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The Islands
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Explore Massachusetts’s Islands for historic harbour towns, Wampanoag heritage, beaches, dunes, seafood and distinctive coastal landscapes.

The Islands is the familiar Massachusetts travel region formed primarily by Martha’s Vineyard and Nantucket, two very different islands south of Cape Cod. Martha’s Vineyard is larger and more varied, with sandy beaches, wooded interior roads, salt marshes, far-reaching western cliffs and six distinct towns. Nantucket is smaller, more compact and strongly shaped by its whaling past, with low dunes, heathland, moors, stone walls and a remarkably preserved historic centre. Both are part of the United States and are reached across the water rather than by bridge.
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Martha’s Vineyard rewards visitors who explore beyond its best-known harbour towns. Vineyard Haven is a working port and year-round community, Oak Bluffs is recognised for its colourful Carpenter Gothic cottages and late-nineteenth-century seaside history, while Edgartown combines white-painted houses, a former whaling port and waterfront walks. West Tisbury and Chilmark lead towards quieter rural landscapes, farm stands and the fishing village of Menemsha; Aquinnah, at the island’s western end, is known for its clay cliffs, lighthouse and longstanding Wampanoag presence. Chappaquiddick, reached from Edgartown by a small seasonal ferry, has beaches, dunes and broad salt-marsh scenery.
Nantucket Town is the island’s historic and commercial centre, where cobbled lanes, grey-shingled houses, old merchants’ residences and former warehouses reflect the wealth generated by the nineteenth-century whaling industry. Beyond town, Siasconset has a distinctive village character, while the island’s eastern and western reaches open into beaches, dunes, cranberry bogs, wildlife habitat and open moorland protected through extensive conservation work. Walking, cycling, birdwatching, sailing and beach-going are central to the island experience, although wind, tides and weather can change conditions quickly.
The Islands’ cultural identity is both maritime and contemporary. Wampanoag history remains especially important on Martha’s Vineyard, and the islands also preserve African American, Portuguese, Irish and other community histories shaped by seafaring, seasonal work and migration. Seafood features prominently in local dining, alongside produce from island farms and bakeries. Summer brings the largest crowds and the fullest calendar, while spring and autumn offer a quieter landscape but fewer services and more variable transport. Reservations, especially for vehicle ferries and accommodation, require careful planning because available space is limited during peak periods.

Getting to and around The Islands

How to get there

Most visitors arrive by ferry from mainland Massachusetts. Steamship Authority services connect Woods Hole, Hyannis and, for some routes, New Bedford with Martha’s Vineyard or Nantucket; Woods Hole is outside The Islands and is the principal mainland gateway to Martha’s Vineyard, while Hyannis is a major gateway to both islands. Private passenger-ferry services also operate on selected routes, but schedules and terminals vary seasonally. Martha’s Vineyard and Nantucket each have airports with domestic service, though routes are limited compared with mainland hubs and may be seasonal. Boston and Providence are useful broader air gateways, but both are outside the region and require onward road, bus, rail or ferry travel.

Transportation

Martha’s Vineyard and Nantucket have local bus networks, taxis, bicycle-rental services and pedestrian-friendly historic centres, although rural roads and beaches can be widely dispersed. A car is useful for reaching outlying parts of Martha’s Vineyard and Nantucket, but parking is constrained in town centres and summer traffic can be slow. Vehicle space on ferries is limited and normally requires advance reservation. Bicycles are practical on many routes, but visitors should use care on narrow or busy roads and be prepared for wind. The small ferry to Chappaquiddick is a distinct local connection from Edgartown and may be affected by weather, tides or seasonal arrangements.

Top city travel guides in The Islands

The cities of The Islands, and the easiest places to base yourself.

