Dinner Cruises

  • Delicious Dinners

  • Amazing Views

  • Lifetime Memories

  • Fantastic Drinks

Private Charter


Now Accepting

If you want your day to be out of this world, then leave the world behind.


Due to Covid 19,

charters are not available this season

We hope to see you next year!

Please keep us in mind for your 2021 vacation.

Our Trips fit your trips


Overnight Trips,

and Midcoast Maine's only Dinner Cruises

click pictures for more information

Nobody Does it Boyder
Schooner sail Katie .jpg

Captain Katie 

Captain, mixologist, mom, badass.

From a background of Great Lakes racing and Tall Ship sailing, she moved to Maine in 2008 to crew aboard the historic three-masted Victory Chimes.

Manifest in our instructional programs, her passion for preservation, instruction, service and nature are fueled by her 5 years with Outward Bound.

Being captain suits Katie so well that she founded and runs two other local businesses! 

sailing maine boyd team .jpg

Boyd N Sheppard

This is the schooner that almost wasn't.

Battered in the harbor by a winter storm, the great schooner had an uncertain future.


Built in 1886 and saved by the passion and vision of the McKinlays - and bought for a dollar! - she sails again, under her original name, and in newly bright shape.

Charming, historic and spry, she sails the midcoast, adding to Maine's beauty wherever she goes. 

Maine Sailing Andy McKinlay.jpg

Chef Adam

Chef, teacher, dad, mariner.


Adam has more than eighteen year's experience using a wood-fired stove/ oven to work his magic.


His creations include elements from his extensive travels and enhances the traditional New England delights.


The food served is locally sourced, ethically raised, and utilizes local farm produce as much as possible.


By procuring the provisions locally and day-of sailing, he can cater to many different diet types and food restrictions.

Sail into the Extraordinary

The BOYD N. SHEPPARD, built in 1886, has a unique cruising program to complement your Maine experience.


We provide an opportunity to sail and explore Maine for an afternoon or dine among the sights of this magical area.

Both Captain Katie and Chef Adam have sailed on a multitude of vessels, holding all manner of positions, for over 20 years.


Adam comes with a degree in outdoor recreation leadership. His passion to teach and explore has guided him into this industry forever. Katie has come up through the "hawsepipe" so to speak, she learned to sail at the age of 12 and became serious about it in her early 20's. The rest is history in the making. 

Adam and Katie's worldly travels have shaped a diverse menu that introduces elements from outside of New England and enhances the traditional fare. The food we serve is locally sourced, ethically raised, and utilizes local farms and produce as much as possible. By procuring the provisions locally and day-of sailing, our meals aboard are as fresh and delicious as possible.

Schooner Boyd N. Sheppard

11 Front St

Rockland ME 04841


© 2020

Custom site design & copy: Q. Donleavy

Contributing Photography: Q. Donleavy

Sonya Siedlaczek