The millionaires and billionaires who frequent the island have headed ashore for shopping, dining, and a break from boating (and the occasional court dispute), as seen by the superyachts and megayachts that are clogging up Nantucket Harbor. Everybody with too much money to count will find something on the island, from the nuclear bunker built for President Kennedy to an exclusive golf club that is frequented by Bill Gates and Warren Buffett. The wealthiest visitors to Nantucket typically stay and play here.
Where the Rich Stay on NantucketThis WauwinetThe Wauwinet is an adults-only, ultra-luxury beach resort rooted in New England and Nantucket history and is widely regarded as Nantucket’s coveted jewel hotel. The Wauwinet is a top pick for the superrich who want the ease of a hotel stay in a location with a stellar reputation for service. As a Forbes verified luxury hotel, it is also. The Wauwinet, according to managing director Sean Burpee, is the perfect place to disconnect and take in Nantucket island’s natural beauty. “We are the only hotel on the island with access to two private beaches and Nantucket’s only Relais & Chateaux hotel,” said Burpee. The Wauwinet, a well-liked location for weekend vacations and weddings, is the greatest location on the island for watching sunsets based on the volume of visitors.
Harborside Hotel The White ElephantThe White Elephant Nantucket is a resort establishment that caters to families and convenience, and it is a premium hotel with Forbes verification. Large parties with young children will enjoy taking the fast ferry into Nantucket and then using the free shuttle service to get to the hotel, which is close to Children’s Beach.) The White Elephant offers top-notch services and amenities and is a short stroll from Nantucket’s businesses. These include Priority Bicycle beach cruisers, a house car for getting around town for dining or shopping, and a private courtyard with recliners that overlooks the water. In May, the iconic Harborside Hotel reopened following a multi-million dollar restoration.
Inn at Jared CoffinThe history of Nantucket Island as the world’s whaling center is evident in every nook and cranny of this classic hotel. The only local magnate whose home survived a fire in 1846 was Coffin, a prosperous owner of whaling ships. As a monument to the 19th-century magnificence that made Nantucket a popular summer vacation destination, the three-story estate still stands better than ever. Famous guests who have stayed at the Coffin House over the years include Joe Biden and Herman Melville. Visitors are drawn outside by the hotel’s proximity to the beach (only a three-block walk away), but they find it hard to leave because of its retro appeal and dependable WiFi. If you decide to go, schedule a bike rental and take your time.
Rentals For Luxury Estates And Other Estates In Nantucket ShoresThe luxurious Nantucket Shores Luxury Estate is just one of the numerous Nantucket properties that THIRDHOME’s coveted Reserve program, an exclusive, under-the-radar club, makes available to members. Members have access to high-end properties all over the world for a fraction of the regular rental costs. A few feet away from this six-bedroom, six-bath, 5,000-square-foot mansion are panoramic views of the ocean. The estate has a feeling of being all-inclusive because to its pebble-tech pool, private tennis court, flower and vegetable garden, and a variety of eating options. The Nantucket Shores Luxury Estate can be rented for as little as $34,500 per week, while THIRDHOME membership begins at $295 annually.
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If you’re looking for the most upscale locations on the island for homeowners and summer rentals, don’t pass up Polpis because of its fantastic harbor views and close proximity to the city, Baxter Road in the Siasconset Beach neighborhood, or Lincoln Circle. Many Baxter homeowners own their own dock and commute into town on their Boston Whaler instead of their cars. This upscale neighborhood is renowned for limiting the number of homes that can receive docks and slips, creating more room and larger estates. The Galley Beach restaurant and the lovely waterfront views near Lincoln Circle made it a popular destination. Hedge funders are fast to properties in the $25 to $35 million area on Dionis Beach, west of the city. You can spend the weekend as their neighbor by visiting any well-known vacation rental website.
