Nantucket, a small island off the coast of Cape Cod, Massachusetts, is one of the world’s best islands for a relaxed luxury weekend getaway. Nantucket offers miles of beautiful beaches, luxury hotels, excellent restaurants, chic boutiques, a variety of watersports and a very relaxed vibe. Nantucket was originally a whaling community but, as whaling gave way to tourism over a century ago, Nantucket was careful to preserve the beauty and charm of its villages and its environment -- you won't find any fast food shops or traffic lights on the islands, the height and style of new buildings are strictly regulated and almost half of the island’s environment is protected by land trusts. Today, the small towns and villages of Nantucket feel as if they have not changed much since the days of whaling ships.

Friday

For this luxury weekend getaway, we recommend the Wauwinet, the most luxurious hotel on the island. The Wauwinet, Nantucket’s only Relais & Chateau property, is located in a secluded corner of the island on narrow peninsula between the Atlantic Ocean and Nantucket Bay. The hotel, first opened in 1877, offers 32 luxurious rooms and four separate cottage suites. While the Bayview rooms have fabulous views overlooking Nantucket Bay, we prefer the very private and romantic Cottage Suites, which are located in separate cottages away from the main building. These cottage suites, decorated in a comfortable New England style, include a separate sitting room with stone fireplace, lofty beds, integrated entertainment system and a private deck with comfortable lounge chairs.

In front of the main hotel building is a beautiful vibrant green lawn filled with plush green cushioned lounge chairs that overlooks a beautiful section of Nantucket Bay. Settle into one of the lounge chairs, order a glass of champagne and enjoy one of the most magnificent vistas in Nantucket.

The Wauwinet // 120 Wauwinet Rd. // website

Afternoon

After getting settled, head into Nantucket Town, which is filled with historic buildings dating from the 18th century, art galleries, chic boutiques and excellent restaurants. Upon entering the town, the first thing you will notice are hundreds of yachts, sailboats and fishing boats moored in the harbor and filling every slip in the boat docks. As you wander along the cobblestone streets and brick walkways, you fill see that the town has been very careful to preserve its provincial charm. Instead of chain stores, you will find charming family owned stores and boutiques. Many of these stores have been in business for decades, including Murray’s Toggery Shop (home of the famous Nantucket Red, the brick-red shorts and pants seen all over the island), Nantucket Looms (known for its excellent selection of home furnishings and handwoven linens since 1968) and Mitchell’s Book Corner (a classic bookstore that has been in business since 1968).

Evening

After an afternoon of exploring Nantucket Town, we recommend stopping for a pre-dinner cocktail at the chic Galley Beach Bar, which is one best spots on the island for watching the sunset. From their enormous deck that spills onto the sand you can watch the sun slip below the horizon while enjoying a glass rosé wine or one of one of their famous cocktails, like their ACK Mule made with local 888 vodka, lime juice and ginger beer.

Galley Beach Bar // 54 Jefferson Ave. // website

After drinks at the Galley Beach Bar, head to the Pearl, which is one of the most popular seafood restaurants in Nantucket. The Pearl’s is known for its creative pan-Asian seafood dishes and award-winning wine list. Highlights include their signature Tuna Martini and Wok-Fried Salt & Pepper Lobster Lo Mein. If you want to stay for a drink after dinner, the bar gets lively as the evening goes on and you may find yourself sitting next to one of the island’s many vacationing celebrities.

The Pearl // 12 Federal Street // website

After dinner, wander over to the Juice Bar, an ice cream shop that is something of an institution on NantucketHere you will find dozens of creative ice cream flavors served in freshly baked waffle cones (as well as healthy juices). Some of the favorite flavors include cookies ‘n cream, butter pecan and blackberry. It is very popular so be prepared for a long line (but the line moves quickly).

Juice Bar // 12 Broad Street // facebook page

Saturday

Morning

Nantucket is a biker’s paradise with over 30 miles of bicycle paths and, because the island is relatively small and flat, it is easy to bike almost anywhere on the island. If you are feeling energetic, borrow a bike from the hotel and ride into Siasconset (generally known as Sconset), a quaint village at the far eastern edge of the island. Sconset is one of the oldest U.S. whaling towns and many of the village’s cottages date from the 18th and 19th century. The village has a general store, a couple of tiny boutiques and a handful of restaurants, as well as a beautiful white sand beach that is seldom crowded.

From the center of the village you can ride your bike or you can walk along the Sconset Rose Path, a public pathway that runs through many backyards along Sconset Bluff, to the 1850’s Sankaty Head Lighthouse.

If you don’t feel like biking, the Wauwinet hotel offers many other activities, including spa treatments, sailing, kayaking and paddle boarding. In addition, the hotel offers local tours in its Woody, boat excursions around the bay, cooking classes, surfcasting and even an opportunity to try your hand at lobstering.

Lunch

For lunch, we absolutely love Cru, which serves extraordinary seafood and has the best raw bar on Nantucket. Cru is located in a picturesque spot at the end of Nantucket Town’s main dock overlooking the yachts and sailboats that fill the harbor and the décor is pure nautical, with sailing accessories throughout and sail sheets decoratively hanging from the ceiling. During your lunch, you can watch the boats gliding by on their way to and from the Nantucket Sound. We recommend starting with their seafood tower, which is filled with icy oysters (request the local Fifth Bend oysters that are exclusive to Cru), littleneck clams, jumbo shrimp and blue crab or lobster cocktail, together with a glass of crisp white or rosé wine. For the main course, we highly recommend their classic lobster roll filled with huge chunks of lobster dressed in mayonnaise and served in a buttery brioche roll. Delicious!