Best attractions in The Islands

The Islands offer a balance of maritime history, coastal scenery and outdoor activity rather than one concentrated collection of attractions. On Martha’s Vineyard, visitors can explore the harbour towns of Vineyard Haven, Oak Bluffs and Edgartown, travel west to Aquinnah’s clay cliffs and lighthouse, or follow roads through Chilmark, West Tisbury and Menemsha. Beaches, salt marshes, conservation land and open farmland support walking, cycling, birdwatching, kayaking and sailing. Chappaquiddick adds a more remote landscape of dunes and wetlands. Nantucket combines museums and historic buildings in Nantucket Town with beaches, moors, cranberry-growing country and protected habitats around the island. The Nantucket Whaling Museum explains the port’s maritime past, while lighthouses, old shipyards and historic villages reveal the hazards and prosperity of the whaling era. Seasonal boat trips, fishing, wildlife observation and arts events broaden the offering, but weather and ferry capacity can affect plans. The most rewarding itineraries leave time for landscapes between the headline towns rather than treating either island as a single waterfront resort.

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Best landmarks in The Islands

The Islands’ most recognisable landmarks express their maritime, religious and coastal history. On Martha’s Vineyard, the Gay Head Lighthouse stands above the clay cliffs at Aquinnah, an area of geological and cultural importance to the Wampanoag Tribe of Gay Head (Aquinnah). Oak Bluffs’ Wesley Hotel and densely arranged Carpenter Gothic cottages recall the town’s nineteenth-century Methodist camp-meeting origins, while Edgartown Lighthouse overlooks a harbour once central to whaling and shipping. Nantucket Town is itself a landmark landscape: cobbled streets, grey-shingled houses, former counting houses and brick merchant buildings preserve the physical scale of a major whaling port. Brant Point Lighthouse marks the approach to Nantucket Harbour, and Sankaty Head Light stands near the island’s eastern edge above a shifting coastline. The Old Mill in Nantucket’s western district reflects an earlier agricultural economy, while the long beaches, dunes and moors provide natural landmarks shaped by wind, waves and erosion. These places are significant not merely for appearance but for the economic and cultural forces they represent.

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Explore The Islands on the map

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Best restaurants in The Islands

Island dining is closely tied to the sea, with oysters, clams, scallops, lobster, striped bass and other locally landed or regionally sourced seafood commonly appearing on menus. Martha’s Vineyard’s harbour communities support seafood shacks, bakeries, cafés, pubs and restaurants ranging from casual seasonal counters to more polished dining rooms, while farm stands and community markets showcase produce from the island’s agricultural districts. Nantucket offers a similarly maritime menu, alongside bread, pastries, ice cream and produce suited to a strong summer trade. Menemsha is particularly associated with a working fishing setting and informal seafood eating, although the availability of catches and businesses changes. Restaurants are busiest in summer, and smaller communities may have limited evening choice outside the main season. Visitors should distinguish genuinely local products from dishes simply marketed with an island theme; the strongest regional identity comes from fresh seafood, farm produce and the continuing relationship between food, boats and working waterfronts.

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Best bars in The Islands

The Islands’ evening life is generally sociable and seasonal rather than centred on a large nightclub scene. In Edgartown, Oak Bluffs, Vineyard Haven and Nantucket Town, visitors find traditional pubs, hotel bars, restaurants with late seating, wine bars and places offering live music during the busier months. Oak Bluffs has a particularly active summer social calendar, while Nantucket Town concentrates much of Nantucket’s evening choice within walkable historic streets. Outside the main centres, evenings tend to revolve around coastal restaurants, village inns, small music events and private gatherings rather than dedicated clubs. Breweries and craft-drink venues form part of the contemporary offer, but opening patterns and entertainment schedules vary by season. Taxis and buses may be less frequent late at night, so arranging transport in advance is sensible, especially after travelling between towns or staying in a rural area.

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Best nightclubs in The Islands

The Islands’ evening life is generally sociable and seasonal rather than centred on a large nightclub scene. In Edgartown, Oak Bluffs, Vineyard Haven and Nantucket Town, visitors find traditional pubs, hotel bars, restaurants with late seating, wine bars and places offering live music during the busier months. Oak Bluffs has a particularly active summer social calendar, while Nantucket Town concentrates much of Nantucket’s evening choice within walkable historic streets. Outside the main centres, evenings tend to revolve around coastal restaurants, village inns, small music events and private gatherings rather than dedicated clubs. Breweries and craft-drink venues form part of the contemporary offer, but opening patterns and entertainment schedules vary by season. Taxis and buses may be less frequent late at night, so arranging transport in advance is sensible, especially after travelling between towns or staying in a rural area.

