Sample Itineraries

For your stay in Maine

There is so much to do in and around Freeport!  The itineraries here are to provide some ideas.  Choose what suits you best.  We also have plenty of other ideas, so please ask.

If you have 3 days to vacation in Maine:

Arrive in Freeport and plan on spending at least 2 days here to wander the streets, shop at L.L. Bean (open 24-hours a day!), and our other retail stores and outlets; hike beautiful Wolfe’s Neck State Park; enjoy a scenic cruise from the harbor; visit the Freeport Historical Society; relax to a wonderful dinner and return to the James Place Inn for a good rest.

On Day 3, travel just 15 minutes to Portland to explore the Old Port’s fine shopping and wonderful architecture.  Perhaps take a cruise on a mailboat from Casco Bay Lines – a great way to see the surrounding islands.  Or take a ferry to Peaks Island for a look at how islanders live.  This is ideal if you are looking for a slower, more relaxed pace.  Whale-watching cruises are also available from Portland or Boothbay Harbor (just 45 minutes north).  Enjoy one of the many great restaurants here or head back to home-base in Freeport for dinner and and evening stroll.

If you have 5 days to vacation in Maine:

Follow the itinerary above for the first 3 days.  On your fourth day, drive north on U.S. 1 and visit Brunswick, jut 10 minutes away.  Stroll the streets of this delightful college town, home to Bowdoin College.  There are wonderful shops to enjoy, including several great antique stores and fine galleries.  Enjoy lunch at “Fat Boys,” a local favorite for fried clams, lobster rolls, and other Maine treats.  After lunch another ten minutes north on U.S. 1 will bring you to Bath, home of the Maine Maritime Museum.  This is a must-see for a wonderful presentation on ship building and history.  After your visit here, enjoy the charming town of Bath and a nice meal at one of the local spots.  Return to Freeport for an evening stroll and perhaps a concert in the L.L. Bean Discovery Park, free every Saturday night between mid-June and Labor Day weekend.  Or catch a performance of the Mainse State Theatre on your way back through Brunswick.

On your fifth day, head north again to visit Reid State Park, where you can climb up the ledges and watch the waves crash on the rocks below.  Head on to the delightful town of Boothbay Harbor.  Visit the beautiful Botanical Gardens, browse the antique shops and art galleries or enjoy some time on the water with a whale sightseeing cruises or Puffin cruise.  Next, travel just a few miles fruther north to Wiscasset and enjoy a lobster roll at “Red’s Eats.”  These are the best in Maine, we think!  They are well worth the wait and the view along the river is delightful.  Head back to Freeport and the James Place Inn to relax before moving on tomorrow.

If you have 7 days to vacation in Maine:

Take a day to relax and enjoy one of our beautiful beaches.  We have several to choose from, from our local Winslow Park, less than 10 minutes away, or the spectacular Popham Beach, just 35 minutes north. Pack a picnic lunch and relax to the sound of the waves and the smell of salt air.  Want a little more action at your beach?  The Old Orchard Beach provides arcades, a boardwalk, and great people watching, not to mention pizza by-the-slice and fried dough!

For your last day, enjoy a tour of the lighthouses.  There are many to see within easy driving distance.  Portland Head Light is at Cape Elizabeth, just south of Portland.  Two Lights lighthouse may also be seen here.  Enjoy the streets of Portland yet again, visiting the Portland Museum of Art, Victoria Mansion, and Wadsworth Longfellow House.  Enjoy more lobster and seafood before moving on.