For the 50+ Traveler

An island playground for the rich and famous, Nantucket is the place to see and be seen during the summer. Almost 50 percent of the island is designated as open space. Always beautiful, Nantucket has lots to offer year-round for a weekend getaway: glorious natural habitats, soft and sandy beaches, rich history, and plenty of outdoor adventures.

Here’s everything you need to know when planning a weekend in Nantucket.

How To Get There

Getting to Nantucket is easy, and you can bring your own car or bicycle. Alternatively, there are taxis, or you could rent a car or bike to get around the island.

The Steamship Authority in Hyannis, Massachusetts, offers two different options: a ferry that takes 2 hours and 15 minutes to reach the island, and a seasonal passenger-only ferry that takes just 1 hour. Hy-Line Cruises, which also operates out of Hyannis, offers a 1-hour ferry to Nantucket.

The Wauwinet resort in Nantucket.

Where To Stay

Pretty much everywhere you look, there is a beautiful beach or a quaint downtown street. You will need to book ahead, since Nantucket is a small island, and weekend accommodations book quickly.

Here are some of my favorite accommodation options.

The Wauwinet

If you want a stay where you will be pampered to the max, reserve a room at The Wauwinet, the perfect luxury resort. You’ll love the private beach, daily port and cheese hour, exquisite ocean views, and excellent service.

Rental Cottages

They don’t come cheap, but Nantucket rental cottages are charming and readily available on the island. Great Point Properties is a good place to start. It offers in-town and beachfront cottages where your family will be sure to have a fantastic time.

Private Yachts

When in Nantucket, do what the locals do and rent a private yacht. Airbnb offers several options, including this classic yacht with bicycles. Imagine being a gangplank away from the harbor and all that it has to offer. Enjoy a coffee and breakfast al fresco as you watch Nantucket Harbor come to life.

Oysters and caviar from CRU Oyster Bar.

Where To Eat

Island dining experiences usually involve fresh seafood. Nantucket offers that along with spectacular views, beachside options, and romantic sunsets. Keep an eye out for celebrities as you eat.

CRU Oyster Bar

Come for the oysters and Champagne, and stay for the lobster rolls and gorgeous sunsets. CRU Oyster Bar is perfectly situated on the waterfront in Nantucket Harbor. It's the quintessential romantic island spot.

Millie’s Nantucket

Millie’s is a local favorite. It’s a traditional seaside fish shack, but a high-end version. Takeout is available for lunch and dinner. Think mini oyster tacos and a blackened swordfish po’boy on a blanket at the beautiful Madaket Beach.

Sandbar At Jetties Beach

Beachside picnic tables, burgers, sandwiches, and a raw bar round out the experience at the Sandbar. This seasonal, toes-in-the-sand joint is exactly what you need after a long day of fun in the sun.

Queequeg’s Restaurant

Housed in a weathered, shake-shingled Cape-style building, Queequeg's offers classic American cuisine. Its seasonal menu changes based on availability, but the food is always good. Queequeg’s is open for dinner and occasionally brunch.

A beach in Nantucket.

What To Do

Enjoy The Beautiful Sandy Beaches

The beaches of Nantucket are perfect for sunbathers, bodysurfers, and castle builders.

Ladies Beach is a semiprivate beach near Cisco Brewers (just a short walk through the dunes from the parking lot). This beach is best for surfers and strong swimmers.

The 40th Pole Beach is perfect for families. You can -- with a beach permit -- drive your four-wheeler onto the beach, eliminating the need for carrying all the beach toys and paraphernalia. There is also an off-beach parking lot.

Other drive-on beaches include Nobadeer Beach, Smith Point, Point of Breakers Beach, Low Beach, Great Point Beach, and Coskata-Coatue. The permits are pricey, but the experience of off-road beach driving is unique and totally worth it.

Other beaches to consider are Codfish Park, Cisco Beach, Madequecham Beach, Settler’s Landing, Surfside Beach, and Water Tower Beach.

