Combining Colonial, Victorian and Greek Revival architectural elements, Nantucket isn’t just any coastal island—it’s the archetype from which the nautical theme evolved. Of course, no duplication ever lives up to the original, and the timeless, one-of-a-kind Nantucket vacation experience guests enjoy remains as inviting today as it did centuries ago.
Nicknamed the “Grey Lady” by 17th century whalers for its misty mornings in the earliest hours, staying at a Nantucket vacation rental is like walking through a window into the past. Travelers follow in the footsteps of the centuries-old whalers Herman Melville immortalized in Moby Dick as they arrive through Nantucket’s harbor in Brant Point, known for its iconic lighthouse, open-air dining and kid-friendly beaches.
The best way to explore Nantucket is via bike or moped, either of which can be easily rented near the harbor or elsewhere on the island. Beach-hoping is typically where vacations in Nantucket start. There are more than 25 public beaches across the 14-mile-long island, each with its own distinct charm and personality. It is an unofficial requirement to explore each and every one.
Visitors will want to make Madaket among their first stops. Known for its jaw-dropping sunsets, meandering beach trails and Millie’s beach restaurant, the area rewards those who venture all the way out to Smith’s Point on the western tip of the island. Depending on the season, Smith’s Point is a great place to spot local wildlife such as the grey seal, snowy owl or a wide variety of songbirds and other aviary species.
On the Eastern side of the island, Sconset is essentially a fairytale town which appears as if it were stuck in the late 19th century with its picturesque cottages and magnificent gardens. In an effort to preserve the neighborhood’s original vibe and culture, there is only one establishment—a “General Store” where one can find most essentials—adding to the neighborhood’s charm and appeal. Ride or stroll through Sconset Bluff Walk to the Sankaty Head Lighthouse, another iconic Nantucket treasure dating back to 1850.
In between Madaket and Sconset, visitors will find numerous bike trails beckoning exploration, quaint houses with grey-shingled roofs, cobblestone streets and classic Americana reminiscent of a Norman Rockwell painting. The Naushop community is an ideal place to call home-base while on the island due to its close proximity to town, well-appointed and generous amenities, including tennis courts, a refreshing community pool and a pickleball court.
Foodies will find no shortage of options during the busy season from fine dining establishments to crave-worthy outdoor eateries. Popular picks include Galley Beach, The Nautilus, Straight Wharf and Breeze.
It doesn’t take long to find out why the laid-back Nantucket culture, bespoke experiences, and exemplary cuisine all but ensures first-time visitors will find themselves returning to the Grey Lady again and again. Luxury vacation rentals such as Rozel Nantucket will be happy to welcome you back!