14 days in United States Itinerary

14 days in United States Itinerary

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Route & dates

14 days in United States Itinerary

Start: Chicago
Fly:  4 h
1
Boston
— 2 nights
Bus:  2 h
2
Newport
— 1 night
Drive:  1 h 30 min
3
Falmouth
— 1 day
Drive:  2 h
4
Provincetown
— 1 night
Drive:  3 h
5
Salem
— 1 night
Drive:  1 h
6
Kittery
— Few hours
Drive:  1 h
7
Portland
— 1 night
Drive:  2 h
8
Camden
— 2 nights
Drive:  2 h
9
Acadia National Park, Mount Desert Island
— 2 nights
Drive:  30 min
10
Bar Harbor, Mount Desert Island
— 2 nights
Drive:  5 h 15 min
11
Boston
— 1 night
Fly:  4 h
End: Chicago

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 Freedom Trail. On the 19th (Sun), contemplate the long history of Gibson House Museum, pause for some photo ops at Making Way for Ducklings Statues, and then appreciate the extensive heritage of Freedom Trail.

To find traveler tips, ratings, reviews, and more tourist information, go to the Boston online travel route planner.

Chicago to Boston is an approximately 4- hour flight. You can also do a combination of flight and bus; or drive. Traveling from Chicago to Boston, you'll lose 1 hour due to the time zone difference. In July, daily temperatures in Boston can reach 83°F, while at night they dip to 67°F. On the 21st (Tue), wrap the sightseeing up by early afternoon so you can take a bus to Newport.

Things to do in Boston

Historic Sites Museums
Highlights from your plan
Gibson House Museum ©
Gibson House Museum
Freedom Trail ©
Freedom Trail
Making Way for Ducklings Statues ©
Making Way for Ducklings Statues

1
night
Newport

Newport ©
With coastline on the west, south, and east, Newport is a maritime city with a rich history.
Your day-by-day itinerary now includes Cliff Walk. Start off your visit on the 21st (Tue): get to know the fascinating history of Cliff Walk, steep yourself in history at Rough Point, then admire the landmark architecture of Kingscote, then Head underground at Purgatory Chasm, and finally sample the tasty concoctions at Newport Craft Brewing & Distilling Co..

To see maps, where to stay, more things to do, and other tourist information, read our Newport day trip planning site.

You can take a bus from Boston to Newport in 2 hours. Alternatively, you can drive; or do a combination of train and bus. In July, daytime highs in Newport are 80°F, while nighttime lows are 66°F. Finish up your sightseeing early on the 22nd (Wed) so you can go by car to Falmouth.

Things to do in Newport

Historic Sites Parks Trails

Side Trip

Purgatory Chasm
Highlights from your plan
Rough Point ©
Rough Point
Kingscote ©
Kingscote
Newport Craft Brewing & Distilling Co. ©

1
day
Falmouth

Falmouth ©
Falmouth is a town in Barnstable County, Massachusetts, United States; Barnstable County is coextensive with Cape Cod. Your day-by-day itinerary now includes Old Silver Beach, Nobska Point Lighthouse and Falmouth Heights Beach. Kick off your visit on the 22nd (Wed): kick back and relax at Old Silver Beach, then enjoy the sand and surf at Falmouth Heights Beach, then enjoy the sea views from Nobska Point Lighthouse, and finally explore the world behind art at Highfield Hall & Gardens.

To see ratings, traveler tips, other places to visit, and other tourist information, you can read our Falmouth journey planner.

Getting from Newport to Falmouth by car takes about 1.5 hours. Other options: take a bus; or do a combination of bus and train. Expect a daytime high around 80°F in July, and nighttime lows around 64°F. Wrap up your sightseeing on the 22nd (Wed) to allow time to drive to Provincetown.

