14 days in United States Itinerary

14 days in United States Itinerary

Created using Inspirock United States Trip Planner

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Route & dates

14 days in United States Itinerary

Start: Bologna
+3
train + bus + Fly + bus:  19​h 30​min
1
New York City
— 4 nights
Drive:  4​h
2
Boston
— 2 nights
Drive:  30​min
3
Salem
— 1 day
Drive:  30​min
4
Gloucester
— 1 night
Drive:  1​h 45​min
5
Kennebunkport
— Few hours
Drive:  45​min
6
Portland
— 1 night
Drive:  30​min
7
Freeport
— Few hours
Drive:  1​h
8
Boothbay Harbor
— Few hours
Drive:  3​h 15​min
9
Acadia National Park
— 1 night
Drive:  30​min
10
Bar Harbor
— 2 nights
bus + ferry:  10​h
11
Provincetown
— 1 night
Drive + Fly:  18​h 30​min
End: Bologna


Learn more about your trip

4
nights
New York City

New York City ©
Writer Pearl Buck once called New York City “a place apart,” and this giant urban center remains unlike any other in the world.
You've added Empire State Building, Circle Line Cruises, Central Park, and other attractions to your itinerary. Satisfy your inner culture vulture at Times Square and St. Patrick's Cathedral. There's still lots to do: browse the eclectic array of goods at Chelsea Market.

To see more things to do, ratings, other places to visit, and tourist information, read New York City trip itinerary maker.

Bologna, Italy to New York City is an approximately 19.5-hour flight. Traveling from Bologna to New York City, you'll gain 6 hours due to the time zone difference. Traveling from Bologna in September, plan for somewhat warmer nights in New York City, with lows around 22°C. Wrap up your sightseeing on the 28th (Fri) early enough to travel to Boston.

Things to do in New York City

Parks Outdoors Museums
Highlights from your plan
Central Park ©
Central Park
St. Patrick's Cathedral ©
St. Patrick's Cathedral
Times Square ©
Times Square

2
nights
Boston

Boston ©
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.
Your day-by-day itinerary now includes Harvard University, Newbury Street and Freedom Trail. Kick off your visit on the 28th (Fri): buy something for everyone on your list at Quincy Market and then get to know the fascinating history of Freedom Trail. On the next day, take in the architecture and design of Harvard University, then don't miss a visit to Newbury Street, and then buy something for everyone on your list at Faneuil Hall Marketplace.

For traveler tips, more things to do, ratings, and more tourist information, use the Boston trip builder.

You can do a combination of flight and bus from New York City to Boston in 3.5 hours. Other options are to drive; or take a bus. In September, Boston is slightly colder than New York City - with highs of 27°C and lows of 17°C. Finish your sightseeing early on the 30th (Sun) to allow enough time to drive to Salem.

Things to do in Boston

Historic Sites Shopping Neighborhoods

Side Trip

Harvard University
Highlights from your plan
Freedom Trail ©
Freedom Trail
Harvard University ©
Harvard University
Newbury Street ©
Newbury Street

1
day
Salem

Salem ©
Best known for its 1692 witch trials, Salem has a number of significant historical sites, a bustling downtown, and many witch-themed attractions.
On the 30th (Sun), tour the pleasant surroundings at Nahant Beach, contemplate the long history of The House of the Seven Gables, and then stop by Omen: Psychic Parlor and Witchcraft Emporium.

To find photos, more things to do, reviews, and more tourist information, go to the Salem trip itinerary maker.

Salem is just a stone's throw from Boston. Traveling from Boston in September, Salem is little chillier at night with lows of 13°C. Wrap up your sightseeing on the 30th (Sun) early enough to drive to Gloucester.

Things to do in Salem

Beaches Outdoors Parks

Side Trip

Nahant Beach
Highlights from your plan
Nahant Beach ©
Nahant Beach
The House of the Seven Gables ©
The House of the Seven Gables

1
night
Gloucester

Gloucester
The still waters off the Gloucester shore are immortalized in paintings and prints produced by the hundreds of artists who visit this town.
To see more things to do, other places to visit, photos, and tourist information, read Gloucester online itinerary creator.

Gloucester is very close to Salem. In September, plan for daily highs up to 26°C, and evening lows to 13°C. You will leave for Kennebunkport on the 30th (Sun).

Things to do in Gloucester

Parks Outdoors Tours

few
hours
Kennebunkport

Kennebunkport
Kennebunkport is a town in York County, Maine, United States. Start off your visit on the 1st (Mon): enjoy the sand and surf at Footbridge Beach.

To see maps, more things to do, photos, and tourist information, you can read our Kennebunkport itinerary maker.

