6 days in Portland, Kennebunkport & Boston Itinerary

6 days in Portland, Kennebunkport & Boston Itinerary

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Route & dates

6 days in Portland, Kennebunkport & Boston Itinerary

Start: San Francisco
+2
Fly + foot + bus:  10​h
1
Portland
— 1 day
Drive:  45​min
2
Kennebunkport
— 2 nights
Drive:  1​h 45​min
3
Boston
— 2 nights
Fly:  7​h 15​min
End: San Francisco

1
day
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 22nd (Mon): wander the streets of Old Port, then sample the fine beverages at Sweetgrass Winery & Distillery Old Port Tasting Room and Shop, then see what you can catch with a fishing tour, and finally look and learn at Portland Observatory.

To see ratings, other places to visit, photos, and more tourist information, use the Portland tour itinerary builder website .

San Francisco to Portland is an approximately 10-hour combination of flight and bus. You can also fly; or drive. The time zone difference when traveling from San Francisco to Portland is 3 hours. While traveling from San Francisco, expect somewhat warmer days and about the same nights in Portland, ranging from highs of 79°F to lows of 61°F. Finish your sightseeing early on the 22nd (Mon) to allow enough time to drive to Kennebunkport.

Things to do in Portland

Tours Wildlife Outdoors
Highlights from your plan
Fishing Charters & Tours
Portland Observatory ©
Portland Observatory
Old Port ©
Old Port

2
nights
Kennebunkport

Kennebunkport ©
Kennebunkport is a town in York County, Maine, United States. Kick off your visit on the 23rd (Tue): enjoy the sea views from Cape Neddick Nubble Lighthouse, kick back and relax at Short Sands Beach, and then kick back and relax at Ogunquit Beach. Here are some ideas for day two: take in the architecture and atmosphere at St. Ann's Episcopal Church, admire all the interesting features of Walker's Point, cruise along Ocean Ave, then shop like a local with Compliments, and finally stop by Scalawags Pet Boutique.

To see ratings, other places to visit, reviews, and tourist information, read our Kennebunkport road trip planning website .

Traveling by car from Portland to Kennebunkport takes an hour. Alternatively, you can take a bus; or do a combination of train and bus. In July, daily temperatures in Kennebunkport can reach 81°F, while at night they dip to 58°F. Finish up your sightseeing early on the 24th (Wed) so you can go by car to Boston.

Things to do in Kennebunkport

Outdoors Beaches Scenic Drive

Side Trips

Ogunquit Beach, Short Sands Beach, Cape Neddick Nubble Lighthouse
Highlights from your plan
Short Sands Beach ©
Short Sands Beach
St. Ann's Episcopal Church ©
St. Ann's Episcopal Church
Walker's Point ©
Walker's Point

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.
Start off your visit on the 25th (Thu): enjoy the sand and surf at Nantasket Beach, steep yourself in history at Old North Church & Historic Site, then steep yourself in history at Captain Jackson’s Historic Chocolate Shop and the Printing Office of Edes and Gill, and finally take a stroll through Beacon Hill. On the 26th (Fri), you'll have a packed day of sightseeing: explore the wealth of natural beauty at Adams National Historical Park, take a stroll through Waterfront, and then explore the different monuments and memorials at Sleepy Hollow Cemetery.

For photos, reviews, other places to visit, and tourist information, use the Boston trip planner .

Traveling by car from Kennebunkport to Boston takes 2 hours. Alternatively, you can take a bus; or take a train. Traveling from Kennebunkport in July, Boston is somewhat warmer at night with lows of 67°F. Wrap up your sightseeing on the 26th (Fri) early enough to travel back home.

Things to do in Boston

Historic Sites Parks Neighborhoods

Side Trips

Sleepy Hollow Cemetery, Nantasket Beach, Adams National Historical Park
Highlights from your plan
Nantasket Beach ©
Nantasket Beach
Adams National Historical Park ©
Adams National Historical Park
Sleepy Hollow Cemetery ©
Sleepy Hollow Cemetery

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