15 days in New England & Chicago's North Shore Itinerary

15 days in New England & Chicago's North Shore Itinerary

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15 days in New England & Chicago's North Shore Itinerary

London
Fly + bus:  9​h 45​min
Boston
— 4 nights
Drive:  1​h 30​min
Ogunquit
— 2 nights
Drive:  2​h 45​min
Newport
— 3 nights
+4
bus + Fly + bus + foot + bus:  8​h
Wheeling
— 1 night
+3
bus + foot + bus + Fly:  6​h 30​min
Provincetown
— 4 nights
Fly:  8​h 30​min
London

4
days
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.
Do some cultural sightseeing at Freedom Trail and Museum of Fine Arts. Get out of town with these interesting Boston side-trips: Concord (Louisa May Alcott's Orchard House & Walden Pond State Reservation), Sandwich (Heritage Museums & Gardens & Sandwich Glass Museum) and Plymouth Rock (in Plymouth). Next up on the itinerary: explore and take pictures at Fenway Park, admire the landmark architecture of Trinity Church, appreciate the extensive heritage of Louisburg Square, and take an in-depth tour of USS Constitution Museum.

To find traveler tips, reviews, and more tourist information, read our Boston trip itinerary maker.

London, UK to Boston is an approximately 10-hour combination of flight and bus. The time zone difference when traveling from London to Boston is minus 5 hours. In May, daytime highs in Boston are 22°C, while nighttime lows are 12°C. Finish your sightseeing early on the 11th (Fri) so you can drive to Ogunquit.

Things to do in Boston

Museums Historic Sites Parks

Side Trips

Sandwich, Concord, Plymouth Rock
Highlights from your plan
Museum of Fine Arts
Museum of Fine Arts
Freedom Trail
Freedom Trail
Heritage Museums & Gardens
Heritage Museums & Gardens

1
day
Ogunquit

Ogunquit ©
Ogunquit means "beautiful place by the sea" in the language of the Native Americans who inhabited the region long ago, and this remains an accurate description of this holiday destination today.
Kick off your visit on the 12th (Sat): tour the pleasant surroundings at Ogunquit Beach, get to know the fascinating history of Marginal Way Walkway, and then visit a coastal fixture at Cape Neddick Nubble Lighthouse.

To find where to stay, reviews, more things to do, and tourist information, use the Ogunquit travel itinerary planner.

Traveling by car from Boston to Ogunquit takes 1.5 hours. Alternatively, you can take a train; or take a bus. Traveling from Boston in May, Ogunquit is slightly colder at night with lows of 8°C. Wrap up your sightseeing on the 13th (Sun) to allow time to drive to Newport.

Things to do in Ogunquit

Historic Sites Outdoors Parks

Side Trip

Cape Neddick Nubble Lighthouse
Highlights from your plan
Marginal Way Walkway ©
Marginal Way Walkway
Ogunquit Beach ©
Ogunquit Beach
Cape Neddick Nubble Lighthouse ©
Cape Neddick Nubble Lighthouse

3
days
Newport

Newport ©
With coastline on the west, south, and east, Newport is a maritime city with a rich history.
Your cultural itinerary includes sights like Cliff Walk and Beavertail Lighthouse and Park. Escape the urban bustle at Shining Sea Bikeway and Old Silver Beach. There's lots more to do: take a memorable drive along Ocean Drive Historic District, examine the collection at The Breakers, and tour the pleasant surroundings at Fort Adams State Park.

For photos, reviews, ratings, and tourist information, go to the Newport vacation builder.

You can drive from Ogunquit to Newport in 3 hours. Alternatively, you can take a bus. In May, plan for daily highs up to 21°C, and evening lows to 11°C. On the 16th (Wed), you're off toWheeling.

Things to do in Newport

Parks Outdoors Historic Sites

Side Trips

Falmouth, Beavertail Lighthouse and Park
Highlights from your plan
Cliff Walk ©
Cliff Walk
The Breakers ©
The Breakers
Ocean Drive Historic District ©
Ocean Drive Historic District

few
hours
Wheeling

Wheeling ©
Wheeling is a city in the State of West Virginia and is the county seat of Ohio County, but it also has some subdivisions in Marshall County. To see traveler tips, ratings, more things to do, and other tourist information, go to the Wheeling trip itinerary maker.

Getting from Newport to Wheeling by combination of bus and flight takes about 8 hours. Other options: drive; or do a combination of bus and train. Traveling from Newport in May, you will find days in Wheeling are somewhat warmer (25°C), and nights are about the same (12°C). You will have some time to spend on the 17th (Thu) before leaving for Provincetown.
Highlights from your plan
West Virginia Independence Hall ©
West Virginia Independence Hall

3
days
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.
Get a sense of the local culture at Pilgrim Monument & Provincetown Museum and Provincetown Art Association and Museum (PAAM). Take a break from the city and head to Cape Cod National Seashore and Herring Cove Beach. Explore the numerous day-trip ideas around Provincetown: Nauset Beach (in Orleans) and Coast Guard Beach (in Eastham). There's still lots to do: enjoy the sand and surf at Race Point Beach.

For maps, where to stay, ratings, and more tourist information, read Provincetown online itinerary creator.

You can do a combination of bus and flight from Wheeling to Provincetown in 6.5 hours. Other options are to drive; or do a combination of bus, train, and ferry. While traveling from Wheeling, expect little chillier days and about the same nights in Provincetown, ranging from highs of 20°C to lows of 10°C. On the 21st (Mon), you'll travel back home.

Things to do in Provincetown

Outdoors Parks Beaches

Side Trips

Cape Cod National Seashore, Coast Guard Beach, Nauset Beach
Highlights from your plan
Cape Cod National Seashore ©
Cape Cod National Seashore
Race Point Beach ©
Race Point Beach
Nauset Beach
Nauset Beach

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