Take extra time on a Boston World Cup trip to spend a day on an iconic Massachusetts island. We saddled up to explore the best of Nantucket
I can be guilty of cramming itineraries with activity while my family would prefer to take it a tad slower, frequently grumbling when I stipulate an early rendezvous. Today, however, I have no need to rouse my husband Jimmy and 24-year-old-daughter Erin. At eight-thirty, along with throngs of tourists donning flip-flops, sun hats, tote bags, and shades, we’re in Hyannis Harbour boarding the Hy-Line Cruise’s Grey Lady high-speed ferry for a day trip to Nantucket—summer stomping ground of the US elite.
Once the whaling capital of the world (circa 1750-1850), sailors often relied on one of three lighthouse beams to guide them to shore when frequent, thick fog blanketed the island, transforming the landmass into a mysterious grey hue and earning the island its nickname “The Grey Lady”. On our crossing, however, Nantucket’s moniker belies the small island 30 miles off the Cape Cod peninsula, and we gaze across a sun-drenched Nantucket Sound sipping Bloody Marys. Within the hour, the white tower of Brant Point Lighthouse clearly comes into view, and we’re docking alongside iconic unpainted, cedar-shingled buildings balanced on stilts, gently lapped by the rippling water.
Alighting, many of our fellow passengers stroll towards the historic town centre littered with fine restaurants and upmarket shops or nose towards Jetties Beach to bag a sunbathing spot to get lost in an Elin Hilderbrand beach read (the Nantucket based author has penned around 30 novels set on the Massachusetts island). Jimmy and Erin look wistfully toward couples sipping cappuccino at a chic harbourside cafe as I steer them towards the family run Young’s Bicycle Shop on Broad Street where I have pre-booked our transport. At only 14 miles long and 3.5 miles wide, one of the best ways to explore the island is on two wheels. Over half the land mass is protected from development, with a well-maintained network of cycle paths weaving through a richly biodiverse landscape to sand-dunned backed beaches, quintessential New England villages, farm shops and Cisco Brewery — the final stop on our planned bike tour.
Instantly perspiring in the soaring July temperatures, we shakily navigate the landmark cobblestones, dodging giddy tourists captivated by the setting, sauntering the streets in a style reminiscent of a Disney theme park, drivers crawling along patiently navigating the hordes. While cars are permitted on Nantucket, most visitors opt to walk, cycle or hop on the Wave — a free shuttle bus regularly traversing the island. We make a quick exit and head east on Milestone Road to make the 8.2-mile journey to Siasconset and within minutes, the crowds dissipate and we are coasting along a quiet tree-lined path bordered with wildflowers to the sound of birdsong and pollinators busy gorging on the colourful feast.
Settled in the 17th century, Siasconset (aka Sconset) is the epitome of New England fishing villages. Nestled at the end of the road we find quaint, shingled cottages, covered in roses with huge pink and blue hydrangeas spilling over perfect white picket fences and a peaceful, lazy atmosphere. A handful of charming shops entice visitors to browse and we take the bait. Hungry cyclists feast on homemade sandwiches at Claudette’s or grab a coffee and a pastry at Siasconset Market. At the delightful Sconset Bookstore Wines an array of carefully curated wines, beers and spirits can be purchased, making the perfect accompaniment to a picnic at Siasconset Beach – our next scheduled attraction.
The wide, pale sand stretches in the distance, strong waves breaking on the shore and as compensation for our efforts, only a handful of sun seekers soak up the rays. A limited area of the beach is patrolled by Nantucket Lifeguards during summer season, but the spot is renowned for strong surf and caution is advised when taking to the water. Although we have come prepared with swimwear, we decide simply to dip our toes and chill for a while, enjoying the serenity and spectacular views. Seals are frequently spotted along the coastline here, but despite vigilantly perusing the horizon, we fail to be rewarded with a sighting of the playful animals. With much to see and do, it’s time to move on.
The ten-mile coastal route via Polpis Road back to Nantucket passes the red and white striped tower of Sankaty Head Light and several farm shops, before we pull up for a well-earned lunch at Millie’s on the rotary on the outskirts of town. The Cliff Road Salad with blackened salmon, goats’ cheese and basil vinegarette hits the spot, full of flavour and much-needed nutrients to refuel for the final leg of our journey. Before returning our bikes, we have one last destination that has been high on my beer-loving husband’s agenda – Cisco Brewery.
Bikes clutter the car park, and we follow the sound of music and laughter to claim our wristband before entering a crowded courtyard full of happy customers. Named after nearby Cisco Beach, the Massachusetts beer hole screams surf vibes, and for non-ale lovers, the Cisco Social Club also provides an excellent selection of wines from the Nantucket Vineyard and spirits and cocktails from the Triple Eight Distillery as well as low alcoholic beverages and soft drinks. Rustic wooden shacks serving drinks and food encircle the outdoor space where its standing room only and kids lark about in flip flops, creating summertime memories. A band is setting up under a gazebo to entertain the post-beach crowd as we head to the merch shop (my husband always needs a t-shirt as a memento — he has hundreds) and with his cycle basket laden with cans, we saddle up and make tracks for to catch dinner booking in town.
In the height of summer, a restaurant pre-booking is essential. At six o’clock, relieved of our bikes, I’m sipping Nantucket pinot gris with grilled salmon in the Cisco Kitchen at the iconic Brotherhood of Thieves whaling bar and tavern. Operating since 1972, the pub honours an anti-slavery movement of the same name whose mob rioted in 1872, against Nantucket’s clergy and social hierarchy. Reminding us of the historical events over 150 years ago, the characterful sign above the establishment’s door depicts a minister with horns.
Next door in the Nantucket Bookworks, I pick up a copy of Daughters of Nantucket, by Julie Gerstenblatt, a fictional tale set on the island in 1846, bringing historical events to life through the challenges and triumphs of three stoic women. Early in the evening, the well-stocked store is buzzing and a friendly local also recommends reading Pulitzer Prize winning Nathaniel Philbrick’s Away Off Shore, a non-fictional account of island history from its settlement to the decline of whaling. I’ve maxed out the literary patience of my husband and daughter, and with time slipping away, we spend the last couple of hours wandering the streets and harbour soaking up the atmosphere.
With weary legs we take refuge on a bench overlooking the harbour. Under twinkling fairy lights, we savour magnificent ice cream cones from Jack and Charlie’s Ice Cream, another family affair, and gaze out at the yachts and fishing boats lightly dancing in the water. My pre-planning has delivered an action-filled day in this glorious, surprisingly unpretentious, bolthole of the rich. As we set sail towards Hyannis it’s my turn to be melancholy. I want to stay longer; slow things down and fully appreciate island life. For now, I’ll just have to lose myself in a book and conjure up the sights, sounds and smells of this Massachusetts paradise.
