We Offer a Festive and Completely Unique

Variety of Sailing Options:

  • 3 hour weekday cruises

  • 1 & 2 night getaway cruises

  • MidCoast Maine's only Gourmet Dinner Cruises

  • Private Charters & Events

All Sailing from Rockland, Maine

Best Food, Best Drinks, Best Sailing

  • Best Sailing - Penobscot Bay has world class sailing.

  • Best Drinks - Katie, the Captain, is also a renowned mixologist.

  • Best Food - Adam, the Chef, is also a veteran sailor, cooking on wood-fired ovens and stoves to make meals aboard savory, delicious and special.

Nobody Does It Boyder

Private Charter


Now Accepting

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


Our Trips fit your trips


Overnight Trips,

and Midcoast Maine's only Dinner Cruises

Family Business

click pictures for more information

Schooner sail Katie .jpg

Katie McKinlay

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, built in 1900.

It was then she met Adam, he was crew on The Heritage, and their stories have been twined like line ever since. They also both worked for Outward Bound which helps to fuel their passion for preservation, instruction, service and nature. 

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

Adam McKinlay

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