Island Character
Nantucket has a strong, consistent look. Gray shingles, white trim and roses climbing over cottage roofs repeat everywhere, from Main Street to the tiny lanes of 'Sconset on the east shore. Chain stores are rare. The town is the center of everything. Beyond it the island opens into heathland and ponds that turn red in fall when the cranberry bogs are flooded. It feels curated and calm.
Martha's Vineyard is more of a patchwork. Edgartown has white clapboard captains' houses and a lighthouse at the harbor. Oak Bluffs is louder, with candy-colored gingerbread cottages and a busier bar scene. Up-island, West Tisbury and Chilmark look like farm country by the sea. Aquinnah has cliffs sacred to the Wampanoag Tribe.
The Vineyard also feels more lived in, with plenty of families who have summered here for generations. Nantucket feels more like a beautifully kept village where the whole island is the attraction.
Ferries and Flights
Getting to Martha's Vineyard is easier. The Steamship Authority runs a year-round ferry from Woods Hole on Cape Cod to Vineyard Haven that takes about 45 minutes. Walk-on passengers do not need reservations. Seasonal passenger boats also leave from Falmouth, Hyannis, New Bedford, Quonset Point in Rhode Island and even New York City. Martha's Vineyard Airport (MVY) has year-round flights from Boston plus seasonal service from New York and Washington, DC.
Nantucket takes a bit more effort. Most couples fly to Boston, travel to Hyannis and take a ferry: about an hour on the high-speed boat or a little over two on the traditional one. Nantucket Memorial Airport (ACK) has seasonal nonstops from New York, Boston and Washington plus year-round service from Boston on small planes. Fares run high and fog delays are common.
On either island, leave the car behind. Ferry car space is expensive and sells out early. Bikes, buses, shuttles and the occasional taxi cover what you need.
Inns and Hotels
Nantucket's two honeymoon classics are very different. White Elephant sits on the harbor in town, a short stroll from Main Street, with rooms and cottages facing the water. The Wauwinet, a Relais and Chateaux inn eight miles out, sits on a narrow strip between the harbor and the Atlantic with a beach on each side. It opens seasonally and offers a shuttle into town. Small historic inns in former captains' houses are often better value and still walkable to dinner. Cottage rentals in 'Sconset add village charm.
On the Vineyard, Edgartown is the classic base. The Harbor View Hotel looks out to the lighthouse and Chappaquiddick. The Charlotte Inn is a small, antique-filled inn on a quiet street with old-fashioned polish. The Winnetu Oceanside Resort near South Beach in Katama gives you more space and sand nearby. Up-island inns and rentals trade walkable dinners for silence and starry skies.
The Vineyard's range is a little wider, especially if you are flexible on location.
What It Costs
Neither island is cheap in summer. Nantucket is usually the pricier of the two. In July and August, its harbor hotels and top inns run roughly $800 to well over $1,500 a night. The Wauwinet often starts around $750. Restaurant tabs reflect the island's location. Flights into ACK can cost more than you expect.
On Martha's Vineyard, good inns typically run from about $500 to well over $1,000 a night in peak season. The Charlotte Inn often starts around $550. The shorter ferry is cheaper too. The island's bus system makes going car-free simple.
On both islands, September brings real savings along with warm water and thinner crowds. June can be a good deal on the Vineyard. Weekend rates around July 4 and in August are the highest of the year. All prices here are approximate and change with dates and demand, so check directly before you set a budget.
Beaches and Sunsets
Nantucket's beaches split by shore. The north side faces the harbor and Nantucket Sound with calmer water. The south shore faces the open Atlantic with surf and strong currents, so swim where lifeguards are on duty. The signature evening is a six-mile bike ride through moors and pines to Madaket Beach on the west end for sunset. Great Point, a wild sandy spit with a lighthouse and seals, is reached on an over-sand tour.
The Vineyard's showpiece is the west end. The clay cliffs at Aquinnah glow red and ochre in late afternoon, with a lighthouse above. Admire them from the beach and overlooks without climbing or taking clay. Menemsha is where much of the island gathers at dusk, takeout seafood in hand, as the boats come home. South Beach in Katama is the big public surf beach.
One quirk to know: some up-island beaches on the Vineyard are reserved for residents and renters in summer. Public beaches such as South Beach and the Aquinnah shore are open to all.
Food, Drink and Evenings Out
Seafood rules on both. Expect lobster rolls, chowder, fried clams and local oysters. In late fall, both islands celebrate bay scallops, small and sweet and best seared in butter.
Nantucket punches above its size for dining, with fine dining rooms in historic houses and lively places by the water. Reservations in summer can be needed weeks ahead. Cisco Brewers, a short ride from town, is a relaxed afternoon of beer, wine and live music outdoors.
The Vineyard spreads its dining across towns. Edgartown has the most polished rooms for a celebration dinner. Oak Bluffs has the noise and Back Door Donuts, a late-night window with a line most summer evenings. Up-island farm stands sell sweet corn, tomatoes and pies. The West Tisbury farmers market makes a fine Saturday outing.
For a buzzier night out, the Vineyard has more choice.
Seasons and Weather
Both islands run on the same calendar. Peak season is late June or July through Labor Day, with warm days in the 70s and low 80s, swimmable water and everything open. Fog and cool evenings are part of the deal, so pack a sweater and a light rain jacket for both of you.
September is the locals' favorite month on each island. The water stays warm, crowds thin and prices ease. Early October is crisp and quiet, with cranberry harvests on Nantucket and changing marsh grasses on the Vineyard, though some seasonal businesses close.
Winter is where they differ a little. Martha's Vineyard keeps more of a year-round community. Some inns stay open with fires lit and winter rates. Nantucket is very quiet from November to April. Its big exception is the Christmas Stroll in early December, a lively festive weekend.
Ticks are common in grassy areas on both islands. Stay on paths and check each other after walks.
Seeing Both Islands
Splitting a week between them works well. Start on Martha's Vineyard for three or four nights, with a base in Edgartown and a day up-island for Aquinnah and Menemsha. Then cross to Nantucket for three or four nights of biking, beaches and long dinners in town.
In summer, a seasonal passenger boat has linked Oak Bluffs with Nantucket, which makes the hop simple, so check the current schedule when you plan. Short flights between the two airports are another option. If neither suits your dates, you can return to the Cape and take the ferry from Hyannis, which turns the transfer into most of a day.
Travel light, since you will be carrying bags on and off boats. Book ferries and inns early for July and August. For a shorter honeymoon of four or five nights, pick one island and settle in rather than spending a day in transit.
