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.

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.

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 charming Camden.

Depart Camden 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 bake by the water in Stonington—a true local experience. Settle in for the night surrounded by the serene charm of Deer Isle.

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.

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.

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.

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. After the cruise, enjoy a relaxing evening at a conveniently located hotel near the Portland airport, resting up before your journey home.

After a memorable week exploring Maine’s stunning coastline, it’s time to say goodbye as you depart from Portland International Jetport (PWM). Take with you the unforgettable memories of charming seaside towns, rugged landscapes, and warm New England hospitality—until your next adventure!