Penobscot Bay is one of the richest fishing grounds in the world, producing more of the famous Maine Lobster than any other body of water. During your six-day multi-sport adventure, you will bike, hike, and kayak in and around the Bay.
From Pemaquid Point, the center of pre-colonial commerce in the new world, To the rugged beauty of Monhegan Island and the charming towns of Rockland and Camden, You will enjoy fabulous cycling, stunning views, and a bounty of fresh food.
171 km / 106 mi
Cycle, Hike, Sail and Kayak along the Maine Coast
Explore charming towns and coastal villages
Discover hidden coves and stunning coastline
Enjoy a variety of Maine delicacies, from lobster and smoked salmon to fresh blueberries and the local favorite “whoopee pies”
Deposit $500.- pp
Easy = untrained, normal physical condition Moderate = regular cyclist, good condition Challenging = experienced, well trained
Guided = with cycling guide(s) - support van Self Guided = individual - directions+maps
40-60 km / 25-37 mi
171 km / 106 mi
Deluxe = 4-5 star hotel or excellent B&B Basic = 1-2 star hotel/motel or B&B Camping = tent, sports hall or campus
Deluxe, room & breakfast
Daily luggage transfers
14 May 2023 - 17 Sep 2023
Tour starts any Monday from Mid May to Mid-September
A minimal of 2 participants in one booking
Airport at start
Portland Int. Jetport (PWM)
Airport at finish
Portland Int. Jetport (PWM)
Prices *Please note the prices are subject to change depending availability*
Price per person / please note the prices are subject to change depending availability
If you travel alone a single supplement is charged. With some group tours you can avoid a single supplement by sharing a room with another rider.
Included / Not Included – lodging
Day 1: Discover Pemaquid Point
One of our staff will meet you at our waterfront pick-up location for the transfer to the charming village of Damariscotta. Take time to explore the town before cycling back roads to Pemaquid Point. Visit the Pemaquid Point Light and the Colonial Pemaquid Historic Site before arriving at the inn.
Cycling options: 24 miles, elevation gain: 1200 ft Meals: none, Lodging: The Bradley Inn
Day 2: To Monhegan Island
Begin your day with a quick 5-mile cycle to New Harbor and the ferry to Monhegan Island. You will lock your bikes at the ferry as you hop on the ferry. Located ten miles off the coast, Monhegan has inspired artists for decades. You can spend the day hiking the perimeter of the island for stunning ocean views and still have plenty of time to relax in an Adirondack chair and enjoy the island vibes.
Cycling: 15 miles, Meals: B, Lodging: Monhegan Island Inn
Day 3: Port Clyde to Rockland
Today you will catch a different ferry that will carry you back to the mainland and the fishing village of Port Clyde. Take time to browse the artist studios before cycling the Marshall Point Light; Forrest Gump ran here. Tonight’s destination is Rockland, home to the Farnsworth Museum of American Art and many shops and galleries.
Cycling: 32 miles, Meals: B, Lodging: The Berry Manor Inn
Day 4: Cycle to Camden and Sail
You have a lot of choices today. The ride from Rockland to Camden is only 10 miles. Camden is one of the most picturesque towns on the Maine Coast, featuring a well-sheltered harbor surrounded by hills lush with forests. In the afternoon, you sail Penobscot Bay on a classic wooden schooner.
Cycling options: 24 or 35 miles, elevation gain: 1800 ft Meals: B, Lodging: The Hartstone Inn
Day 5: Kayaking
You begin the day kayaking Camden Harbor on a guided kayak tour. You will enjoy beautiful views of the Camden Hills and Curtis Island Lighthouse. After kayaking, you will have time for lunch before an early afternoon transfer back to Portland.
A two hour Kayak tour, meals: B
*Tour itineraries are subject to change and modification based on the group, available accommodations and other unforeseen circumstances including weather, wildfires, flooding, hurricanes, landslides and/or other acts of nature. Please view this itinerary as an outline as to what to expect on this tour.
Up to five nights’ lodging, six breakfasts.
All lodging taxes and gratuities.
Hybrid bike with panniers
Detailed route notes and maps plus turn by turn navigation using the Ride with GPS app (no cellular data needed)
Daily Luggage Transfers
Sailing and Kayaking
Tour operators Souvenirs – cycling water bottle and t-shirt (available in men’s & women’s fit)
Airfare to and from the tour
Night before and night after the tour
The Bradley Inn.
Monhegan Island Inn
The Berry Manor Inn
The Hartstone Inn
Map & Routes
We feature high-quality Norco hybrid and Trek road bicycles equipped with bags and rear racks. Feel free to bring your own pedals and/or your own saddle and our guides will install them on a rental bike for you.
available for $250.- extra fee.
More information about this tour
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