14 days in Martha's Vineyard, Cape Cod & Berkshires Itinerary

14 days in Martha's Vineyard, Cape Cod & Berkshires Itinerary

Created using Inspirock Massachusetts trip builder

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Make it your trip
Fly
1
Edgartown
— 2 nights
Bus to Marthas Vineyard Terminal, Ferry to Hyannis
2
Hyannis
— 4 nights
Drive
3
Provincetown
— 4 nights
Drive
4
Pittsfield
— 3 nights
Drive

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Edgartown

— 2 nights
Edgartown is a town located on Martha's Vineyard in Dukes County, Massachusetts, United States. Edgartown is known for historic sites, beaches, and nature. Your plan includes some of its best attractions: visit a coastal fixture at Edgartown Lighthouse, explore the striking landscape at Aquinnah Cliffs, admire the natural beauty at Mytoi, and take a stroll through Martha's Vineyard Camp meeting Association (MVCMA).

Plan a Edgartown trip in moments using our itinerary builder.

New York City to Edgartown is an approximately 3-hour flight. You can also do a combination of car and ferry; or do a combination of bus, ferry, and car. Expect a bit cooler temperatures when traveling from New York City in August; daily highs in Edgartown reach 79°F and lows reach 59°F. Finish your sightseeing early on the 3rd (Tue) to allow enough time to travel to Hyannis.

Things to do in Edgartown

Parks · Outdoors · Historic Sites · Beaches

Side Trips

Hyannis

— 4 nights

Capital of Cape Cod

"The Capital of the Cape," Hyannis serves as Cape Cod's main transportation and commercial hub.
Explore the numerous day-trip ideas around Hyannis: Nickerson State Park (in Brewster), Nauset Beach (in Orleans) and Chatham (Chatham Lighthouse Beach, Chatham Railroad Museum, &more). There's much more to do: see majestic marine mammals with Hyannis Whale Watcher Cruises, look for gifts at Titcomb's Bookshop, grab your bike and head to Shining Sea Bikeway, and tour the pleasant surroundings at Old Silver Beach.

For ratings, more things to do, traveler tips, and other tourist information, refer to the Hyannis travel planner.

Getting from Edgartown to Hyannis by combination of bus and ferry takes about 2.5 hours. Other options: do a combination of car and ferry. In August, plan for daily highs up to 79°F, and evening lows to 63°F. Finish up your sightseeing early on the 7th (Sat) so you can go by car to Provincetown.

Things to do in Hyannis

Parks · Outdoors · Wildlife · Museums

Side Trips

Provincetown

— 4 nights

Birthplace of American Liberty

A small resort town with a year-round population of just 3,000, Provincetown draws nearly 60,000 annual visitors with its scenic beaches, art colonies, galleries, theaters, and shops.
Explore Provincetown's surroundings by going to Eastham (Coast Guard Beach & Nauset Light Beach). There's still lots to do: look for all kinds of wild species at Wildlife Areas, take a leisurely stroll along MacMillan Wharf, appreciate the history behind Pilgrim Monument & Provincetown Museum, and enjoy the sand and surf at Marconi Beach.

To find maps, traveler tips, photos, and tourist information, go to the Provincetown online journey planner.

Drive from Hyannis to Provincetown in 1.5 hours. Alternatively, you can take a bus. In August, daily temperatures in Provincetown can reach 78°F, while at night they dip to 62°F. Wrap up your sightseeing on the 11th (Wed) early enough to travel to Pittsfield.

Things to do in Provincetown

Outdoors · Parks · Beaches · Museums

Side Trips

Pittsfield

— 3 nights
Pittsfield is the largest city and the county seat of Berkshire County, Massachusetts, United States. Change things up with these side-trips from Pittsfield: Zipline (in Charlemont), The Clark Art Institute (in Williamstown) and MASS MoCA (in North Adams). There's still lots to do: explore the world behind art at Norman Rockwell Museum, contemplate the long history of The Mount, Edith Wharton's Home, stroll through Ashuwillticook Rail Trail, and explore the landscape on two wheels at Village Bike Rentals.

To find ratings, reviews, traveler tips, and tourist information, go to the Pittsfield trip builder website.

You can drive from Provincetown to Pittsfield in 4.5 hours. Plan for slightly colder nights when traveling from Provincetown in August since evenings lows in Pittsfield dip to 55°F. Cap off your sightseeing on the 14th (Sat) early enough to go by car back home.

Things to do in Pittsfield

Museums · Outdoors · Parks · Historic Sites

Side Trips

Martha's Vineyard travel guide

4.4
Beaches · Lighthouses · Landmarks
Martha's Vineyard is an island located south of Cape Cod in Massachusetts that is known for being an affluent summer colony. It includes the smaller Chappaquiddick Island which is usually connected to the Vineyard, though storms and hurricanes have been known to separate the two. The last such separation of the islands was in 2007 and the two islands are again connected as of April 2, 2015.It is the 58th largest island in the United States, with a land area of 100sqmi, and the third largest on the East Coast of the United States, after Long Island and Mount Desert Island. The island constitutes the bulk of Dukes County, Massachusetts, which also includes the Elizabeth Islands and the island of Nomans Land.The Vineyard was home to one of the earliest known deaf communities in the United States; consequently, a special sign language developed on the island called Martha's Vineyard Sign Language (MVSL).The 2010 census reported a year-round population of 16,535 residents, although the summer population can swell to more than 100,000 people. About 56% of the Vineyard's 14,621 homes are seasonally occupied.

Source

Cape Cod travel guide

4.4
Beaches · Dolphin & Whale Watching · Specialty Museums
Located on the southern shore of Massachusetts, Cape Cod contains some 15 towns and two islands. The arm-shaped peninsula is a popular holiday destination throughout the year because of its historical attractions, art galleries, award-winning restaurants, and a scenic coastline dotted by sandy beaches. Start your sightseeing in Provincetown, located at the very tip of the cape and famous for being the site of the first Pilgrims' landing in 1620. From there you can hit up all of the Cape's other small towns, renowned for their comfortable bed and breakfasts and distinctive cuisine of fresh fish and oyster dishes. This maritime community features more than a dozen lighthouses. Part of experiencing the Cape means a trip to its two islands--which showcase several lighthouses and numerous restaurants.

Berkshires travel guide

4.6
Art Museums · Historic Sites · Zipline