Getting Between Stops
Fly into Providence (PVD) or Boston (BOS) and home from Nantucket (ACK) or Boston. You need a car only for Newport and the drive to the ferry.
Newport to Woods Hole is about an hour and a half by car. The Steamship Authority ferry from Woods Hole to Vineyard Haven takes about 45 minutes and runs year-round. Walk-on passengers do not need reservations.
Getting from the Vineyard to Nantucket is the tricky leg. A seasonal inter-island passenger ferry has run between Oak Bluffs and Nantucket in summer, so check schedules for your dates. Outside that season, take the ferry back to Woods Hole, take a taxi about 40 minutes to Hyannis and take the high-speed ferry, about an hour, to Nantucket. Small planes also connect the islands with Boston, though fog can delay them. Arrange a one-way rental that you can return in Falmouth, near Woods Hole, before you board.
Where to Stay
In Newport, Castle Hill Inn is the waterfront classic on its own point. The Chanler at Cliff Walk is a mansion hotel at the start of the Cliff Walk. The Vanderbilt, part of Auberge Resorts, is steps from Thames Street restaurants.
On Martha's Vineyard, Edgartown is the honeymoon base. The Charlotte Inn is small, quiet and full of antiques. The Harbor View Hotel overlooks the lighthouse and the Chappaquiddick channel. Oak Bluffs is livelier and less formal.
On Nantucket, White Elephant puts you on the harbor a short walk from Main Street. The Wauwinet is secluded, with two beaches and a free shuttle into town. Historic inns in former captains' houses are often cheaper and still walkable.
In July and August, expect top hotels on Nantucket to run about $800 to well over $1,500 a night (approximate). Newport and Edgartown run a little less.
When to Go
June and September are the best months for most couples. Days are mild, crowds are thinner and rates are lower than in midsummer. September is often the local favorite, since the water holds its summer warmth after Labor Day.
July and August are peak season, with warm days in the 70s and low 80s Fahrenheit, swimmable water and everything open. Ferries fill, rates jump and the towns get busy, especially on weekends and around July 4.
Late May and early October are pretty but cool, with some seasonal businesses not yet open or starting to close. From November to April, much of both islands shuts and Newport turns quiet and windy. Fog can roll in at any time of year, delaying small planes, so leave a buffer before flights home.
Budget and Booking
Book Nantucket first, since its best inns sell out early for summer. Then book Edgartown, Newport and your flights. Reserve a car on the ferry only if you truly need it, since it is expensive and spaces sell out months ahead.
As an approximate guide, expect $400 to $1,200 a night for good inns and harbor hotels, with Nantucket's top hotels higher in July and August. Weekdays are cheaper than weekends, especially in Newport. Ferries, bikes and island buses are inexpensive compared with the rooms.
Many inns have minimum stays of two or three nights in summer, which this route already allows for. Mention your honeymoon when you book. Small inns often leave a bottle or a treat in the room and may help with dinner reservations.
Staying Comfortable and Safe
Atlantic water is cool even in summer and south-facing beaches can have strong surf and rip currents. Swim at lifeguarded beaches and watch the flags.
On the islands, ticks are common in tall grass and on trails. Use repellent, wear long pants on walks through brush and check each other at night. Tick-borne illnesses, including Lyme disease, are present.
Wear helmets when you bike and use lights at dusk, since island roads can be narrow and busy in summer. Bring a warm layer each for evenings and boat rides, which can be chilly even in July. On the Cliff Walk, some southern sections are rough and rocky, so wear proper shoes. Dress is relaxed, though Newport and Nantucket's best dining rooms lean smart casual for both of you.
Make It Shorter or Longer
For an 8-day trip, drop Newport and fly into Boston. Spend three nights on Martha's Vineyard and four on Nantucket.
For 13 to 14 days, add two nights in Boston at the start, or add three nights in Bar Harbor and Acadia National Park after Nantucket, flying from Boston to Bangor. Maine brings granite, pine forests and lobster pounds.
Couples who want a single base can spend the whole trip on Nantucket, with a day trip to the Vineyard if the inter-island ferry is running. Another option is splitting Nantucket between town and 'Sconset or The Wauwinet, which gives you walkable dinners and quiet nights in one stay.
