19 days in New England Itinerary

19 days in New England Itinerary

Created using Inspirock New England trip itinerary builder

Make it your trip
Fly
1
Boston
— 4 nights
Fly
2
Provincetown
— 2 nights
Drive
3
Sandwich
— 2 nights
Drive
4
Newport
— 3 nights
Drive
5
Ogunquit
— 1 night
Drive
6
North Conway
— 2 nights
Drive
7
Bar Harbor, Mount Desert Island
— 3 nights
Fly

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Boston

— 4 nights

Beantown

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.
Venture out of the city with trips to Salem (Pickering Wharf, The House of the Seven Gables, &more). The adventure continues: explore the world behind art at Museum of Fine Arts, take an in-depth tour of New England Holocaust Memorial, get lost in a book at John F. Kennedy Presidential Museum & Library, and step aboard Boston Tea Party Ships & Museum.

To see more things to do, ratings, reviews, and more tourist information, read our Boston trip maker site.

Tel Aviv, Israel to Boston is an approximately 13.5-hour flight. You'll gain 7 hours traveling from Tel Aviv to Boston due to the time zone difference. In October, Boston is a bit cooler than Tel Aviv - with highs of 20°C and lows of 11°C. Finish your sightseeing early on the 14th (Thu) to allow enough time to travel to Provincetown.

Things to do in Boston

Museums · Historic Sites · Parks · Shopping

Side Trips

Provincetown

— 2 nights

Birthplace of American Liberty

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 15th (Fri), tour the pleasant surroundings at Race Point Beach, admire the masterpieces at Atwood Museum, and then stroll through Chatham Lighthouse Beach. Keep things going the next day: browse the exhibits of Pilgrim Monument & Provincetown Museum and then enjoy the sand and surf at Cape Cod National Seashore.

To find other places to visit, photos, reviews, and more tourist information, you can read our Provincetown day trip planning app.

Fly from Boston to Provincetown in 2 hours. Alternatively, you can ride a ferry; or drive. In October, daily temperatures in Provincetown can reach 20°C, while at night they dip to 11°C. Finish up your sightseeing early on the 16th (Sat) so you can go by car to Sandwich.

Things to do in Provincetown

Beaches · Outdoors · Parks · Museums

Side Trips

Sandwich

— 2 nights
Sandwich is a town in Barnstable County, Massachusetts, United States. Kick off your visit on the 17th (Sun): get up close to creatures of the deep with Hyannis Whale Watcher Cruises, get curious at Sandwich Glass Museum, then experience rural life at Coonamessett Farm, and finally contemplate the waterfront views at Cape Cod Canal. On the 18th (Mon), you'll have a packed day of sightseeing: take an in-depth tour of Plimoth Patuxet, then pause for some photo ops at Plymouth Rock, then steep yourself in history at Mayflower II, and finally make a trip to Old King's Hwy.

To see photos, other places to visit, maps, and more tourist information, you can read our Sandwich travel itinerary planner.

Drive from Provincetown to Sandwich in 1.5 hours. Alternatively, you can take a bus. Expect a daytime high around 20°C in October, and nighttime lows around 9°C. Wrap up your sightseeing on the 18th (Mon) early enough to drive to Newport.

Things to do in Sandwich

Museums · Tours · Outdoors · Wildlife

Side Trips

Newport

— 3 nights

City by the Sea

With coastline on the west, south, and east, Newport is a maritime city with a rich history.
You'll find plenty of places to visit near Newport: Mystic Seaport Museum (in Mystic), Skip's Dock (in South Kingstown) and Lizzie Borden House (in Fall River). There's still lots to do: examine the collection at The Breakers, admire the striking features of Marble House, explore and take pictures at Ocean Drive Historic District, and appreciate the extensive heritage of Cliff Walk.

For more things to do, photos, and more tourist information, use the Newport route maker tool.

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 October, plan for daily highs up to 20°C, and evening lows to 11°C. Cap off your sightseeing on the 21st (Thu) early enough to go by car to Ogunquit.

Things to do in Newport

Historic Sites · Museums · Outdoors · Tours

Side Trips

Ogunquit

— 1 night
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.
On the 22nd (Fri), get to know the fascinating history of Marginal Way Walkway, explore the striking landscape at Perkins Cove, then visit a coastal fixture at Nubble Lighthouse, and finally head outdoors with Fisherman's Walk.

To see traveler tips, where to stay, other places to visit, and other tourist information, read Ogunquit day trip planning app.

You can drive from Newport to Ogunquit in 3 hours. Other options are to take a bus; or do a combination of bus and train. Traveling from Newport in October, Ogunquit is a bit cooler at night with lows of 3°C. Finish your sightseeing early on the 22nd (Fri) to allow enough time to drive to North Conway.

Things to do in Ogunquit

Historic Sites · Parks · Nature · Outdoors

Side Trip

North Conway

— 2 nights
North Conway combines colonial New England architecture with outlet shops selling goods from some of the world's most recognizable brands, all set amid the scenery of the White Mountains.
On the 23rd (Sat), look and learn at Mount Washington Observatory Weather Discovery Center, delve into the lush surroundings at White Mountain National Forest, and then explore and take pictures at Kancamagus Highway. Get ready for a full day of sightseeing on the 24th (Sun): surround yourself with nature on Bretton Woods Canopy Tour, then explore and take pictures at Mt. Washington Auto Road, and then admire the sheer force of Glen Ellis Falls.

To see more things to do, traveler tips, photos, and tourist information, read our North Conway day trip planning tool.

You can drive from Ogunquit to North Conway in 2 hours. Another option is to take a bus. Plan for a bit warmer nights when traveling from Ogunquit in October since evenings lows in North Conway dip to 8°C. Wrap up your sightseeing on the 24th (Sun) early enough to drive to Bar Harbor.

Things to do in North Conway

Outdoors · Scenic Drive · Parks · Wildlife

Side Trips

Bar Harbor, Mount Desert Island

— 3 nights
Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. Step out of Bar Harbor with an excursion to Schoodic Point in Winter Harbor--about 46 minutes away. And it doesn't end there: take in the awesome beauty at Cadillac Mountain, explore the landscape on two wheels at Carriage Roads, hike along Great Head Trail, and explore the activities along Jordan Pond Path Trailhead.

To find photos, reviews, other places to visit, and more tourist information, you can read our Bar Harbor trip itinerary planner.

Traveling by car from North Conway to Bar Harbor takes 4.5 hours. Alternatively, you can do a combination of car and bus; or do a combination of bus and flight. In October, daytime highs in Bar Harbor are 17°C, while nighttime lows are 6°C. Finish your sightseeing early on the 27th (Wed) so you can travel back home.

Things to do in Bar Harbor

Parks · Outdoors · Trails · Nature

Side Trips