Sail into the Extraordinary

Daysail Descriptions

We offer Daysail Schooner Tours of MidCoast Maine sailing out of Rockland.


"...Captain Katie was easy going and knowledgeable and really fun to get to know. Chef Adam prepared an amazing dinner which we enjoyed on deck in a calm area of the harbor. We ended with a delicious dessert as we sailed back toward the dock. Everything was perfect. The whole crew was so welcoming and helpful. The food was top notch..."

Daysails, Evening Cruises

& Special events




"What More Do You Want?"

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See her sailing!

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Day sails 

  Capacity: 34 people

       Children's Fares: 

5 and under: Free

6-13: 45

14 and over: Adult Fare

Dinner Cruises

  Capacity: 25 people

       Children's Fares:

5 and under free

6-13: 45

14 and over: Adult Fare


Monday 10 - 1

Arrive 15-20 mins. prior

Rockland is a wonderful harbor to sail out of for a daysail; even before we pass by the scenic sentinel of the harbor, the breakwater lighthouse, you'll see an impressive variety of sailboats, motor yachts, lobster boats and island ferries.


The hustle and bustle of the harbor quickly gives way to the world-renowned sailing waters of Penobscot Bay. Speckled with local islands, curious seals and beautiful sailboats, our sails are a wonderful way to see the rugged beauty and famous sights of the Maine coast.


A sail aboard the historic BOYD N SHEPPARD is a charming, unique way to experience Maine's magic and create wonderful memories of your Maine trip.

$60 per person

Monday Fun Day


Mondays 5 - 8

Arrive 15-20 mins. prior

The "Red Lead Drinkery" is open and in full swing Tuesdays.

We feature specialty cocktails, beer and wine cash bar. Note that this cruise is for passengers 21 & over. 


The Boyd Sheppard is the only schooner with a liquor license and operating bar that sails out of Rockland - and we celebrate this fact every week!

Don't wait for the weekend to have a good time. Make a Friday out of your Tuesday. 

There's no better way to celebrate a good day, or unwind after a stressful day, than a happy hour sail aboard the BOYD N. SHEPPARD. A fine breeze and great scenery always makes for a happy few hours.​

Click here to see the Specialty Drink Menu.

$60 per person

Happy Hour Cruise



 Chef Adam & the Wood-fired Dining Experience

Boyd N Sheppard is the MidCoast's only schooner offering gourmet dinner cruises.


Using fresh local ingredients, cooked aboard on a wood-fired stove, Chef Adam's creations are second only to the Maine scenery.

While the food is being prepared,  if you stand by the chimney, you'll smell the cozy incense of a wood fire going below decks and the aroma of his next delicious creations.



Tuesdays 10 - 1
Arrive 15-20 mins. prior

Start your day with a lovely cruise around Penobscot Bay. Heading out into the bay, we'll pass right by the local landmark of the Breakwater Lighthouse. It's special experience to see it from the water and sail into the bright, open beauty of our famous sailing waters.

Off to the north you'll see the rolling blue hills of Camden's, Mt. Battie with Mt. Megunticook looming majestically behind. Some days you can see all the way to Blue Hill, with the foreground peppered with the local islands of North Haven and Vinalhaven.

Walk the swarthy decks of our rugged, historic schooner while the beauty of maritime Maine glides by. You'll see quaint lighthouses, rocky shorelines, working lobsterboats, chugging island ferries and the blue, beautiful waters of Penobscot Bay.

Seeing the sights from the water is a wonderful way to enjoy Maine's rugged coast, and it's a great way to get your day off to a memorable start. ​This cruise will give you a whole new appreciation for what makes our home a uniquely special place. 

$60 per person

Tuesday Cruise Day


Tuesdays 5 - 8
Arrive 15-20 mins. prior

With an a la carte menu and drinks served aboard, you can feast and imbibe to your taste and make this event as merry and filling as you wish. We warn you that Chef Adam's cooking, all on a wood-fired stove, is masterful, fragrant, special and in-demand! 


Some places offer a nice view with dinner; aboard the BOYD N SHEPPARD, the boat itself, in addition the magnificent bay views, is part of the spectacular view. Built in 1886, this schooner is an authentic piece of living history, handsome and oozing with seagoing charm.

These events are as memorable as they are delicious. Punctuate your time in Maine with one of these gourmet dinner cruises because, in addition to the food and scenery, we always serve up lifetime memories.

$60 per person

Chef's Choice Dinner Cruise



Schooner Boyd N. Sheppard

11 Front St

Rockland ME 04841


© 2020

Custom site design & copy: Q. Donleavy

Contributing Photography: Q. Donleavy

Sonya Siedlaczek