8 days in United States Itinerary

8 days in United States Itinerary

Created using Inspirock United States tour builder

Make it your trip
Fly
1
Freeport
— 1 day
Drive
2
Kennebunkport
— 1 night
Drive
3
Kittery
— 1 night
Drive
4
Portsmouth
— 1 night
Drive
5
West Tisbury
— 1 night
Drive
6
Boston
— 1 night
Drive
7
Salem
— 2 nights
Fly

S M T W T F S
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Freeport

— 1 day
Freeport is a town in Cumberland County, Maine, United States. Kick off your visit on the 12th (Tue): immerse yourself in nature at Bradbury Mountain State Park and then get some fabulous bargains at L.L. Bean Factory Store.

To find ratings, where to stay, traveler tips, and other tourist information, go to the Freeport road trip website.

New York City to Freeport is an approximately 3-hour flight. You can also drive; or take a train. Prepare for a bit cooler weather when traveling from New York City in October: high temperatures in Freeport hover around 60°F and lows are around 39°F. Finish your sightseeing early on the 12th (Tue) so you can drive to Kennebunkport.

Things to do in Freeport

Nature · Parks · Shopping

Kennebunkport

— 1 night
Kennebunkport is a town in York County, Maine, United States. On the 13th (Wed), enjoy the sand and surf at Mother's Beach, then take a memorable drive along Walker's Point, and then take an in-depth tour of Seashore Trolley Museum.

To see more things to do and other tourist information, refer to the Kennebunkport tour itinerary site.

Drive from Freeport to Kennebunkport in an hour. Alternatively, you can do a combination of train and bus; or take a bus. In October, plan for daily highs up to 62°F, and evening lows to 38°F. Finish your sightseeing early on the 13th (Wed) to allow enough time to drive to Kittery.

Things to do in Kennebunkport

Outdoors · Scenic Drive · Beaches · Parks

Side Trip

Kittery

— 1 night
Kittery is a town in York County, Maine, United States. Kick off your visit on the 14th (Thu): walk around Fort McClary State Historic Site and then look for gifts at When Pigs Fly Company Store.

For maps, other places to visit, and tourist information, you can read our Kittery trip itinerary planner.

You can drive from Kennebunkport to Kittery in an hour. Traveling from Kennebunkport in October, you can expect nighttime temperatures to be somewhat warmer in Kittery, with lows of 44°F. Finish your sightseeing early on the 14th (Thu) to allow enough time to drive to Portsmouth.

Things to do in Kittery

Parks · Shopping

Side Trip

Highlights from your trip

Portsmouth

— 1 night
Portsmouth is a city in Rockingham County, New Hampshire, in the United States. Kick off your visit on the 15th (Fri): visit a coastal fixture at Portsmouth Harbor Lighthouse, then see the interesting displays at USS Albacore Museum, and then take an in-depth tour of Strawbery Banke Museum.

To find where to stay, photos, reviews, and more tourist information, go to the Portsmouth tour itinerary builder site.

Portsmouth is just a short distance from Kittery. In October, plan for daily highs up to 62°F, and evening lows to 44°F. Finish your sightseeing early on the 15th (Fri) to allow enough time to travel to West Tisbury.

Things to do in Portsmouth

Museums · Historic Sites

Side Trip

West Tisbury

— 1 night
West Tisbury is a town located on Martha's Vineyard in Dukes County, Massachusetts, United States. On the 16th (Sat), stroll through Katama Beach/ South Beach, then enjoy the sea views from Edgartown Lighthouse, then make a trip to Flying Horses Carousel, and finally take a stroll through Martha's Vineyard Camp meeting Association (MVCMA).

For maps, more things to do, where to stay, and other tourist information, go to the West Tisbury sightseeing website.

Traveling by car from Portsmouth to West Tisbury takes 3.5 hours. Alternatively, you can drive. Expect a daytime high around 65°F in October, and nighttime lows around 46°F. Finish up your sightseeing early on the 16th (Sat) so you can travel to Boston.

Things to do in West Tisbury

Beaches · Outdoors · Neighborhoods · Parks

Side Trips

Boston

— 1 night

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.
On the 17th (Sun), get a sense of history and politics at Old State House, contemplate the long history of Charlestown Navy Yard, then contemplate the long history of Longfellow House Washington's Headquarters National Historic Site, then explore the different monuments and memorials at Mount Auburn Cemetery, and finally steep yourself in history at John F. Kennedy National Historic Site.

To see photos and tourist information, read our Boston tour planner.

You can drive from West Tisbury to Boston in 2.5 hours. Alternatively, you can drive. October in Boston sees daily highs of 64°F and lows of 50°F at night. Finish your sightseeing early on the 17th (Sun) to allow enough time to drive to Salem.

Things to do in Boston

Historic Sites · Museums

Side Trips

Salem

— 2 nights

Witch City

Best known for its 1692 witch trials, Salem has a number of significant historical sites, a bustling downtown, and many witch-themed attractions.
Kick off your visit on the 18th (Mon): get engrossed in the history at Witch House, then stop by Hex: Old World Witchery, and then see the interesting displays at Gallows Hill Museum/Theatre. Keep things going the next day: take in the history at Minute Man National Historical Park, get engrossed in the history at Louisa May Alcott's Orchard House, and then stroll the grounds of Sleepy Hollow Cemetery.

For photos, other places to visit, traveler tips, and tourist information, use the Salem attractions planner.

You can drive from Boston to Salem in an hour. Other options are to take a train; or take a bus. Plan for slightly colder nights when traveling from Boston in October since evenings lows in Salem dip to 45°F. Finish your sightseeing early on the 19th (Tue) to allow enough time to fly back home.

Things to do in Salem

Museums · Historic Sites · Nature · Shopping

Side Trip

United States travel guide

4.5
Specialty Museums · Beaches · History Museums
More than the country of car-packed streets seen in TV shows and movies, the United States of America is a complex and diverse home to over 300 million people living in a wide range of landscapes and climates. From its big-city skyscrapers to its sprawling natural parks, the country's ''melting pot'' combines many ethnic groups that share a strong sense of national identity despite their cultural differences. A country of road trips and big blue skies, the United States harbors orderly cities filled with restaurants, parks, museums, and innumerable sightseeing opportunities, as well as pristine natural areas perfect for a holiday in the great outdoors. To see as much as you can of this diverse land quickly, drive over some of the more than 6 million km (4 million mi) of highways leading through deserts, mountain peaks, fertile fields, and giant urban centers.

Martha's Vineyard travel guide

4.3
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.

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