Martha's Vineyard and Nantucket – The resort islands south of Cape Cod

The two beautiful islands south of Cape Cod – Martha's Vineyard and the smaller Nantucket to its east, in the southeastern corner of Massachusetts, were once shipping empires closely tied to whaling. Today, the islands are a great tourism destination (not just for the wealthy) with plenty of hotels for vacationing and touring.

• The islands are a stunning example of the unique character and style of New England, with charming fishing villages, countless sailboats, and a large number of high-quality seafood restaurants, including lobsters and fish dishes.
• The islands were the home ports for whaling ships in the 18th and 19th centuries, which led to their prosperity and wealth during that time.
• Important processing facilities and export of marine mammal products were established on the islands.
• As the importance of the whaling industry declined, the islands transformed and became important recreational and tourist destinations.
• Wealthy individuals from New England and New York placed their estates on the islands, primarily following the stylish estates of the Kennedy family.

How much time do you need for a trip to Martha's Vineyard and Nantucket?

If you're coming for a relaxing vacation, you can spread the trip over a few especially pleasant summer days. To visit all the sites and towns on the islands, it's recommended to dedicate at least two days.

During a trip to Martha's Vineyard and Nantucket, it's recommended to find a place to stay for at least one night

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7 Must-See and Do Things in Martha's Vineyard and Nantucket

1. Whale watching (not literally hunting but observing from one of the ships specializing in following the pods)
2. Edgartown and the large island of Chappaquiddick
3. The great lawn of Ocean Park in Oak Bluffs
4. The fishing boats and charming shacks of Menemsha village
5. The magical beaches on the western part of Martha's Vineyard and the cliffside beaches around Aquinnah
6. Travel back in time in Siasconset
7. Enjoy the heart of Nantucket town

How to Get to Martha's Vineyard and Nantucket?

There are two ways to reach the islands, one by air and the other by sea

1. Martha's Vineyard has a small airport, Martha's Vineyard Airport – MVI, accessible by flights from New York, Chicago, Boston, and other major airports. It's primarily for small planes. Flights to the island are seasonal, operating from mid-spring to late summer. During winter, flights are only available from Nantucket and Cape Cod. Nantucket also has a small airport, Nantucket Memorial Airport – ACK, with flights from Boston, New York, Chicago, and other major US airports. These flights are also seasonal. Off-season, flights are only available from Cape Cod (Hyannis Airport) and from Martha's Vineyard.
2. The second way to reach the islands is by ferry from Hyannis or Falmouth in southern Cape Cod. There are also ferries between the two islands.

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Map of Martha's Vineyard and Nantucket Islands

When to Visit Martha's Vineyard and Nantucket Islands?

• As summer approaches, tourism to the islands expands massively. The summer on the islands is simply perfect and it's the best time to visit
• In the height of summer, it's advisable to book accommodations in advance since the islands are highly sought after
• It's highly recommended to also include a ship cruise for whale watching, perhaps the most important attraction on the islands
• The trip to both islands is seasonal only and there's no point in visiting during winter
• In winter, only the residents are on the islands, and many tourist businesses are closed
• As spring arrives, the tourist season begins, the snow melts, and the islands' nature is especially blooming

How to Plan a Trip Itinerary in Martha's Vineyard and Nantucket Islands?

• Combine a trip to both islands with all the attractions and places worth visiting in Southeast Massachusetts
• The islands are satellites of Cape Cod and are an integral part of the magnificent mainland journey
• The town of Plymouth, landing site of the Mayflower in 1620 and the first British settlement in New England, is also located a short drive from Cape Cod
• The entire area can be accessed from the city of Boston, the largest and most important city in New England, or from New York
• The route in Martha's Vineyard includes the major towns of Vineyard Haven, Oak Bluffs, and Edgartown, from which access to Chappaquiddick Island is available. From there, it's recommended to take a car trip through the entire western part of the island, a charming rural area with two delightful villages – Aquinnah, an upscale estate village, and Menemsha, a charming fishing village that epitomizes all we know about New England.

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Accommodation and Hotels in Martha's Vineyard and Nantucket

Both islands are popular tourist destinations and they offer quite a few accommodation options.

• In Martha's Vineyard, most hotels are centered in the heart of Oak Bluffs near the coastline or in the heart of Edgartown
• On the outskirts of the towns, there are motel-style hotels, and in their centers, there are three or four-star hotels
• In Nantucket, most of the hotels are located in the northern part of the town center, with a mix of three and four-star hotels
• All the hotels on the islands are excellent plus, and as the season peaks, their prices also increase
• Since there's high demand for accommodation on the islands, it's advisable to book a place in advance

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Martha's Vineyard

Martha's Vineyard, or ‘The Vineyard' to the locals, is the third largest island on the Atlantic coast of the USA after Long Island and Mount Desert Island in the Acadia National Park, Maine. It's actually the largest island on the East Coast of the USA that isn't adjacent to the mainland and is not connected by a bridge. East of the island lies a satellite island called Chappaquiddick, which is part of Edgartown town.

