Martha's Vineyard & Nantucket Itinerary: The New England Island Week

Boarding is in Newport — Newport Shipyard or by tender from the harbor — with Providence forty minutes away and Boston about ninety. The captain and chef meet the group at the dock, run the welcome briefing, and get under way by early afternoon for the twenty-four-mile run east across Rhode Island Sound to the tail of the Elizabeth Islands, the chain Bartholomew Gosnold charted in 1602 before the Pilgrims ever raised the Cape.

Cuttyhunk is the deliberate opening move: a village of a few dozen year-round residents, one store, golf carts for traffic, and a fifteen-minute walk up Lookout Hill to a 360-degree view spanning the week ahead — the Vineyard filling the eastern horizon, Buzzards Bay north, open Atlantic south. It is the least famous stop on the route and, for many groups by Friday, the one they talk about most.

At six, the island's raw-bar skiff works the anchorage, shucking farm oysters and littlenecks straight over the rail — the chef builds the first dinner around whatever comes aboard. The anchorage goes dark and silent early. Tomorrow the week gets busier by design; tonight is the baseline the islands get measured against.

A morning run down Vineyard Sound with the current under the keel — the captain times the tide, which runs hard enough here to matter — and by midday the yacht is picking up its held mooring inside Edgartown Harbor, with the Edgartown Light on its sand spit to port and Chappaquiddick a stone's throw across the channel where the three-car On Time ferry shuttles back and forth all day.

Edgartown is the Vineyard at its most polished: the Greek Revival captains' houses along North Water Street built on whaling money in the 1840s, the Old Whaling Church's massive columns a block inland, and a walkable grid of galleries, bookshops, and bars between them. The afternoon ashore covers it easily, with a stop at the rooftop above the harbor or the 1742 Newes from America pub depending on the group's register.

The evening choice sets up the Vineyard's range. Dinner ashore in Edgartown runs from clam shacks to l'étoile's tasting menu; dinner aboard comes with the harbor's mooring-field glow and the lighthouse blinking at the entrance. Either way, the tender is five minutes from the dock, which is the entire logistical footprint of the day.

The lay day covers the island the harbor town can't. Oak Bluffs, a short hop up-island, is Edgartown's Victorian opposite: three hundred–plus painted gingerbread cottages ringed around the old Methodist campground, the 1876 Flying Horses — the country's oldest operating platform carousel — and Circuit Avenue's bars running at full July volume. The contrast with North Water Street's white clapboard is the whole point of seeing both.

The island's west end is the wild end. A car out through West Tisbury and Chilmark reaches Aquinnah, where the Gay Head cliffs stack a hundred feet of rust-and-ochre clay under the 1856 brick lighthouse — sacred ground to the Wampanoag tribe that still holds it. On the way back, Menemsha is the fishing village the movies borrowed: lobster boats unloading at the dock, Larsen's Fish Market selling off the boats, and a beach where the whole harbor turns out to applaud the sunset.

Groups that would rather stay on the water point the tender at Cape Pogue and the outer beaches of Chappaquiddick instead — miles of barrier sand with nobody on them, the chef's beach lunch in the shade of an umbrella line the crew set before the group arrived. Both versions of the day end back in Edgartown; the second one ends saltier.

The morning crossing runs the shoal water of Nantucket Sound — twenty-five miles of strong tide and sandbars that made this some of the most heavily piloted water of the nineteenth century, when Nantucket whaleships came home around these banks from four-year voyages. The modern version is easier: the captain rides the current, the group rides the flybridge, and Brant Point Light comes up on the bow by early afternoon.

Nantucket town is the country's best-preserved whaling port — the whole island is a National Historic Landmark district — and the first afternoon belongs to it. Cobblestoned Main Street climbs from Straight Wharf between brick merchant houses; the Whaling Museum, built into an 1847 spermaceti candle factory, hangs a forty-six-foot sperm whale skeleton over the story of the island's rise and near-collapse; and the wharf lanes are all galleries, oysters, and boat traffic.

