Sail Away on the Eastwind Schooner
For me there is one constant in travel which plagues me nearly as much as the decision of whether to keep my hair long or to cut it shorter again. When my hair is long I dream of short hair which is easy to take care of, and when it is short, visions of glorious long curls dance through my head. Never has short hair been easy for me to take care of, and the glorious curls appear maybe once every two months. These contrasts in fortune have been my experience in travel adventures as well.
In travel I want both new exciting things to try and a vacation where I am never uncomfortable. Usually I over-romanticize travel and then get a rude awakening, as happened when I booked an experience to go horse-back riding through Tuscany. Doesn’t that sound like a romantic adventure? Instead I got put on a horse whose sole interest in life was biting the farting horse in front of her.
When this same group of girlfriends and I made plans for a July 4th vacation in Maine I was at first hesitant to suggest a new adventure. They would never forget the horse-back riding fiasco (fiasco for me, not them) and if I picked a second thing that went awry my reputation would be set forever. A lot was riding on my success this time for a new experience.
Sailing is an incurable interest of mine. Since about 18-years-old I have had five basic desires:
learn to dance
write a book
go horseback riding on hills, anywhere
get married
go sailing
Thus far I have learned to dance and ridden on a horse over hills and far away, but writing a book, marriage, and sailing eluded me.
On July 3rd, 2025, my life changed. I helped a sailor hoist the mainsail.
I was tempted to fall in love with the captain and knock out two things at once on the list, but refrained since four girls nearer to him seemed to be occupied in the same business of falling in love and as a result he was also occupied.
WELCOME TO MY DREAM
Goin’ my way, sailor?
We met the crew at the docks where the Eastwind was to set sail. It was the company’s bigger boat and we were joined by approximately 16-20 other people. The air already had a chill in it as we clutched our sweaters and our pearls and climbed aboard.
First things first the first mate, or was she the boatswain (?) asked for volunteers to help hoist the sails. Um, hello. Here I am. We had a great time with me bumbling every other grip and her doing her professional thing while entertaining all of us. She was a fabulous entertainer and in between her other duties and conversations would come over to exclaim how much I looked like her sister. There was some resemblance there but most of us thought I looked more like her.
We were free to move about the boat if we wanted and I guess I moved too quickly at one point because the middle-aged lady with the blonde hair, pictured above, gasped loudly because she thought I was going to jump overboard. I’ve thought about that moment a lot. Do some people live their lives waiting for other people to jump?
The photo above is one that I would like to frame for the adventure and beauty wall of my home. The golden light of the near-sunset spilling out over the blue water and old wood of the schooner was hauntingly beautiful. We skirted some rain clouds on the way and as a reward witnessed a rainbow over the water.
Dinner and Aperol spritzers aboard the Eastwind.
Did you know that sailor speak is real? It was glory to hear all the terms I’ve only read about in books get thrown about. I did not write them down which is why if you want to hear them you should also go to Boothbay Harbor, Maine and sail on either the Eastwind or the Applejack.
We sailed around the harbor for a few hours as the evening drew on and the blue of water and sky deepened. A moon came out to shine upon us and peace settled.
The evening touched me with its beauty. Sometimes when I don’t want to put in the effort to articulate what water and boats and cool breezes do to quiet my soul and make me feel unutterably happy it’s easier to joke about falling in love with a captain.
There is rarely a greater happiness for me than when I am on the water, any water, in nearly any kind of boat or craft. Sailboats, speedboats, paddle boards, kayaks, it doesn’t seem to matter. One of my favorite kid films is Moana because she gets it. She is drawn to the open water the way I am and her soul craves to be out there.
It’s a dream that may not be fulfilled on the old earth, but nevertheless I persist to dream it for here and the new earth. Boats bring me into heaven for just a moment and this sail was everything I wanted.
Good night friends. We anchor here.
