Discover Penobscot Bay Multi-Sport

Booking Form
Contact Us
Full Name*
Email Address*
Number of People*
Your Inquiry*
* I agree with Terms of Service and Privacy Statement.
Please agree to all the terms and conditions before proceeding to the next step

Book Now

Save To Wish List

Adding item to wishlist requires an account

  • 5 Days
  • 2024 DatesMay - Oct
  • Difficulty LevelModerate - I Own Bike Shorts

Discover Penobscot Bay on Our Multi-Sport Adventure

Renowned as one of the most fertile fishing locations worldwide, Penobscot Bay outshines its counterparts in the production of the world-famous Maine Lobster. This Bay provides the scenic backdrop for our exciting five-day multi-sport adventure, where you’ll experience a blend of biking, hiking, and kayaking.

Beginning your journey at Pemaquid Point, a significant hub of pre-colonial commerce in the New World, you will immerse yourself in the historical echoes of Maine’s past.

Pedal, Hike, and Kayak through the Natural Beauty of Maine’s Coastline

Your journey continues to the rugged allure of Monhegan Island and through the charming coastal towns of Rockland and Camden. Along the way, you’ll indulge in unforgettable cycling experiences, absorb stunning panoramic views, and enjoy plenty of fresh local food.

With each pedal, step, and paddle, you’ll uncover Maine’s scenic coast’s diverse beauty and rich history through this unparalleled multi-sport adventure.

If you have any questions, please get in touch

What's Included

  • Four nights’ lodging
  • All lodging taxes and gratuities
  • 4 Breakfasts
  • Detailed route notes and maps plus turn by turn navigation using the Ride with GPS app (no cellular data needed)
  • Daily Luggage Transfers
  • Emergency Support
  • Hybrid bike with panniers
  • Round trip ferry Rockland to Vinalhaven
  • Summer Feet Souvenirs – cycling water bottle and t-shirt (available in men’s & women’s fit)
  • Ferry Transfers
  • Sailing and Kayaking


  • 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”

Pick Up/Drop Off

Portland, Maine (PWM)

2023 -2024 Dates

Tour starts any Sunday from Mid May to Mid-October


$2295.00 per person double occupancy



Day 1Discover 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
  • Lodging: The Bradley Inn
  • Meals: None

Day 2To 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.

Day 3Port 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.

Day 4Cycle 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
  • Lodging: The Hartstone Inn
  • Meals: Breakfast


Day 5Kayaking

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: Breakfast

Please Ask a Question or give us a call at 1.866-857-9544 if you have any questions.


Related Tours

Pedal the Coast

Boothbay to Bar Harbor Self-Guided

7 Days
The coast of Maine offers amazing diversity as it travels almost 400 hundred miles from Kittery to the Canadian border.
Maine’s Gold Coast

Maine’s Gold Coast Tour

6 Days
Your guides lead you through Acadia National Park, around a picturesque island. There’s plenty of time off-bike to taste, touch, see and do.