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Best shops in The Islands

Shopping is concentrated in the historic centres of Edgartown, Oak Bluffs, Vineyard Haven and Nantucket Town, where independent clothing shops, bookshops, galleries, homeware stores, jewellers and maritime-themed retailers occupy restored buildings. Nantucket is particularly associated with locally styled textiles, basketry, art and design, while Martha’s Vineyard offers galleries, craft goods, island-made food products and shops reflecting the different character of its harbour towns and rural communities. Farm stands and seasonal markets are useful for produce, baked goods, preserves and other edible gifts, although availability follows the agricultural calendar. Visitors can also find ceramics, paintings, photography and handmade work from artists with connections to the islands. Retail selection is broader in summer and more restricted in winter, when some seasonal businesses close. The most appropriate souvenirs are durable products made by identifiable local artists or producers rather than generic nautical merchandise, and visitors should respect restrictions on purchasing or removing natural materials from protected beaches and conservation land.

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The Islands essentials

Currency and Payment
The currency is the United States dollar (USD), as throughout Massachusetts and the United States. Cards and contactless payments are widely accepted in accommodation, restaurants, shops and transport-related businesses, but carrying some cash is sensible for small purchases, tips, occasional market stalls and places where connectivity or card equipment is temporarily unreliable. Prices can be higher than on the mainland, particularly during the summer season, because goods and supplies must be transported across the water. International visitors should notify their card provider about travel and check foreign-transaction charges.
Safety
The main visitor concerns are ordinary property security, road safety, changing coastal conditions and the practical limitations of island services. Keep valuables out of unattended vehicles and take particular care on bicycles, where roads may be narrow and traffic increases in summer. Dunes, cliffs and beaches can be unstable or exposed to strong wind, surf and rip currents; follow local warnings and never assume calm-looking water is safe. Sun protection, drinking water and sensible footwear are important on long beach, nature-reserve and moorland walks. Wild landscapes may have ticks, so check clothing and skin after time in grass or brush.
Emergency Situations
Call 911 anywhere in The Islands for police, fire or ambulance assistance; this is the national emergency number used throughout the United States. Give the dispatcher the island, town, road or beach access point and any nearby landmark, since precise location information can be difficult in rural areas. For emergencies at sea or on the coast, 911 can connect callers with the appropriate response, including Coast Guard resources where relevant. Mobile coverage can be inconsistent in some remote areas, so do not rely solely on a phone when undertaking long walks, boating or cycling excursions.
Do's and Don'ts
Do respect private property, posted beach restrictions, historic buildings and the rights of Wampanoag communities, particularly around Aquinnah. Do keep to marked paths in dunes and protected habitats, carry rubbish away when facilities are limited and observe local parking signs. Do allow pedestrians and cyclists space on narrow roads. Do not remove shells, plants or historic objects from protected places, and do not climb unstable cliffs or cross barriers. Tipping is customary in the United States for table service, taxis and many personal services; check the bill and tip according to the service received rather than assuming a gratuity is included.
Local Tips
Build an itinerary around ferry geography: Vineyard Haven, Oak Bluffs and Edgartown are separate Martha’s Vineyard gateways or centres, while Nantucket Town is the island’s principal arrival point. Early and late seasons can provide a quieter atmosphere, but some businesses, tours and transport services operate less frequently outside summer. On Martha’s Vineyard, west-island journeys take longer than a map may suggest, and Chappaquiddick requires a separate ferry crossing. On Nantucket, reserve time for beaches and conservation land beyond the historic centre, but check access rules because habitats and roads can change with weather and coastal erosion.
Eve, your Evendo local guide

From Eve

Local phrases worth knowing

You don't need to get them perfect. A few words go a long way, and locals appreciate the effort.

