16 days in New England Itinerary

16 days in New England Itinerary

Created using Inspirock New England tour planner

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Route & dates

16 days in New England Itinerary

Start: Hartford
Drive:  3​h
1
Ogunquit
— 1 night
Drive:  1​h 30​min
2
Boston
— 5 nights
ferry:  1​h 30​min
3
Provincetown
— 3 nights
Drive:  1​h 30​min
4
Sandwich
— 4 nights
Drive:  1​h 30​min
5
Newport
— 2 nights
Drive:  2​h
End: Hartford

1
night
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 16th (Thu): visit a coastal fixture at Cape Neddick Nubble Lighthouse, then contemplate the long history of Elizabeth Perkins House, and then appreciate the extensive heritage of Marginal Way Walkway. Keep things going the next day: admire all the interesting features of Perkins Cove, view the masterpieces at Mast Cove Galleries, then take in the exciting artwork at W. Robert Paine Gallery, and finally kick back and relax at Ogunquit Beach.

To see photos, more things to do, where to stay, and more tourist information, you can read our Ogunquit day trip planner.

Hartford to Ogunquit is an approximately 3-hour car ride. You can also take a bus. Expect a bit cooler temperatures when traveling from Hartford in May; daily highs in Ogunquit reach 66°F and lows reach 43°F. Wrap up your sightseeing on the 17th (Fri) early enough to drive to Boston.

Things to do in Ogunquit

Parks Historic Sites Museums

Side Trips

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

5
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.
Boston is known for historic sites, museums, parks, shopping, and nightlife. Your plan includes some of its best attractions: admire all the interesting features of Fenway Park, explore the world behind art at Museum of Fine Arts, take in nature's colorful creations at Boston Public Garden, and stroll through Boston Common.

For maps, traveler tips, reviews, and tourist information, refer to the Boston route maker site .

Traveling by car from Ogunquit to Boston takes 1.5 hours. Alternatively, you can take a train; or take a bus. Traveling from Ogunquit in May, plan for somewhat warmer nights in Boston, with lows around 50°F. Finish your sightseeing early on the 22nd (Wed) to allow enough time to ride a ferry to Provincetown.

Things to do in Boston

Museums Parks Historic Sites

Side Trips

Brookline Booksmith, Mount Auburn Cemetery
Highlights from your plan
Fenway Park ©
Fenway Park
Museum of Fine Arts ©
Museum of Fine Arts
Freedom Trail ©
Freedom Trail

3
nights
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 out of town with these interesting Provincetown side-trips: Nickerson State Park (in Brewster) and Captain Penniman House (in Eastham). Next up on the itinerary: pause for some photo ops at Pilgrim Monument & Provincetown Museum, look for all kinds of wild species at Wildlife Areas, get lost in a book at Provincetown Library, and learn more about the world around you at Sea Space Marine Discovery Center.

To find other places to visit, maps, where to stay, and other tourist information, go to the Provincetown trip itinerary maker app .

Traveling by ferry from Boston to Provincetown takes 1.5 hours. Alternatively, you can do a combination of bus and flight; or drive. In May, daily temperatures in Provincetown can reach 63°F, while at night they dip to 48°F. Finish your sightseeing early on the 25th (Sat) to allow enough time to drive to Sandwich.

Things to do in Provincetown

Outdoors Parks Beaches

Side Trips

Nickerson State Park, Captain Penniman House
Highlights from your plan
Dolphin & Whale Watching
Race Point Beach ©
Race Point Beach
Long Point ©
Long Point

4
nights
Sandwich

Sandwich ©
Sandwich is a town in Barnstable County, Massachusetts, United States. Explore Sandwich's surroundings by going to Chatham (Chatham Lighthouse Beach & Monomoy National Wildlife Refuge), Falmouth (Falmouth Museums on the Green, Highfield Hall & Gardens, & more) and Edward Gorey House (in Yarmouth Port). There's lots more to do: examine the collection at Heritage Museums & Gardens, admire the masterpieces at Sandwich Glass Museum, explore the activities along Cape Cod Canal, and don't miss a visit to Mayflower II.

To see photos, more things to do, maps, and more tourist information, use the Sandwich trip itinerary planning website .

You can drive from Provincetown to Sandwich in 1.5 hours. Another option is to take a bus. Expect a daytime high around 65°F in May, and nighttime lows around 47°F. Finish your sightseeing early on the 29th (Wed) so you can drive to Newport.

Things to do in Sandwich

Museums Parks Historic Sites

Side Trips

Falmouth, Plymouth, Chatham, Cape Cod Canal, Edward Gorey House
Highlights from your plan
Heritage Museums & Gardens ©
Heritage Museums & Gardens
Shining Sea Bikeway ©
Shining Sea Bikeway
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 30th (Thu): appreciate the extensive heritage of Cliff Walk, then examine the collection at The Breakers, then explore and take pictures at Ocean Drive Historic District, and finally view the masterpieces at Thames Glass. Get ready for a full day of sightseeing on the 31st (Fri): admire the landmark architecture of The Elms, let your taste buds guide you at a local gastronomic tour, and then enjoy the sea views from Beavertail Lighthouse and Park.

For more things to do, ratings, photos, and other tourist information, go to the Newport route planner .

Drive from Sandwich to Newport in 1.5 hours. Alternatively, you can do a combination of taxi and bus; or take a bus. In May, daytime highs in Newport are 65°F, while nighttime lows are 49°F. Finish up your sightseeing early on the 31st (Fri) so you can go by car back home.

Things to do in Newport

Historic Sites Outdoors Parks

Side Trip

Beavertail Lighthouse and Park
Highlights from your plan
Ocean Drive Historic District ©
Ocean Drive Historic District
The Breakers ©
The Breakers
The Elms ©
The Elms

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