11 days in New England Itinerary

11 days in New England Itinerary

Created using Inspirock New England travel planner

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Route & dates

11 days in New England Itinerary

Start: Tampa, Florida
Fly:  6​h 30​min
1
Portland
— 1 night
Drive:  1​h 45​min
2
Rockland
— 1 night
Drive:  2​h 15​min
3
Bar Harbor, Mount Desert Island
— 1 night
Fly:  5​h 30​min
4
Nantucket
— 1 day
Drive:  3​h 15​min
5
Provincetown
— 2 nights
Ferry:  1​h 30​min
6
Boston
— 2 nights
Drive:  1​h 30​min
7
Newport
— 2 nights
Fly:  7​h
End: Tampa, Florida

1
night
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.
Start off your visit on the 1st (Tue): take in the architecture and atmosphere at St. Ann's Episcopal Church.

For more things to do, photos, reviews, and tourist information, go to the Portland trip itinerary planner .

Tampa to Portland is an approximately 6.5-hour flight. You can also do a combination of flight and bus; or drive. Plan for much colder temperatures traveling from Tampa in October, with highs in Portland at 62°F and lows at 43°F. Finish up your sightseeing early on the 2nd (Wed) so you can go by car to Rockland.

Things to do in Portland

Museums Neighborhoods Historic Sites

Side Trips

St. Ann's Episcopal Church, Maine Maritime Museum
Highlights from your plan
Maine Maritime Museum ©
Maine Maritime Museum
Victoria Mansion ©
Victoria Mansion
St. Ann's Episcopal Church ©
St. Ann's Episcopal Church

1
night
Rockland

Rockland ©
Rockland is a city in Knox County, Maine, in the United States. Start off your visit on the 3rd (Thu): admire the masterpieces at Farnsworth Art Museum, examine the collection at Owls Head Transportation Museum, enjoy the sea views from Owls Head Lighthouse, then visit a coastal fixture at Rockland Breakwater Light, then make a trip to Keag River Gallery, and finally go for a walk through Finnish Church and Heritage House.

To find maps, more things to do, traveler tips, and more tourist information, read Rockland online visit planner .

You can drive from Portland to Rockland in 2 hours. Alternatively, you can take a bus. In October, plan for daily highs up to 58°F, and evening lows to 42°F. Wrap up your sightseeing on the 3rd (Thu) early enough to drive to Bar Harbor.

Things to do in Rockland

Historic Sites Museums Shopping

Side Trips

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

1
night
Bar Harbor, Mount Desert Island

Bar Harbor ©
Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. On the 4th (Fri), contemplate the waterfront views at Jordan Pond Path Trailhead, cruise along Park Loop Road, then don't miss a visit to Land Bridge to Bar Island, then look for all kinds of wild species at Shore Path, and finally go for a walk through Compass Harbor Trail.

For traveler tips, maps, other places to visit, and more tourist information, you can read our Bar Harbor vacation planning tool .

You can drive from Rockland to Bar Harbor in 2.5 hours. Alternatively, you can take a bus. Expect a daytime high around 59°F in October, and nighttime lows around 42°F. Finish up your sightseeing early on the 4th (Fri) so you can travel to Nantucket.

Things to do in Bar Harbor

Parks Nature Outdoors

Side Trip

Acadia National Park
Highlights from your plan
Shore Path ©
Shore Path
Jordan Pond Path Trailhead ©
Jordan Pond Path Trailhead
Compass Harbor Trail ©
Compass Harbor Trail

1
day
Nantucket

Nantucket ©
Nantucket is an island about 30mi by ferry south from Cape Cod, in the American state of Massachusetts. On the 5th (Sat), visit a coastal fixture at Sankaty Head Lighthouse, get to know the fascinating history of Altar Rock, visit a coastal fixture at Brant Point Lighthouse, then examine the collection at Whaling Museum, and finally brush up on your knowledge of spirits at Cisco Brewers.

To find other places to visit, traveler tips, maps, and more tourist information, read our Nantucket vacation site .

