10 days in Boston & Maine Itinerary

10 days in Boston & Maine Itinerary

Created using Inspirock United States holiday planner

Make it your trip
Fly
1
Boston
— 2 nights
Drive
2
Kennebunkport
— 2 nights
Drive
3
Portland
— 2 nights
Drive
4
Rockland
— 1 night
Drive
5
Bar Harbor, Mount Desert Island
— 2 nights
Fly

S M T W T F S
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Boston

— 2 nights

Beantown

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 19th (Mon), appreciate the history behind The Mapparium, then wander the streets of Back Bay, then explore the landscape on two wheels at Charles River Bike Path, and finally work some fitness into your day at Charles River Esplanade. On the 20th (Tue), you'll have a packed day of sightseeing: contemplate the long history of Captain Jackson’s Historic Chocolate Shop and the Printing Office of Edes and Gill, admire the striking features of Marriott's Custom House, wander the streets of North End, then head off the coast to George's Island, and finally step off the mainland to explore Castle Island.

To find photos, maps, traveler tips, and more tourist information, go to the Boston trip itinerary planning tool.

Kansas City to Boston is an approximately 6-hour flight. You can also drive; or take a train. You'll lose 1 hour traveling from Kansas City to Boston due to the time zone difference. Expect slightly colder temperatures when traveling from Kansas City in July; daily highs in Boston reach 83°F and lows reach 67°F. Wrap up your sightseeing on the 20th (Tue) to allow time to drive to Kennebunkport.

Things to do in Boston

Parks · Outdoors · Nature · Neighborhoods

Side Trip

Kennebunkport

— 2 nights
Kennebunkport is a town in York County, Maine, United States. Start off your visit on the 21st (Wed): relax and rejuvenate at Cottage Breeze Day Spa & Boutique, enjoy the sand and surf at Mother's Beach, then kick back and relax at Wells Beach, and finally get outside with Fisherman's Walk. Get ready for a full day of sightseeing on the 22nd (Thu): stop by Maine-ly Drizzle, take a tour by water with Boat Tours & Water Sports, appreciate the extensive heritage of Parson's Way, then don't miss a visit to President Bush Compound, and finally take in the exciting artwork at Compliments.

For where to stay, reviews, ratings, and other tourist information, refer to the Kennebunkport road trip site.

Getting from Boston to Kennebunkport by car takes about 2 hours. Other options: take a bus; or do a combination of train and bus. Expect a bit cooler evenings in Kennebunkport when traveling from Boston in July, with lows around 58°F. Finish up your sightseeing early on the 22nd (Thu) so you can go by car to Portland.

Things to do in Kennebunkport

Outdoors · Parks · Beaches · Shopping

Side Trips

Portland

— 2 nights

The Forest City

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.
On the 23rd (Fri), contemplate the long history of Wadsworth-Longfellow House, do a tasting at Maine Mead Works, then tour the pleasant surroundings at Back Cove Trail, and finally kick back and relax at East End Beach.

To find more things to do, maps, and more tourist information, refer to the Portland trip itinerary builder website.

You can drive from Kennebunkport to Portland in an hour. Alternatively, you can take a bus; or do a combination of bus and train. Expect a daytime high around 79°F in July, and nighttime lows around 61°F. Wrap up your sightseeing on the 24th (Sat) to allow time to drive to Rockland.

Things to do in Portland

Parks · Outdoors · Historic Sites · Trails

Rockland

— 1 night
Rockland is a city in Knox County, Maine, in the United States. Start off your visit on the 24th (Sat): go for a walk through Belfast Harborwalk, explore the landscape on two wheels at Passy Rail Trail, and then walk around Camden Harbor Park and Amphitheatre. Keep things going the next day: identify plant and animal life at Beech Hill Reserve, then learn about winemaking at Sweetgrass Farm Winery and Distillery, then visit a coastal fixture at Maine Lighthouse Museum, and finally cast your line with Morning In Maine Boat Tour.

For traveler tips, other places to visit, more things to do, and more tourist information, read our Rockland day trip app.

You can drive from Portland to Rockland in 2 hours. Alternatively, you can take a bus. While traveling from Portland, expect slightly colder days and about the same nights in Rockland, ranging from highs of 74°F to lows of 58°F. Cap off your sightseeing on the 25th (Sun) early enough to go by car to Bar Harbor.

Things to do in Rockland

Parks · Wildlife · Outdoors · Historic Sites

Side Trips

Bar Harbor, Mount Desert Island

— 2 nights
Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. Kick off your visit on the 26th (Mon): stop by Christmas Spirit Shop, play a few rounds at Kebo Valley Golf Club, then stroll through Bar Island Trails, and finally look for all kinds of wild species at Shore Path.

For traveler tips, reviews, more things to do, and tourist information, go to the Bar Harbor route planner.

You can drive from Rockland to Bar Harbor in 2.5 hours. Another option is to take a bus. In July, plan for daily highs up to 75°F, and evening lows to 58°F. You will have some time to spend on the 27th (Tue) before leaving for home.

Things to do in Bar Harbor

Parks · Outdoors · Wildlife · Trails

Maine travel guide

4.6
Beaches · Lighthouses · Mountains
The Pine Tree State
The easternmost state in New England, Maine features an indented coastline and forested interior, carved eons ago by receding glaciers. Maine includes more lighthouses and quaint resort villages than you could ever hope to explore in a single trip, but the state is also one of the country's most sparsely populated, the majority of its land pristine and uninhabited wilderness. The temperate coastal regions, historically supported by fishing and lobstering, contain most of the state's urban centers and are the most popular spots in the state for holidays. The sea is the focus here, so it shouldn't come as a surprise that water plays an important role in the distinct character of the state, shaping its economy, tourism, cuisine, politics, sports, and art.