Island Hopping

How to spend 72 Hours on Martha’s Vineyard and Nantucket

Text and Photography by Christopher Setterlund

MARTHA’S VINEYARD is visible from the south coast of the Cape, from Woods Hole to Mashpee. It seems so close that you could touch it yet feels so far away. Thirty miles off the coast of Cape Cod sits NANTUCKET, one of the most well-known islands on Earth. It is an island seemingly untouched by the hustle and drama of 21st-century life. There is not even a street light to be found on its shores. One could spend weeks on both of these islands’ heavenly shores and still not see and experience all they have to offer. What follows is only one of a million ways to spend 72 hours on the Vineyard and Nantucket. For the sake of this article, we will be traveling to both islands by car. However, there are several options to get around, including by bicycle or public transportation.


Day 1

Taking the ferry to Oak Bluffs is a summer-only option that’s highly recommended. After disembarking from the ferry, take time to enjoy Ocean Park, a lush green welcome mat to the island with a wide open space, a fountain and a grand gazebo bandstand.

A short walk from Ocean Park is the Martha’s Vineyard Camp Meeting Association (MVCMA) and its delightful gingerbread houses. Colorful and unique, more than 300 cottages cover 34 acres of land seemingly torn right from a fairy tale. Though worth a visit anytime, these homes are breathtaking during the Grand Illumination event in August, when they are adorned with colorful lights and lanterns.

For lunch, take a walk over to the highly regarded Martha’s Vineyard Chowder Company, with its award-winning chowder and delicious seafood and steaks. Afterward, take a ride on the famous Flying Horses Carousel. This historic landmark is the oldest platform carousel in the country—built in 1876 and brought to the Vineyard from Coney Island in 1884. Grab the brass ring and you win a free ride!

Later on, head south through Oak Bluffs to Joseph Sylvia State Beach. Walk the sands along the Atlantic, sit and listen to the lapping of the ocean waves, and take in all of the wondrous scenery from the American Legion Memorial Bridge, the setting of one of the most famous scenes in the movie “Jaws.”

Continue on into Edgartown for some shopping and dinner. Along Main Street and Water Street, there are many shops worth checking out, including the original Vineyard Vines clothing store and Murdick’s Fudge. If it’s mealtime, choose The Wharf Pub or Seafood Shanty, or the more upscale l’etoile. After dinner, settle in for the night at one of Edgartown’s fine accommodations, The Charlotte Inn or Winnetu Oceanside Resort.

Day 2

In the morning, take the Chappy Ferry over to Chappaquiddick. Chappy has many incredible sights, such as Mytoi Gardens. A 14-acre Japanese garden complete with authentic-looking bridges over the rivers and ponds, Mytoi is a serene place where one can enjoy the beautiful landscape and flowers.

A trip to Chappaquiddick should include a stop at Wasque, a Trustees of Reservations property with an allure all its own. The pleasant drive out to this southwest corner of Chappy leads to Norton Point Beach, which stretches out to meet Wasque Point.

After relaxing at Wasque, spend the rest of the afternoon taking a guided tour of the 1,000-acre Cape Poge Wildlife Refuge, another Trustees property with stunning natural beauty and the must-see remote Cape Poge Lighthouse.

Day 3

On your last day, start by driving out to the Vineyard’s western side where you’ll find the soul of the island. Here, you’ll find the awe-inspiring clay cliffs of Lucy Vincent Beach, a landmark that must be seen to be believed.

Getting hungry? Grab a snack at Wampanoag-run Orange Peel Bakery in Aquinnah, owned by Julianne Vanderhoop. In an effort to bring the community together, she hosts community pizza nights twice a week, Wednesday and Saturday. Bring your own toppings, and make new friends.

Continue on to one of the most famous landmarks on the Vineyard, Gay Head Lighthouse. Recently moved back from the eroding cliffs, it is instantly recognizable both by islanders and people from around the world. Just to the north of the lighthouse are the Aquinnah Cliffs.

