Sail into the Extraordinary

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.

Descriptions of our 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..."


"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


Mondays 5 - 8 Arrive 15-20 mins. prior      $60 per person

Happy Hour Cruise 

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The "Red Lead Drinkery" is open and in full swing Mondays!

We feature specialty cocktails, beer and wine cash bar and a tasty small plate menu. Oysters are always available 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; put some Friday in your Monday! 

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.​

Mondays 10 - 1 Arrive 15-20 mins. prior      $60 per person

MOnday Fun Day



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.

Tuesdays 10 - 1 Arrive 15-20 mins. prior     $60 per person

Tuesday Cruise Day



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.

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. 

Tuesdays 5 - 8 Arrive 15-20 mins. prior     $100 per person

chef's choice dinner Cruise

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With a Prix Fixe menu and drinks served aboard, these dinners are the perfect way to experience the magic of Maine and the charm of our ship.


Chef Adam's cooking, all on a wood-fired stove, is masterful, fragrant, special and in-demand! You don't want to miss it.


Some places offer a nice view with dinner; with us we are part of 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.


 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.


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Wednesdays 10 - 1 Arrive 15-20 mins. prior     $60 per person

bay breezes day starter


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Put some weekend in your Wednesday with a relaxing, scenic tour of Penobscot Bay. 

A lovely jaunt out into the bay will do you good: the crisp air, the sparkling seas, the feel of our 1886 schooner gently rising and falling as it gracefully glides along. Few things are better for your time in Maine than a sailing tour of the area.

Another neat thing about this daysail is that you can come back later the same day for our Happy Hour! Do this: after your sail, head into town for a leisurely lunch at one of the many Foodie-praised hotspots; then wander the galleries and shops of Rockland. Right about the time you're a bit tired from walking around, you'll be right on time to join us for a relaxing Happy Hour.

Time can really fly when you're getting into the rhythm of sailing. The only way to counteract the "time flies when you're having fun" effect - is to have more fun, and this daysail, with a Happy Hour Chaser, is definitely that. Try it!

Wednesdays 2 - 4:30 Arrive 15-20 mins. prior     $60 per person

Midday Rambler


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This afternoon sail is a great way to relax after a delicious lunch at one of Rockland's many great restaurants. Rockland has a lot of them, so it won't be an easy choice, but how to best enjoy your afternoon afterwards is an easy thing to agree on - a wonderful, scenic sail aboard our historic schooner!

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.

Middle of the week, middle of the day, out in the middle of the bay; a perfect combination​ of vacation elements, all together for a scenic boat tour. 

Seeing the sights of coastal Maine from the water will give you a whole new appreciation for what makes our home a uniquely special place. 

Wednesdays 5 - 8 Arrive 15-20 mins. prior     $60 per person

Hump Day Happy Hour


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How do make Wednesday more downhill towards Friday than uphill from Monday? Hump Day Happy Hour, that's how.

Featuring a small plate menu, specialty cocktails, beer & wine cash bar - and oysters always available! -  this sail will lift you from feeling under if your 21 & over. 


Our ship is the only schooner with a liquor license and operating bar that sails out of Rockland, so book ahead because here's nothing happy about missing out on hours of relaxation aboard our ship.

If you've never sailed on a charming wooden schooner into the sunset as part of your Happy Hour, was it ever really "happy?"

Nobody Does it Boyder. Click here to see the Specialty Drink Menu.

Thursdays 5 - 8 Arrive 15-20 mins. prior     $100 per person

Farm to Galley Dinner Cruise


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The menus for our Farm to Galley Dinner Cruises are based on fresh Farmer’s Market finds that Chef Adam discovers locally. 

You might not know what the meal is going to be, but you can be sure that it's going to be wicked tasty!

And because Chef Adam cooks aboard on a wood-fired, cast iron stove, you'll be treated to the savory scents of his chosen wood and discovered delicacies. The wafting scent of the stove and cooking dinner is completely unique to the area because we are the midcoast's only Gourmet Dinner cruise.


Beyond Chef Adam's gourmet cooking, these dinner cruises are a feast for the senses: The sights of the coast, the sounds of sailing and the touch of a wooden schooner combine with the fine taste of the meal to create a completely unique event and lasting memory.

JUL 10 ONLY 1 - 4:30 Arrive 15-20 mins. prior        $80 per person

parade of sail special event

FRIDAY july 10

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We'll be serving a cheese board, Maine oysters on the half shell, and our Specialty Drinks. Passengers are welcome and encouraged to otherwise bring their own food for a Parade Picnic out in the bay!

On this special sailing tour we'll be amongst the finest ships in the region, the Windjammer Fleet. The fleet is made up a group of charming schooners like ours that sail longer trips along the Maine coast.

It's not often that we're all seen together, so you don't want to miss this special event. It's a fun combination of sailing adventure and relaxing tour: All of us out and about, trading passes and reveling in the spectacle and fellowship of it all.  


Being aboard our1886 schooner is always a charming experience of immersion into the history and swagger of these old ships, so imagine being surrounded by a whole group of beautiful ships and passionate captains! 

Fridays 5 - 8 Arrive 15-20 mins. prior        $60 per person

Weekend Kickoff Happy Hour



The key to a great weekend is a good Friday.

Can you imagine anything "gooder" than kicking back on a classic, wooden schooner, sipping away at your new favorite drink?

We couldn't come up with anything better either, that's why we end our Fridays, and start our weekends, with this Happy Hour sail.

Chef Adam's masterful small plate menu pairs perfectly with Captain Katie's concoctions. She's a masterful mixologist, has been for years - renowned in port and at sea - so when she helms the bottles and shakers, it's well worth it to be witness and customer to her magic.

And the scenery! Let's not forget - in all the Happy Hour talk - that we'll be roaming some of the best sailing waters in the world. There's a reason we call Maine "The Great State of Maine." The crisp, clear air, the majestic, rocky coast, the lighthouses, the variety of other boats we encounter - it's amazing and this cruise is a wonderful way to experience so much of what makes Maine great. All while kicking off the weekend in style!

Click here to see the Specialty Drink Menu.