the wine list is full of delights.

EXPLORE

Stroll the delightful cobbled streets of the town of Nantucket, full of boutiques and art galleries. The Travel Office can arrange private yacht cruises, seasonal oyster tours and picnic lunches on a private beach. At The Wauwinet, hourly shuttle service to and from town and complimentary bikes are available.