Getting from Bar Harbor to Nantucket by flight takes about 5.5 hours. Other options: do a combination of car and flight; or do a combination of car and ferry. Plan for a bit warmer nights when traveling from Bar Harbor in October since evenings lows in Nantucket dip to 51°F. Finish up your sightseeing early on the 5th (Sat) so you can go by car to Provincetown.

Things to do in Nantucket

Historic Sites Museums Wineries
Highlights from your plan
Sankaty Head Lighthouse ©
Sankaty Head Lighthouse
Brant Point Lighthouse ©
Brant Point Lighthouse
Cisco Brewers ©
Cisco Brewers

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.
Kick off your visit on the 6th (Sun): take a leisurely stroll along MacMillan Wharf, get up close to creatures of the deep with a dolphin and whale watching tour, make a trip to Commercial Street, get lost in a book at Provincetown Library, then tour the pleasant surroundings at Herring Cove Beach, and finally appreciate the history behind Pilgrim Monument & Provincetown Museum. On the 7th (Mon), you'll have a packed day of sightseeing: enjoy the sand and surf at Race Point Beach, then enjoy the sea views from Nauset Lighthouse, and then tour the pleasant surroundings at Cape Cod National Seashore.

To see where to stay, traveler tips, more things to do, and tourist information, go to the Provincetown tour itinerary planner .

Drive from Nantucket to Provincetown in 3.5 hours. In October, daytime highs in Provincetown are 63°F, while nighttime lows are 49°F. Finish up your sightseeing early on the 7th (Mon) so you can catch the ferry to Boston.

Things to do in Provincetown

Outdoors Beaches Parks

Side Trips

Nauset Lighthouse, Cape Cod National Seashore
Highlights from your plan
Nauset Lighthouse ©
Nauset Lighthouse
Cape Cod National Seashore ©
Cape Cod National Seashore

2
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.
Kick off your visit on the 8th (Tue): steep yourself in history at Granary Burying Ground, take in the architecture and atmosphere at Old North Church & Historic Site, stroll the grounds of Old Burying Point Cemetery, then see the interesting displays at Peabody Essex Museum, and finally steep yourself in history at The House of the Seven Gables. Keep things going the next day: wander the streets of Beacon Hill, explore the world behind art at Isabella Stewart Gardner Museum, then take in the architecture and design of Harvard University, and finally take a stroll through Waterfront.

Plan my trip to Boston with suggested itineraries provided by Inspirock.

Ride a ferry from Provincetown to Boston in 1.5 hours. Alternatively, you can fly; or drive. In October, daily temperatures in Boston can reach 64°F, while at night they dip to 50°F. Wrap up your sightseeing on the 9th (Wed) early enough to drive to Newport.

Things to do in Boston

Historic Sites Museums Neighborhoods

Side Trips

Salem, Harvard University
Highlights from your plan
The House of the Seven Gables ©
The House of the Seven Gables
Old North Church & Historic Site ©
Old North Church & Historic Site
Old Burying Point Cemetery ©
Old Burying Point Cemetery

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 10th (Thu): examine the collection at Rosecliff, admire the landmark architecture of Marble House, then examine the collection at Battleship Cove, then explore the galleries of Lizzie Borden House, and finally appreciate the extensive heritage of WaterFire Providence. Here are some ideas for day two: contemplate the long history of Fort Adams State Park, admire the landmark architecture of The Elms, and then examine the collection at New Bedford Whaling Museum.

To see maps, other places to visit, ratings, and tourist information, read Newport itinerary planner .

You can drive from Boston to Newport in 1.5 hours. Other options are to take a bus; or do a combination of train and bus. In October, daytime highs in Newport are 64°F, while nighttime lows are 50°F. Finish up your sightseeing early on the 11th (Fri) so you can travel back home.

Things to do in Newport

Museums Historic Sites Nightlife

Side Trips

Fall River, WaterFire, New Bedford Whaling Museum
Highlights from your plan
Lizzie Borden House ©
Lizzie Borden House
Battleship Cove ©
Battleship Cove
New Bedford Whaling Museum ©
New Bedford Whaling Museum

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