15 days in New England Itinerary

15 days in New England Itinerary

Created using Inspirock New England trip itinerary planner

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Make it your trip
Fly
1
Bar Harbor, Mount Desert Island
— 4 nights
Drive
2
Rockland
— 2 nights
Drive
3
Kennebunkport
— 3 nights
Drive
4
Provincetown
— 2 nights
Taxi to Hyannis, MA, Ferry to Nantucket
5
Nantucket
— 3 nights
Fly

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Bar Harbor, Mount Desert Island

— 4 nights
Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. Visiting Sand Beach and Kayaking & Canoeing will get you outdoors. You'll discover tucked-away gems like Ocean Path and Carriage Roads. There's much more to do: hike along Great Head Trail, explore the activities along Frenchman Bay, tee off at Pirate's Cove Miniature Golf, and tour the pleasant surroundings at Cadillac Mountain North Ridge Trail.

To see reviews, maps, and tourist information, you can read our Bar Harbor trip planner.

Pittsburgh to Bar Harbor is an approximately 5.5-hour flight. You can also drive; or take a bus. Expect a bit cooler temperatures when traveling from Pittsburgh in September; daily highs in Bar Harbor reach 70°F and lows reach 52°F. Finish your sightseeing early on the 30th (Thu) so you can drive to Rockland.

Things to do in Bar Harbor

Outdoors · Parks · Trails · Nature

Side Trip

Rockland

— 2 nights
Rockland is a city in Knox County, Maine, in the United States. Kick off your visit on the 1st (Fri): admire the masterpieces at Farnsworth Art Museum, enjoy the sea views from Maine Lighthouse Museum, and then take a tour by water with Boat Tours & Water Sports. On the 2nd (Sat), you'll have a packed day of sightseeing: see the interesting displays at Marshall Point Lighthouse Museum, visit a coastal fixture at Rockland Breakwater Light, and then immerse yourself in nature at Camden Hills State Park.

For reviews, where to stay, photos, and more tourist information, you can read our Rockland trip planner.

Drive from Bar Harbor to Rockland in 2.5 hours. Alternatively, you can take a bus. September in Rockland sees daily highs of 69°F and lows of 51°F at night. Wrap up your sightseeing on the 2nd (Sat) to allow time to drive to Kennebunkport.

Things to do in Rockland

Historic Sites · Museums · Nature · Outdoors

Side Trips

Kennebunkport

— 3 nights
Kennebunkport is a town in York County, Maine, United States. Get in touch with nature at Wells Beach and Long Sands Beach. Visit Footbridge Beach and Kennebunk Beach for some beach relaxation. There's much more to do: head outdoors with Outdoor Activities, go for a walk through Rotary Park, tour the pleasant surroundings at Rachel Carson National Wildlife Refuge, and take a memorable drive along Ocean Ave.

To find traveler tips, where to stay, photos, and more tourist information, use the Kennebunkport online road trip planner.

Drive from Rockland to Kennebunkport in 2.5 hours. Alternatively, you can take a bus; or do a combination of bus and train. In October, daily temperatures in Kennebunkport can reach 62°F, while at night they dip to 38°F. Finish up your sightseeing early on the 5th (Tue) so you can go by car to Provincetown.

Things to do in Kennebunkport

Outdoors · Parks · Beaches · Scenic Drive

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 6th (Wed), kick back and relax at Marconi Beach, then kick back and relax at Nauset Light Beach, and then enjoy the sand and surf at Coast Guard Beach. Keep things going the next day: visit a coastal fixture at Highland Light, stroll through Herring Cove Beach, then take in the waterfront at MacMillan Wharf, and finally get outside with Art's Dune Tours.

For ratings, more things to do, photos, and tourist information, use the Provincetown journey planner.

Drive from Kennebunkport to Provincetown in 4.5 hours. Alternatively, you can do a combination of bus and ferry; or do a combination of bus, train, and ferry. Traveling from Kennebunkport in October, Provincetown is a bit warmer at night with lows of 49°F. Finish your sightseeing early on the 7th (Thu) so you can travel to Nantucket.

Things to do in Provincetown

Outdoors · Parks · Beaches · Wildlife

Side Trips

Nantucket

— 3 nights
Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. Your itinerary includes some good beach time at Madaket Beach and Siasconset Beach. Visit Brant Point Lighthouse and Great Point Light for their historical value. There's still lots to do: kick back and relax at Surfside Beach, stroll through Cisco Beach, visit a coastal fixture at Sankaty Head Lighthouse, and sample the fine beverages at Cisco Brewers.

To see traveler tips, other places to visit, more things to do, and more tourist information, read Nantucket journey maker tool.

You can do a combination of taxi and ferry from Provincetown to Nantucket in 3 hours. Alternatively, you can do a combination of bus and ferry. Expect a daytime high around 64°F in October, and nighttime lows around 51°F. Finish your sightseeing early on the 10th (Sun) so you can fly back home.

Things to do in Nantucket

Outdoors · Parks · Beaches · Historic Sites