Custom Sailing Charters
Rockland, Maine
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We pride ourselves on flexibility. Our private sailing charters are not constrained by any schedule but your own, we create an experience just for you. Whether you are interested in a 2-hour coastal sight seeing sail, an all day island hopping cruise, or an overnight adventure, the choice is yours

Our 2022 Season will begin on June first and run through October fifth. We look forward to welcoming you aboard. 

Penobscot Bay plays host to some of the most beautiful and diverse scenery on the Maine coast. From the rugged rocky cliffs and bays of the many islands to the gently wooded shorelines of the mainland, the views will charm and captivate you. Penobscot Bay is home to some of the most beautiful lighthouses in the state. There are more than 200 islands, providing no shortage of sights to see and places to explore in this ocean playground aboard our custom sailing charters.


Let us be the venue for your most memorable event.  We will create the perfect atmosphere for your marriage proposal, elopement, photo shoot, reunion, bachelor or bachelorette party, the highlight of your family vacation, any special event you envision.  What more elegant way for a bride and her attendants to arrive at her island wedding, or for the the newly married couple to depart their celebration

For special events please contact us. 

We dodged thunderstorms and we're rewarded with a picture perfect maine sunset!  With _reneelaplante


Welcome to On The Wind Sailing. We offer private sailing charters in Rockland, Maine on beautiful Penobscot bay, inviting you to design your own personalized and flexible excursion. Founded in 2015, On The Wind Sailing is based upon the simple idea that a smaller more intimate setting creates a more enjoyable on-the-water experience.

We offer an exclusive alternative because we operate on a private-charter-only basis, providing an intimate, comfortable, customized sailing experience suited to the needs and desires of our guests, second to none.



Please call us to book your private charter or special event and to discuss your personalized details. 

We can be reached by phone at: 207-318-3025

You can also reach us via e-mail at: info@sailcascobay.