9 days in Boston, Newport & Portland Itinerary

9 days in Boston, Newport & Portland Itinerary

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Route & dates

9 days in Boston, Newport & Portland Itinerary

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

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.
Appreciate the collections at Hancock-Clarke House and Beauport, the Sleeper-McCann House. Eschew the tourist crowds and head to Ogunquit Museum of American Art and Back Bay. Venture out of the city with trips to Strawbery Banke Museum (in Portsmouth), Marginal Way Walkway (in Ogunquit) and Louisa May Alcott's Orchard House (in Concord). There's still lots to do: explore the world behind art at Museum of Fine Arts, steep yourself in history at Captain Jackson’s Historic Chocolate Shop and the Printing Office of Edes and Gill, take an in-depth tour of Buckman Tavern, and appreciate the extensive heritage of Freedom Trail.

To find traveler tips, more things to do, and other tourist information, you can read our Boston online trip itinerary builder .

San Juan, Puerto Rico to Boston is an approximately 7-hour flight. You can also do a combination of flight and bus; or do a combination of car and flight. The time zone difference when traveling from San Juan to Boston is minus 1 hour. Prepare for much colder weather when traveling from San Juan in October: high temperatures in Boston hover around 20°C and lows are around 11°C. Cap off your sightseeing on the 15th (Tue) early enough to go by car to Newport.

Things to do in Boston

Museums Historic Sites Neighborhoods

Side Trips

Lexington, Ogunquit, Beauport, the Sleeper-McCann House, Strawbery Banke Museum, Louisa May Alcott's Orchard House
Highlights from your plan
Museum of Fine Arts ©
Museum of Fine Arts
Strawbery Banke Museum ©
Strawbery Banke Museum
Ogunquit Museum of American Art ©
Ogunquit Museum of American Art

3
nights
Newport

Newport ©
With coastline on the west, south, and east, Newport is a maritime city with a rich history.
The Preservation Society of Newport County and Florence Griswold Museum will appeal to history buffs. Explore hidden gems such as St. Mary's Catholic Church and Touro Synagogue. Venture out of the city with trips to Old Lighthouse Museum (in Stonington) and The Submarine Force Museum (in Groton). Next up on the itinerary: see the interesting displays at International Tennis Hall of Fame, don't miss a visit to Queen Ann Square, contemplate the long history of Chateau-sur-Mer, and stroll around Fort Adams State Park.

For ratings, photos, where to stay, and tourist information, use the Newport trip app .

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. Expect a daytime high around 20°C in October, and nighttime lows around 11°C. Finish your sightseeing early on the 18th (Fri) so you can drive to Portland.

Things to do in Newport

Museums Historic Sites Parks

Side Trips

The Submarine Force Museum, Florence Griswold Museum, The Stonington Lighthouse Museum
Highlights from your plan
Touro Synagogue ©
Touro Synagogue
Florence Griswold Museum ©
Florence Griswold Museum
Fort Adams State Park ©
Fort Adams State Park

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 19th (Sat): steep yourself in history at Wadsworth-Longfellow House, then make a trip to Portland Observatory, then indulge your thirst for a good beer at Allagash Brewery, and finally take in the architecture and atmosphere at St. Ann's Episcopal Church. On the 20th (Sun), you'll have a packed day of sightseeing: get engrossed in the history at Victoria Mansion, enjoy the sea views from Portland Breakwater Lighthouse, and then indulge your thirst for a good beer at Rising Tide Brewing Company.

To find traveler tips, other places to visit, maps, and other tourist information, read our Portland trip builder app .

Traveling by car from Newport to Portland takes 3.5 hours. Alternatively, you can take a bus; or take a bus. Traveling from Newport in October, you can expect nighttime temperatures to be slightly colder in Portland, with lows of 7°C. Wrap up your sightseeing on the 20th (Sun) early enough to travel back home.

Things to do in Portland

Historic Sites Breweries & Distilleries Museums

Side Trips

Portland Breakwater Lighthouse, St. Ann's Episcopal Church
Highlights from your plan
Wadsworth-Longfellow House ©
Wadsworth-Longfellow House
St. Ann's Episcopal Church ©
St. Ann's Episcopal Church
Victoria Mansion ©
Victoria Mansion

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