10 days in Maine Itinerary

10 days in Maine Itinerary

Created using Inspirock Maine trip planner
Make it your trip
Fly to Boston, Bus to Portland
— 1 night
Old Orchard Beach
— 2 nights
— 1 night
— 3 nights
Bailey Island
— 2 nights


Portland — 1 night

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.
Kick off your visit on the 9th (Sun): enjoy the sea views from Portland Head Light and then admire the masterpieces at Portland Museum of Art.

To see reviews, other places to visit, photos, and more tourist information, read our Portland day trip planner.

Phoenix to Portland is an approximately 8.5-hour combination of flight and bus. You can also drive; or do a combination of bus and train. The time zone difference when traveling from Phoenix to Portland is 2 hours. Traveling from Phoenix in October, expect Portland to be cooler, temps between 62°F and 43°F. Wrap up your sightseeing on the 10th (Mon) early enough to drive to Old Orchard Beach.
Neighborhoods · Museums · Historic Sites · Breweries & Distilleries
Side Trip

Old Orchard Beach — 2 nights

Old Orchard Beach is a town and census-designated place (CDP) in York County, Maine, United States. Kick off your visit on the 10th (Mon): browse for treasures at Arundel Antiques.

Discover how to plan a Old Orchard Beach trip in just a few steps with Inspirock's itinerary builder.

Old Orchard Beach is very close to Portland. October in Old Orchard Beach sees daily highs of 62°F and lows of 43°F at night. You'll have a few hours on the 12th (Wed) to wrap things up before traveling to Hallowell.
Parks · Shopping · Wildlife · Outdoors
Side Trips

Hallowell — 1 night

Hallowell is a city in Kennebec County, Maine, United States. On the 12th (Wed), stop by Scrummy Afters Candy Shoppe, then admire the landmark architecture of State Capitol, then take an in-depth tour of Maine State Museum, and finally steep yourself in history at Fort Western. On the 13th (Thu), you'll have a packed day of sightseeing: pick up a one of a kind souvenir at Hallowell Antique Mall, snap pictures at Two Cent Bridge, and then explore the world behind art at Colby College Museum of Art.

To find where to stay, reviews, traveler tips, and more tourist information, read Hallowell online trip maker.

You can drive from Old Orchard Beach to Hallowell in 1.5 hours. Another option is to drive. In October, daily temperatures in Hallowell can reach 60°F, while at night they dip to 43°F. Finish up your sightseeing early on the 13th (Thu) so you can go by car to Jonesport.
Museums · Shopping · Historic Sites
Side Trips

Jonesport — 3 nights

Jonesport is a town in Washington County, Maine, United States. Kick off your visit on the 14th (Fri): immerse yourself in nature at Roque Bluffs State Park, enjoy the sand and surf at Jasper Beach, and then step off the mainland to explore Machias Seal Island. On the 15th (Sat), you'll have a packed day of sightseeing: step off the mainland to explore Great Wass Island Preserve, then experience rural life at Wild Blueberry Land, and then learn about winemaking at Catherine Hill Winery.

To find maps, photos, where to stay, and tourist information, refer to the Jonesport trip itinerary builder tool.

Drive from Hallowell to Jonesport in 3 hours. Alternatively, you can drive. In October in Jonesport, expect temperatures between 59°F during the day and 42°F at night. Finish your sightseeing early on the 16th (Sun) so you can drive to Bailey Island.
Parks · Nature · Wildlife · Outdoors
Side Trips

Bailey Island — 2 nights

Start off your visit on the 16th (Sun): look for gifts at Land's End Gift Shop, then hike along Giant's Stairs Trail, and then snap pictures at Bailey Island Bridge.

To see ratings, more things to do, other places to visit, and tourist information, you can read our Bailey Island trip site.

Drive from Jonesport to Bailey Island in 4 hours. Alternatively, you can drive. In October, plan for daily highs up to 62°F, and evening lows to 43°F. You'll set off for home on the 18th (Tue).
Outdoors · Parks · Trails · Shopping

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.