Discover Penobscot Bay Multi-Sport


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  • 5 Days
  • 2023 DatesMay - Oct
  • Difficulty LevelModerate - I Own Bike Shorts

Tour Overview

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. 


What's Included

  • Five nights’ lodging
  • All lodging taxes and gratuities
  • 5 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 Bar Harbor to Winter Harbor
  • Summer Feet Souvenirs – cycling water bottle and t-shirt (available in men’s & women’s fit)
  • Ferry Transfers
  • Sailing and Kayaking

Pick Up/Drop Off

Portland, Maine (PWM)


  • 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”

2023 Dates

Tour starts any Monday from Mid May to Mid-September


$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


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