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Explore Casco Bay

Itinerary

What’s Included

Reviews

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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

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
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Lynne Voncanon
★★★★★

Views were amazing. Guides were friendly and personable. Lobster roll was delicious. I upgraded to the ebike (first time riding one) and 10/10 recommend it. I wasn’t looking for a workout. Just wanted to see the sights and enjoy myself. Portland was my favorite stop from a New England cruise.

Michael Brown
★★★★★

Five Stars to Rick (our guide) and the folks at Summer Feet Cycling. The ride was perfectly tailored to our group of nine middle aged individuals. The sights were terrific and the lobster role for lunch was the best I have ever eaten. Thanks for making our time in Maine a memorable experience.

Marsha Walton
★★★★★

Our Summer Feet cycle along the Maine coast was glorious. In early September, we had perfect weather. We cycled along breathtaking views. Then we caught our breath in quaint Maine towns and fishing villages. Each evening our luggage was waiting for us at a charming inn, where we were served breakfast before heading out the next morning. The Summer Feet staff were friendly and efficient. We will hope to plan another Summer Feet trip soon! Pedal The Coast

Lynne Voncanon
★★★★★

Views were amazing. Guides were friendly and personable. Lobster roll was delicious. I upgraded to the ebike (first time riding one) and 10/10 recommend it. I wasn’t looking for a workout. Just wanted to see the sights and enjoy myself. Portland was my favorite stop from a New England cruise.

Michael Brown
★★★★★

Five Stars to Rick (our guide) and the folks at Summer Feet Cycling. The ride was perfectly tailored to our group of nine middle aged individuals. The sights were terrific and the lobster role for lunch was the best I have ever eaten. Thanks for making our time in Maine a memorable experience.

Marsha Walton
★★★★★

Our Summer Feet cycle along the Maine coast was glorious. In early September, we had perfect weather. We cycled along breathtaking views. Then we caught our breath in quaint Maine towns and fishing villages. Each evening our luggage was waiting for us at a charming inn, where we were served breakfast before heading out the next morning. The Summer Feet staff were friendly and efficient. We will hope to plan another Summer Feet trip soon! Pedal The Coast

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