Things to do in Falmouth

Parks Outdoors Beaches
Highlights from your plan
Highfield Hall & Gardens ©
Highfield Hall & Gardens
Nobska Point Lighthouse ©
Nobska Point Lighthouse
Falmouth Heights Beach ©
Falmouth Heights Beach

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.
On the 22nd (Wed), enjoy the sea views from Race Point Lighthouse.

To find ratings, maps, traveler tips, and more tourist information, refer to the Provincetown day trip tool.

Traveling by car from Falmouth to Provincetown takes 2 hours. Alternatively, you can take a bus. In July in Provincetown, expect temperatures between 79°F during the day and 64°F at night. You will have some time to spend on the 23rd (Thu) before leaving for Salem.

Things to do in Provincetown

Historic Sites Parks Outdoors
Highlights from your plan
Long Point ©
Long Point
Race Point Lighthouse ©
Race Point Lighthouse
Old Harbor Life Saving Museum ©
Old Harbor Life Saving Museum

1
night
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.
You've now added Salem Witch Trials Memorial to your itinerary. Kick off your visit on the 23rd (Thu): admire the landmark architecture of Phillips House, then steep yourself in history at Salem Maritime National Historic Site, and then stroll around Salem Witch Trials Memorial.

For more things to do, reviews, and more tourist information, read Salem route planner.

Getting from Provincetown to Salem by car takes about 3 hours. Other options: fly; or ride a ferry. Expect a daytime high around 82°F in July, and nighttime lows around 64°F. Wrap up your sightseeing on the 24th (Fri) to allow time to drive to Kittery.

Things to do in Salem

Historic Sites Parks Museums
Highlights from your plan
Phillips House ©
Phillips House
Salem Maritime National Historic Site ©
Salem Witch Trials Memorial ©
Salem Witch Trials Memorial

few
hours
Kittery

Kittery ©
Kittery is a town in York County, Maine, United States. Kick off your visit on the 24th (Fri): visit a coastal fixture at Portsmouth Harbor Lighthouse.

To see ratings, maps, and tourist information, read Kittery trip maker.

Traveling by car from Salem to Kittery takes an hour. July in Kittery sees daily highs of 81°F and lows of 63°F at night. On the 24th (Fri), you'll have the morning to explore before heading off to Portland.

Things to do in Kittery

Historic Sites

Side Trip

Portsmouth Harbor Lighthouse
Highlights from your plan
Portsmouth Harbor Lighthouse ©
Portsmouth Harbor Lighthouse

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.
You've now added Old Port to your itinerary. Start off your visit on the 24th (Fri): visit a coastal fixture at Portland Head Light, then take a stroll through Old Port, and then sample the tasty concoctions at Geary Brewing Company.

To find more things to do, other places to visit, ratings, and more tourist information, go to the Portland online tour planner.

Traveling by car from Kittery to Portland takes an hour. In July, plan for daily highs up to 79°F, and evening lows to 61°F. Wrap up your sightseeing on the 25th (Sat) early enough to drive to Camden.

Things to do in Portland

Neighborhoods Historic Sites Breweries & Distilleries

Side Trip

Portland Head Light
Highlights from your plan
Old Port ©
Old Port
Portland Head Light ©
Portland Head Light
Geary Brewing Company ©
Geary Brewing Company

2
nights
Camden

Camden ©
Camden is a town in Knox County, Maine, United States. Your day-by-day itinerary now includes Camden Hills State Park, Megunticook Lake and Mount Battie. On the 25th (Sat), explore the activities along Megunticook Lake, then stop by High Street Historic District, and then stroll around Camden Harbor Park and Amphitheatre. Get ready for a full day of sightseeing on the 26th (Sun): immerse yourself in nature at Camden Hills State Park and then take in the awesome beauty at Mount Battie.

For where to stay, maps, ratings, and other tourist information, read our Camden sightseeing planner.

