16 days in New England Itinerary

16 days in New England Itinerary

Created using Inspirock New England trip planner

Plan created by another user. Make it yours
Fly to Boston, Ferry to Provincetown
1
Provincetown
— 1 night
Taxi to Hyannis, MA, Ferry to Nantucket
2
Nantucket
— 2 nights
Fly to Boston, Foot to Terminal A
3
Boston
— 2 nights
Drive
4
Portland
— 3 nights
Drive
5
Rockland
— 2 nights
Drive
6
Bar Harbor, Mount Desert Island
— 5 nights
Fly

S M T W T F S
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1
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1
night
Provincetown

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.
Kick off your visit on the 17th (Fri): appreciate the history behind Pilgrim Monument & Provincetown Museum and then take a tour by water with Art's Dune Tours. On the 18th (Sat), you'll have a packed day of sightseeing: take an in-depth tour of Salt Pond Visitor Center, tour the pleasant surroundings at Coast Guard Beach, and then enjoy the sand and surf at Nauset Beach.

For maps, traveler tips, where to stay, and tourist information, refer to the Provincetown trip itinerary builder tool.

Milan, Italy to Provincetown is an approximately 14.5-hour combination of flight and ferry. The time zone difference when traveling from Milan to Provincetown is minus 6 hours. Expect slightly colder weather when traveling from Milan in September: highs in Provincetown hover around 25°C, while lows dip to 16°C. Wrap up your sightseeing on the 18th (Sat) to allow time to travel to Nantucket.

Things to do in Provincetown

Outdoors · Beaches · Parks · Museums

Side Trips

2
nights
Nantucket

Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. Kick off your visit on the 19th (Sun): visit a coastal fixture at Sankaty Head Lighthouse, brush up on your knowledge of spirits at Cisco Brewers, and then enjoy the sand and surf at Madaket Beach. Keep things going the next day: see the interesting displays at Whaling Museum, visit a coastal fixture at Brant Point Lighthouse, and then tour the pleasant surroundings at Siasconset Beach.

To see other places to visit, where to stay, traveler tips, and more tourist information, use the Nantucket trip itinerary builder app.

Getting from Provincetown to Nantucket by combination of taxi and ferry takes about 3 hours. Other options: do a combination of bus and ferry. September in Nantucket sees daily highs of 25°C and lows of 17°C at night. Wrap up your sightseeing on the 20th (Mon) early enough to travel to Boston.

Things to do in Nantucket

Beaches · Parks · Historic Sites · Outdoors

2
nights
Boston

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.
Start off your visit on the 21st (Tue): take a tour by water with Boat Tours & Water Sports, then browse the different shops at Faneuil Hall Marketplace, then take a stroll through North End, and finally appreciate the extensive heritage of Freedom Trail. Keep things going the next day: take in the architecture and atmosphere at King's Chapel, then explore the world behind art at Museum of Fine Arts, then walk around Boston Public Garden, and finally stroll around Boston Common.

To see traveler tips, maps, other places to visit, and tourist information, refer to the Boston online driving holiday planner.

You can fly from Nantucket to Boston in 3 hours. Alternatively, you can do a combination of ferry and car; or do a combination of flight and bus. In September, daily temperatures in Boston can reach 28°C, while at night they dip to 17°C. Wrap up your sightseeing on the 22nd (Wed) to allow time to drive to Portland.

Things to do in Boston

Parks · Historic Sites · Museums · Neighborhoods

3
nights
Portland

The Forest City

Maine's biggest and perhaps most vibrant city, Portland was established as a fishing village in 1633 and grew to become New England's largest port.
Discover out-of-the-way places like Pemaquid Point Lighthouse and Maine Maritime Museum. You'll find plenty of places to visit near Portland: Kennebunkport (Boat Tours & Water Sports & St. Ann's Episcopal Church), Marginal Way Walkway (in Ogunquit) and Wells Beach (in Wells). And it doesn't end there: head off the coast to Casco Bay Islands, sample the tasty concoctions at Allagash Brewing Company, and make a trip to Portland Observatory.

To find photos, ratings, where to stay, and tourist information, use the Portland day trip tool.

Traveling by car from Boston to Portland takes 2 hours. Alternatively, you can take a bus; or take a train. Traveling from Boston in September, Portland is slightly colder at night with lows of 13°C. Finish up your sightseeing early on the 25th (Sat) so you can go by car to Rockland.

Things to do in Portland

Historic Sites · Parks · Outdoors · Beaches

Side Trips

2
nights
Rockland

Rockland is a city in Knox County, Maine, in the United States. On the 26th (Sun), see the interesting displays at Owls Head Transportation Museum, enjoy the sea views from Rockland Breakwater Light, then take a tour by water with Boat Tours & Water Sports, and finally don't miss a visit to Curtis Island Light. Here are some ideas for day two: admire the masterpieces at Farnsworth Art Museum, then immerse yourself in nature at Camden Hills State Park, and then take in the awesome beauty at Mount Battie.

To see ratings, where to stay, maps, and more tourist information, read our Rockland trip itinerary planner.

You can drive from Portland to Rockland in 2 hours. Another option is to take a bus. In September, daily temperatures in Rockland can reach 24°C, while at night they dip to 12°C. Wrap up your sightseeing on the 27th (Mon) to allow time to drive to Bar Harbor.

Things to do in Rockland

Parks · Nature · Historic Sites · Museums

Side Trips

5
nights
Bar Harbor, Mount Desert Island

Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. You'll discover tucked-away gems like Frenchman Bay and Otter Cliff. The adventure continues: hike along Gorham Mountain Trail, explore the striking landscape at Thunder Hole, stroll around Village Green, and take in the spiritual surroundings of St. Saviour's Church :.

To find other places to visit, reviews, and tourist information, refer to the Bar Harbor online trip planner.

Getting from Rockland to Bar Harbor by car takes about 2.5 hours. Other options: take a bus. In September, daily temperatures in Bar Harbor can reach 24°C, while at night they dip to 13°C. Finish your sightseeing early on the 2nd (Sat) so you can travel back home.

Things to do in Bar Harbor

Parks · Outdoors · Trails · Nature

Side Trip