Basic Women’s Sail Training

3-Day Overnight PRogram

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 competence, confidence, and courage, both on and off the water.

Friday 1 pm - Sunday 5 pm
South Freeport Town Dock
Cost: $795

2025 Sessions:

September 5 to 7, 2025
July 25 to 27, 2025 - Waitlist

New for August:
Women’s 2-Day Overnight Program
Women’s Weekend Day Sailing Program

In the company of other women, you will develop your sailing skills practicing operating a 36’ fiberglass sloop, including maneuvering under power and sail, hoisting and trimming sails, navigating using electronic and paper charts, managing the dinghy, observing the weather, learning safety procedures and basic rules of the road, mooring, and anchoring. SV Brightside has eight bunks accommodating four students, a USCG licensed Captain, and a deckhand/educator.

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

Together, as women, we will sail into our strength, acknowledging and honoring our authentic experience and vulnerabilities, holding ourselves and each other with genuine care and compassion as we stand up to each challenge with courage and resilience, celebrating our successes. With this foundation, we’ll step into our roles aboard as we connect with ourselves, each other, and the wider environment of the natural world, collaborating and playfully engaging with it all!

Read this account of our program this summer or go ahead and take a step forward below.

Note: We reserve the right to cancel any program due to unforeseen circumstances.

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.

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

Sailing Ships Maine is a 501(c)(3) non-profit organization. Your contribution is tax-deductible to the fullest extent of the law (EIN 47-3101784).

Sailing Ships Maine creates life-changing opportunities for teens of all abilities and income levels so that they may discover the ocean environment and expand leadership skills while being encouraged to consider further maritime training.  Through public events, we support the marine economy, provide access to the ocean and traditional sailing ships and preserve our maritime heritage.