9 days in Portland, Newport & Boston Itinerary

9 days in Portland, Newport & Boston Itinerary

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Route & dates

9 days in Portland, Newport & Boston Itinerary

Start: San Juan, Puerto Rico
+2
Fly + foot + bus:  8​h 30​min
1
Portland
— 2 nights
Drive:  3​h 30​min
2
Newport
— 3 nights
Drive:  1​h 30​min
3
Boston
— 2 nights
Fly:  7​h
End: San Juan, Puerto Rico

2
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.
Kick off your visit on the 13th (Sun): take a stroll through Diamond Cove, contemplate the long history of Fort Gorges, visit a coastal fixture at Portland Breakwater Lighthouse, then sample the tasty concoctions at Rising Tide Brewing Company, and finally do a tasting at Maine Mead Works. On the next day, see the interesting displays at Maine Jewish Museum, then tour the pleasant surroundings at Eastern Prom Trail, and then get to know the fascinating history of Parson's Way.

For photos, ratings, maps, and more tourist information, read Portland online travel route planner .

San Juan, Puerto Rico to Portland is an approximately 8.5-hour combination of flight and bus. You can also fly; or do a combination of car and flight. Traveling from San Juan to Portland, you'll gain 1 hour due to the time zone difference. Prepare for cooler weather when traveling from San Juan in October: high temperatures in Portland hover around 62°F and lows are around 43°F. Finish up your sightseeing early on the 14th (Mon) so you can go by car to Newport.

Things to do in Portland

Historic Sites Outdoors Trails

Side Trips

Parson's Way, Portland Breakwater Lighthouse
Highlights from your plan
Fort Gorges ©
Fort Gorges
Portland Breakwater Lighthouse ©
Portland Breakwater Lighthouse
Rising Tide Brewing Company ©
Rising Tide Brewing Company

3
nights
Newport

Newport ©
With coastline on the west, south, and east, Newport is a maritime city with a rich history.
Eschew the tourist crowds and head to Old Lighthouse Museum and Hoxie House. Wing Fort House and Chepstow will appeal to museum buffs. You'll find plenty of places to visit near Newport: Green Briar Nature Center and Jam Kitchen (in East Sandwich), Fort Phoenix State Reservation (in Fairhaven) and Dexter’s Grist Mill (in Sandwich). Next up on the itinerary: pause for some serene contemplation at St. Mary's Catholic Church, steep yourself in history at Isaac Bell House, and enjoy the sea views from Ned's Point Lighthouse.

To find maps, photos, where to stay, and tourist information, refer to the Newport holiday maker app .

Traveling by car from Portland to Newport takes 3.5 hours. Alternatively, you can take a bus; or take a bus. Traveling from Portland in October, Newport is somewhat warmer at night with lows of 50°F. Wrap up your sightseeing on the 17th (Thu) to allow time to drive to Boston.

Things to do in Newport

Historic Sites Museums Parks

Side Trips

Sandwich, The Stonington Lighthouse Museum, Ned's Point Lighthouse, Fort Phoenix State Reservation
Highlights from your plan
The Stonington Lighthouse Museum ©
The Stonington Lighthouse Museum
St. Mary's Catholic Church ©
St. Mary's Catholic Church
Dexter’s Grist Mill ©
Dexter’s Grist Mill

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.
On the 18th (Fri), steep yourself in history at Hancock-Clarke House, get engrossed in the history at Buckman Tavern, stroll the grounds of Sleepy Hollow Cemetery, then pause for some serene contemplation at The First Church of Christ, Scientist, and finally take in the architecture and atmosphere at Church of the Covenant. Get ready for a full day of sightseeing on the next day: take an in-depth tour of Cape Ann Museum, then examine the collection at Beauport, the Sleeper-McCann House, then steep yourself in history at Saugus Iron Works, and finally get to know the fascinating history of Charlestown Navy Yard.

To see where to stay, more things to do, reviews, and tourist information, refer to the Boston online attractions planner .

You can drive from Newport to Boston in 1.5 hours. Other options are to take a bus; or do a combination of bus and train. In October, daytime highs in Boston are 64°F, while nighttime lows are 50°F. Finish your sightseeing early on the 19th (Sat) so you can travel back home.

Things to do in Boston

Historic Sites Museums

Side Trips

Gloucester, Lexington, Saugus Iron Works, Sleepy Hollow Cemetery
Highlights from your plan
Hancock-Clarke House ©
Hancock-Clarke House
Sleepy Hollow Cemetery ©
Sleepy Hollow Cemetery
Buckman Tavern ©
Buckman Tavern

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