You will enjoy fabulous cycling, stunning views, and a bounty of fresh food. 
Discover Penobscot Bay multi sport
During your six-day multi-sport adventure, you will bike, hike, and kayak in and around the Penobscot Bay.

Discover Penobscot Bay multi sport

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. 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.

Highlights

  • 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”

Details

TypeHybrid bike
Duration5 days
LevelModerate
SupportSelf guided
Daily distanceDaily choise of mileage options
LodgingHotels
BicycleIncluded, E-bike extra fee
MonthMay, June, July, August, September, October
StartPortland, Maine
FinishPortland, Maine
States or countryMaine
Airport startPortland Int. Jetport (PWM)
Airport finishPortland Int. Jetport (PWM)

Starting from $ 2,295.00

*Please note the prices are subject to change depending availability *

Persons number of persons
Tour date
Itinerary
Bicycle
Lodging
Included / not included
Pricing / Tour dates
Conditions

Itinerary

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: 26 miles, elevation gain: 1437 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: 3 miles, hike 1.5 miles Meals: Breakfast, 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, elevation gain 1,537 ft Meals: Breakfast, 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: 10 -32 miles, elevation gain: 692-2,319 ft1800 ft Meals: Breakfast, Lodging: The Harbor House

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: Breakfast

* This is a general itinerary. Tour itineraries are subject to change based on the group, available accommodations and other unforeseen circumstances such as the weather, local conditions, government intervention, that may affect the quality of the trip and/or safety of the participants. Please view this itinerary as an outline as to what to expect on this tour.

Bicycle

Hybrid bike with panniers included
E-bikes available for $250.- extra fee.
Feel free to bring your own pedals and/or your own saddle and our guides will install them on a rental bike for you.

Lodging

Discover Penobscot Bay multi sport

The Bradley Inn.
Monhegan Island Inn
The Berry Manor Inn
The Blue Harbor House

Included:

  • four nights’ lodging, four 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
  • Emergency Support
  • Ferry Tickets to and from Monhegan
  • Round trip ferry Rockland to Vinalhaven
  • Sailing and Kayaking

Not included:

  • Airfare to and from the tour
  • Night before and night after the tour

Pricing / Tour dates

Tour price 2026 from: $2295.-pp. single fee ask for price
Extra fee E-bike rental $250.-
Tour date 2026:
Tour starts any Sunday from Mid May to Mid-October

Conditions

Deposit $500.- pp
The deposit payment for a tour must be paid within two weeks after the booking is confirmed.
The remaining payment is due 90 days before the start of the tour.
For tours that are booked within 90 days before the start of the tour you will pay 100% of the tour price

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