8 days in New England Itinerary

8 days in New England Itinerary

Created using Inspirock New England trip itinerary planner

Make it your trip
Fly
1
Boston
— 3 nights
Drive
2
Newport
— 1 night
Taxi to Point Judith Ferry Terminal, Narragansett, RI, Ferry to New Shoreham
3
New Shoreham, Block Island
— 1 night
Unknown
4
Chilmark, Martha's Vineyard
— 1 night
Unknown
5
Nantucket
— 1 night
Fly

S M T W T F S
16
17
18
19
20
21
22
23
24
25
26
27
28
29

Boston

— 3 nights

Beantown

Rich in museums, restaurants, shops, and historical sites, Boston attracts over 16 million visitors each year. New England's largest and most influential city, Boston ranks among the world's major centers of education and culture.
Get some historical perspective at Marginal Way Walkway and Freedom Trail. Museum of Fine Arts and Newbury Street are good opportunities to explore the local culture. You'll find plenty of places to visit near Boston: Ogunquit Beach (in Ogunquit), Dolphin & Whale Watching (in Gloucester) and Just Us Chickens Gallery (in Kittery). The adventure continues: visit North End, get a taste of the local shopping with Faneuil Hall Marketplace, stroll around Boston Public Garden, and get engrossed in the history at John F. Kennedy Presidential Museum & Library.

To see traveler tips, where to stay, ratings, and tourist information, you can read our Boston tour itinerary maker site.

Greenville to Boston is an approximately 6-hour flight. You can also drive; or do a combination of bus and train. In May, Boston is little chillier than Greenville - with highs of 67°F and lows of 50°F. Cap off your sightseeing on the 25th (Tue) early enough to go by car to Newport.

Things to do in Boston

Outdoors · Museums · Historic Sites · Wildlife

Side Trips

Find places to stay May 22 — 25:

Newport

— 1 night

City by the Sea

With coastline on the west, south, and east, Newport is a maritime city with a rich history.
Kick off your visit on the 26th (Wed): take a tour by water with Boat Tours & Water Sports, then examine the collection at The Breakers, and then admire all the interesting features of Cliff Walk.

To see reviews, more things to do, and more tourist information, use the Newport driving holiday planning tool.

Drive from Boston to Newport in 2 hours. Alternatively, you can take a bus; or do a combination of train and bus. May in Newport sees daily highs of 65°F and lows of 49°F at night. Wrap up your sightseeing on the 26th (Wed) to allow time to travel to New Shoreham.

Things to do in Newport

Outdoors · Museums · Trails · Tours
Find places to stay May 25 — 26:

New Shoreham, Block Island

— 1 night
New Shoreham is a town in Washington County, Rhode Island, United States. Start off your visit on the 27th (Thu): enjoy the sand and surf at Mansion Beach, explore the striking landscape at Mohegan Bluffs, then shop like a local with Jessie Edwards Studio, and finally shop like a local with Spring Street Gallery.

For photos, more things to do, other places to visit, and tourist information, read our New Shoreham journey planning website.

Getting from Newport to New Shoreham by combination of taxi and ferry takes about 2.5 hours. Other options: ride a ferry. May in New Shoreham sees daily highs of 61°F and lows of 50°F at night. Wrap up your sightseeing on the 27th (Thu) early enough to travel to Chilmark.

Things to do in New Shoreham

Trails · Beaches · Outdoors · Parks
Find places to stay May 26 — 27:

Chilmark, Martha's Vineyard

— 1 night
Chilmark is a town located on Martha's Vineyard in Dukes County, Massachusetts, United States. Kick off your visit on the 28th (Fri): kick back and relax at Menemsha Hills, then visit a coastal fixture at Gay Head Lighthouse, then stop by Chilmark Chocolates, and finally tour the pleasant surroundings at Menemsha Public Beach.

For more things to do, maps, where to stay, and tourist information, refer to the Chilmark road trip planning tool.

You can travel from New Shoreham to Chilmark in 4.5 hours. In May, daytime highs in Chilmark are 65°F, while nighttime lows are 47°F. Wrap up your sightseeing on the 28th (Fri) early enough to travel to Nantucket.

Things to do in Chilmark

Beaches · Outdoors · Parks · Wildlife

Side Trips

Find places to stay May 27 — 28:

Nantucket

— 1 night
Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. Kick off your visit on the 29th (Sat): enjoy the sand and surf at Madaket Beach and then kick back and relax at Jetties Beach.

To see photos, ratings, other places to visit, and other tourist information, refer to the Nantucket online trip itinerary maker.

Travel from Chilmark to Nantucket in 3 hours. Expect a daytime high around 62°F in May, and nighttime lows around 49°F. Cap off your sightseeing on the 29th (Sat) early enough to travel back home.

Things to do in Nantucket

Beaches · Outdoors · Parks
Find places to stay May 28 — 29:
Highlights from your trip

Block Island travel guide

4.3
Geologic Formations · Lighthouses · Beaches
Block Island is located off the coast of the U.S. state of Rhode Island, named after Dutch explorer Adriaen Block. It is located in the Atlantic Ocean about 14mi east of Montauk Point, Long Island, New York, and 13mi south from mainland Rhode Island, from which it is separated by Block Island Sound.The United States Census Bureau defines Block Island as census tract 415 of Washington County, Rhode Island. As of the 2010 Census, the island's population is 1,051 living on a land area of 9.734sqmi. The island is part of the Outer Lands region, a coastal archipelago.The Nature Conservancy added Block Island to its list of "The Last Great Places", which consists of 12 sites in the western hemisphere. About 40 percent of the island is set aside for conservation. Presidents Bill Clinton, Dwight D. Eisenhower, Franklin Delano Roosevelt, and Ulysses S. Grant have visited Block Island. Other famous visitors include Amelia Earhart and Charles Lindbergh, who each visited the island in 1929.

Source

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