Nine-day Portland to Portland Itinerary
Portland, Maine, is outdoorsy and artsy, full of activities and welcoming locals. This Portland to Portland itinerary begins and ends in Portland at the Fore Points Marina.
Days 1-3 | Portland
As you begin your journey, take a cycling tour and view rustic lighthouses and the rugged Maine coastline. Summer Feet Cycling Adventures provides a tour that stops at Fort Williams. Here you can tour Portland Headlight, explore the forts, and stroll along the cliff walk. Alternatively, venture south and take a walk around Kennebunkport.
In the afternoon, stroll the beaches or the cobblestone streets and boutiques of the Old Port. In the evening, watch the sunset from the top of Bayside Bowl.
The next day, ride the Maine Brew Bus to sample local beers, take in the culture, and meet local brewmasters. Afterward, dine at one of the town’s award-winning restaurants. Then, take in a concert at Thompson’s Point, a casual outdoor arena featuring national acts and local beers.
On day three, go surfing at Higgins Beach or hire an experienced guide for white water rafting. For a more laid-back experience, have a leisurely float down the Saco River.
Day 4 | Boothbay Harbor
Boothbay Harbor (35 NM from Portland) is a beautiful and quaint mid-Maine stopping point between Casco Bay and Penobscot Bay. Its idyllic flat waters are great for sailing.
Be sure to visit the lovely village of Boothbay Harbor. Visit the Coastal Maine Botanical Gardens, the largest public gardens in the country, where you can arrive by land or tender. Afterward, visit the Boothbay Craft Brewery at the Watershed Tavern. Later, explore the village.
Days 5 and 6 | Bar Harbor
Continue to Bar Harbor. Bar Harbor (77 NM from Boothbay Harbor) is a town on Mount Desert Island along Maine’s Frenchman Bay. It is a gateway to the Acadia National Park. Towering over the park, Cadillac Mountain has trails and views of the town, the bay, and the Cranberry Islands. From the town pier, the Shore Path winds along the bay overlooking the Porcupine Islands.
Things to do:
- Hike, bike, and enjoy the fantastic scenery. Spend the evening strolling the town, or go to the Improve Acadia for a show.
- Take a helicopter tour with Scenic Flights of Acadia for a unique perspective of lighthouses, the national park, and Somes Sound.
- Go to the Great Maine Lumberjack Show with axe throwing, log rolling, pole climbing, and more.
- Taste local oysters.
Day 7 | Rockland
As you cruise back to Portland, spend the night at another charming mid-coast village. Dock at Journey’s End in Rockland, a classic family-operated marina adjacent to Main Street.
Things to do:
- Take a morning stroll through the town.
- Visit Owl’s Head Transportation Museum full of vintage vehicles and aircraft.
- Dine at Cafe’ Miranda.
Days 8 and 9 | Portland
Return to Portland and spend time relaxing and exploring.
Things to do:
- Merrill Auditorium
- Portland Ballet
- On the first Friday of each month, walk the city to view famous and local artists and rising designers from the Maine College of art.
- Try Paddle Board Yoga
- Kayak through Casco Bay.
Day 10 | End Your Portland to Portland Itinerary
Disembark for your flight home.
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