After admiring the cliffs at Aquinnah, it is time to head back to Oak Bluffs and catch the ferry to the mainland. Seventy-two hours has flown by. This is not enough time to see all the Vineyard has to offer, but the short trip will whet your appetite until you return.


Day 1

Upon arrival by ferry downtown, the best way to begin a few days on Nantucket is to head away from the center of town and go west. Madaket Beach, located in the southwestern corner of the island, is a perfect starting place. The beach is great for surfing and for sunsets. After relaxing on the sand, venture a little farther and learn about Madaket Millie. Millie Jewell, known for her volunteer work with the Coast Guard, was a local legend of the 20th century. A bridge going across Hither Creek to Smith Point is named after her, as well as a restaurant not far from the beach—a perfect spot to grab lunch.

After lunch, take a left off of Madaket Road and follow Warrens Landing Road out to Eel Point in the northwest corner of Nantucket. The 100-acre Eel Point, a picturesque landscape owned by the Nantucket Conservation Foundation, is a great place to bird watch or hike down to the ocean.

Take the rural Eel Point Road back east toward downtown, but make sure to stop by one of the most amazing spots on the island: Steps Beach. Located off the beaten path on Indian Avenue, Steps Beach has a one-of-a kind landscape. The dirt path that leads to the beach opens up to a stunning view at the top of the stairs. The beach is also a good place to go for a swim. Head back into town and enjoy dinner at Lola 41 (their sushi is exquisite.) For the first night on the island, one cannot go wrong with one of the spectacular bed-and-breakfasts near Lola 41: The Periwinkle, Brass Lantern Inn or The Veranda House.

Day 2

The next morning, it is time to explore the eastern half of Nantucket. The Milestone Road Bike Path leads from downtown straight out to the quiet village of Siasconset. Follow Main Street down to Gully Road. Take a walk up onto the Sconset Footbridge, from which there are stunning views east to Sconset Beach.

The journey north from the footbridge takes you to one of the more unique spots on the island, the Sconset Bluff Walk. After the bluff walk, head north along the coast to Sankaty Head Lighthouse. Located next to a golf course, it is the highest point on the island, with a breathtaking view.

Head back into town and enjoy lunch at Fog Island Café or Something Natural. Then spend the rest of the afternoon taking in the Nantucket Whaling Museum, which showcases the rich whaling history of the island in great detail. The museum closes at 5 p.m. during the summer, so make sure to leave enough time to explore the collection.

Grab dinner at one of the top downtown establishments like Dune, Le Languedoc Inn & Bistro or Brotherhood of Thieves. Afterward, hunker down for the night at a posh downtown hotel, such as The Nantucket or White Elephant, and enjoy a good night’s sleep before your last day on the island.

Day 3

Start the morning off with a sunrise trip to Brant Point Lighthouse, one of the most photographed lighthouses in the world. After taking in the beauty of this site, head south slightly out of town to enjoy some heralded blueberry pancakes at Downyflake Doughnuts on Sparks Avenue. It is worth the trip.

The rest of the last day on Nantucket should be spent wandering the cobblestone streets downtown. There are popular shops like Murray’s Toggery, The Hub and Mitchell’s Book Corner, and wonderful dining establishments like The Rose & Crown and Provisions. Don’t forget to check out historical highpoints like the Nantucket Atheneum, where Frederick Douglass once spoke, and the First Congregational Church, which has a view of the harbor from its tower. If time allows, take a short walk over to Sunset Hill Lane and the Jethro Coffin House, also known as The Oldest House. Built in 1686, it is the only structure remaining from the original Nantucket settlement.

Before catching the ferry back to the mainland, there is no better way to end a trip to Nantucket than with a beer from the Cisco Brewery on Bartlett Farm Road. It is a bit of a hike outside of downtown, but worth it to visit the island’s only brewery in a laidback rural location.

It is now time to head back to the ferry. Seventy-two hours is barely enough time to scratch the surface of what Nantucket has to offer, but it is a start. Make sure the next trip to this quaint island is as long as possible so you can fully appreciate it!

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