Basic Sail Training for Women

Taught by Women for Women

Welcome Aboard!

Join us and spend 3 days and two nights aboard our 36’ sail training sloop Brightside sailing along the Maine Coast, anchoring each evening and learning to sail in a hands-on, immersive, supportive environment. Whether you own a boat or not, here is a program to increase your self-reliance, self-confidence, and courage both on and off the water.

Friday 1 p.m. thru Sunday 5 p.m South Freeport, Maine
Cost: $795

June 20 to 22, 2025
June 27 to 29, 2025

In the company of other women, you will develop your sailing skills practicing operating a 36’ fiberglass sloop and its inboard diesel engine, handling sails, piloting, managing the dinghy, predicting the weather, learning safety procedures, rigging, sail trim, maneuvering under power and sail, right of way, mooring, anchoring and practical navigation using electronic and paper charts. SV Brightside has eight comfy bunks accommodating four students, a USCG licensed Captain, and a deckhand/educator.

Traditionally, sailing has been a male-dominated sport with women in support roles punctuated by a few rare examples of amazing women sailors (Cole Brauer or Google Kirsten Neuschäfer or watch the movie Maiden). Let’s follow their lead!

Perhaps you’ve had some experience on sailboats and want to build your competence and confidence. Maybe you’re new to sailing but eager to learn how you can go cruising. Maybe you have been sailing for decades. Whatever your experience, you are welcome aboard!

We’ll be here together, as women, to hopefully sail beyond some of our perceived limitations. We begin by acknowledging and honoring our authentic feelings and vulnerabilities and then holding ourselves with genuine care and self-compassion. From there, we stand up to each challenge with courage and resilience, celebrating our successes with pride and humility. With this foundation, we’ll step into our roles aboard and we’ll connect with ourselves, each other and the wider environment of water, sky, and the natural world. We’ll collaborate, co-create, and playfully engage with it all!

Reach out on the form below to let us know your interest.

Photos copyrighted (c) by Amy Wilton Photography

To find out more, fill out this form to tell us something about yourself and we’ll get back to you.

Can you say EMPOWERMENT?


Read what some women have to say about our weekends, and scroll down for even more pictures.

"I learned a ton and had lots of fun and laughs with our mighty crew of four intrepid women plus very capable Captain and First Mate. This program taught me more in a weekend than I have learned in my many hours on sailboats with various partners. Sailing Into Your Strength women's sail training through Sailing Ships Maine is a bad ass program." —JoAnn

"I would never have asked to take the helm and was pleasantly surprised when encouraged to do so. It was empowering and it helped after I had seen the Navionics course and the depths and saw the day before what to look out for. I had an angel at my shoulder reminding me of things, too. So, I felt surrounded by gentle encouragement and made to feel that sailing was complex but could be broken down to its parts and then compiled again during the voyage. It was like breathing in and breathing out." —Carol

"Thank you for the amazing experience as a participant in the Sailing into your Strength weekend. You offered a skillful blend of navigational instruction, the opportunity for hands-on time at the helm, and discussion regarding claiming our competence and experience to feel more confident in a role of leadership on the boat. For me personally, the all-female environment was particularly supportive for gaining confidence having grown-up in a patriarchal sailing family where I was encouraged to relax, tidy-up, prepare food and function as a first mate but rarely encouraged to consider navigation, boat maintenance or the other responsibilities of the captain." —Willow

"This trip gave me a sense of joy and peace that I had been longing for. Honestly, I cried a few times on my drive home as I processed how this trip touched me on an emotional level -- facing fears and self doubt, feeling the bliss of being on the water, finding a place that feels like home in a place so unfamiliar. Before it was over, I kept circling the question of how to do this again and how long it may take me to get 365 days at sea." —Emily

"That was such an adventure for me. Super fun and filled with riding my edge of learning. I feel so blessed and touched deep in the sea of my heart. It was amazing to be with such an easy group of women. I felt birthed into the sailing world with your support! I am a water baby! I look forward to growing these sea legs and new confidence of navigating the wildness of it. I was surprised at how comfortable I actually felt. Show tunes and great food helped! Natasha is one amazing captain. So graceful and filled with the knowledge, beauty, abundance and wisdom of the sea." —Jules