8 days in Maine Itinerary

8 days in Maine Itinerary

Created using Inspirock Maine trip builder

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Make it your trip
Fly
1
Portland
— 3 nights
Drive
2
Kennebunkport
— 2 nights
Drive
3
Bar Harbor, Mount Desert Island
— 2 nights
Fly

S M T W T F S
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Portland

— 3 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.
Explore the numerous day-trip ideas around Portland: North Conway (Mount Washington Observatory Weather Discovery Center & Kancamagus Highway), Maine Heritage Village (in Wiscasset) and South End Dog Park (in Bath). There's much more to do: sample the tasty concoctions at Allagash Brewing Company, enjoy the sea views from Portland Head Light, admire the masterpieces at Portland Museum of Art, and get engrossed in the history at Victoria Mansion.

To find photos, traveler tips, where to stay, and other tourist information, you can read our Portland trip itinerary planning tool.

Tampa to Portland is an approximately 5-hour flight. You can also drive; or take a bus. Expect colder temperatures when traveling from Tampa in October; daily highs in Portland reach 62°F and lows reach 43°F. Finish your sightseeing early on the 9th (Sun) so you can drive to Kennebunkport.

Things to do in Portland

Breweries & Distilleries · Museums · Parks · Scenic Drive

Side Trips

Kennebunkport

— 2 nights
Kennebunkport is a town in York County, Maine, United States. Start off your visit on the 10th (Mon): explore the striking landscape at Perkins Cove, then get to know the fascinating history of Marginal Way Walkway, and then visit a coastal fixture at Nubble Lighthouse. Get ready for a full day of sightseeing on the next day: take in the exciting artwork at Compliments, take a memorable drive along Ocean Ave, then cruise along Walker's Point, and finally take in the architecture and atmosphere at St. Ann's Episcopal Church.

To find other places to visit, ratings, where to stay, and more tourist information, refer to the Kennebunkport trip itinerary maker site.

You can drive from Portland to Kennebunkport in an hour. Other options are to take a bus; or do a combination of train and bus. Traveling from Portland in October, expect little chillier with lows of 38°F in Kennebunkport. Finish your sightseeing early on the 11th (Tue) to allow enough time to drive to Bar Harbor.

Things to do in Kennebunkport

Historic Sites · Scenic Drive · Outdoors · Nature

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 12th (Wed): get a new perspective on things with Boat Tours & Water Sports, then take a memorable drive along Park Loop Road, then explore the activities along Jordan Pond Path Trailhead, and finally take in the pleasant sights at Compass Harbor Trail. Get ready for a full day of sightseeing on the 13th (Thu): look for gifts at Sherman's Books & Stationery and then take in the awesome beauty at Cadillac Mountain.

To see photos, maps, ratings, and more tourist information, use the Bar Harbor trip builder website.

Drive from Kennebunkport to Bar Harbor in 4 hours. Alternatively, you can do a combination of bus, train, and flight; or do a combination of bus and train. Expect a daytime high around 59°F in October, and nighttime lows around 42°F. Wrap up your sightseeing by early afternoon on the 13th (Thu) to allow time for the flight back home.

Things to do in Bar Harbor

Nature · Parks · Outdoors · Scenic Drive

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.