Cape Cod is a lot easier to spot in a picture — all those iconic white clapperboard houses, picturesque lighthouses and wild beaches recalling any number of Edward Hopper paintings — than it is to find in real life.
Unlike the coastal strip of Massachusetts known collectively as North of Boston, where one charming township follows another, this old fishing ground — only latterly reinvented as a tourist destination — is a sprawl of mainland and island communities with no visible centre
Unless, that is, you count Boston itself, where every Cape Cod trip must start. It is a splendidly maritime, as well as cultured, city, surrounded by water on all sides. Fine hotels with sea views include the new Intercontinental — close to the handsome new Instituted of Contemporary Art — and the Seaport Hotel, even more convenient for those planning a trip to the Cape after a city stopover as it is right opposite the terminal from where a fast ferry whizzes passengers all the way to Provincetown at the far end of the Cape — a trip which would take hours by car.
This lively, historic and attractive town ticks all the boxes and unlike many of its neighbours, Provincetown has a sound tourist infrastructure, with lovely inns, restaurants and attractions, if less lovely shops.
Inns abound, but it would be hard to find a better location than the Lands End Inn, which has been lovingly restored and has a huge verandah from which to enjoy the sunset.
Fine fish dinners await almost opposite at the Red Inn, overlooking the harbour. No visitor should leave town without visiting the library, housed in a spectacular old church, which astonishingly has a historic schooner suspended from its ceiling
What one really wants from Provincetown is another boat headed straight for the pair of delightful islands — Martha’s Vineyard and Nantucket — which are the glory of the Cape. However, for the moment one must pootle halfway back to Boston along the mainland to take a ferry from either Hyannisport — forever associated with the nearby Kennedy compound — or Woods Hole.
The two islands are quite different, but both very much worth a visit, though “the Vineyard” — as the many celebs who holiday or have second homes there call it —is larger, easier to get around and offers more variety.
Boats arrive at Vineyard Haven or Oak Bluffs. The former is the de facto centre with a pleasant range of shops and a nice family inn, the Mansion House, which has a Jewish owner.
The town is also where the island’s resident “royal family” — also Jewish — holds court. They are the Simons — Carly, the songwriter, and her photographer brother Peter. Each has a great shop: Carly’s is a real hive of island retail therapy with its great furniture, fabrics, books and china.
The best part about Peter’s shop, hung with his pictures of Swinging Sixties celebs, is the exquisite jewellery made by his wife, Ronni. Fans of Gossip Girl will have seen some of Ronni’s gold wire earrings studded with fragments of semi-precious stones dangling off the lobes of the lovely Serena.
An efficient bus service allows travellers to get around the island with a roving daily bus ticket, and a visit to Oak Bluffs is a must. Built originally for devout Christians, the community of colourful gingerbread summer houses at its heart is now open to homeowners of all denominations — though they still require a reference from their rabbi or priest testifying to their moral fibre before residence is approved. A half-hour walking tour is a great way to learn the settlement’s history.
Some visitors may never get further than the two ferry-ports, but it is really worth continuing to Menemsha, a rustic, ramshackle corner of the island with a great jetty where you can sit and eat freshly-caught and cooked fish, watching the boats bob on the water.
The island’s most charming souvenirs are the large shells, hand-painted with nautical scenes, and the wooden model boats made by the husband-and-wife team who have run Menemsha’s tiny gift shop for decades.
Although this tiny fishing village looks like there’s absolutely nothing fancy hereabouts, appearances can be deceptive. Meg Ryan and James Taylor have summer homes here, and one of the most laid-back yet desirable places to stay (and eat) is the Beach Plum Inn. Just a short walk away, it serves wonderful candlelit dinners.
As if all these varied island riches were not enough, Edgartown is considered the jewel in the crown of Martha Vineyard. An elegant village of cobbled streets awash with smart red-brick homes and inns, it also has one of the best restaurants in America — the award-winning Detente, which displays a level of sophistication that would not be out of place in New York.
Edgartown is also home to the splendid English Butler tea-room, run by a Brit, Alison David, who came to the island in search of Carly Simon; now the star comes for the cuppas served in bone china. The town’s Victorian Inn is the place to stay.
If you never get over to Nantucket — a 15-minute hop by plane, longer by ferry — Edgartown will give you an idea what its eponymous town looks like, though the latter is larger and somewhat grander. One family owns several hostelries, making a mix and match scenario easy even without a car. Start at the Summer House in the heart of town, whose little garden cottages are utterly divine, then ask to be brought to their delightfully laid-back and countrified beach-side inn at Siasconset, where delicious dinners are served to piano accompaniment and cottages can be booked for an overnight stay.
Back in Boston (after allowing a couple of hours en route to explore the truly fascinating glass museum at Sandwich), do allow a day or two to enjoy America’s most cultured and refined city. Faneuil Hall and its lively surrounding shops are a must, and the nearby North End is home to numerous Italian restaurants. You can also nip up to the ritzy Back Bay, explore the Newbury Street shops and end the day at the elegant Beacon Hill Bistro.
Although Virgin serves Boston daily, their flights are often full. The answer is to fly (at the same price) into New York and take the excellent LimoLiner, a business class-style coach which transports travellers to the heart of Boston in enormous comfort (think reclining seats, wi-fi and complimentary snacks) in just four hours.
Jewish Cape Cod
● Jews arrived in Boston in the 17th century. The modern community, mainly based in Brookline and Newton, numbers 200,000.
● Of the many synagogues, the oldest is the Vilna Shul on Beacon Hill, and the largest Temple Israel.
● “Jewish Friendship Walks” take place around the city, including Cambridge, home to Harvard and the suburb of Brookline.
● There are Reform synagogues at Hyannis on Cape Cod, and Vineyard Haven on Martha’s Vineyard.
● Kosher restaurants can be found in Brookline and Newton.