Traveling by car from Gloucester to Kennebunkport takes 2 hours. Alternatively, you can do a combination of train and taxi. In October in Kennebunkport, expect temperatures between 17°C during the day and 4°C at night. On the 1st (Mon), wrap the sightseeing up by early afternoon so you can drive to Portland.

Things to do in Kennebunkport

Beaches Outdoors Parks

Side Trip

Footbridge Beach

1
night
Portland

Portland
Maine's biggest and perhaps most vibrant city, Portland was established as a fishing village in 1633 and grew to become New England's largest port.
To find reviews, other places to visit, where to stay, and tourist information, go to the Portland itinerary builder.

Traveling by car from Kennebunkport to Portland takes an hour. Alternatively, you can do a combination of taxi and train. In October in Portland, expect temperatures between 19°C during the day and 7°C at night. Wrap up your sightseeing on the 2nd (Tue) to allow time to drive to Freeport.

Things to do in Portland

Historic Sites

Side Trip

Portland Breakwater Lighthouse

few
hours
Freeport

Freeport
Freeport is a town in Cumberland County, Maine, United States. To see traveler tips, more things to do, where to stay, and other tourist information, read our Freeport trip itinerary planner.

Freeport is very close to Portland. In October, daily temperatures in Freeport can reach 17°C, while at night they dip to 5°C. On the 2nd (Tue), you're off toBoothbay Harbor.

Things to do in Freeport

Outdoors Parks Tours

few
hours
Boothbay Harbor

Boothbay Harbor ©
Boothbay Harbor is a town in Lincoln County, Maine, United States. For photos, where to stay, other places to visit, and tourist information, read Boothbay Harbor travel planner.

You can drive from Freeport to Boothbay Harbor in an hour. In October, daytime highs in Boothbay Harbor are 17°C, while nighttime lows are 4°C. Finish up your sightseeing early on the 2nd (Tue) so you can go by car to Acadia National Park.

Things to do in Boothbay Harbor

Shopping Nightlife
Highlights from your plan
Opera House at Boothbay Harbor ©
Opera House at Boothbay Harbor
Coastal Maine Popcorn Co ©
Coastal Maine Popcorn Co

1
night
Acadia National Park

Acadia National Park
The first national park east of the Mississippi River, Acadia National Park draws visitors with its rugged landscape of ocean shoreline, low-slung granite mountains, dense woodlands, and pristine lakes.
To see maps, other places to visit, where to stay, and tourist information, read our Acadia National Park travel planner.

Traveling by car from Boothbay Harbor to Acadia National Park takes 3.5 hours. Alternatively, you can do a combination of taxi and bus. In October in Acadia National Park, expect temperatures between 17°C during the day and 7°C at night. On the 2nd (Tue), you'll travel to Bar Harbor.

Things to do in Acadia National Park

Parks Outdoors Trails

2
nights
Bar Harbor

Bar Harbor ©
Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. On the 3rd (Wed), stop by A Little Mad, look for gifts at FIORE Artisan Olive Oils & Vinegars, then relax and rejuvenate at some of the top local wellness centers, and finally enjoy the sea views from Egg Rock Light. Get ready for a full day of sightseeing on the 4th (Thu): stop by The Rock & Art Shop, stop by Ben & Bill's Chocolate Emporium, then indulge your thirst for a good beer at Atlantic Brewing Company, and finally do a tasting at Bar Harbor Cellars.

To see other places to visit, where to stay, ratings, and more tourist information, read Bar Harbor itinerary maker.

Bar Harbor is just a short distance from Acadia National Park. In October, plan for daily highs up to 17°C, and evening lows to 6°C. Cap off your sightseeing on the 5th (Fri) early enough to travel to Provincetown.

Things to do in Bar Harbor

Shopping Breweries & Distilleries Historic Sites
Highlights from your plan
A LITTLE MAD ©
A LITTLE MAD
Egg Rock Light ©
Egg Rock Light
Bar Harbor Cellars Winery ©
Bar Harbor Cellars Winery

1
night
Provincetown

Provincetown ©
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.
To see other places to visit, ratings, maps, and other tourist information, you can read our Provincetown tour planner.

You can do a combination of taxi and flight from Bar Harbor to Provincetown in 3.5 hours. Alternatively, you can drive; or do a combination of bus and ferry. Plan for somewhat warmer nights when traveling from Bar Harbor in October since evenings lows in Provincetown dip to 11°C. Wrap up your sightseeing on the 6th (Sat) early enough to travel back home.

Things to do in Provincetown

Historic Sites Parks Wildlife

Side Trips

Wellfleet Bay Wildlife Sanctuary, Salt Pond Visitor Center, Highland Light
Highlights from your plan
Highland Light ©
Highland Light
Salt Pond Visitor Center ©
Salt Pond Visitor Center

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