Drive from Portland to Camden in 2 hours. Alternatively, you can take a bus. Traveling from Portland in July, expect nights in Camden to be about the same, around 58°F, while days are slightly colder, around 74°F. Wrap up your sightseeing by early afternoon on the 27th (Mon) to allow enough time to drive to Acadia National Park.

Things to do in Camden

Parks Nature Historic Sites
Highlights from your plan
High Street Historic District ©
High Street Historic District
Camden Hills State Park ©
Camden Hills State Park
Megunticook Lake ©
Megunticook Lake

2
nights
Acadia National Park, Mount Desert Island

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.
On the 27th (Mon), delve into the lush surroundings at Indian Point Blagden Preserve, then stroll through Echo Lake Beach, and then hike along Acadia Mountain Trail. On the 28th (Tue), you'll have a packed day of sightseeing: trek along Gorham Mountain Trail, then kick back and relax at Little Hunters Beach, and then explore the striking landscape at Otter Cliff.

To see traveler tips, reviews, and tourist information, you can read our Acadia National Park planning website.

Traveling by car from Camden to Acadia National Park takes 2 hours. Alternatively, you can take a bus. In July in Acadia National Park, expect temperatures between 75°F during the day and 58°F at night. Wrap up your sightseeing by early afternoon on the 29th (Wed) to allow time for the car ride to Bar Harbor.

Things to do in Acadia National Park

Parks Outdoors Trails

Side Trip

Indian Point Blagden Preserve
Highlights from your plan
Echo Lake Beach ©
Echo Lake Beach
Gorham Mountain Trail ©
Gorham Mountain Trail
Otter Cliff ©
Otter Cliff

2
nights
Bar Harbor, Mount Desert Island

Bar Harbor ©
Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. Kick off your visit on the 29th (Wed): take an in-depth tour of Bar Harbor Historical Society Museum, go for a walk through The Gorge Path, and then go for a walk through Compass Harbor Trail. On the 30th (Thu), you'll have a packed day of sightseeing: trek along Bar Island Trails, explore the striking landscape of Eagle Lake Acadia National Park, and then admire the natural beauty at Wild Gardens of Acadia.

To see more things to do, traveler tips, where to stay, and more tourist information, go to the Bar Harbor trip planner.

Bar Harbor is just a stone's throw from Acadia National Park. July in Bar Harbor sees daily highs of 75°F and lows of 58°F at night. Finish your sightseeing early on the 31st (Fri) to allow enough time to travel to Boston.

Things to do in Bar Harbor

Parks Nature Trails

Side Trip

Acadia National Park
Highlights from your plan
Bar Island Trails ©
Bar Island Trails
Eagle Lake Acadia National Park ©
Eagle Lake Acadia National Park
Bar Harbor Historical Society Museum ©

1
night
Boston

Boston ©
Start off your visit on the 31st (Fri): explore the galleries of USS Cassin Young and then contemplate the long history of Charlestown Navy Yard. Here are some ideas for day two: walk around Rose Kennedy Greenway, pause for some photo ops at The Mapparium, take in the architecture and atmosphere at Shrine of Saint Anthony, then get engrossed in the history at Old South Meeting House, then pick up some local products at Boston Public Market, and finally explore the different monuments and memorials at Mount Auburn Cemetery.

To find reviews, where to stay, photos, and other tourist information, use the Boston online vacation planner.

Traveling by flight from Bar Harbor to Boston takes 4.5 hours. Alternatively, you can do a combination of car and flight; or drive. Prepare for a bit warmer weather when traveling from Bar Harbor in July: high temperatures in Boston hover around 83°F and lows are around 67°F. Wrap up your sightseeing on the 1st (Sat) to allow time to travel back home.

Things to do in Boston

Historic Sites Museums Shopping

Side Trip

Mount Auburn Cemetery
Highlights from your plan
Mount Auburn Cemetery ©
Mount Auburn Cemetery
Charlestown Navy Yard ©
Charlestown Navy Yard
Old South Meeting House
Old South Meeting House

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