9 days in Portland, Newport & Boston Itinerary

9 days in Portland, Newport & Boston Itinerary

Created using Inspirock United States trip maker

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

Route & dates

9 days in Portland, Newport & Boston Itinerary

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

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.
Museum-lovers will get to explore Portland Head Light and Portland Observatory. Your inner history buff will appreciate Marginal Way Walkway and Wadsworth-Longfellow House. You'll find plenty of places to visit near Portland: Compliments (in Kennebunkport) and Ogunquit (Perkins Cove & Ogunquit Beach). The adventure continues: sample the tasty concoctions at Allagash Brewery, visit a coastal fixture at Cape Neddick Nubble Lighthouse, take an in-depth tour of Victoria Mansion, and take a stroll through Old Port.

For more things to do, traveler tips, maps, and tourist information, you can read our Portland road trip site .

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. The time zone changes from Atlantic Standard Time (AST) to Eastern Standard Time (EST), which is usually a -1 hour difference. In October, Portland is much colder than San Juan - with highs of 62°F and lows of 43°F. Finish up your sightseeing early on the 15th (Tue) so you can go by car to Newport.

Things to do in Portland

Parks Historic Sites Museums

Side Trips

Ogunquit, Nubble Lighthouse, Compliments, 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
Newport

Newport ©
With coastline on the west, south, and east, Newport is a maritime city with a rich history.
Start off your visit on the 16th (Wed): take in the exciting artwork at Thames Glass, see the interesting displays at The Breakers, then appreciate the extensive heritage of Cliff Walk, and finally take a memorable drive along Ocean Drive Historic District. Get ready for a full day of sightseeing on the 17th (Thu): contemplate the long history of The Elms, sample the tasty concoctions at Newport Craft Brewing & Distilling Co., then steep yourself in history at Lizzie Borden House, and finally get to know the fascinating history of WaterFire Providence.

For other places to visit, more things to do, maps, and other tourist information, you can read our Newport trip builder site .

You can drive from Portland to Newport in 3.5 hours. Alternatively, you can take a bus; or take a bus. Traveling from Portland in October, plan for a bit warmer nights in Newport, with lows around 50°F. Finish your sightseeing early on the 17th (Thu) so you can drive to Boston.

Things to do in Newport

Historic Sites Outdoors Museums

Side Trips

Lizzie Borden House, WaterFire
Highlights from your plan
The Breakers ©
The Breakers
Ocean Drive Historic District ©
Ocean Drive Historic District
Lizzie Borden House ©
Lizzie Borden House

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), explore the world behind art at Museum of Fine Arts, get to know the fascinating history of Freedom Trail, and then take a stroll through North End. Get ready for a full day of sightseeing on the next day: get your bearings at John F. Kennedy Presidential Museum & Library, wander the streets of Newbury Street, and then explore the galleries of The House of the Seven Gables.

For where to stay, photos, and other tourist information, read our Boston trip itinerary planning tool .

You can drive from Newport to Boston in 1.5 hours. Alternatively, you can take a bus; or do a combination of bus and train. October in Boston sees daily highs of 64°F and lows of 50°F at night. Wrap up your sightseeing on the 19th (Sat) to allow time to travel back home.

Things to do in Boston

Museums Historic Sites Neighborhoods

Side Trip

The House of the Seven Gables
Highlights from your plan
Museum of Fine Arts ©
Museum of Fine Arts
Freedom Trail ©
Freedom Trail

Similar Plans

12 days in United States BY A USER FROM UNITED STATES July, teens, kids, culture, outdoors, beaches, historic sites, museums, wildlife, popular & hidden gems PREFERENCES: July, teens, kids, culture, outdoors, beaches, historic sites, museums, wildlife ATTRACTION STYLE: Popular & hidden gems PACE: Medium 13 days in Boston & New York City BY A USER FROM ISRAEL June, culture, outdoors, beaches, historic sites, museums, shopping, hidden gems PREFERENCES: June, culture, outdoors, beaches, historic sites, museums, shopping ATTRACTION STYLE: Hidden gems PACE: Medium 10 days in United States BY A USER FROM UNITED STATES April, outdoors, beaches, historic sites, popular & hidden gems PREFERENCES: April, outdoors, beaches, historic sites ATTRACTION STYLE: Popular & hidden gems PACE: Medium 10 days in Arlington, Washington DC & Nags Head BY A USER FROM UNITED STATES June, kids, beaches, historic sites, museums, shopping, popular sights PREFERENCES: June, kids, beaches, historic sites, museums, shopping ATTRACTION STYLE: Popular sights PACE: Medium 11 days in Portland BY A USER FROM UNITED STATES September, culture, outdoors, relaxing, beaches, historic sites, shopping, popular & hidden gems PREFERENCES: September, culture, outdoors, relaxing, beaches, historic sites, shopping ATTRACTION STYLE: Popular & hidden gems PACE: Medium 10 days in Boston & Nantucket BY A USER FROM CANADA August, teens, beaches, historic sites, museums, popular sights PREFERENCES: August, teens, beaches, historic sites, museums ATTRACTION STYLE: Popular sights PACE: Medium 13 days in United States BY A USER FROM UNITED STATES July, kids, outdoors, historic sites, museums, popular sights PREFERENCES: July, kids, outdoors, historic sites, museums ATTRACTION STYLE: Popular sights PACE: Medium 10 days in United States BY A USER FROM UNITED STATES July, teens, kids, popular sights PREFERENCES: July, teens, kids ATTRACTION STYLE: Popular sights PACE: Medium 10 days in United States BY A USER FROM UNITED STATES August, slow & easy, popular sights PREFERENCES: August ATTRACTION STYLE: Popular sights PACE: Slow & easy 10 days in Boston & Nantucket BY A USER FROM UNITED STATES September, beaches, historic sites, museums, popular sights PREFERENCES: September, beaches, historic sites, museums ATTRACTION STYLE: Popular sights PACE: Medium
View more plans