Discover Cape Cod and its neighbouring islands on this coastal road trip

The sun glows a fiery shade of orange as it starts to dip below the watery Nantucket horizon. At the helm of the boat, captain John Stobaugh casually steers the wheel with his palm as he serenades the setting sun and the small cluster of guests on board with a melodic sea shanty. It’s a folksy tale of drunken sailors, long-lost love and the hope of fairer weather ahead: lyrics that have rung out across these waters for centuries.

These days, the ballads are sung to curious out-of-towners on sunset cruise tours, organised by the family-run boating company Nantucket by Water and departing from Nantucket harbour. Once call-and-response work songs used to rouse sailors aboard New England’s sailing vessels in the 19th century, today sea shanties are a way to conserve and celebrate the region’s rich maritime traditions.

I’ve come to Cape Cod and the neighbouring islands of Martha’s Vineyard and Nantucket to explore the revival of its seafaring culture. Shaped like a fish hook that extends into the Atlantic Ocean from the southeastern corner of Massachusetts, the area is celebrated for its windswept shoreline, pristine beaches and the romantic allure of its beaming lighthouses. The cape was originally the Indigenous home of the Wampanoag, and in 1620 the Mayflower Pilgrims sailed here from Europe and attempted to down anchor, before deciding to instead journey onwards to Plymouth.

Over time the coast has witnessed a renaissance. Whaling and agriculture have given way to tourism, aided in no small part by the area’s long-running association with Hollywood stars and presidents, including the Kennedy family, who favoured it as a summertime retreat. Fifteen distinctive towns now line the cape’s peninsula, home to around 230,000 people. This number swells in the warmer months as a steady stream of visitors arrive, beckoned by the region’s powdery white shores, beautiful shingled houses and laid-back character.

The beachy island of Nantucket has a reputation as a seaside playground for the rich and famous. Joe Biden has celebrated Thanksgiving here, Bill Gates tees off at the golf club and Drew Barrymore holidays on the island with her family. The local film festival even has actor Ben Stiller as a founder. Nantucket is situated 25 miles off the Massachusetts coast, accessible on an hour-long high-speed ferry from Hyannis Port on the Mid-Cape mainland. Passengers disembark at Nantucket town and inhale a deep breath of salty sea air, visibly relaxing.

Its cobblestone streets are flanked with Colonial and Federal architecture, mostly built as homes for 19th-century whaling merchants and often finished with plaques displaying the names of bygone captains and the years in which the houses were built. There’s a refreshing absence of chain stores, their place taken instead by nautical-themed boutiques and oceanfront restaurants that offer freshly caught seafood, usually served with a splash of white wine.

Meandering a couple of streets from the ferry dock, the morning after my sailing trip, I discover the Scrimshander Gallery, a tucked-away basement store owned by Boston-born Mike Vienneau. Hunched under a fluorescent light at the back of the gallery, with a whale’s tooth in one hand and an engraving needle delicately poised between the fingers of the other, Mike explains that his interest in scrimshaw, the rare art of engraving onto bone or ivory, was sparked during sun-kissed childhood holidays back in the 1960s.

“My parents would rent a house in Nantucket in the summer,” Mike says, examining his painstakingly intricate work scraping a miniature tableau into the surface of the tooth. “There would be barrels of whales’ teeth at the front of gift shops, selling for a couple of bucks each,” he recalls. “All the kids around here taught themselves to scrimshaw as a hobby.” Hanging on the adjacent wall is the enormous jaw of a sperm whale, etched by Mike’s steady hand and retailing for a cool $40,000 (£31,000).

Sea-lore has it that this handicraft originated with bored sailors on long voyages, who would wile away their days at sea by decorating the bones and teeth of whales and tusks of walruses. “You can’t buy the teeth anymore, so I just work with what I already have in my collection,” Mike tells me. He swung open the doors to his business in 1974. “A tooth like this will take me two or three weeks to complete. There’s a lot of preparation involved beforehand: polishing the tooth, making a stand, drawing the image out and then engraving it.”

I leave Mike to concentrate on his fiddly task and venture on to nearby Hadwen House, a grand, white-columned Greek Revival mansion originally built in 1846 for the wealthy whaling merchant William Hadwen. It’s now a local history museum stacked high with glass cabinets crammed with examples of Nantucket’s arts and crafts.

