15 days in United States Itinerary

15 days in United States Itinerary

Created using Inspirock United States trip itinerary planner
Make it your trip
Fly
1
Plymouth
— 1 day
Drive
2
West Tisbury, Martha's Vineyard
— 1 night
Drive
3
Hyannis
— 3 nights
Drive
4
Provincetown
— 1 night
Drive
5
Montpelier
— 1 night
Drive
6
Stowe
Drive
7
Jeffersonville
— 1 night
Drive
8
Burlington
Drive
9
Bristol
— 1 night
Drive
10
Middlebury
Drive
11
Woodstock
— 1 night
Drive
12
Newburyport
— 1 night
Drive
13
Waltham
Drive
14
Boston
— 3 nights
Taxi
15
Cambridge
— 1 night
Fly

S M T W T F S
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Plymouth — 1 day

Rightly calling itself "America's Hometown," Plymouth holds a prominent place in the nation's history and culture as the site of the first Puritan colony.
On the 16th (Sat), learn about winemaking at Plymouth Bay Winery, then steep yourself in history at Plymouth Rock, then get engrossed in the history at Mayflower II, and finally pause for some photo ops at National Monument to the Forefathers.

Quickly create a custom-made itinerary for Plymouth using our trip planner.

Los Angeles to Plymouth is an approximately 7-hour flight. You can also drive; or take a bus. Due to the time zone difference, you'll lose 3 hours traveling from Los Angeles to Plymouth. Plan for a bit cooler temperatures traveling from Los Angeles in October, with highs in Plymouth at 65°F and lows at 46°F. Finish your sightseeing early on the 16th (Sat) so you can drive to West Tisbury.
Historic Sites · Parks · Nature · Museums

West Tisbury, Martha's Vineyard — 1 night

West Tisbury is a town located on Martha's Vineyard in Dukes County, Massachusetts, United States. Start off your visit on the 17th (Sun): kick back and relax at Katama Beach/ South Beach, then visit a coastal fixture at Edgartown Lighthouse, and then don't miss a visit to Flying Horses Carousel.

For photos, traveler tips, other places to visit, and more tourist information, go to the West Tisbury trip planner.

Traveling by car from Plymouth to West Tisbury takes 2 hours. In October, daily temperatures in West Tisbury can reach 65°F, while at night they dip to 46°F. Finish your sightseeing early on the 17th (Sun) so you can drive to Hyannis.
Parks · Beaches · Outdoors · Historic Sites
Side Trips

Hyannis — 3 nights

"The Capital of the Cape," Hyannis serves as Cape Cod's main transportation and commercial hub.
Get ready for a full day of sightseeing on the 18th (Mon): take a stroll through Main Street Hyannis, get curious at Sandwich Glass Museum, and then examine the collection at Heritage Museums & Gardens.

For traveler tips, more things to do, maps, and more tourist information, you can read our Hyannis driving holiday tool.

Getting from West Tisbury to Hyannis by car takes about 2 hours. In October, plan for daily highs up to 64°F, and evening lows to 48°F. You will have some time to spend on the 20th (Wed) before leaving for Provincetown.
Museums · Shopping · Neighborhoods · Childrens Museums
Side Trips

Provincetown — 1 night

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.
Kick off your visit on the 20th (Wed): pause for some photo ops at Pilgrim Monument & Provincetown Museum and then take a tour by water with Boat Tours & Water Sports. Get ready for a full day of sightseeing on the 21st (Thu): tour the pleasant surroundings at Race Point Beach, take in the exciting artwork at Rice-Polak Gallery, and then view the masterpieces at Charles-Baltivik Gallery and Sculpture Garden.

To see more things to do, maps, and tourist information, read our Provincetown attractions planner.

Traveling by car from Hyannis to Provincetown takes 1.5 hours. Alternatively, you can take a bus. In October, daily temperatures in Provincetown can reach 63°F, while at night they dip to 49°F. Finish up your sightseeing early on the 21st (Thu) so you can travel to Montpelier.
Museums · Shopping · Outdoors · Parks

Montpelier — 1 night

Montpelier is the capital city of the U.S. state of Vermont and the seat of Washington County. For other places to visit, traveler tips, and other tourist information, read Montpelier trip itinerary maker website.

Traveling by car from Provincetown to Montpelier takes 5 hours. Alternatively, you can do a combination of car and flight. Expect slightly colder temperatures when traveling from Provincetown in October; daily highs in Montpelier reach 58°F and lows reach 38°F. On the 22nd (Fri), you'll travel to Stowe.
Shopping · Parks · Museums · Outdoors

Stowe

Stowe bustles in winter when skiers and snowboarders flock here to challenge themselves on the long, steep trails careening down Vermont's tallest peak, Mt.
On the 22nd (Fri), sample the tasty concoctions at The Alchemist and then trek along Stowe Recreation Path.

For photos, ratings, maps, and other tourist information, use the Stowe day trip app.

Stowe is just a stone's throw from Montpelier. Expect a daytime high around 60°F in October, and nighttime lows around 39°F. Finish your sightseeing early on the 22nd (Fri) so you can drive to Jeffersonville.
Trails · Parks · Outdoors · Breweries & Distilleries

Jeffersonville — 1 night

Jeffersonville is a village in the town of Cambridge, Vermont, United States. Kick off your visit on the 23rd (Sat): sample the fine beverages at Smugglers' Notch Distillery - Maple Products - Gift Shop - Local Products and then brush up on your knowledge of spirits at Boyden Valley Winery & Spirits.