6 phrase groups · English, local and pronunciation

Basics
EnglishLocalSay it
HelloHowdy[Haud-ee]
GoodbyeSee ya[See yah]
YesYep[Yep]
NoNah[Nah]
Please/You're welcomeSure thing[Shoor thing]
Thank youThanks a lot[Thangs a lot]
Excuse me/SorryPardon me[Pardon me]
How are you?How's it going?[How's it goin'?]
Fine. And you?Good. You?[Good. You?]
Do you speak English?You speakin' English?[You speakin' English?]
I don't understandI ain't followin'[I ain't followin']
Eating & Drinking
EnglishLocalSay it
I'd like to see the menu, pleaseCan I see the menu?[Can I see the menu?]
I don't eat meatI ain't eatin' meat[I ain't eatin' meat]
Cheers!Cheers![Cheers!]
I would like to pay, pleaseCan I get the check?[Can I get the check?]
Emergencies
EnglishLocalSay it
Help!Help![Help!]
Go away!Get outta here![Get outta here!]
Call the Police!Call the cops![Call the cops!]
Call a doctor!Get a doc![Get a doc!]
I'm lostI'm turned around[I'm turned around]
I'm illI don't feel good[I don't feel good]
Shopping
EnglishLocalSay it
I'd like to buy...I wanna buy...[I wanna buy...]
I'm just lookingJust browsin'[Just browsin']
How much is it?What’s the price?[What’s the price?]
That's too expensiveThat's a bit pricey[That's a bit pricey]
Can you lower the price?Can you knock down the price?[Can you knock down the price?]
Time & Numbers
EnglishLocalSay it
What time is it?What time we got?[What time we got?]
It's one o'clockIt's one o'clock[It's one o'clock]
Half past (10)Half past ten[Half past ten]
MorningMornin'[Mornin']
AfternoonAfternoon[Afternoon]
EveningEvenin'[Evenin']
YesterdayYesterday[Yesterday]
TodayToday[Today]
TomorrowTomorrow[Tomorrow]
1One[One]
2Two[Two]
3Three[Three]
4Four[Four]
5Five[Five]
6Six[Six]
7Seven[Seven]
8Eight[Eight]
9Nine[Nine]
10Ten[Ten]
Transport & Directions
EnglishLocalSay it
Where's a/the...?Where's the...?[Where's the...?]
What's the address?What's the address?[What's the address?]
Can you show me (on the map)?Can you point it out?[Can you point it out?]
When's the next (bus)?When's the next bus?[When's the next bus?]
A ticket (to ....)One ticket to... please[One ticket to... please]

History of The Islands

Wampanoag Homelands before European Settlement

Martha’s Vineyard and Nantucket are part of the ancestral homelands of the Wampanoag people, whose communities developed sophisticated coastal economies based on fishing, shellfishing, farming, hunting and trade. The islands’ waters, beaches and wetlands were not empty landscapes but lived-in cultural environments with established place names and seasonal movements. Wampanoag communities survived the severe disruption brought by European settlement, epidemic disease and land loss. On Martha’s Vineyard, the Wampanoag Tribe of Gay Head (Aquinnah) remains a federally recognised nation, and Aquinnah continues to be an important centre of Wampanoag identity and cultural life.

Seventeenth-Century English Colonisation

English settlement expanded across the islands during the seventeenth century, following the establishment of colonial communities on Martha’s Vineyard and Nantucket. Land ownership, religious activity and political authority were contested and negotiated between settlers and Wampanoag communities. Nantucket became associated with Quaker influence, while Martha’s Vineyard developed several separate townships rather than one dominant urban centre. Many present-day roads, town boundaries and settlement patterns have roots in this colonial period, although the surviving landscape must be understood alongside the continuing history of the Wampanoag people.

