The small but charming island of Nantucket, Massachusetts, has become a leading luxury holiday destination in the last few decades.

Located 30 miles south of Cape Cod and near Martha’s Vineyard, it is home to some of New England’s most expensive properties, exclusive boutiques, and fine dining restaurants.

So, if you are planning a relaxed but sophisticated vacation, Nantucket is one of the best choices in the country.

Nantucket has everything you will need for a memorable getaway with its record-breaking number of pre-civil war buildings, untouched nature, pristine beaches, and remarkable whaling history.

Here are some ideas for planning your perfect upscale vacation there.

1. Book a luxurious house or mansion

Known as “Billionaire’s Isle,” Nantucket is a top choice for a summer property location for the rich and the famous.

If you want to experience the true feeling of residing in one of those stunning houses or mansions, you can rent one of the many exclusive residences available on the island.

You can choose a grand waterfront mansion with a manicured lawn and garden, a pool, a spa and sauna, and all amenities you can find in the best 5-star hotels worldwide.

If you are in luck, you can book one of these properties with its own pier to enjoy sailing and kayaking in the turquoise ocean.

There are also some gorgeous historic houses, shingle-style cottages, and other properties offered for short-term rent in all neighborhoods of Nantucket. They are restored meticulously to their original look from centuries ago and yet feature the latest state-of-the-art appliances for a luxurious and comfortable stay.

2. Shop at high-end boutiques

Every summer, the top celebrities, influencers, and entrepreneurs choose Nantucket for a high-end vacation. So, although it has no bright neon signs or fast food chain restaurants, the island is home to some of the most fashionable boutiques, galleries, antique shops, and stores.

The island is perfect for an upscale shopping spree for lavish jewelry, the latest fashion lines, fragrances, handcrafted décor items, furniture, and art.

Top boutiques and stores to add to your shopping list include Lily Pulitzer, Susan Lister Locke, Sernella, Olivela, Goldsmiths, Diana Kim England, and Victoria Greenhood Designs.

You can purchase exquisite and unique jewelry from Nantucket Estate Jewelry, the Nantucket Pearl Company, and Katherine Grover Fine Jewelry.

Nantucket Looms is one of the most famous stores on the island and offers deluxe hand-woven fabric items made from the highest quality silk, wool, cashmere, and mohair by the leading local artisans. Some of its famous customers through the years, including Princess Grace, Jackie Onassis, Bill Gates, Louis Vuitton, and Chanel 

Of course, don’t forget to buy a pair of preppy coastal Nantucket Reds pants, shorts, or other apparel from Murray’s Toggery Shop on Main Street.

3. Join a cruise

One of the best ways to explore the island and enjoy its stunning views is from the sea. 

You can book a small or a super yacht with professional stewards, chefs, crew, and captains for a one-day or longer 6-star luxury cruise in the Atlantic or Nantucket Sound.

There are also various other sailing cruises that you can choose for an unforgettable tour around the harbor or island.

There are cocktail cruises where you can sit back and enjoy the views of the yachts and the Nantucket Harbor and island while sipping a delicious handcrafted cocktail. Or, you can go on a sunset cruise for a romantic evening or date.

If you are looking for something more special to celebrate an event, you can also hire a private charter cruise.

4. Know the best fine-dining places

In recent years, Nantucket has established itself as one of the top culinary centers with some of the best fine-dining restaurants in New England.

If you want to experience the best of the select upscale dining on the island, then you should book a table well ahead of time because there is often a long waiting list.

Some of the top luxurious restaurants to enjoy an exceptional brunch, lunch, or dinner in Nantucket include Cru, Topper’s, Dune, Brant Point Grill, The Seagrille, Oran Mor Bistro, and Via Mare Greydon House.

In any of these and many other restaurants and eateries, you can try the unique elevated takes of the leading chefs on traditional New England, European and worldwide dishes.

The island is known for some of the best-tasting and freshest seafood delicacies, including local lobsters, raw oysters, scallops, clams, and fresh fish from the Atlantic. The chefs rely on the best organic local produce, freshly caught seafood, and their culinary skills to create some of the best dishes in the country.

The leading restaurants also offer award-winning wine lists and excellent handcrafted cocktails.

5. Enjoy the sunset with a glass of rosé

After a long day on the yacht or beach or exploring the beauties of the island, you can enjoy a glass of the best French chilled rosé or a handcrafted cocktail on the beach at the élite Galley Beach bar.

This high-end restaurant and bar is set on the sand of the island’s northwest shore and offers an exceptional view of the Nantucket Sound.

With its award-winning menu, rich 100-year-old history, and impeccable service, Galley Beach is among the most famous restaurants on the island. It has an open-air dining room, a beach bar, and a canopied lounge with fire pits, so you can enjoy a meal or drink with your feet in the sand.

Galley Beach has a curated wine list of more than 5,000 of the best wines from around the world and has hosted famous guests, presidents, celebrities, and more.

It is one of the best places to enjoy the mesmerizing sunsets on Nantucket and a top location for special events and casual chic nights out.