Portland Schooners Co.

“Sailing a boat calls for quick action, a blending of feeling with the wind and water as well as with the very heart and soul of the boat itself. Sailing teaches alertness and courage, and gives in return a joyousness and peace that but few sports afford.” ~ George Matthew Adams

Two years ago, to celebrate my old age, my best friend took me on a sail boat. By sail boats, I mean those old time Schooners. The type of boat that makes you feel like you are in a scene from Pirates of the Caribbean. Larger then life, so real that it takes you back to Black Beard, corsets, and  high sea larceny.


I had seen them person from the distant shore and of course in movies and television. But much to my shame this mermaid, had never been on one. I know! It was criminal! It was something which needed to be rectified, and my best friend did just that.


Sailing out of Portland Harbor, the windjammer known as Wendameen set sail, giving us picturesque views of Casco Bay, light houses and the islands that inhabit the Maine Coast.  It was instant love, as they hoisted the sails (even getting my chance at the tiresome job) letting the wind take us whichever which way she so chose.


Since that first mind-blowing mermaid adventure, it has become a birthday tradition. This year was no different, despite my friend having moved to Bar Harbor this past year. She travelled down and I travelled across to make the journey, this time on the Windjammer called Bagheera.


We began our morning as any hip long lost mer-fashionistas would; boozy brunch at the Front Room which is near East Prom. After reuniting, enjoying some excellent food and each others company, we made our way down to the Harbor to buy tickets. It was a cloudy, slightly blustery day, – which despite the cooler temperatures – at least would make for a great day of sailing.

Perhaps Neptune was taking pity on us, or Tiffany and I were channeling our inner mermaids and had the mystical powers to prophesize. Only an hour before, at brunch we had been talking about renting our own private Schooner in a very Kim K move. Fortunately for us, other people were turned off by the weather and we ended up with our very own private sail.

A boat that fit forty-two people set sail with just the crew and the two of us. It was pure mermaid heaven.


With the wind giving strong attitude, we made it all the way out past Portland Headlight, viewing the light house from a different, but still stunningly spectacular, perspective.


Through out the sail, the captain and crew were incredibly attentive, talkative and full of knowledge; from the history of Schooner, to stories about the harbor and surrounding islands. Even sharing details of a private island with its’ very own fort!

Tiffany and I both looked at each other, laughing and joking that yes we would totally buy it with all our millions.

“Life goals,” as they say.

It was an incredible day, one I can not wait to do again.


This was my third sail with this company, and while each time was different in terms of how far we sailed and quantity of people. Each time has become more and more enjoyable. The staff is absolutely phenomenal. You can tell they are passionate, not only about sailing, but about making sure our experience is second to none.

I can not wait for our next trip…Is it next year yet?


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10 thoughts on “Portland Schooners Co.

    1. Hehe thanks:) I agree! I grew up just over the boarder in New Hampshire, but I feel like a Mainer. Two Lights is by far my favorite place! Thanks for reading!

            1. Fort Williams is so cool! I wish you it wasn’t so cordoned off though. I am hoping to go to George’s Island this weekend and explore Fort Warren which is really cool!

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