14 days in New England Itinerary

14 days in New England Itinerary

Created using Inspirock New England route planner

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Route & dates

14 days in New England Itinerary

Start: New York City
Drive:  5​h 15​min
1
Ogunquit
— 2 nights
Drive:  1​h 30​min
2
Boston
— 4 nights
ferry:  1​h 30​min
3
Provincetown
— 3 nights
Drive:  1​h 15​min
4
Sandwich
— 2 nights
Drive:  1​h 15​min
5
Newport
— 2 nights
Drive:  3​h 45​min
End: New York City

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 20th (Sun): grab your bike and head to Beth Condon Pathway. Keep things going the next day: take in the architecture and atmosphere at St. Ann's Episcopal Church, examine the collection at Portland Head Light, and then enjoy the sand and surf at Ogunquit Beach.

To find more things to do, photos, maps, and other tourist information, go to the Ogunquit trip itinerary maker tool .

New York City to Ogunquit is an approximately 5.5-hour car ride. You can also do a combination of flight and bus; or do a combination of flight and bus. Traveling from New York City in September, things will get little chillier in Ogunquit: highs are around 74°F and lows about 48°F. Finish your sightseeing early on the 22nd (Tue) to allow enough time to drive to Boston.

Things to do in Ogunquit

Historic Sites Parks Outdoors

Side Trips

Beth Condon Pathway, Nubble Lighthouse, Portland Head Light, St. Ann's Episcopal Church
Highlights from your plan
Marginal Way Walkway ©
Marginal Way Walkway
Portland Head Light ©
Portland Head Light
Nubble Lighthouse ©
Nubble Lighthouse

4
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.
Take a break from Boston with a short trip to Dolphin & Whale Watching in Gloucester, about 50 minutes away. There's still lots to do: explore the world behind art at Museum of Fine Arts, take a tour by water with Boat Tours & Water Sports, walk around Boston Common, and get a taste of the local shopping with Faneuil Hall Marketplace.

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

Traveling by car from Ogunquit to Boston takes 1.5 hours. Alternatively, you can take a train; or take a bus. Expect a bit warmer evenings in Boston when traveling from Ogunquit in September, with lows around 59°F. Finish your sightseeing early on the 26th (Sat) to allow enough time to ride a ferry to Provincetown.

Things to do in Boston

Museums Tours Parks

Side Trip

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

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.
Change things up with these side-trips from Provincetown: Nauset Beach (in Orleans) and Salt Pond Visitor Center (in Eastham). Next up on the itinerary: pause for some photo ops at Pilgrim Monument & Provincetown Museum, kick back and relax at Cape Cod National Seashore, browse the collection at Provincetown Library, and stroll through Herring Cove Beach.

For other places to visit, where to stay, reviews, and tourist information, use the Provincetown online visit planner .

Traveling by ferry from Boston to Provincetown takes 1.5 hours. Alternatively, you can fly; or drive. September in Provincetown sees daily highs of 71°F and lows of 57°F at night. Finish up your sightseeing early on the 29th (Tue) so you can go by car to Sandwich.

Things to do in Provincetown

Outdoors Parks Beaches

Side Trips

Salt Pond Visitor Center, Cape Cod National Seashore, Marconi Beach, Nauset Beach
Highlights from your plan
Cape Cod National Seashore ©
Cape Cod National Seashore
Race Point Beach ©
Race Point Beach

2
nights
Sandwich

Sandwich ©
Sandwich is a town in Barnstable County, Massachusetts, United States. Kick off your visit on the 30th (Wed): see the interesting displays at Heritage Museums & Gardens, engage your brain at Sandwich Glass Museum, then explore the landscape on two wheels at Shining Sea Bikeway, and finally pause for some photo ops at Plymouth Rock. On the 1st (Thu), you'll have a packed day of sightseeing: examine the collection at John F Kennedy Hyannis Museum, kick back and relax at Chatham Lighthouse Beach, then get engrossed in the history at Plimoth Plantation, and finally contemplate the waterfront views at Cape Cod Canal.

To see maps and other tourist information, refer to the Sandwich trip itinerary builder tool .

Traveling by car from Provincetown to Sandwich takes 1.5 hours. Alternatively, you can take a bus. In September, daily temperatures in Sandwich can reach 73°F, while at night they dip to 55°F. Cap off your sightseeing on the 1st (Thu) early enough to go by car to Newport.

Things to do in Sandwich

Museums Parks Outdoors

Side Trips

Plymouth, Cape Cod Canal, John F Kennedy Hyannis Museum, Chatham Lighthouse Beach, Shining Sea Bikeway
Highlights from your plan
Heritage Museums & Gardens ©
Heritage Museums & Gardens
Plimoth Plantation ©
Plimoth Plantation
Sandwich Glass Museum ©
Sandwich Glass Museum

2
nights
Newport

Newport ©
With coastline on the west, south, and east, Newport is a maritime city with a rich history.
Start off your visit on the 2nd (Fri): take a memorable drive along Ocean Drive Historic District, examine the collection at The Breakers, and then appreciate the extensive heritage of Cliff Walk. Keep things going the next day: contemplate the long history of The Elms, identify plant and animal life at Seapowet Marsh and Point Fishing Area, and then get up close and personal with brilliant marine life at Mystic Aquarium.

For where to stay, ratings, traveler tips, and tourist information, read Newport trip planner .

Drive from Sandwich to Newport in 1.5 hours. Alternatively, you can take a bus; or do a combination of bus and train. In October, plan for daily highs up to 64°F, and evening lows to 50°F. Finish your sightseeing early on the 3rd (Sat) so you can drive back home.

Things to do in Newport

Historic Sites Parks Outdoors

Side Trips

Mystic Aquarium, Seapowet Marsh and Point Fishing Area
Highlights from your plan
The Breakers ©
The Breakers
Ocean Drive Historic District ©
Ocean Drive Historic District
The Elms
The Elms

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