14 days in Maine Itinerary

14 days in Maine Itinerary

Created using Inspirock Maine vacation builder

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Make it your trip
Fly to Bangor International Airport, Drive to Gouldsboro
1
Gouldsboro
— 1 day
Drive
2
Bar Harbor, Mount Desert Island
— 2 nights
Drive
3
Castine
Drive
4
Rockland
— 2 nights
Drive
5
Freeport
— 2 nights
Drive
6
Portland
— 2 nights
Drive
7
Kennebunkport
— 4 nights
Drive
8
Kittery
— 1 night
Drive to General Edward Lawrence Logan International Airport, Fly to Asheville Regional Airport

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Gouldsboro

— 1 day
Gouldsboro is a town and municipality in Hancock County, Maine, United States on the Schoodic Peninsula. Start off your visit on the 1st (Wed): stop by Winter Harbor 5&10, view the masterpieces at Whopaints Gallery, then view the masterpieces at Chapter Two Art Gallery, then explore the striking landscape at Schoodic Point, and finally take in the exciting artwork at Spring Woods Gallery.

To find traveler tips, other places to visit, and more tourist information, read Gouldsboro day trip planning website.

Asheville to Gouldsboro is an approximately 8.5-hour combination of flight and car. You can also drive. Expect little chillier temperatures when traveling from Asheville in September; daily highs in Gouldsboro reach 70°F and lows reach 52°F. Cap off your sightseeing on the 1st (Wed) early enough to go by car to Bar Harbor.

Things to do in Gouldsboro

Shopping · Museums · Nature · Parks

Side Trips

Bar Harbor, Mount Desert Island

— 2 nights
Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. Start off your visit on the 2nd (Thu): kick back and relax at Sand Beach, get engrossed in the history at Somesville Historical Museum and Gardens, then visit a coastal fixture at Bass Harbor Head Lighthouse, and finally get a taste of the local shopping with Little Village Gifts. Keep things going the next day: examine the collection at The Seal Cove Auto Museum and then stop by Naturalist's Notebook.

To see traveler tips, more things to do, and other tourist information, you can read our Bar Harbor trip builder.

Getting from Gouldsboro to Bar Harbor by car takes about an hour. Expect a daytime high around 70°F in September, and nighttime lows around 52°F. Finish your sightseeing early on the 3rd (Fri) so you can drive to Castine.

Things to do in Bar Harbor

Museums · Shopping · Beaches · Parks

Side Trips

Castine

Castine is a town in Hancock County in eastern Maine, USA, which served from 1670 to 1674 as the capital of Acadia. Start off your visit on the 3rd (Fri): visit a coastal fixture at Fort Point Lighthouse.

For ratings, reviews, other places to visit, and more tourist information, refer to the Castine road trip website.

You can drive from Bar Harbor to Castine in 1.5 hours. In September, daily temperatures in Castine can reach 70°F, while at night they dip to 52°F. Wrap up your sightseeing on the 3rd (Fri) early enough to drive to Rockland.

Things to do in Castine

Historic Sites

Side Trip

Highlights from your trip

Rockland

— 2 nights
Rockland is a city in Knox County, Maine, in the United States. On the 4th (Sat), don't miss a visit to Curtis Island Light, get engrossed in the history at Belfast Historical Society & Museum, enjoy the sea views from Rockland Breakwater Light, then admire the masterpieces at Olson House, and finally get a taste of the local shopping with Linda Bean’s Maine Wyeth Gallery. Here are some ideas for day two: enjoy the sea views from Owls Head Lighthouse, then enjoy the sea views from Maine Lighthouse Museum, and then contemplate the long history of Farnsworth Art Museum.

To find traveler tips, reviews, maps, and tourist information, refer to the Rockland road trip planning tool.

You can drive from Castine to Rockland in 1.5 hours. September in Rockland sees daily highs of 69°F and lows of 51°F at night. Finish up your sightseeing early on the 5th (Sun) so you can go by car to Freeport.

Things to do in Rockland

Museums · Historic Sites · Shopping

Side Trips

Freeport

— 2 nights
Freeport is a town in Cumberland County, Maine, United States. On the 6th (Mon), examine the collection at Maine Maritime Museum, then revel in the low prices at L.L. Bean Factory Store, and then kick back and relax at Popham Beach State Park. On your second day here, steep yourself in history at Joshua L. Chamberlain Museum and then steep yourself in history at Fort Popham State Historic Site.

For other places to visit, maps, where to stay, and other tourist information, refer to the Freeport travel planner.

Traveling by car from Rockland to Freeport takes 1.5 hours. In September, daily temperatures in Freeport can reach 72°F, while at night they dip to 50°F. Finish your sightseeing early on the 7th (Tue) to allow enough time to drive to Portland.

Things to do in Freeport

Museums · Historic Sites · Shopping · Beaches

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.
Start off your visit on the 7th (Tue): kick back and relax at Old Orchard Beach. On the 8th (Wed), you'll have a packed day of sightseeing: take in panoramic vistas at Portland Observatory, get engrossed in the history at Victoria Mansion, then enjoy the sea views from Portland Head Light, and finally admire the masterpieces at Portland Museum of Art.

For traveler tips, other places to visit, ratings, and tourist information, use the Portland road trip planner.

Portland is just a short distance from Freeport. September in Portland sees daily highs of 73°F and lows of 52°F at night. You will have some time to spend on the 9th (Thu) before leaving for Kennebunkport.

Things to do in Portland

Museums · Beaches · Shopping · Parks

Side Trips

Kennebunkport

— 4 nights
Kennebunkport is a town in York County, Maine, United States. Your list of things to see and do now includes First Families Kennebunkport Museum, Scalawags Pet Boutique, Farm + Table, and other attractions. You'll explore and learn at Seashore Trolley Museum and Compliments. The adventure continues: kick back and relax at Wells Beach and stop by Mainely Murders Bookstore.

To see maps, reviews, more things to do, and other tourist information, refer to the Kennebunkport online trip builder.

Getting from Portland to Kennebunkport by car takes about an hour. Other options: take a bus; or do a combination of train and bus. Expect a daytime high around 74°F in September, and nighttime lows around 48°F. Cap off your sightseeing on the 13th (Mon) early enough to go by car to Kittery.

Things to do in Kennebunkport

Shopping · Beaches · Parks · Outdoors

Side Trips

Kittery

— 1 night
Kittery is a town in York County, Maine, United States. You've added Seapoint Beach, Kittery Trading Post, Yummies Candy and Nuts, and other attractions to your itinerary. On the 13th (Mon), look for gifts at Kittery Trading Post, kick back and relax at Ogunquit Beach, then look for gifts at Yummies Candy and Nuts, then look for gifts at Just Us Chickens Gallery, and finally look for gifts at When Pigs Fly Company Store. Keep things going the next day: get all the information you need at Maine Visitor Information Center, then revel in the low prices at Kittery Premium Outlets, and then kick back and relax at Seapoint Beach.

To see ratings, photos, reviews, and tourist information, read Kittery trip itinerary planner.

You can drive from Kennebunkport to Kittery in an hour. Traveling from Kennebunkport in September, Kittery is a bit warmer at night with lows of 54°F. Finish up your sightseeing early on the 14th (Tue) so you can travel back home.

Things to do in Kittery

Shopping · Beaches · Parks · Outdoors

Side Trip

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.