12 days in Boston, Plymouth & Portland Itinerary

12 days in Boston, Plymouth & Portland Itinerary

Created using Inspirock United States trip itinerary planner

This plan was created by another user.  Make it your plan

Route & dates

12 days in Boston, Plymouth & Portland Itinerary

Start: Boston
1
Boston
— 2 nights
Drive:  1​h
2
Plymouth
— 2 nights
3
Plymouth
— 2 nights
Drive:  2​h 45​min
4
Portland
— 4 nights
Fly:  7​h 45​min
End: New Orleans

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.
Visit Freedom Trail and The Paul Revere House for their historical value. You'll visit kid-friendly attractions like Fenway Park and Boston Public Garden. There's still lots to do: stroll the grounds of Mount Auburn Cemetery.

To find where to stay, photos, maps, and more tourist information, go to the Boston road trip planner .

Use the Route module to find suitable travel options from your home destination to Boston. In July in Boston, expect temperatures between 83°F during the day and 67°F at night. Finish up your sightseeing early on the 15th (Mon) so you can go by car to Portland.

Things to do in Boston

Historic Sites Parks Museums

Side Trip

Mount Auburn Cemetery
Highlights from your plan
Freedom Trail ©
Freedom Trail
Fenway Park ©
Fenway Park
Boston Public Garden ©
Boston Public Garden

2
nights
Plymouth

Plymouth ©
Rightly calling itself "America's Hometown," Plymouth holds a prominent place in the nation's history and culture as the site of the first Puritan colony.
Start off your visit on the 16th (Tue): tour the pleasant surroundings at Shining Sea Bikeway and then contemplate the long history of Hoxie House. Get ready for a full day of sightseeing on the next day: see majestic marine mammals with a dolphin and whale watching tour, contemplate the long history of Mayflower II, and then get curious at Sandwich Glass Museum.

For maps, reviews, traveler tips, and tourist information, go to the Plymouth day trip planner .

Traveling by car from Boston to Plymouth takes an hour. Alternatively, you can take a bus; or take a train. In July in Plymouth, expect temperatures between 82°F during the day and 64°F at night. Finish your sightseeing early on the 17th (Wed) to allow enough time to travel to Plymouth.

Things to do in Plymouth

Outdoors Tours Wildlife

Side Trips

Sandwich, Shining Sea Bikeway
Highlights from your plan
Shining Sea Bikeway ©
Shining Sea Bikeway
Sandwich Glass Museum ©
Sandwich Glass Museum
Dolphin & Whale Watching

2
nights
Plymouth

Plymouth ©
Here are some ideas for day two: enjoy the sea views from Nobska Point Lighthouse, kick back and relax at Old Silver Beach, then steep yourself in history at Lizzie Borden House, and finally admire the majestic nature at National Monument to the Forefathers.

To find reviews, maps, photos, and tourist information, read Plymouth trip itinerary builder website .

Cap off your sightseeing on the 19th (Fri) early enough to go by car to Portland.

Things to do in Plymouth

Parks Historic Sites Museums

Side Trips

Sandwich, Falmouth, Lizzie Borden House, John F Kennedy Hyannis Museum, Cape Cod Canal
Highlights from your plan
Lizzie Borden House ©
Lizzie Borden House
Nobska Point Lighthouse ©
Nobska Point Lighthouse

4
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.
Attractions like Popham Beach State Park and Long Sands Beach make great kid-friendly stops. Visit Ogunquit Beach and Drakes Island Beach for some beach relaxation. Explore Portland's surroundings by going to Moody Beach (in Wells), Marginal Way Walkway (in Ogunquit) and St. Ann's Episcopal Church (in Kennebunkport). There's lots more to do: kick back and relax at Sandy Point Beach, stroll through Ferry Beach, get a sense of history and politics at Portland City Hall, and take in the architecture and atmosphere at The Cathedral Of The Immaculate Conception.

For reviews, where to stay, maps, and more tourist information, read Portland trip planner.

Traveling by car from Boston to Portland takes 2 hours. Alternatively, you can take a bus; or take a train. Traveling from Boston in July, plan for slightly colder nights in Portland, with lows around 61°F. Cap off your sightseeing on the 19th (Fri) early enough to travel back home.

Things to do in Portland

Beaches Outdoors Parks

Side Trips

Ogunquit, Wells, Sandy Point Beach, Long Sands Beach, Popham Beach State Park
Highlights from your plan
Marginal Way Walkway ©
Marginal Way Walkway
Popham Beach State Park ©
Popham Beach State Park
Ogunquit Beach ©
Ogunquit Beach

Similar Plans

13 days in Boston & Hull BY A USER FROM UNITED STATES May, teens, culture, outdoors, relaxing, beaches, historic sites, museums, popular & hidden gems PREFERENCES: May, teens, culture, outdoors, relaxing, beaches, historic sites, museums ATTRACTION STYLE: Popular & hidden gems PACE: Medium 15 days in United States BY A USER FROM FRANCE June, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife, popular & hidden gems PREFERENCES: June, culture, outdoors, relaxing, romantic, beaches, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 13 days in New York City, New Haven & Washington DC BY A USER FROM MALAYSIA May, culture, outdoors, relaxing, romantic, historic sites, museums, shopping, wildlife, popular sights PREFERENCES: May, culture, outdoors, relaxing, romantic, historic sites, museums, shopping, wildlife ATTRACTION STYLE: Popular sights PACE: Medium 15 days in Boston BY A USER FROM ISRAEL May, culture, outdoors, romantic, historic sites, museums, shopping, popular sights PREFERENCES: May, culture, outdoors, romantic, historic sites, museums, shopping ATTRACTION STYLE: Popular sights PACE: Medium 16 days in Boston & New York City BY A USER FROM UNITED STATES June, teens, culture, outdoors, relaxing, historic sites, shopping, popular sights PREFERENCES: June, teens, culture, outdoors, relaxing, historic sites, shopping ATTRACTION STYLE: Popular sights PACE: Medium 15 days in United States BY A USER FROM ROMANIA October, culture, historic sites, museums, shopping, popular & hidden gems PREFERENCES: October, culture, historic sites, museums, shopping ATTRACTION STYLE: Popular & hidden gems PACE: Medium 15 days in Boston, Washington DC & New York City BY A USER FROM MALAYSIA July, teens, kids, culture, historic sites, museums, popular & hidden gems PREFERENCES: July, teens, kids, culture, historic sites, museums ATTRACTION STYLE: Popular & hidden gems PACE: Medium 15 days in Washington DC, New Orleans & Orlando BY A USER FROM COLOMBIA April, culture, historic sites, museums, slow & easy, popular sights PREFERENCES: April, culture, historic sites, museums ATTRACTION STYLE: Popular sights PACE: Slow & easy 15 days in Maine, Boston & New York City BY A USER FROM ISRAEL May, culture, outdoors, relaxing, beaches, historic sites, museums, shopping, popular sights PREFERENCES: May, culture, outdoors, relaxing, beaches, historic sites, museums, shopping ATTRACTION STYLE: Popular sights PACE: Medium
View more plans