Newport & Narragansett Bay Itinerary: The Classic New England Charter Week

The charter begins in Newport — boarding at Newport Shipyard or by tender from a harbor mooring, depending on the yacht. Providence (PVD) is forty minutes by car; Boston (BOS) about ninety. The captain and chef meet you at the dock, stow the luggage, and walk the group through the yacht and the week's chart while the harbor does what Newport Harbor does: launches running, a 12 Metre ghosting past the moorings, the church spires and shingled waterfront stacked behind Bowen's Wharf.

There is no reason to rush off. Newport rewards the first afternoon — a walk down Thames Street and the wharves, a chowder at The Black Pearl on Bannister's Wharf, or nothing at all beyond the aft deck and the harbor traffic. Late in the day, lines come off for the shortest leg of the week: five nautical miles across the East Passage to Conanicut Island and the quiet side of the bay.

The first night sets the register. Dutch Harbor on Jamestown's west side is a working mooring field with a sunset over the West Passage; Mackerel Cove, a sand-bottomed notch on the island's south end, is the at-anchor alternative when the wind agrees. The chef serves the welcome dinner aboard — local seafood, and it will not be the last time — with Newport's glow across the water and almost none of its noise.

The morning run rounds Beavertail Light at the southern tip of Conanicut Island — the third-oldest lighthouse site in the country — and points offshore. Block Island sits about twelve miles off the Rhode Island coast, and the twenty-two-mile leg from Jamestown is the week's first taste of open Atlantic water. The captain times it for the morning calm; motor yachts make it inside two hours, and on a sailing yacht it is a proper passage with the island growing on the horizon.

The entrance to the Great Salt Pond is a narrow cut on the island's west side, and the pond inside is one of the best natural harbors on the East Coast — a mile-wide bowl of protected water known locally as New Harbor. The afternoon belongs to the island: the tender runs guests in for rented bikes or a taxi south to Mohegan Bluffs, where a wooden staircase drops a hundred and fifty feet of clay cliff to the beach below and the 1875 Southeast Light stands where erosion forced it to be moved bodily inland in 1993.

Evenings in the pond are their own tradition. The Oar overlooks the mooring field with several hundred boat oars nailed to its ceiling, and a dark-and-stormy there while the launch traffic winds down is the standard first-night move. Dinner is the chef's aboard, or ashore in the Old Harbor village on the island's east side — a fifteen-minute taxi across the island.

The lay day is why Block Island earns two nights. Nearly half the island is conservation land — the Nature Conservancy counted it among its 'last great places' in the Western Hemisphere — and the distances are bicycle-scale. The standard loop runs south past Painted Rock to the bluffs, east through the Victorian hotels of Old Harbor, and north along Corn Neck Road to the stone North Light at Sandy Point, with farm stands and stone walls the whole way.

The beaches are the other half of the day. Crescent Beach runs two-plus miles of clean sand up the island's east side within walking distance of Old Harbor; Mansion Beach at its north end is the quieter stretch with the ruins of a Gilded Age foundation in the dunes behind it. The water in late summer runs warmer than most first-timers expect — low seventies in August — and the chef packs the tender for a beach afternoon whenever the group wants one.

For the evening, Payne's Dock in the pond sells its famous sugared donuts as the sun drops, and Dead Eye Dick's serves a proper swordfish a short walk from the dinghy dock. Guests who want the full island dinner take the taxi to Old Harbor; guests who have found their rhythm stay aboard, where the chef's raw bar and the mooring-field lights do the work. Both answers are correct.

The week's longest leg crosses Rhode Island Sound eastward — about twenty-five nautical miles from the Great Salt Pond to the tail of the Elizabeth Islands, the chain that runs southwest off Cape Cod between Buzzards Bay and Vineyard Sound. The captain runs it in the morning; by lunch the yacht is closing on Cuttyhunk, an island Bartholomew Gosnold landed on in 1602, decades before the Pilgrims saw the Cape.

Cuttyhunk is the anti-Newport, and that is exactly why it is on the route. A few dozen people live here year-round. There is one small store, a church, a one-room schoolhouse, and a grass-strip of a town where golf carts outnumber cars. The walk up Lookout Hill takes fifteen minutes and pays out a 360-degree view — the Vineyard east, Buzzards Bay north, the open Atlantic south — from old WWII bunker mounts at the top.