• Over the years, the island has become one of the most favored vacation spots for the wealthy from Long Island and New York.
• Nowadays, the island is home to lavish private estates owned by all the who's who (those with a lot of money, of course).
• The island developed as a vacation spot following the Kennedys' estate on the island.
• Since the island was isolated from the mainland during the 18th and 19th centuries, a large portion of its residents married within their families. This led to a high rate of deafness among the island's inhabitants and the development of a unique sign language.
• The island was the filming location for Steven Spielberg's movie Jaws, making it even more attractive in popular culture.

Two famous events related to the Bostonian aristocratic family occurred on the island:

1. The first event where Ted Kennedy left a woman to die in an accident on Chappaquiddick Island, in 1969, about 6 years after his brother President John F. Kennedy was assassinated.
2. About 30 years later, in July 1999, John F. Kennedy's son, John John, and his wife were killed when the plane he was piloting crashed near the island's shore.

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Vineyard Haven and Oak Bluffs

The port town of the island is also its largest settlement. The center of Vineyard Haven is the ferry port, above which stretches the main street of the town. This area is considered the important urban center on the charming natural island, with upscale restaurants, shops, and galleries. Just south of the port, the long peninsula stretches across the bay towards the town of Oak Bluffs. At the tip of the peninsula is the VH-OB bridge, a low bascule bridge.

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Oak Bluffs is the foundation on which tourism in Martha's Vineyard developed, and it can also be reached by ferries from Cape Cod towns. In the center of the town is the large lawn – Ocean Park, which was once a huge campsite for summer tent vacations.

Around the square, you'll find charming vacation homes and beautiful streets lined with restaurants and shops. Nearby is the Flying Horses Carousel, the oldest operating carousel in the USA.

Edgartown

The town of Edgartown is located a fifteen-minute drive south of Oak Bluffs, along the island's eastern coast. Adjacent to the town on the east is the large island of Chappaquiddick, filled with natural activities including a large golf course in its northern part. The town developed during the 19th century as the home of sailors and ship owners who ventured into the ocean to hunt whales.

Many of the old sea captains' homes have remained intact to this day and are considered highly sought-after residences for the wealthy of New England. Edgartown's main street is also one of the important urban centers in the town, filled with restaurants, hotels, and shops. At the northeastern tip of the town is the Edgartown Harbor Light, one of the most beautiful lighthouses on the islands.

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The Western Shoreline of Martha's Vineyard

While most of the island's tourism is concentrated in the larger towns of the eastern coastline, between Vineyard Haven and Edgartown, the western coastline of the island is dedicated to two main things – nature and massive private estates. The coastline is filled with stunning natural beaches. The scattered village of Aquinnah, formerly known as Gay Head, sits on a fish-shaped peninsula at the western tip of the island. The peninsula boasts spectacular cliffside beaches, alongside some of the largest private estates in Martha's Vineyard.

Opposite the peninsula of the village of Aquinnah, at its northern end, lies the charming fishing village of Menemsha. The village is known for the sight of fishing boats attached to the wooden cabins of its residents. This village is considered one of the most beautiful in the entire island and preserves the original atmosphere of the island before the influx of estate owners.

Nantucket Island

Nantucket Island is located 20 km east of Martha's Vineyard and 40 km south of Cape Cod. Nantucket was one of the wealthiest places in the USA during the 18th and 19th centuries, all linked to whale hunting. The island hosted a massive harbor where ships related both to hunting and processing raw materials extracted from whales, such as the bones and fat of the giant marine mammal used for lighting, anchored. The island was the base from which the ship Pequod set out in Herman Melville's famous novel “Moby-Dick”.

• In the mid-19th century, the thriving island began to suffer economically due to the use of other oils and fuels for lighting, impacting the whaling industry.
• Additionally, in 1846, the town of Nantucket, the main settlement on the island, was engulfed in a massive fire.
• Since then, the town didn't recover until the mid-20th century, when, like Martha's Vineyard to the west, Nantucket Island became a very sought-after tourist destination.
• About 15 thousand people live in the town of Nantucket itself, and its center is filled with hotels and restaurants for the benefit of tourists who visit the island every summer.
• Overlooking the entrance to the town's harbor is the charming Brant Point Lighthouse, which has become a popular tourist attraction.

The village of Siasconset is the second settlement on the island besides the main town of Nantucket. It is a twenty-minute drive from the town center. The village is a collection of charming cottages and houses, some of which are historic, and is filled with lanes overlooking the ocean waters. In the northern part of the village is the gigantic Sankaty Head Lighthouse, which guides ship traffic towards New York.