The Nantucket Island School of Design and the Arts sponsors an annual Sculpture and Sandcastle Day, a fun, family-focused event at Jetties Beach in late July.

There is no shortage of beautiful beaches on this island paradise.

Take The Sconset Bluff Walk To The Sankaty Head Lighthouse

The Sconset Bluff Walk is a public path that winds along the bluffs on the island’s eastern shore. Park in town in Siasconset, and you will find the head of the trail near Codfish Park. The bluff walk winds behind cottages, luxurious summer homes, and sweetly scented rose hedges on its way to Sankaty Head Lighthouse. The trail can be narrow and at times washed out, making the walk steep and difficult. Take care when rerouting to avoid walking on private property.

The view from the bluffs is well worth the fairly arduous walk. You’ll love the magnificent ocean views with a backdrop of spectacular seaside mansions.

Different beers on tap at Cisco Brewery.

Head To The Brewery

Cisco Brewers, Triple Eight Distillery, and Nantucket Vineyard are Nantucket institutions. After a sun-filled day at the beach, locals and visitors alike join in the hip, fun vibe at Cisco for some libations, casual food-truck dining, and live music.

One of the best spots for vacationing (and watching for celebrities), Cisco Brewers is the place to gather in Nantucket. Take a tour of the facilities, sample a few options, and let the party begin.

Take In A Festival

Nantucket has a few holiday options to consider. When you visit during the off-season, you will experience smaller crowds and get to hobnob with the locals.

The Nantucket Chamber Christmas Stroll takes place in early December. Sponsored by the Nantucket Chamber of Commerce, the weekend includes a storefront decoration contest, a tree festival, theatrical performances, tours, Christmas fairs, beverage tastings, and plenty of great food. A true, old-time Christmas experience, it is a fun time to enjoy the holiday festivities.

The Daffodil Festival, held the last weekend of April, celebrates spring's arrival. The weekend includes an antique car parade, a tailgate picnic, tours, art shows, a hat contest, a children’s bike parade, a window-decorating contest, and other quaint, small-town festivities.

Go On A Tour

A great way to get a feel for the island is by taking a tour. Nantucket Island Tours offers excursions to all the important spots on the island, including the Old Mill, Siasconset Village, Sankaty Head Lighthouse, and more.

The first stop is six blocks away from the Hy-Line Dock. There are some accessible buses -- be sure to ask when booking.

Views of Nantucket, Massachusetts.

Learn About Nantucket’s History

Rich with history, from the Quaker settlement to the whaling boom, Nantucket has lots to offer history buffs. The Nantucket Historical Association manages several historic properties that offer seasonal tours. The Hadwen House & Garden, the Quaker Meeting House, the Old Mill, and the Thomas Macy House are just a few of the buildings you can visit.

The Whaling Museum covers life in Nantucket during the late 18th and early 19th centuries, when Nantucket was the whaling capital of the world. Visit the scrimshaw exhibit, or venture up to Tucker’s Roofwalk for a panoramic view of the island. Explore the whaling ship gallery that highlights the Essex, the ship that was the inspiration for Melville’s Moby Dick.

Go Shopping

Nantucket is home to numerous specialty shops and boutiques. You could spend a glorious day popping in and out of little shops while strolling along the waterfront or downtown. Stop for lunch at a seaside cafe to revitalize, and then renew your hunt for that perfect souvenir.

Old South Wharf has a variety of one-of-a-kind shops. Find the Brown Basket Gallery, which offers pretty baskets, and Pete’s Fresh Fish Prints, where you can pick up unique fish-related artwork.

Centre Street offers island fashion establishments like trendy Cattivo, and the Valentiva Kova luxury women’s boutique can be found on South Beach Street.

Nantucket’s shopping guide is a useful source of information for planning your shopping expedition.

Pro Tip: Nantucket is not a place to wing it -- plan ahead, make reservations, and your weekend getaway will meet all of your expectations.