New England Islands: Nantucket, Martha's Vineyard, Block Island

Destination Guide · New England

The three major islands of southern New England — Nantucket, Martha's Vineyard, and Block Island — form a roughly triangular cruising ground that has been a summer sailing destination since recreational sailing became a thing Americans did. They are close enough to the mainland and to each other that a sailor with a week can visit all three. They are different enough in character that each visit is distinct. And they are crowded enough in July and August that a sailor without reservations or the patience for a raft-up can find the experience more stressful than enjoyable.

The argument for visiting them anyway, even in season, is that the sailing to get there — across Buzzards Bay, through the rips and eddies of Vineyard Sound, or out across Block Island Sound — is genuine sailing, the kind that requires a watch, some judgment, and the occasional reduction of sail. These are working passages, not motor-sailing channels. They remind you what the boat is for.

Getting There: The Crossings

Buzzards Bay is the triangle of water between the Massachusetts mainland and the Cape Cod Canal to the north and Vineyard Sound to the south. The bay is oriented southwest-northeast, which means the dominant summer southwesterly blows directly up its length and builds a chop that, in 15–20 knots, makes for an uncomfortable motor-sail and an excellent beat. Buzzards Bay squally afternoons are a summer institution; the local sailors leave early.

Vineyard Sound, between Martha's Vineyard and the Elizabeth Islands, has the current running through it that a geography-driven sound acquires from tidal differential — it can be 2 knots against you or with you depending on timing. Cross the shipping lane with attention; vessels transiting through the Sound on their way to or from New Bedford and Providence are there every day.

Block Island Sound is open water — a clear shot across from Point Judith or Montauk with no particular shelter. In a southwest 15–20, it is a beam reach to Block Island from either direction. In an easterly, it is lumpy. Timing the approach to the Great Salt Pond entrance against the current makes life easier.

Nantucket: Expensive, Beautiful, Worth It

Nantucket is the expensive island. The mooring fees are the highest of the three, the marine services are priced for a fleet that includes serious offshore racing boats and hundred-foot motor yachts, and a dinner ashore for two will remind you that Nantucket knows what it is. It is also genuinely beautiful — the grey-shingled town, the cobblestone streets, the maritime history that is not decorative but structural (the whaling economy built this place and you can see it in the architecture) — and worth experiencing on its own terms.

The mooring field off Nantucket Town is managed by the Nantucket Boat Basin. Moorings are available, but "available" in July and August means calling ahead — the basin fills fast and the informal queue for free anchorage spots is real. The holding in the outer harbor is sand and acceptable, but the anchorage is exposed to southwesterly swell and uncomfortable when the wind pipes up in the afternoon. Most sailors who come to Nantucket take a mooring. A few anchor out and dingy in. Nobody anchors off Nantucket for free in August without eventually regretting the decision.

September Nantucket is a different island. The population drops, the prices in the restaurants become almost reasonable, the scallop boats start working the harbor, and the light changes to the particular golden-grey of New England fall. Fresh Nantucket bay scallops, available from roadside stands in October, are one of the better arguments for the visit.

Martha's Vineyard: Bigger, More Towns, Menemsha

Martha's Vineyard is the larger island with more cruising variety. Vineyard Haven is the main harbor — convenient, protected, with good services and a large mooring field managed by the town. Edgartown, on the island's southeast, is the elegant option: a meticulously preserved colonial town with a harbor that has been photographed as many times as any anchorage in New England. The mooring field in Edgartown is run by the Edgartown Harbormaster; the waiting list for moorings in August is real. The anchorage is crowded but workable for boats with settled weather.

Menemsha, on the island's western end, is the fishing village that the rest of the Vineyard uses as evidence that it is still connected to its working waterfront. It is small, genuinely commercial, and worth the sail around the west end of the island. The fish market at the dock sells whatever came in that day. The holding in Menemsha Pond is good and the anchorage is mostly quiet. The entrance is narrow and the current is notable; enter near slack.

Block Island: The Great Salt Pond

Block Island is the smallest of the three and, in the view of many experienced cruisers, the most interesting. The island is 35% land-conserved, which means the development that has consumed the shoreline elsewhere in southern New England has not happened here. The cliffs on the island's southeastern end — the Mohegan Bluffs — are 200 feet of red clay dropping straight to the water. There are no chain restaurants. The town of New Shoreham is small and self-contained.

The Great Salt Pond, Block Island's harbor, is the best hurricane hole in New England. It is completely enclosed, with depths sufficient for serious draft boats, and the natural protection from wind from any direction makes it genuinely reliable in severe weather. During the active part of hurricane season, boats that cannot haul out routinely duck into the Great Salt Pond. In normal summer conditions, it is simply the most protected overnight anchorage in the triangle — calm water, adequate depth, and the kind of quiet that Nantucket harbor does not offer.

The raft-up culture in the Great Salt Pond during the summer social season has its own character — boats come alongside each other in chains of three and four, dinghies circulate between boats at cocktail hour, the evening produces the particular sound of 50 boats at close quarters on a calm night. If you want solitude, anchor in the far northwest corner of the pond. If you want to meet the fleet, raft up in the center and let the afternoon develop.

The Summer Crowd Problem

All three islands are genuinely overcrowded from the Fourth of July through Labor Day. This is not a matter of opinion — the mooring fields fill to capacity, the restaurants have two-hour waits, and the dinghy docks at the fuel marinas require patience. None of this is unique to sailing; the ferry crowds are worse. The mitigation is planning: book moorings in advance where that is possible, arrive on weekdays rather than Fridays, budget two to three nights at each island rather than one, and accept that the provisioning run to the one grocery store on Block Island will take longer than you expect.

The other mitigation is September. After Labor Day, the transformation of all three islands is rapid and complete. Within two weeks the mooring fields have space, the restaurants are open but not full, and the sailing on Vineyard Sound in a northwest 15 with clear autumn sky is worth the whole summer of planning.

← All Destinations  |  Massachusetts Marinas →