The evening is the island's signature moment: the raw-bar skiff from the Cuttyhunk shellfish farm motors through the anchorage around six, pulling alongside to shuck oysters and littlenecks straight into the cockpit. The chef builds dinner around what comes over the rail. There is no nightlife and no reservation to make — the anchorage goes quiet early, and after Block Island at peak, that is the point.

A morning run back west across the sound, and by early afternoon the yacht is standing in past Castle Hill Light — the small 1890 lighthouse on the rocks below the Castle Hill Inn — and into Newport Harbor. The approach from seaward is the way the harbor was always meant to be seen: Fort Adams to port, the mansion rooflines along the Cliff Walk to starboard, and the mooring field opening up behind Goat Island.

The afternoon is for the Gilded Age. The Breakers — the Vanderbilts' seventy-room Italian Renaissance palace above the Cliff Walk — anchors the Bellevue Avenue mansion row, with Marble House and Rosecliff a walk or short drive apart. Guests who prefer the water's view of it all walk the Cliff Walk itself: three and a half miles between the mansions' back lawns and the surf. The crew arranges cars and timing so nobody thinks about either.

Newport dinner reservations are worth having, and the crew books ahead. The Clarke Cooke House on Bannister's Wharf has fed the sailing crowd since before the Cup left town; the White Horse Tavern has been pouring since 1673 and calls itself the oldest operating restaurant in the country; Castle Hill Inn does the special-occasion table above the harbor entrance. The night ends back aboard on the mooring, the harbor lights doing what they have done for a century and a half.

The bay north of Newport is the stretch most visitors never see, and it is some of the easiest cruising of the week — twelve miles of protected water past Prudence Island's conservation shoreline to Bristol, a colonial harbor town that has run its Fourth of July parade every year since 1785, the country's oldest.

Bristol's claim on this route is the Herreshoff Marine Museum, on the site of the family yard that built five consecutive America's Cup defenders between 1893 and 1920 and effectively invented the modern racing yacht. The museum's hall of boats — and the America's Cup Hall of Fame inside it — is a half-day for anyone who cares about why Newport matters to sailing, and a good hour even for guests who don't. Hope Street's colonial houses and small storefronts fill the rest of an easy afternoon ashore.

The evening stays simple: a lobster dinner in town at the harbor's long-standing spots, or the chef's version aboard with the anchorage nearly to yourselves. Colt State Park's shoreline lawns catch the sunset just north of the mooring field. After the season's crowds further south, Bristol feels like being let in on something.

A short morning run returns the yacht to Newport for the week's finale, and the last full day is built around the harbor itself. This is the day to sail aboard a 12 Metre — several of the America's Cup boats that raced off Newport still day-sail and match-race out of the harbor all season, and the crew can have the group aboard one by late morning. Two hours of grinding winches (or declining to) on a Cup boat in Rhode Island Sound is the single most Newport thing it is possible to do.

The afternoon fills itself. Fort Adams — the harbor's massive 19th-century fortress point, home of the Newport Folk and Jazz Festivals — is a tender-accessible walk; the shops and galleries off Thames Street and the sailing-hardware windows of Bannister's Wharf absorb the rest. Guests with energy left for one more house tour take Marble House or Rosecliff; guests without settle onto the aft deck and watch the harbor's evening shift change.

The chef cooks the farewell dinner aboard — New England's version of the greatest-hits menu, lobster included — as the mooring field lights come up. The week ends where it started, which was always the design: Newport read differently after Block Island's bluffs, Cuttyhunk's silence, and Bristol's boatbuilding history than it did on boarding day.

A slow last breakfast aboard, and disembarkation by mid-morning at Newport Shipyard or the town dock. Providence (PVD) is forty minutes by car and Boston (BOS) about ninety — the crew arranges the transfer, and guests connecting through Boston are at the gate by early afternoon. Step off with the Gilded Age harbor, Block Island's clay bluffs, a raw bar delivered to the cockpit at Cuttyhunk, and the yard that built the Cup defenders all inside one week — and no passport used at any point.