For reviews, traveler tips, other places to visit, and more tourist information, read Jeffersonville driving holiday planner.

Traveling by car from Stowe to Jeffersonville takes an hour. October in Jeffersonville sees daily highs of 60°F and lows of 39°F at night. Finish your sightseeing early on the 23rd (Sat) so you can drive to Burlington.
Breweries & Distilleries · Wineries
Side Trip

Burlington

Burlington is the most populous city in the U.S. state of Vermont and the seat of Chittenden County. To see reviews, where to stay, more things to do, and other tourist information, read Burlington trip itinerary builder app.

Traveling by car from Jeffersonville to Burlington takes an hour. In October, plan for daily highs up to 62°F, and evening lows to 44°F. You'll set off for Bristol on the 23rd (Sat).
Parks · Outdoors · Shopping · Museums

Bristol — 1 night

Bristol is a town in Addison County, Vermont, United States. To find maps, where to stay, reviews, and other tourist information, use the Bristol day trip app.

Drive from Burlington to Bristol in an hour. October in Bristol sees daily highs of 61°F and lows of 42°F at night. On the 24th (Sun), you'll travel to Middlebury.
Parks · Nature · Outdoors · Museums

Middlebury

Middlebury is the shire town (county seat) of Addison County, Vermont, United States. On the 24th (Sun), look for gifts at Danforth Pewter.

To see maps, traveler tips, ratings, and more tourist information, read Middlebury attractions planner.

Middlebury is just a stone's throw from Bristol. October in Middlebury sees daily highs of 61°F and lows of 42°F at night. Finish up your sightseeing early on the 24th (Sun) so you can go by car to Woodstock.
Shopping
Highlights from your trip

Woodstock — 1 night

Woodstock is the shire town of Windsor County, Vermont, United States. Kick off your visit on the 25th (Mon): explore the wealth of natural beauty at Marsh - Billings - Rockefeller National Historical Park.

To find ratings, more things to do, photos, and tourist information, read our Woodstock trip planner.

You can drive from Middlebury to Woodstock in 1.5 hours. In October, daily temperatures in Woodstock can reach 62°F, while at night they dip to 40°F. Wrap up your sightseeing on the 25th (Mon) early enough to travel to Newburyport.
Historic Sites · Parks · Nature

Newburyport — 1 night

Newburyport is a small coastal city in Essex County, Massachusetts, United States, northeast of Boston. To find traveler tips, other places to visit, more things to do, and tourist information, read Newburyport trip planner.

You can drive from Woodstock to Newburyport in 2.5 hours. Traveling from Woodstock in October, you can expect nighttime temperatures to be a bit warmer in Newburyport, with lows of 46°F. Wrap up your sightseeing by early afternoon on the 26th (Tue) to allow time for travel to Waltham.
Parks · Beaches · Outdoors
Side Trip
Highlights from your trip

Waltham

The heart of the American Industrial Revolution and an important place for the labor movement, Waltham was a prototype of industrial city planning in the 19th century.
Kick off your visit on the 26th (Tue): snap pictures at The Old North Bridge.

For ratings, where to stay, and more tourist information, go to the Waltham trip planner.

Traveling by car from Newburyport to Waltham takes an hour. Expect a daytime high around 64°F in October, and nighttime lows around 42°F. Wrap up your sightseeing on the 26th (Tue) to allow time to drive to Boston.
Historic Sites
Side Trip

Boston — 3 nights

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.
You'll explore and learn at John F. Kennedy Presidential Museum & Library and The House of the Seven Gables. Do some cultural sightseeing at North End and Peabody Essex Museum. When in Boston, make a side trip to see Salem Witch Museum in Salem, approximately Salem away. There's lots more to do: make a trip to Faneuil Hall Marketplace, take an in-depth tour of Boston Tea Party Ships & Museum, get to know the fascinating history of Freedom Trail, and stroll around Charles River Esplanade.

To see maps, reviews, and other tourist information, read our Boston trip itinerary maker tool.

Boston is just a stone's throw from Waltham. Traveling from Waltham in October, you can expect nighttime temperatures to be a bit warmer in Boston, with lows of 50°F. Finish your sightseeing early on the 29th (Fri) so you can drive to Cambridge.
Museums · Historic Sites · Parks · Neighborhoods
Side Trip

Cambridge — 1 night

Best known as the location of two internationally renowned universities, Cambridge sits just across the Charles River from Boston.
On the 30th (Sat), learn more about the world around you at The Harvard Museum of Natural History, then get a taste of the local shopping with MIT Museum, and then contemplate the waterfront views at Charles River.

To see where to stay, other places to visit, more things to do, and other tourist information, go to the Cambridge attractions planner.

Cambridge is very close to Boston. In October, daytime highs in Cambridge are 64°F, while nighttime lows are 50°F. Finish your sightseeing early on the 30th (Sat) to allow enough time to fly back home.
Museums · Childrens Museums · Scenic Drive · Shopping

United States travel guide

4.5
Specialty Museums · Nightlife · Beaches
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.

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.