Day 2: Island Hopping Maine Style!

I had this great idea that while my  husband and I were on vacation, we should try and visit as many of the islands as possible. I looked into what it would cost to take a ferry ride with our car to each island and that started to get a little expensive. Hence where my great idea comes in! Online I found this little bike rental place called Summer Feet Cycling, and decided on the ‘Explore Casco Bay’ tour. They have a few other tours available as well, one being a ‘Bikes and Brews’ tour for all of you who love sipping on some beer from craft breweries!

Our tour started out in the morning and was approximately 20 miles in length with a few hills. We first took a ferry ride thru Casco Bay and made a few stops on a couple islands en route to Chebeague Island. We were filled with some history and fun details with the islands as we passed them. The Casco Bay Islands in Maine are sometimes called the Calendar Islands because at differing times of the year there can be up to 365 islands, which is said that you could explore a different island each day of the year.

One major stop en route to Chebeague Island was at Diamond Cove. There is a beautiful restaurant there that was having a delivery made. For someone from the Midwest, it was a very different experience seeing a delivery made via boat vs via semi!

Once we docked at Chebeague Island, we got ourselves prepared for our mini RAGBRAI (I say this because RAGBRAI was actually happening at the exact same time we were on vacation. And for those of you who are wondering what RAGBRAI is, RAGBRAI stands for Register’s Annual Great Bicycle Ride Across Iowa and it is a week long biking event in the state of Iowa where you start on the western side of the state with your back tire dipped in the Missouri River and end the week on the eastern side of the state with your front tire dipped in the Mississippi River). Once set, we began our little island adventure and made a pit stop by the only post office on the island. I couldn’t get over how lush and green all the trees were, all the beautiful flowers that were present (most of the flowers they had in Maine we also have in Iowa due to the fact that many plants are hardy meaning they can sustain up to -40 degrees F and are annuals).

We cruised the 5 miles around the island and made a little stop near the islands edge to take a look at the gorgeous view. I cannot begin to explain how peaceful, gorgeous, and secluded this place was. I was falling in love with Maine and for this reason!


We made our way to Chebeague Island Inn where we had lunch. This cute Inn was beautiful. It had such a quaint feel to it with some of the best views of the ocean. There was also a beautiful golf course right next door. So if you’re a big golfer and want a quiet little get-away, this just may be your place! PS, they had the BEST lobster rolls around.

Check out that view at Chebeague Island Inn!

At 2 pm sharp, we were ready to take yet another ferry ride over to Cousin’s Island where we would continue our trek back to Portland. Once on Cousin’s Island, we slowly pedaled our way thru the island, made a pit stop at a church/day care to use the restrooms. (You use them when you can since there are no other bathrooms readily available!) The cool thing with this island is that it is connected to the main land via bridge. As we crossed that bridge onto the mainland we were technically in Falmouth, which is north of Portland. We got to see some beautiful communities in that area with beautiful homes. Not to mention some decent sized hills that we conquered in the process!

A little market available to residents in Falmouth Foreside

We crossed over another bridge which led us into Portland. We were able to ride our bikes along a flat bike path all the way to downtown Portland where we started. The bike path is amazing, well used, and is such a great way to keep the city of Portland an active community. Which, by the way, the city of Portland is such a dog friendly community! I love when towns/cities are dog friendly and accommodate to our furry little friends. The bike path also took us right past Portland Paddle one more time, which was a great reminder of all the fun we had the day before!


We loved the views that this tour gave us, especially the different way of living when it comes to island living. The 20 miles of pedaling and my butt being on a bike seat for those 20 miles, well, I’ll just choose to ignore those feelings!

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