In the museum’s upstairs studio, I find weaver Elizabeth Clyne working on a Nantucket lightship basket. The history of these sturdy baskets, woven with rattan or cane, is intertwined with the history of whaling in the region, which, by the 1850s, was so popular that the East Coast waters had become heavily trafficked. To prevent fatal shipwrecks, the state of Massachusetts commissioned lightships — floating, scaled-down versions of a lighthouse — and basket-weaving is thought to have developed among the crews sent to maintain them.

“The early basket-weavers were men,” Elizabeth tells me as she shapes a thin rattan stave around her polished wood base. “Sailors would bring materials with them on their ships to pass the time.” After tourism boomed in the 1860s, she adds that the baskets soon shape-shifted from utilitarian household items to become desirable keepsakes for summer visitors. In the 20th century, artisans such as Philippines-born José Formoso Reyes, whose studio has been recreated at Hadwen House, transformed the Nantucket lightship basket into high-fashion purses, adorned with elaborately carved birds and flowers.

“Not much has changed in terms of technique since the early days of those lightship baskets,” Elizabeth reflects. “But today you will find plenty of the shops in town selling this style of weaving as decorative clutch bags or bracelets”. She tells me that reclaiming this time-honoured craft has helped her to foster a deeper connection to her island, too. “People here have been doing this type of weaving for generations, so I am just carrying on the legacy,” she says with some pride.

Seeing the light

At daybreak the following morning I’m on a ferry with a rented bike in tow and heading towards the island of Martha’s Vineyard. Cast adrift seven miles south from the mainland of Cape Cod, this summer resort has 125 miles of tidal shoreline, protected by five towering lighthouses that are scattered along its coastline like twinkling gems.

Keen to discover more about these historic beacons, I disembark the ferry at the lively port of Vineyard Haven and take the cycling path to Martha’s Vineyard Museum. At 20 miles long and 10 miles across at its widest point, Martha’s Vineyard is easy to navigate on two wheels. Around 40% of the island is now protected conservation land, and its landscape of farmland, sandy beaches and six harbour towns is a joy to explore on my rented bike. Ice-cream emporiums and traditional New England-style ‘saltbox houses’ fringed with white-picket fences flash by as I make my way along the path.

I arrive at the museum, perched high on a grassy hill, to a chorus of seagulls. It was founded in 1922 to preserve the island’s history, art and culture. Today, its star attraction is the Fresnel lighthouse lens, displayed at the heart of the museum and measuring twice the height of an average adult.

The game-changing lens, shaped like a beehive, used crystal glass prisms to produce a startlingly brilliant beam. Visible from 20 miles out at sea, it was streets ahead of previous lamps in deterring shipwrecks and therefore in saving lives. It was installed at the island’s Gay Head Light in 1856 to much fanfare, but was later replaced with an automated version. Day-trippers now flock to the museum to admire the pioneering beacon in all its kaleidoscopic glory.

Before looping back to the marina, I make a pit stop at East Chop Light in Oak Bluffs, a black-and-white lighthouse overlooking one of the busiest waterways in the world. Pleasure boats, sailing ships and fishing vessels pass under its watchful eye, just as they have done for over 150 years.

Back on the cape’s mainland, I round things off with a visit to the Cape Cod Maritime Museum in Hyannis, an organisation focused on preserving the peninsula’s maritime culture. In its woodworking workshop, surrounded by a wall of shiny metal tools and surfaces covered in a thin blanket of sawdust, executive director Elizabeth York explains how they’re keeping the craft of traditional boat-building alive for a new generation.

“We have groups of local teenagers who come here to work as a team, learning to build a boat from stem to stern,” she tells me as we watch a mentor sand down a handsome Bevin’s Skiff boat made from white oak and cedar wood. “Boats were once the main mode of transport around here and the water is still so pivotal to our lives. Sailing, fishing, ferries, rowing, swimming — it’s what we do.”

When I ask why they still invest in making Cape Cod boats by hand, when buying a kit would make life easier, Elizabeth takes a moment to glance beyond the window at the harbour, where masts rattle like cowbells. “It’s a connection to where we came from and what sets us apart,” she says. “That’s got to be worth preserving.” I look out at the jostling boats, certain they’ll be made by Cape Codders for generations to come, and wonder what shanties will be sung on their decks by future seafarers.