Boating is at the heart of Nantucket, an island with a past and a present that is intrinsically tied to the sea. From the late 18th to early 19th centuries, this crescent-shaped piece of land, located some 30 miles off the coast of Massachusetts, was the whaling capital of the world.

Today, those whaling ships are long gone, and in their place you’ll find megayachts and sailboats floating offshore. And just like the sea captains of yesteryear, modern-day sailors know that some of Nantucket’s most amazing treasures are discovered via the water.

For visitors who fly into ACK with Tradewind Aviation, a number of companies make it possible to get out on the ocean—including ACK Sunset Sail, which runs sunset sailing trips, or Captain James Genthner, who offers daily cruises and private charters on the Endeavor, a reproduction of an early 1900’s single-masted sloop. Island Boat Rental has powerboats ranging from 15 to 20 feet that you can take out for the day and captain yourself. There’s even a vintage 1953 Hinckley that you can rent by the night through AirBnb. And if you really want to get serious about yachting, you can apply to be a member of the prestigious Nantucket Yacht Club or Barton & Gray, which gives members access to gorgeous wooden Hinckleys.

When you’re ready to set sail, chart your course to the best boating destinations around the island. Here are our 10 favorites.

Jetties Beach

Photo credit: Jetties Beach Restaurant

Jetties is one of the more popular beaches on Nantucket — and it’s no wonder, with its placid waters that are ideal for kids. If you want to grab a bite, head to the small beach restaurant on the boardwalk, which serves up killer lobster rolls. Every summer, the Boston Pops performs here and boaters get a front-row view.

Coatue

Photo credit: Flickr via Massachusetts Office of Travel & Tourism

Photo credit: Flickr via Massachusetts Office of Travel & Tourism

Set right beyond the main harbor, this barrier beach on a narrow strip of land feels worlds away. Anchor here overnight and watch the twinkling lights of Nantucket Town in the distance. The shell hunting can’t be beat.

Great Point

This remote spit of sand at the extreme northeastern coast of the Coskata-Coatue Wildlife Refuge has miles of sand for exploring and an iconic lighthouse. This is where serious anglers come to fish for striped bass and bluefish.

Dionis Beach

Photo credit: Yelp

Photo credit: Yelp

Lined with high dunes and wildflower-dotted sea grass, Dionis is the kind of picture-perfect white-sand beach that makes its way onto postcards. Anchor offshore and dive into the warm waters of Nantucket Sound.

CRU Oyster Bar

Photo credit CRU Oyster Bar

Photo credit CRU Oyster Bar

This dockside restaurant in Nantucket’s main harbor is a hit with landlubbers and boaters alike. Tie up your yacht on a slip right out front and stop in for a glass of Rosé and a plate of fresh-shucked oysters that are infused with New England’s briny terroir.

Polpis Harbor

This tranquil harbor is a protected spot where you can anchor for the day and spy on the multimillion-dollar mansions that overlook the water. This is the place for some of the best sunsets on the island.

Madaket

Photo credit: Flickr via James Behnke

Photo credit: Flickr via James Behnke

On the westernmost tip of Nantucket, Madaket is where Fred Rogers (a.k.a. Mr. Rogers) used to spend the summer. There’s a tiny village and great crabbing in the surrounding creeks. Boaters also come here to spend time on the breathtaking beach, wade in the tidal flats, and kayak along the shore.

Tuckernuck Island

Just off the west coast of Nantucket, Tuckernuck is a place that people rarely see. Most of the island is privately owned by a handful of summer residents, and it doesn’t even have paved roads. But for experienced boaters who are able to navigate its ever-changing shoals, Tuckernuck is nirvana, with its empty beaches and rare birds and animals that call the island home.

Muskeget Island

Beyond Tuckernuck is Muskeget Island, an uninhabited dot of land with marshes and windswept dunes. It’s inaccessible to most boaters because of its dangerous shoals and sandbars, but it’s a great place to bob offshore and watch the gray seals that breed here or fish for yellowfin tuna.

Cuttyhunk Island

This island is a quite a bit further afield, but worth the journey from Nantucket. Back in the day, Teddy Roosevelt used to fish here for striped bass, and it hasn’t changed much. With its old fishing village, two-room schoolhouse, and general store, Cuttyhunk feels like a place from another era.

*Featured image courtesy of Flickr via Bob P. B.