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Writer's pictureDaniel Jasinski

Bailey Island, Maine: Dog-Friendly Boat-day

Updated: Sep 9, 2023

Bailey Island is the kind of place where you can experience true silence. Located about an hour north of Portland, ME, it is a remote little island accessible by car.

Bailey Island is just one in the series of islands in this area, but as you can see above, it is the most remote. The Bailey Island Bridge is reported to be the only granite crib-stone bridge in the world, built solely by stacking slabs of granite held together by gravity. The bigger island is Orr's Island, and the greater town is called Harpswell. We visited Bailey Island for two years in a row for Memorial Day after finding this gorgeous little tiny home posted right on a cliff, with a fantastic view. The perfect place to unplug.

The Sand Dollar, Bailey Island, Maine

The coolest part of this particular place is that if the weather is clear, you can see Mt. Washington (the highest peak in the Northeastern US) in New Hampshire, over 100 miles away.

Mt. Washington Sunset view from Maine

Going to Maine on Memorial Day is hit-or-miss activity, mainly because they weather is still classic New England, where you can get all four seasons in one-week. It can go from crystal-clear...

Perfection

...to super hazy...

Hazy Day

Regardless, staying in the place feels like floating on the water; all you can hear is the wind, the waves, and the birds. Truly peaceful. Given the remote-location, we were unsure if we would find any sort of adventure beyond some (really great) hikes around the island, but we were in luck! We found an awesome boat company called Casco Bay Sightseeing, and they were more than happy to have us bring Hazey on the bay tour of the islands. Our captain, Len, was a local of the area, and he knew all the facts. Despite the weather not being 100% cooperative...

Blankets provided by Captain Len

...we had a great time! There is a lot of history to the islands.

"You better not look at Hazey!"

I made sure to keep my eye on them.

How many seals to do you see staring at you?

There were lots of pups playing around as well; it was so cute! The answer is 4 (look closely). We made the best of this hazy, cool day on our island adventure.

There are plenty of restaurants around and a ton of other things to do around the area.


Yvonne-spiration for this trip: 1000 Island Adventures When searching for a place to get away, I always look to Yvonne's Travel for inspiration, but in this case, it was based on one of my favorite memories.


When I was around middle-school age, my mom pulled off some of the best vacations ever. One of her biggest hits was group-camping in 1000 Islands, NY. These trips consisted of 3-6 families, all with kids around the same age, camping together in an amazing state park. Pontoon-boat rentals would often be a staple to these trips, but there was a catch. My childhood dog, Copernicus (Copper), was not allowed on the boat. Obviously, we weren't going to let that stop us from having fun. So we developed a plan. I would take Copper and put him inside my back-pack with kielbasa to keep him busy. Everything was going swimmingly, but the dock attendant took quite a long time to help us get off the dock, and Copper was beginning to grow impatient. I remember signaling my mom that he was getting restless, and she burst into song! Now we have a whole group of adults singing sailor songs like Yo, Ho! (A Pirates Life for Me). Long story short, we got away with it and laughed about it for the whole trip and for many years afterward, and I will never forget it. Oh, and as I recall, we almost sank that boat. This ties into our Bailey Island experience because although it was seemingly perfect, there was one major catch: Hazey was not actually allowed at the Sand Dollar. We almost never risk it when it comes to accommodations, but this place was too perfect not to go for it. So the first year, we are being super careful to watch out for any owners, property managers, etc., and keeping all signs of Hazey's presence to a minimum. I took a page out of the playbook above to ensure the mission's success. The last day, when we're checking out, and it was raining, the owner decided to show up and mow the lawn. Yikes! We hide all the evidence and keep Hazey entertained as we quickly pack up the car. How do we get Hazey from inside the house to the car without this man seeing her? Yep, you guessed it, back-pack and snacks! We put as much good stuff in my pack to keep Hazey quietly snacking so we could zip it up and carry her to the car and make our escape. Of course, this guy decides to spark-up a conversation with us while Hazey is on my back, zipped up and rustling around for treats at the bottom of the bag. Looking him right in the eyes was fun, and acting like nothing was out of the ordinary. The whole time, I thought about that 1000 Islands mission, and this, too, was a success. We were invited to renew our reservation for the following year - and we did. Next time we will find an actual dog-friendly place to stay. Hazey didn't really appreciate the oasis as much as we did...


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