2026088 Coastal Maine

06/09/2026-06/12/2026 Tue-Fri Trip# 2026088

Coastal Maine

Embark on a classic Maine coastal escape filled with ocean breezes, iconic lighthouses, maritime history, and picture-perfect seaside villages. Your getaway begins with a three-night stay at the Anchorage by the Sea in Ogunquit—an oceanfront gem set along the famed Marginal Way—before days of hand-picked experiences unfold. Marvel at the dramatic beauty of Portland Head Light, explore the working waterfronts and boutiques of Portland, discover Freeport’s beloved shops, and dive into Maine’s storied shipbuilding heritage at the Maine Maritime Museum. Wander the charming streets of Kennebunkport, ride the rails at the Seashore Trolley Museum, and feel the salt spray aboard an authentic lobster cruise from Perkins Cove. With a blend of scenic touring, coastal culture, fresh Maine flavors, and unforgettable photo stops—ending at the iconic Nubble Light—this tour captures the very best of “the way life should be.”

Day 1

Tuesday, June 9 - Welcome to Maine
Welcome to Maine-where the state motto proudly declares, "the way life should be." Cross over the Piscataqua River into the charming seaside village of Ogunquit and arrive at the Anchorage by the Sea, your oceanfront home for the next three nights. This beloved coastal resort sits directly along the famed Marginal Way, offering sweeping views of rocky cliffs, sandy coves, and the endless Atlantic. Its beautifully landscaped grounds, inviting Adirondack chairs, and gentle sea breezes set the perfect tone for a relaxing coastal escape. Settle into your room and take time to stroll the oceanside paths as your Maine adventure officially begins. Tonight, enjoy the evening at leisure to dine at your resort or one of the many restaurants in the area.

Day 2

Wednesday, June 10 - Portland Head Light, Portland City Tour, Freeport & Maine Maritime Museum
After breakfast, meet your local Step-On Guide and set out along the coast for your first stop: the iconic Portland Head Light, one of the most photographed and celebrated lighthouses in the country. Commissioned by George Washington and perched dramatically on a rocky bluff overlooking Casco Bay, this is a perfect place for photos and fresh ocean air. Next, enjoy a guided tour of Portland, Maine's largest city and the cultural heart of the coast. Explore its storied waterfront, boutiques, and historic lanes while hearing stories from its early maritime past. Continue north to Freeport, home of the world-famous L.L. Bean flagship store and a delightful collection of Maine-inspired shops. This afternoon, travel to Bath for a fascinating visit to the Maine Maritime Museum, celebrating Maine's rich shipbuilding heritage. Return to Ogunquit to freshen up for a planned dinner, followed by an evening performance at the Ogunquit Playhouse.

B, D

Day 3

Thursday, June 11 - Kennebunkport, Seashore Trolley Museum, Perkins Cove & Lobster Cruise
This morning, meet your Step-On Guide and depart for the charming coastal village of Kennebunkport. Enjoy a guided tour featuring oceanfront views, including a scenic drive past Walker's Point. Next, visit the Seashore Trolley Museum, the oldest and largest electric railway museum in the world, and enjoy a relaxing trolley ride through the Maine Countryside! Continue into Dock Square for time to explore and enjoy lunch on your own. This afternoon, head to Perkins Cove, one of the most picturesque harbors on the Maine coast. Board Finest Kind Cruises for an authentic lobstering experience and lobserbake. Afterward, enjoy leisure time before returning to the hotel.

B, D

Day 4

Friday, June 12 - Picture Stop at Cape Neddick Light & Homeward Bound
After breakfast, begin your journey home with a visit to Cape Neddick Light, affectionately known as "the Nubble." Perched on its rugged offshore island and surrounded by crashing waves, it is one of the most photographed and beloved lighthouses in the world-an unforgettable final glimpse of Maine's stunning coastline. Meals - Breakfast

B=Breakfast, D=Dinner

Tour Inclusions:

Three nights’ accommodations at the Anchorage by the Sea – Tower Rooms

Three breakfasts

Two dinners, including a traditional Lobsterbake

Lobster cruise experience

Evening performance at the Ogunquit Playhouse

Visits to Portland Head Light

Guided tour of Portland

Visit to Freeport & LL Bean

Admission to the Maine Maritime Museum

Guided tour of Kennebunkport