Why Nantucket Is a Vacation Oasis

April 22, 2019

In the summer the prevailing winds blow across coastal Massachusetts and Cape Cod from the southwest. The gentle morning sea breeze often builds throughout the day into a stiff wind that wafts across the exposed crescent that is the is- land of Nantucket. The Wampanoag were the first to ride these winds and settle Nantucket, the “far away land” in their language. European explorers used these winds to sail past the island in the 17th century, and the great whaling ships that once chased sperm whales across the globe called Nantucket harbor their home port. While this glacial remnant that juts out of the ocean 30 miles south of Hyannis is now known for its sandy beaches and stunning vacation homes, sailing—more than anything—defines the Nantucket way of life.

When spending time on the island, it is impossible not to feel the urge to hop aboard a boat and hoist the mainsail. The best place to get a sailing lesson or send the kids to sailing school is Nantucket Community Sailing, a nonprofit organization dedicated to teaching and providing sailing opportunities. Once you learn how to sail, the waters around the island open up to a whole new world.

Oddly enough, Herman Melville had not set foot on Nantucket before writing Moby Dick in 1851. But he knew the history of the infamous whaling ship the Essex from Nantucket, which was rammed and sunk by a sperm whale in the South Pacific. And his book, hailed by some as the Great American Novel, foisted both sailing and the island of Nantucket into the national consciousness.

Nantucket was the hub of America’s whaling fleet from 1715 until the eventual demise of commercial whaling 150 years later. (The last whaler reportedly left the harbor in 1869.) At its peak in the mid-19th century, 72 whaling ships listed Nantucket as their home port. The ships had three masts that hoisted square-rigged sails; three-dozen crew-members would board and set sail from the island on expeditions that lasted as long as three years. That’s quite the contrast from the fleet of recreational day sailors that flit about the harbor or swing with the tide on moorings today.

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Nantucket took to its present-day incarnation as a vacation oasis not long after those whaling ships faded into history, with visitors flocking to the island for the same reason as the original settlers—rugged yet picturesque beauty and a large protected harbor.

The island is actually part of a glacial moraine, formed at the forward edge of the Laurentide Ice Sheet that retreated at the end of the last ice age more than 20,000 years ago. It left behind a 50-square-mile chunk of land in the shape of a crescent moon off the coast of Cape Cod. Melville described it in Moby Dick as an “elbow of sand,” but that’s not exactly right. Parts of the island’s sandy shoreline are still littered with boulders and rocks from the leftover glacial till. Much of the island rises up from the beaches in the form of vast bluffs that provide high vantage points for gazing far across the surrounding waters. The opening to Nantucket Harbor sits in the middle of the crescent, facing north into Nantucket Sound and across to the Cape. There is always at least a little wind.

“Nantucket Sound is just a glorious sailing location,” says Diana Brown, the chief executive of Nantucket Community Sail- ing. “There are steady breezes every day and the water is clear.”

Founded in 1994, Nantucket Community Sailing is dedicated to teaching sailing and making it accessible to people who live in or visit Nantucket. It offers weekly classes for children in season, all taught by instructors certified by US Sailing. Adults and kids alike can sign up for private lessons. “Our primary focus is children,” says Brown. “But we work with sailors from age 5 to 95.”

Youth classes range from absolute beginner all the way up to advanced racing level, and adults can sign up for private lessons at all skill levels. There’s also a woman’s sailing clinic and an adult racing program. Last year, the organization provided sailing opportunities to more than 1,000 kids and 2,000 adults over the season, which lasts mid-June through August, with rentals available through mid-September.

For rentals and lessons, head to Jetties Sailing Center, where Community Sailing keeps its boats. It’s on the beach just off Bathing Beach Road, about a mile from downtown and the docks for the ferries from Oak Bluff and Hyannis. Prospective sailors can rent or take lessons in small one- to two-person boats such as Sunfish and Lasers or larger Rhodes or Marshall Cats or take a trip with a captain aboard a J/105.

All of Jetties Sailing Center’s introductory sailing lessons, as well as rentals, stay inside the protected waters of the harbor. From the center, you can sail past the historic Brant Point Lighthouse, first established as an aid to navigation in 1746. The interior harbor offers protected water where first-timers can learn basic skills such as how to set and trim a sail so that it works to move the boat no matter the wind direction, how to tack and jibe, control the centerboard and how to come about, which is how you change direction.

A lesson aboard the 35-foot J/105 can involve leaving the harbor and exploring the waters surrounding Nantucket. And there is no better way to see the island than from the deck of a boat.

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Heading west along the shoreline leads to the smaller Madaket Harbor, which is more exposed to the elements but offers the best view of Nantucket’s sunset. Sailing farther west and to the north provides the best opportunity to see the privately owned summer community on Tuckernuck Island, or sail beyond to the neighboring Muskeget Island to view the largest population of grey seals in the United States. (Don’t try to swim near them; it’s illegal to get within 150 feet of one, and seals attract sharks.) An article from the Cape Cod Times described the seal-viewing experience this way, “On a foggy day you can smell the island before you can actually see it.” But the chance
to see roughly 3,000 seals in the wild is worth the olfactory assault.

Heading north and east outside of the harbor entrance leads to the Coskata-Coatue Wildlife Refuge, a pristine stretch of grassy sand dunes and marshes that juts north into the ocean, protected at its tip by the Great Point Light, built in 1785 to guide sailors in from Cape Cod. As Ezra G. Perry wrote in his 1898 book A Trip Around Cape Cod, “The long-drawn sandy shores of Great Point are among the first land of the real island sighted on the trip across,” from the Cape. This is another place to watch seals flopping on and off the beaches into the surf, as well as several species of migratory shore birds like American oystercatchers, piping plovers or snowy egrets.

The south shore of Nantucket is exposed to the whims of the Atlantic Ocean, and subject to much larger seas. (It holds great surfing spots, if you want to try that.) But on calm days sailors can cruise along the sandy beaches and observe the famous Nantucket summerhouses perched atop the bluffs.

Sailors with serious experience can venture about 20 miles offshore to the whale feeding grounds, where it’s possible to catch a glimpse of the massive humpback and finback whales that pass through these waters throughout the summer season. And whale watching brings the Nantucket experience back full circle to its days of Captain Ahab and the majestic whaling fleet.

As Melville wrote in Moby Dick of the Nantucket sailor, “For the sea is his; he owns it, as Emperors own empires.”