9 days in Boston, Rockland & Portland Itinerary

9 days in Boston, Rockland & Portland Itinerary

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Route & dates

9 days in Boston, Rockland & Portland Itinerary

Start: Lisbon
Fly:  10​h 15​min
1
Boston
— 3 nights
Fly:  2​h 30​min
2
Rockland
— 1 night
Drive:  1​h 45​min
3
Portland
— 3 nights
bus + Fly:  10​h 30​min
End: Lisbon

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.
Start off your visit on the 18th (Tue): explore and take pictures at Fenway Park. On the 19th (Wed), you'll have a packed day of sightseeing: explore the different monuments and memorials at Granary Burying Ground, then get engrossed in the history at The House of the Seven Gables, and then take a memorable tour with Tours.

To see more things to do, photos, ratings, and more tourist information, read Boston itinerary planning website .

Lisbon, Portugal to Boston is an approximately 10.5-hour combination of flight and bus. You can also do a combination of flight and train. The time zone changes from Western European Time (WET) to Eastern Standard Time (EST), which is usually a -5 hour difference. Expect a bit cooler weather when traveling from Lisbon in September: highs in Boston hover around 28°C, while lows dip to 17°C. Finish your sightseeing early on the 21st (Fri) to allow enough time to travel to Rockland.

Things to do in Boston

Museums Wildlife Tours

Side Trips

Dolphin & Whale Watching, The House of the Seven Gables, Plimoth Plantation
Highlights from your plan
The House of the Seven Gables ©
The House of the Seven Gables
Plimoth Plantation ©
Plimoth Plantation
Museum of Fine Arts ©
Museum of Fine Arts

1
night
Rockland

Rockland ©
Rockland is a city in Knox County, Maine, in the United States. Kick off your visit on the 21st (Fri): admire the masterpieces at Farnsworth Art Museum, then visit a coastal fixture at Owls Head Lighthouse, then examine the collection at Maine Lighthouse Museum, and finally look for gifts at Fiore Artisan Olive Oils and Vinegars. Get ready for a full day of sightseeing on the next day: explore the engaging exhibits at Coastal Children's Museum, then visit a coastal fixture at Rockland Breakwater Light, and then see the interesting displays at Owls Head Transportation Museum.

For more things to do, maps, other places to visit, and more tourist information, read Rockland travel route website .

Traveling by combination of bus and flight from Boston to Rockland takes 2.5 hours. Alternatively, you can do a combination of bus, flight, and taxi; or drive. In September, Rockland is slightly colder than Boston - with highs of 23°C and lows of 12°C. Wrap up your sightseeing on the 22nd (Sat) early enough to drive to Portland.

Things to do in Rockland

Museums Historic Sites Childrens Museums

Side Trip

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

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.
You'll visit kid-friendly attractions like Wells Beach and Popham Beach State Park. Visit Old Orchard Beach and Ogunquit Beach for some beach relaxation. Take a break from Portland with a short trip to Maine Maritime Museum in Bath, about 42 minutes away. There's still lots to do: see the interesting displays at Portland Head Light, revel in the low prices at L.L. Bean Factory Store, and admire the masterpieces at Portland Museum of Art.

To find traveler tips, other places to visit, more things to do, and other tourist information, go to the Portland tour planner .

Drive from Rockland to Portland in 2 hours. Alternatively, you can take a bus. In September in Portland, expect temperatures between 26°C during the day and 13°C at night. Finish your sightseeing early on the 25th (Tue) so you can travel back home.

Things to do in Portland

Parks Outdoors Beaches

Side Trips

Maine Maritime Museum, Popham Beach State Park, Ogunquit Beach, L.L. Bean Factory Store, Wells Beach
Highlights from your plan
Portland Head Light ©
Portland Head Light
Popham Beach State Park ©
Popham Beach State Park
Maine Maritime Museum ©
Maine Maritime Museum

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