Maritime Trade and Coastal Communities

Before whaling transformed the islands, residents depended on fishing, farming, small-scale trade, pilotage and other maritime work. Harbours such as Edgartown, Vineyard Haven and Nantucket Town connected the islands to mainland ports and the wider Atlantic economy. Their exposed locations demanded practical knowledge of shoals, currents and changing weather, while island communities developed distinctive relationships with Cape Cod, New England and overseas trade. The continued presence of working fleets, ferry terminals, boatyards and fishing villages reflects this earlier maritime economy.

The Whaling Era

From the late eighteenth century through much of the nineteenth century, Nantucket became one of the world’s leading whaling ports, while Edgartown and other Martha’s Vineyard communities also benefited from maritime commerce and whaling. Nantucket’s ships travelled extensively in pursuit of sperm and right whales, bringing considerable wealth but also exposing crews and families to dangerous, lengthy voyages. The industry supported merchants, sailmakers, coopers and other trades. Its decline, caused by changing markets, depleted whale populations and the emergence of petroleum, left a powerful architectural and cultural legacy in Nantucket Town and across the region.

Nineteenth-Century Summer Resorts

Improved steamship connections and changing ideas about seaside recreation brought growing numbers of summer visitors during the nineteenth century. Oak Bluffs developed from a Methodist camp-meeting community into a major resort, retaining its closely packed, vividly decorated Carpenter Gothic cottages. Nantucket’s whaling wealth produced substantial houses and commercial buildings that later helped define its historic character. Martha’s Vineyard also became associated with African American summer life and the community of Oak Bluffs, whose social and cultural importance grew over generations.

Conservation and the Modern Island Economy

During the twentieth century, the islands increasingly balanced tourism and second-home development with efforts to protect fragile coastal environments and historic character. Land trusts, public agencies and community organisations helped preserve dunes, moors, wetlands, farmland and open views, while historic-preservation measures shaped the appearance of Nantucket and several Martha’s Vineyard towns. The economy now combines tourism, hospitality, fishing, farming, construction, public services and creative work. Seasonal population changes remain a defining practical and social feature of island life.

The Islands in Photos

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Neighbouring regions of The Islands

The closest regions to The Islands, if you have time for more than one.

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Massachusetts
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Evendo: Your Ultimate Travel Guide to The Islands, Massachusetts

Explore The Islands with Evendo, a 100% free app-based travel guide covering attractions, landmarks, shops, dining, and more for an unforgettable adventure.

  • Comprehensive listings of attractions, landmarks, shops, and more.
  • Easy hotel, tour, and ticket bookings within the app.
  • Rich content including images, descriptions, and local tips.
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More about the Evendo app

Discover the best of The Islands, Massachusetts with Evendo. From famous landmarks to local dining, our free app offers everything you need for an incredible trip.

  • History and travel essentials of The Islands.
  • Curated local advice for authentic experiences.
  • User-friendly navigation and 'Near me' feature for real-time exploration.
  • 100% free with no in-app purchases or hidden costs.

Welcome to Evendo, your comprehensive travel guide to The Islands, Massachusetts. Whether you're planning to explore the iconic Martha's Vineyard or the serene beauty of Nantucket, Evendo has you covered. Our app is designed to be your ultimate travel companion, offering in-depth information on all the best attractions, landmarks, shops, bars, nightclubs, restaurants, hotels, tours, experiences, and activities across The Islands.

Imagine wandering through the beautifully preserved streets of Edgartown or enjoying a scenic bike ride along the Nantucket shores. With Evendo, you can easily plan your itinerary with detailed descriptions, stunning images, and local insights that bring each location to life. Discover the charm of The Islands' famous landmarks like the Gay Head Lighthouse or indulge in culinary delights at top-rated restaurants such as The Red Cat Kitchen or Galley Beach.

Our app simplifies your travel planning by allowing you to book hotels, tours, tickets, and experiences directly within the app. No more hassle of juggling different platforms or missing out on must-see attractions. Plus, with our 'Near me' feature, you can effortlessly find exciting spots and hidden gems around you. Download Evendo today and embark on a seamless journey through The Islands!

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