8 days in Portland, Bar Harbor & Boston Itinerary

8 days in Portland, Bar Harbor & Boston Itinerary

Created using Inspirock United States travel planner

Plan created by another user. Make it yours

Route & dates

1
Portland
— 3 nights
2
Bar Harbor
— 2 nights
3
Boston
— 2 nights

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.
Start off your visit on the 18th (Sun): stop by Old Port. On the 19th (Mon), you'll have a packed day of sightseeing: admire the masterpieces at Portland Museum of Art, thenvisit a coastal fixture at Portland Head Light, and then indulge your thirst for a good beer at Allagash Brewing Company.

To find more things to do, photos, traveler tips, and more tourist information, use the Portland itinerary planner.

Washington DC to Portland is an approximately 4.5-hour flight. You can also drive; or do a combination of train and bus. Traveling from Washington DC in October, things will get a bit cooler in Portland: highs are around °F and lows about °F. Cap off your sightseeing on the 21st (Wed) early enough to go by car to Bar Harbor.

Things to do in Portland

Historic Sites Neighborhoods Parks

Side Trips

Ogunquit, Nubble Lighthouse, Portland Head Light
Highlights from your plan
Marginal Way Walkway ©
Marginal Way Walkway
Portland Head Light ©
Portland Head Light
Nubble Lighthouse ©
Nubble Lighthouse

2
nights
Bar Harbor

Bar Harbor ©
Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. Kick off your visit on the 21st (Wed): take in the awesome beauty at Cadillac Mountain, take in the pleasant sights at Compass Harbor Trail, thencruise along Park Loop Road, and finally contemplate the waterfront views at Jordan Pond Path Trailhead. On the 22nd (Thu), you'll have a packed day of sightseeing: take in the dramatic natural features at Thunder Hole, thenhike along Ocean Path, thenstop by Christmas Spirit Shop, and finally take a tour by water with Boat Tours & Water Sports.

For other places to visit, traveler tips, and tourist information, you can read our Bar Harbor planner.

Drive from Portland to Bar Harbor in 3.5 hours. Alternatively, you can take a bus; or do a combination of bus and flight. In October, daily temperatures in Bar Harbor can reach °F, while at night they dip to °F. Finish your sightseeing early on the 23rd (Fri) to allow enough time to travel to Boston.

Things to do in Bar Harbor

Parks Outdoors Nature

Side Trip

Acadia National Park
Highlights from your plan
Cadillac Mountain ©
Cadillac Mountain
Boat Tours & Water Sports
Park Loop Road ©
Park Loop Road

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.
Start off your visit on the 23rd (Fri): get engrossed in the history at USS Constitution Museum, thenappreciate the history behind Bunker Hill Monument, thentake in nature's colorful creations at Boston Public Garden, and finally walk around Boston Common. On the 24th (Sat), you'll have a packed day of sightseeing: explore the world behind art at Museum of Fine Arts, appreciate the extensive heritage of Freedom Trail, and then visit North End.

To find maps, ratings, where to stay, and other tourist information, go to the Boston itinerary maker app.

Traveling by flight from Bar Harbor to Boston takes 5 hours. Alternatively, you can drive; or take a bus. Traveling from Bar Harbor in October, you can expect nighttime temperatures to be a bit warmer in Boston, with lows of °F. You'll set off for home on the 25th (Sun).

Things to do in Boston

Museums Parks Historic Sites
Highlights from your plan
Museum of Fine Arts ©
Museum of Fine Arts
Boston Public Garden ©
Boston Public Garden
Freedom Trail ©
Freedom Trail

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