Arrive in Portland and ease into your Maine adventure with a relaxing walk through the charming Old Harbor district, where cobblestone streets and historic waterfront views set the tone for the week ahead. On the scenic drive to Boothbay Harbor, we may stop in Freeport—home to the iconic L.L. Bean flagship store and unique local shops. Settle in for the night in the cozy seaside village of Boothbay Harbor, your home base for the next two nights.

Overnight in Boothbay Harbor

Hop aboard a morning ferry and set sail for Monhegan Island, a rugged and remote artist colony 10 miles off the coast. Spend the day exploring scenic cliffside trails, browsing local galleries, and soaking in the island’s peaceful charm and breathtaking ocean views. In the late afternoon, we’ll ferry back to Boothbay Harbor, where you’ll enjoy a second relaxing night in this quaint coastal town.

Overnight in Boothbay Harbor

Leave Boothbay behind as we journey north to the postcard-perfect town of Camden, where the mountains meet the sea. Spend the day exploring boutique shops, harborfront paths, and the timeless beauty of this seaside gem. In the afternoon, step aboard a traditional schooner for a sailing tour along Penobscot Bay—an unforgettable way to experience Maine’s stunning coastline. Enjoy a restful evening and overnight stay in the charming town of Rockport.

Overnight in Rockport

Depart Rockport and travel to the unspoiled beauty of Deer Isle and Stonington, two of Maine’s most scenic and authentic coastal communities. Spend the day exploring the area’s quiet harbors, rocky shores, and hidden gems, where time seems to slow down. In the evening, indulge in a traditional Maine lobster dinner—a true local experience.

Overnight in Bar Harbor

Leave the quiet beauty of Deer Isle behind as we head north to the crown jewel of Maine’s coast—Acadia National Park. Spend the day exploring the park’s dramatic landscapes, from rocky shorelines and sweeping ocean views to the tranquil beauty of Jordan Pond. Wander scenic trails, visit iconic shore points, and take in the crisp autumn air as we soak up the natural splendor of one of America’s most beloved national parks.

Overnight in Bar Harbor

Rise early to witness the unforgettable sunrise from the summit of Cadillac Mountain—the first place in the U.S. to greet the morning sun. Afterward, enjoy time exploring the vibrant shops and waterfront charm of Bar Harbor before we set out on a scenic drive to Maine’s easternmost reaches. Along the way, we’ll visit Eastport and Lubec, home to some of the state’s most picturesque and remote lighthouses, including the striking red-and-white striped West Quoddy Light.

Overnight in Lubec

Journey south from Eastport to the charming coastal town of Rockport, winding through some of Maine’s most picturesque seaside landscapes. Along the way, we’ll stop at Owls Head and the quaint fishing village of Port Clyde—both known for their iconic lighthouses, rugged coastlines, and postcard-perfect views. Spend the evening relaxing in Rockport, surrounded by classic New England charm and coastal tranquility.

Overnight in Rockport Harbor

Depart Rockport and make your way back to Portland for one final coastal adventure—an exhilarating afternoon whale watch. Set sail in search of humpbacks, minkes, and finbacks as you take in the open sea and stunning shoreline views.

Group continues on to North Conway, NH for extension

Due to overwhelming interest, all participants have elected to join the optional post-tour extension, allowing the group to continue traveling together after our Maine program concludes.

Rather than ending the tour in Portland, we will continue south into the beautiful White Mountains of New Hampshire, where we will spend additional time exploring the charming village of North Conway.

Our accommodations for the extension will be at the historic Eastern Slope Inn, located in the heart of North Conway. This iconic New England property offers comfortable accommodations, walkable access to shops and restaurants, and stunning mountain scenery.

The extension provides an opportunity to experience another of New England's most picturesque destinations while enjoying additional time with fellow travelers before returning home.

Sunday – We’ll transfer from Portland to North Conway, stopping along the way to hike the scenic Ledges Trail at Pleasant Mountain in Bridgton, Maine. This moderate 5-mile hike (with about 1,200’ elevation gain) rewards us with sweeping views of the lakes and mountains before settling in for the night in charming North Conway.

Monday – Experience the thrill of the historic Cog Railway to the summit of Mt. Washington, the tallest peak in the Northeast. Above the treeline, we’ll have time to hike and explore this dramatic alpine landscape before riding the Cog back down. Enjoy the rest of the day in North Conway.

Tuesday – Our final hike takes us into the White Mountain National Forest on the Champney Brook Trail to Mt. Chocorua. This 10-mile hike (with about 1,400’ elevation gain) features waterfalls, pools, and sweeping forest trails. If conditions allow, we’ll summit Mt. Chocorua for breathtaking views.

Wednesday – We will return to Portland for one final night, before departures on Thursday.

Lodging at The Eastern Slope Inn, North Conway