Evenings here run on reservations, which the crew has already made. Cru at the end of Straight Wharf does the waterfront oyster-and-champagne register; Straight Wharf Restaurant next door has anchored the harbor's dinner scene for fifty years; and the Nautilus takes the group's livelier nights. The mooring field at night — Brant Point blinking, the last ferry gone — is its own closing argument.

Day five stretches the island to its corners. The signature move is Great Point by tender or four-wheel-drive: seven miles of bare barrier sand running to a solitary 1818-lineage lighthouse, with grey seals hauled out in the hundreds along the rip where Nantucket Sound meets the open Atlantic. It is the emptiest place on one of the busiest summer islands in America, and most visitors never see it.

The island's east side answers with Sconset (Siasconset on the chart) — a village of rose-covered fishermen's cottages above the surf, connected by the Bluff Walk, a public footpath running along the cliff edge through the village's front gardens toward Sankaty Head Light. The route back to town passes the cranberry bogs and the moors that turn red in fall; guests who want one purely local stop add Cisco Brewers' yard, the island's brewery-distillery-winery compound with food trucks and live music most summer afternoons.

The chef's day peaks tonight. Nantucket's day-boat scallops, bluefish, and farm stands stock the galley, and the second Nantucket evening is the one most groups spend aboard — the town seen from the mooring, dinner built from the morning's dock buying, and nothing on the schedule before tomorrow's Cape crossing. A Topper's-at-the-Wauwinet table up-harbor is the ashore alternative, tender-accessible at high water.

The route turns north for its Cape Cod night, and the harbor is the captain's call with the group. Chatham, thirty miles up, is the Cape at its most shingled: the fish pier's afternoon offload draws a crowd of grey seals waiting on scraps, the 1877 lighthouse watches the break in the barrier beach, and Main Street runs to a proper dinner — Chatham Bars Inn's verandah above the fleet being the classic.

Provincetown, at the Cape's fist another two hours on, is the louder finale. The Mayflower anchored here first — five weeks in November 1620 before the move to Plymouth, commemorated by the 252-foot granite Pilgrim Monument over the harbor — and the town has since become the Cape's arts capital, its whale-watch port, and its best people-watching, all compressed onto Commercial Street. The harbor is deep, the moorings are protected, and the sunset over the moored fleet with the monument lit is a legitimate rival to anything the islands offered.

Either version ends the same way: the last full dinner of the loop, ashore at the chosen harbor or aboard, with the homeward crossing on tomorrow's tide. Whale-watch-minded groups note that Stellwagen Bank — the humpback feeding ground — sits just north of Provincetown, and a dawn detour before the run home is a real option in season.

The longest leg of the week runs home to Newport — fifty-five to seventy nautical miles depending on the Cape harbor, and the captain leaves early to carry the fair tide down Vineyard and Rhode Island Sounds. On a motor yacht it is a morning; on a sailing yacht it is the week's one proper passage day, which for sailing-minded groups is a feature. Either way the miles pass with the chef's long breakfast and the islands of the past week sliding by to port.

By mid-afternoon the yacht is standing in past Castle Hill Light into Newport Harbor, and the arrival lands differently after a week among the islands — the mansion rooflines, the fleet, the 12 Metres drifting home from their afternoon races. The evening is Newport's to close: a walk through Bannister's Wharf, drinks at the Clarke Cooke House where the Cup crews used to celebrate, or the Cliff Walk at golden hour for the group's last shore excursion.

The farewell dinner is the chef's — the New England greatest-hits table, lobster and day-boat fish and whatever Nantucket's farm stands sent along — served on the aft deck as the harbor settles. Seven nights, three islands, the Cape, and about a hundred ninety miles of the best-known summer water in America, with the whole coast run on domestic flights and zero customs stops.

Breakfast aboard, luggage handled by the crew, and disembarkation by mid-morning. Providence (PVD) is forty minutes by car, Boston (BOS) about ninety, and guests joining or leaving mid-island can note for next time that Nantucket (ACK) and Martha's Vineyard (MVY) both take seasonal direct flights from the Northeast. Step off with Cuttyhunk's raw bar, Edgartown's captains' houses, Great Point's seals, and the Pilgrim Monument all behind you — the island summer the ferry crowds queue for, run on the yacht's schedule instead.