14 days in New England Itinerary

14 days in New England Itinerary

Created using Inspirock New England sightseeing planner

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Route & dates

14 days in New England Itinerary

Start: Milan
Fly:  12​h 15​min
1
Provincetown
— 3 nights
Drive:  1​h 15​min
2
Sandwich
— 2 nights
Drive:  1​h 15​min
3
Newport
— 2 nights
Drive:  3​h
4
Ogunquit
— 2 nights
Drive:  1​h 30​min
5
Boston
— 3 nights
Fly:  13​h 15​min
End: Milan

3
nights
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.
Shop till you drop at Charles-Baltivik Gallery and Sculpture Garden and Rice-Polak Gallery. Get a sense of the local culture at Chatham Marconi Maritime Center and Pilgrim Monument & Provincetown Museum. Step out of Provincetown with an excursion to Nauset Beach in Orleans--about 48 minutes away. There's lots more to do: kick back and relax at Cape Cod National Seashore, learn about winemaking at Truro Vineyards of Cape Cod, get a sense of history and politics at Provincetown Town Hall, and tour the pleasant surroundings at Marconi Beach.

For ratings, traveler tips, reviews, and more tourist information, read Provincetown trip tool .

Milan, Italy to Provincetown is an approximately 12.5-hour flight. You can also do a combination of flight and bus. You'll gain 6 hours traveling from Milan to Provincetown due to the time zone difference. When traveling from Milan in August, plan for slightly colder days in Provincetown, with highs around 30°C, while nights are about the same with lows around 19°C. Finish your sightseeing early on the 13th (Tue) so you can drive to Sandwich.

Things to do in Provincetown

Beaches Parks Outdoors

Side Trips

Chatham Marconi Maritime Center, Cape Cod National Seashore, Marconi Beach, Truro Vineyards of Cape Cod, Nauset Beach
Highlights from your plan
Cape Cod National Seashore ©
Cape Cod National Seashore
Chatham Marconi Maritime Center ©
Chatham Marconi Maritime Center
Nauset Beach ©
Nauset Beach

2
nights
Sandwich

Sandwich ©
Sandwich is a town in Barnstable County, Massachusetts, United States. Start off your visit on the 14th (Wed): get curious at Sandwich Glass Museum, examine the collection at Heritage Museums & Gardens, then explore the world behind art at Highfield Hall & Gardens, and finally explore the landscape on two wheels at Shining Sea Bikeway. Get ready for a full day of sightseeing on the next day: tour the pleasant surroundings at Craigville Beach, then steep yourself in history at Edward Gorey House, and then enjoy the sand and surf at Chatham Lighthouse Beach.

For photos, ratings, maps, and more tourist information, you can read our Sandwich trip planning tool .

Traveling by car from Provincetown to Sandwich takes 1.5 hours. Alternatively, you can take a bus. In August in Sandwich, expect temperatures between 30°C during the day and 19°C at night. Finish your sightseeing early on the 15th (Thu) so you can drive to Newport.

Things to do in Sandwich

Parks Outdoors Museums

Side Trips

Falmouth, Craigville Beach, Chatham Lighthouse Beach, Edward Gorey House
Highlights from your plan
Shining Sea Bikeway ©
Shining Sea Bikeway
Heritage Museums & Gardens ©
Heritage Museums & Gardens
Edward Gorey House ©
Edward Gorey House

2
nights
Newport

Newport ©
With coastline on the west, south, and east, Newport is a maritime city with a rich history.
Kick off your visit on the 16th (Fri): see the interesting displays at The Breakers, don't miss a visit to Cliff Walk, then cruise along Ocean Drive Historic District, and finally take in the exciting artwork at Thames Glass. Keep things going the next day: kick back and relax at Goosewing Beach Preserve, contemplate the long history of Lizzie Borden House, and then visit a coastal fixture at Beavertail Lighthouse and Park.

To see where to stay, maps, traveler tips, and other tourist information, refer to the Newport online driving holiday planner .

Traveling by car from Sandwich to Newport takes 1.5 hours. Alternatively, you can take a bus; or do a combination of bus and train. In August, daily temperatures in Newport can reach 30°C, while at night they dip to 20°C. Finish your sightseeing early on the 17th (Sat) so you can drive to Ogunquit.

Things to do in Newport

Historic Sites Parks Outdoors

Side Trips

Beavertail Lighthouse and Park, Lizzie Borden House, Goosewing Beach Preserve
Highlights from your plan
Beavertail Lighthouse and Park ©
Beavertail Lighthouse and Park
The Breakers ©
The Breakers
Lizzie Borden House ©
Lizzie Borden House

2
nights
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.
Start off your visit on the 18th (Sun): view the masterpieces at Abacus, take in the dramatic natural features at Perkins Cove, then appreciate the extensive heritage of Marginal Way Walkway, and finally enjoy the sea views from Cape Neddick Nubble Lighthouse. Here are some ideas for day two: enjoy the sand and surf at Ogunquit Beach, then view the masterpieces at Mast Cove Galleries, then take in the exciting artwork at Compliments, and finally enjoy the sand and surf at Wells Beach.

To see where to stay, other places to visit, and tourist information, read our Ogunquit tour planning app .

You can drive from Newport to Ogunquit in 3 hours. Alternatively, you can take a bus; or do a combination of bus and train. Plan for slightly colder nights when traveling from Newport in August since evenings lows in Ogunquit dip to 14°C. Wrap up your sightseeing on the 19th (Mon) early enough to drive to Boston.

Things to do in Ogunquit

Parks Beaches Outdoors

Side Trips

Kennebunkport, Wells Beach, Cape Neddick Nubble Lighthouse
Highlights from your plan
Marginal Way Walkway ©
Marginal Way Walkway
Cape Neddick Nubble Lighthouse ©
Cape Neddick Nubble Lighthouse
Perkins Cove ©
Perkins Cove

3
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.
You'll explore and learn at Museum of Fine Arts and USS Constitution Museum. Shop till you drop at Faneuil Hall Marketplace and Old South Meeting House. Step out of Boston to go to Gloucester and see Dolphin & Whale Watching, which is approximately 50 minutes away. And it doesn't end there: get to know the fascinating history of Freedom Trail, explore and take pictures at Fenway Park, don't miss a visit to Charles Street, and take a stroll through Newbury Street.

For photos, where to stay, more things to do, and more tourist information, read Boston driving holiday site .

Traveling by car from Ogunquit to Boston takes 1.5 hours. Alternatively, you can take a train; or take a bus. Plan for somewhat warmer nights when traveling from Ogunquit in August since evenings lows in Boston dip to 21°C. Wrap up your sightseeing on the 22nd (Thu) early enough to travel back home.

Things to do in Boston

Museums Shopping Neighborhoods

Side Trip

Dolphin & Whale Watching
Highlights from your plan
Museum of Fine Arts ©
Museum of Fine Arts
Freedom Trail ©
Freedom Trail
Dolphin & Whale Watching

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