11 days in New England Itinerary

11 days in New England Itinerary

Created using Inspirock New England trip planner

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Route & dates

11 days in New England Itinerary

Start: Anchorage
Drive + Fly:  12​h 45​min
1
Portland
— 3 nights
Drive:  1​h 45​min
2
Rockland
— 1 night
Fly:  2​h 15​min
3
Boston
— 3 nights
ferry:  1​h 30​min
4
Provincetown
— 2 nights
+4
ferry + foot + bus + Fly + Drive:  12​h 15​min
End: Anchorage

3
nights
Portland

Portland ©
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.
Get a sense of the local culture at Maine Maritime Museum and Portland Museum of Art. Appreciate the collections at Strawbery Banke Museum and North Conway League of NH Craftsmen Fine Arts Gallery. You'll find plenty of places to visit near Portland: Kittery Trading Post (in Kittery), Flume Gorge (in Franconia) and Ogunquit (Ogunquit Beach & Marginal Way Walkway). Next up on the itinerary: visit a coastal fixture at Pemaquid Point Lighthouse, wander the streets of Old Port, see the interesting displays at Portland Head Light, and pause for some serene contemplation at St. Ann's Episcopal Church.

To see more things to do, reviews, and tourist information, go to the Portland tour itinerary site .

Anchorage to Portland is an approximately 13-hour combination of car and flight. You can also do a combination of car, flight, and bus; or drive. Due to the time zone difference, you'll lose 4 hours traveling from Anchorage to Portland. Prepare for a bit warmer weather when traveling from Anchorage in October: high temperatures in Portland hover around 62°F and lows are around 43°F. Wrap up your sightseeing on the 21st (Wed) to allow time to drive to Rockland.

Things to do in Portland

Historic Sites Museums Parks

Side Trips

Ogunquit, Pemaquid Point Lighthouse, Flume Gorge, North Conway League of NH Craftsmen Fine Arts Gallery, Portland Head Light
Highlights from your plan
Strawbery Banke Museum ©
Strawbery Banke Museum
Pemaquid Point Lighthouse ©
Pemaquid Point Lighthouse
Maine Maritime Museum ©
Maine Maritime Museum

1
night
Rockland

Rockland ©
Rockland is a city in Knox County, Maine, in the United States. Kick off your visit on the 22nd (Thu): visit a coastal fixture at Owls Head Lighthouse, then enjoy the sea views from Rockland Breakwater Light, then examine the collection at Owls Head Transportation Museum, and finally explore the world behind art at Farnsworth Art Museum.

To find photos, traveler tips, more things to do, and tourist information, read Rockland itinerary maker .

Traveling by car from Portland to Rockland takes 2 hours. Alternatively, you can take a bus. In October, daytime highs in Rockland are 58°F, while nighttime lows are 42°F. Wrap up your sightseeing on the 22nd (Thu) early enough to travel to Boston.

Things to do in Rockland

Museums Historic Sites Shopping

Side Trip

Owls Head
Highlights from your plan
Owls Head Lighthouse ©
Owls Head Lighthouse
Farnsworth Art Museum ©
Farnsworth Art Museum
Owls Head Transportation Museum ©
Owls Head Transportation Museum

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.
For shopping fun, head to Quincy Market or Newbury Street. Deepen your sense of the past at sights like The House of the Seven Gables and Freedom Trail. Change things up with these side-trips from Boston: Hampton Beach State Park (in Hampton) and Plimoth Plantation (in Plymouth). There's much more to do: contemplate in the serene atmosphere at Old North Church & Historic Site, admire the masterpieces at Museum of Fine Arts, and ponder the world of politics at Old State House.

For reviews, other places to visit, maps, and more tourist information, use the Boston route planner.

Traveling by flight from Rockland to Boston takes 2.5 hours. Alternatively, you can do a combination of taxi and flight; or drive. Traveling from Rockland in October, expect Boston to be a bit warmer, temps between 64°F and 50°F. Finish your sightseeing early on the 25th (Sun) so you can ride a ferry to Provincetown.

Things to do in Boston

Museums Historic Sites Shopping

Side Trips

The House of the Seven Gables, Hampton Beach State Park, Plimoth Plantation
Highlights from your plan
Museum of Fine Arts ©
Museum of Fine Arts
Old State House ©
Old State House
Freedom Trail ©
Freedom Trail

2
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.
Start off your visit on the 26th (Mon): enjoy the sand and surf at Race Point Beach, view the masterpieces at Charles-Baltivik Gallery and Sculpture Garden, and then enjoy the sand and surf at Nauset Beach. On your second day here, enjoy the sand and surf at Herring Cove Beach and then see the interesting displays at Pilgrim Monument & Provincetown Museum.

To find reviews, photos, traveler tips, and more tourist information, refer to the Provincetown trip builder app .

You can ride a ferry from Boston to Provincetown in 1.5 hours. Alternatively, you can fly; or drive. October in Provincetown sees daily highs of 63°F and lows of 49°F at night. Cap off your sightseeing on the 27th (Tue) early enough to travel back home.

Things to do in Provincetown

Parks Beaches Outdoors

Side Trip

Nauset Beach
Highlights from your plan
Nauset Beach ©
Nauset Beach
Herring Cove Beach ©
Herring Cove Beach
Race Point Beach ©
Race Point Beach

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