On Nantucket, where the rich eat and drinkThe Wauwinet’s TOPPER’S TOPPER’S is the only AAA Five-Diamond restaurant on Nantucket. It lives up to its reputation as one of Nantucket Bay’s finest dining venues and one of the best spots to eat while taking pictures of the setting sun. With more than 2,200 labels, it also has the island’s largest wine list. Naturally, the seafood is the menu’s standout item. 300 yards away in the Bay, where the Retsyo oysters are harvested. You don’t have to be rich to order the Billionaire’s Bar for dessert, which consists of shortbread, chocolate and caramel ganache, and caramel ice cream.
The CRU Nantucket
CRU, one of Nantucket’s most popular and well-known lunch and supper spots, is situated near the end of the Straight Wharf. Tourists find it appealing as the harbor is within walking distance, and the wealthy residents frequent it for the cuisine. Madeline Grayson, one of the three co-founders of women’s lifestyle boutique Tuckernuck, described the place as “an iconic location with a lively scene, great food, and amazing setting.” Treat yourself to a great cocktail and plate of oysters upon arrival since reservations are rarely simple to secure.
Brewers CiscoA titan of the billionaire jet-set elite who is best known for appearing on Shark Tank, Kevin O’Leary, recently paid Cisco Brewers a visit for their Fourth of July celebration. Cisco Brewers, a well-known company among locals and tourists, produces The Notch, the country’s first and only island malt whiskey, and distills and sells spirits under its own brand (Triple Eight Distillery). Cisco is a one-stop shop for island drinking because a vineyard and brewery are also located there.
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The Chanticleer, a 1909 cottage restaurant, is situated in Siasconset on the island and offers a charming outdoor dining experience. It is renowned for providing the greatest wines in the world as well as the freshest seasonal foods. Visit Galley Beach for the best oceanfront fine dining. The perfect summer scene is created by the prix fixe meal, which has something for everyone, and white wines served at dusk.
On Nantucket, where the rich shopThe most recognizable store on the island, in Grayson’s opinion, is Murray’s Toggery, which President Biden recently visited. “Murray’s is a family-owned clothing store that has been open since 1945 and is home to the original Nantucket RedsTM, as well as many exclusive designs with Nantucket icons,” says Grayson. … The Atlantic and Erica Wilson are the recommended stores for ladies, according to Grayson. You can only discover locally made, exquisitely designed accessories on Nantucket at the Peter Beaton Hat Shop and Jewelers’ Gallery. For a vintage Nantucket basket handbag created in the 1960s, check out Rafael Osana’s Auctions. For a look at a range of vintage arts and crafts, visit Sylvia Antiques.
Special Nantucket Events Residents of Nantucket go to tremendous measures all year long to maintain the island’s lucrative summer tourism industry. The 1 Percent returns every year because of a few must-attend occasions.
The Nantucket Film Festival, which takes place in June each year, was started by locals in 1996 as a way to promote burgeoning screenwriters. The festival’s board of directors has included actor Ben Stiller from its beginning. Stiller has lived on the island his entire life. … Every May, the Nantucket Wine & Food Festival outshines all others in terms of quality. In a 2016 interview, the festival’s founder, Denis Toner, mentioned that one edition featured a 1961 Bordeaux that sold for about $10,000 at auction. Every April, the charming small-town Nantucket Daffodil Festival brings together antique cars, trendy accessories, and kid-friendly activities. Every July, the Nantucket Dreamland hosts its DreamBIG fundraising event. This nonprofit organization is devoted to supporting the local entertainment scene. It’s an opportunity for interested donors to be visible in front of a live audience while enjoying alcoholic beverages. The local Boys and Girls club benefits from the Tim Russert Summer Groove performance in August, which the 1 Percent attend when their fundraising budget isn’t completely depleted. Following a two-year break brought on by the pandemic, the Boston Pops resumed their yearly performance on Jetties Beach in August 2022. Since John Williams led the first performance in August 1997, the occasion—which supports the Nantucket Cottage Hospital—has become an institution in the community.