Cru // One Straight Wharf // website

Afternoon

After lunch, head to one of Nantucket’s many public beaches. One of the most popular beaches is Seaside, a beautiful wide beach on the south side of the island. The beach has a concession stand and restroom facilities. Given the influence of the Atlantic Ocean, the waves are bigger and the water is a little colder than the beaches along Nantucket Sound. On the opposite side of the island facing Nantucket Sound (where the waves are small and the water warmer), you will find a number of excellent beaches, including Jetties Beach, a family-oriented beach with calm waters, and Step’s Beach, which is next to Jetties Beach and usually less crowded.

After an afternoon at the beach, head to Cisco Brewery, the island’s only distillery, winery and brewer, where you will find an assortment of locals and visitors enjoying flights of locally produced wine, beer and whiskey while listening to live music and grazing on food from food trucks operated by a number of local restaurants. Order a local Cisco beer (their Summer of Lager is excellent), some local oysters, littleneck clams and shrimp from the raw bar and sit back and enjoy the music.

Cisco Brewers // 5 Bartlett Farm Rd // website

Evening

For dinner, you cannot beat the Chanticleer, a romantic and elegant restaurant in the quaint village of Sconset. The restaurant has two separate dining rooms but we recommend dining outside in the romantic and intimate Rose Garden. Chef Jeff Worchester prepares a seasonal cuisine focused on regional produce and seafood. The food is creative and innovative and restaurant’s wine list is excellent. Some recent standout dishes included Ahi Tuna Martini with Scallion Pancakes and local halibut with mushrooms jus. Make sure to save room for their delicious desserts.

The Chanticleer // 9 New St., Siasconset // website

Sunday

Morning

After a leisurely breakfast at the Wauwinet, we suggest a relaxed morning enjoying one of the hotel’s two private beaches. There is a private beach on the Bay side right in front for the hotel and a private beach a short walk from the hotel on the Atlantic side. This beach is part of Great Point Beach, a 7-mile long beach that is one of the nicest beaches on Nantucket. If you want to explore the entire length of Great Point Beach, you will need a 4-wheel drive vehicle and a beach permit.

*Photo courtesy of Bartlett's Ocean View Farm*

On your way to brunch, stop by Bartlett’s Ocean View Farm, Nantucket’s oldest and biggest family-owned farm, where you will fine a beautiful greenhouse and nice market. The farm stand is particularly known for their locally grown tomatoes and corn. During strawberry season, you can pick your own strawberries.

Bartlett’s Ocean View Farm // 33 Bartlett Farm Road // website

Brunch

For brunch, we suggest the Brant Point Grill, which has been consistently named as the best brunch in Nantucket. While the restaurant is known for its lavish Sunday brunch buffet, including a “Create-Your-Own” Bloody Mary bar, we think that the real draw is the spectacular view of Nantucket Harbor. The restaurant is located in the White Elephant Hotel and the best tables are located on the large open deck that looks across a beautiful manicured lawn to the harbor. While enjoying your brunch you can watch the yachts, high-speed ferries and sailboats enter and exit the harbor.

Brant Point Grill // 50 Easton St. // website

Afternoon

For a very special experience, arrange for a late-afternoon private charter of the Endeavor, a 31-foot Friendship sloop built and captained by Jim Genthner. Captain Genthner, who has been sailing the waters of Nantucket for over 30 years, will take you through the harbor filled with yachts and sailboats, past Brant Point Lighthouse (one of the oldest in the U.S.), along the waterfront mansions on Hulbert Avenue and out through the inlet into the beautiful blue waters of Nantucket Sound.

The best time to go is late afternoon when the sun is low on the horizon and everything is bathed in golden light. If you are lucky, you may see some seals or even whales.

Endeavor // Straight Wharf, Slip #1015 // website

Evening

The Wauwinet’s restaurant, Toppers, is a perfect spot for a Sunday night dinner. You can dine in elegant dining room or, if the weather is nice, the more casual outdoor deck, which offers the same menu but affords a magnificent view of the sun setting over Nantucket Bay. The chef prepares a contemporary regional cuisine with an emphasis on local produce and seafood. The restaurant, which has earned the Wine Spectator’s prestigious “Grand Award” since 1996, lists over 1,450 wines and is particularly strong with California, Bordeaux and Burgundy wines. Some recent standout dishes included a summer harvest dish of summer fruits and vegetables, marinated quinoa and Stracciatelli cheese, and Grilled Long Island Swordfish with cranberry beans and braised broccoli rabe.

Toppers // 120 Wauwinet Rd. // website

After dinner, you can lounge next to the firepit on the Wauwinet’s veranda while enjoying a selection from the hotel’s excellent after-dinner drink menu. Later, you can select from one of the hotel’s 200 in-room movie selections and the hotel will deliver hot buttered popcorn to your room to accompany your movie.

Final Thoughts

When to Go

The island is a popular summer retreat for New Englanders and the population swells during July and August. Many think that the best time to visit is early September when the crowds have departed, the weather is beautiful and the water is at its warmest.

Getting Around

Although the island is small and it is easy to get around by taxi or bicycle, we recommend renting a car for the weekend. If you want to drive on the beach, rent a 4-wheel drive jeep with a beach permit that allows access to the beaches that allow vehicles. Otherwise, a convertible Mini is perfect for zipping around the sometimes narrow roads while enjoying the fresh open air and sunshine with the top down. Since parking in Nantucket Town can be challenging during the peak periods (and the town is vigilant about enforcing their parking regulations), we suggest using the public valet services located in a few spots in town. If you are staying at the Wauwinet and do not want to drive, the hotel offers an hourly shuttle to town, as well as a cocktail-hour boat from the hotel to the main town.