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Explore Casco Bay

Itinerary

What’s Included

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2026 Dates

Memorial Day to Columbus Day

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7 Hours Approx
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Difficulty Level

Easy/Moderate - I Own Bike Shorts

Two cyclists pausing to look out over Casco Bay, Maine

Explore Casco Bay Bike Tour

You’ll begin the day with a scenic bike ride of about 17 miles, following quiet coastal roads and paths as you make your way toward the water. From there, a short ferry ride from Littlejohn Island to Chebeague carries you across the bay and onto island time.

Once on Chebeague, you’ll bike quiet island roads with wide views and plenty of space to slow down and enjoy where you are. The day wraps up with a longer, scenic ferry ride back to Portland — a relaxing finish and a chance to take in Casco Bay from the water.

Explore Littlejohn and Chebeague Islands

 

Any questions about this tour? Please get in touch. 

And if you’re looking for a longer adventure, explore our Multi-Day Cycling Tours in Maine.

 

Highlights

  • Scenic 17-mile bike ride
  • Cycling quiet island roads on Chebeague,
  • Enjoy lunch overlooking the ocean
  • A scenic ferry ride back to Portland
  • Friendly, knowledgeable local guides
Pricing

Tour Price: $245 per person

2026 Dates

Daily Memorial Day to Columbus Day
(no Sunday trips)

Pickup/Drop Off
Tours depart at 9:00 am from the Portland Encyclepedia (located at 6 Commercial Street) and usually return around 3:00 pm.

Casco Bay Cycling Tour Itinerary

Daily Tour

Leaders will meet you at the Portland Encyclepedia at 9:00  am to fit you for your bike.  The morning ride will take you through the affluent neighborhood of Falmouth and then on to Littlejohn Island, a local favorite.

A short ferry ride carries you to Chebeague Island, the largest island in Casco Bay.  Chebeague’s quiet roads, quaint homes, and ocean views offer a wonderful experience of island life.  We have time to explore the island’s quiet roads and many beaches.  In the afternoon, we return to Portland via the mail boat as it cruises through Casco Bay.

Participants should be comfortable cycling 25 miles.  Please wear athletic clothing and close-toed shoes.

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

Join us for a relaxed day exploring Casco Bay

 

What's Included

  • Bicycle and Helmet rental
  • Scenic Ferry Ride
  • Lunch
  • Experienced Guide(s) Local Guides
  • Rear Bike Bag to hold your extra layer, water bottle, and essentials
Book Now
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- Teresa L
★★★★★

Outstanding tour! It was a beautiful ride. We enjoyed our guide Rick’s company and his attention to detail. It’s been a highlight of our vacation.

- Brandyn F
★★★★★

Art was the best tour guide, told many funny stories! 

- Judy M
★★★★★

Wow what a nice cycle ride around Portland, Maine. My bike was perfectly managed as in mechanical. Our tour guide gave us considerable interesting information about all sorts of things. It was a soul expanding experience. 

- James O
★★★★★

Great cycle tour of Casco Bay and great local guide, Emma, who was very kind, friendly and knowledgeable about the area.

Frequently asked questions

Is Explore Casco Bay right for me?

We certainly think so — especially if you enjoy variety. This tour blends 17 miles of cycling with time on the water for a well-balanced day.

There are actually two boat rides … a short ferry from Little John Island to Chebeague Island and a longer ride from Chebeague back to Portland … and yes, both boat rides are included in your trip cost.

Seeing Casco Bay from both land and water creates a richer, more complete experience than doing either as a stand-alone experience.

We have been guiding bike tours for over 25 years, We design days that flow naturally. Nothing feels rushed, and every transition is thoughtfully planned.

Couples and travelers who want an active day that still leaves time to relax and take it all in.

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