9 days in Maine Itinerary

9 days in Maine Itinerary

Created using Inspirock Maine tour itinerary maker
Make it your trip
Fly to Portland International Jetport, Drive to South Portland
South Portland
— 1 night
— 2 nights
— 1 night
Bar Harbor, Mount Desert Island
— 4 nights


South Portland — 1 night

South Portland is a city in Cumberland County, Maine, United States, and is the fourth-largest city in the state, incorporated in 1898. On the 20th (Tue), stroll around Bug Light Park, then enjoy the sand and surf at Casco Bay, and then enjoy the sea views from Portland Breakwater Lighthouse. On the next day, enjoy the sea views from Spring Point Ledge Lighthouse, learn about winemaking at Maine Mead Works, then contemplate the long history of Wadsworth-Longfellow House, and finally see what you can catch with a fishing tour.

For maps, reviews, photos, and other tourist information, read our South Portland travel planner.

Chicago to South Portland is an approximately 5-hour combination of flight and car. You can also drive. The time zone difference moving from Central Standard Time (CST) to Eastern Standard Time (EST) is 1 hour. In September, South Portland is little chillier than Chicago - with highs of 73°F and lows of 52°F. Wrap up your sightseeing on the 21st (Wed) early enough to drive to Rockland.
Historic Sites · Outdoors · Parks · Tours
Side Trip

Rockland — 2 nights

Rockland is a city in Knox County, Maine, in the United States. Kick off your visit on the 22nd (Thu): browse the exhibits of Marshall Point Lighthouse Museum, enjoy the sea views from Owls Head Lighthouse, and then see what you can catch with A Morning In Maine. Here are some ideas for day two: see the interesting displays at Owls Head Transportation Museum, examine the collection at Maine Lighthouse Museum, then do a tasting at Cellardoor Winery, and finally make a trip to Curtis Island Light.

For other places to visit, reviews, more things to do, and tourist information, read Rockland trip itinerary site.

You can drive from South Portland to Rockland in 2 hours. In September, plan for daily highs up to 69°F, and evening lows to 51°F. Finish your sightseeing early on the 23rd (Fri) so you can drive to Greenville.
Museums · Historic Sites · Outdoors · Tours
Side Trips

Greenville — 1 night

Greenville is a town in Piscataquis County, Maine, United States. On the 24th (Sat), surround yourself with nature on a nature and wildlife tour, then contemplate the waterfront views at Moosehead Lake, and then immerse yourself in nature at Lily Bay State Park.

To see photos, more things to do, traveler tips, and more tourist information, refer to the Greenville tour itinerary planner.

You can drive from Rockland to Greenville in 3 hours. Alternatively, you can drive. September in Greenville sees daily highs of 68°F and lows of 50°F at night. Finish your sightseeing early on the 24th (Sat) so you can drive to Bar Harbor.
Parks · Nature · Outdoors · Tours

Bar Harbor, Mount Desert Island — 4 nights

Bar Harbor is a town on Mount Desert Island in Hancock County, Maine, United States. Popular historic sites such as St. Saviour's Church : and Egg Rock Light are in your itinerary. Explore hidden gems such as Gorham Mountain Trail and Village Green. There's lots more to do: play a few rounds at Pirate's Cove Miniature Golf, explore the activities along Frenchman Bay, indulge your thirst for a good beer at Atlantic Brewing Company, and indulge in some personalized pampering at some of the best spas.

For other places to visit, ratings, reviews, and more tourist information, go to the Bar Harbor day trip planner.

You can drive from Greenville to Bar Harbor in 3 hours. Another option is to drive. In September, daily temperatures in Bar Harbor can reach 70°F, while at night they dip to 52°F. Finish your sightseeing early on the 28th (Wed) so you can fly back home.
Parks · Outdoors · Breweries & Distilleries · Historic Sites
Side Trip

Maine travel guide

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.