Sail into the Extraordinary

Daysail Descriptions

We offer a variety of Daysail Schooner Tours of MidCoast Maine,

all 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..."

We offer a variety of Daysails

and even Overnights

Click choice below or scroll to explore your options.

Boyd icon.png




"What More Do You Want?"

click pic for quick vid 

See her sailing!

click pic for quick vid 

Day sails 

  Capacity: 34 people

       Children's Fares: 

5 and under free

6-13: 35

14 and over: Adult Fare

Dinner & Brunch Cruises

  Capacity: 25 people

       Children's Fares:

5 and under free


brunch: 80/child           (1/3 discount) 

dinner cruise: 85/child   (~35% discount)

14 and over: Adult Fare


$120 per person

Bay Brunch Cruise


Every other Sunday 10 - 2

Arrive 15-20 mins. prior

Lollygag your Sunday underway and spoil yourself with Chef Adam's sumptuous brunch.


This fantastic way to finish your weekend and set the tone for the day also features tasty creations from the "Red Lead Drinkery."


Imagine the sun on your skin, the fresh air of the sea, and the amazing scenery of Maine's gem - the midcoast - all around you from aboard our historic schooner. 


It's not just a Brunch, it's a Boyd Brunch - by Chef Adam; it's the finest kind there is in Maine.


Note that the AUG 25th Brunch will include a special wine tasting! Bank Burana of South Portland Wine guides us through a tasting of this year's best sparkling wines from around the world and Chef Adam presents us with pairings to taste, go global in a tiny bubble. Pricing for this special event will be determined when the wine list is finalized. 


The dates for this tasty touring event are:

June: 2,16,30

July: 14,28

August: 25 - this is a special Wine Tasting Brunch! See above. This also the last brunch of the season because of our One Day Wonder schedule in September. 

$60 per lesson, sign up for all four is only 200

Ladies Sailing Series


One Sunday a month, JUN - SEP, 3 - 6

Arrive 15-20 mins. prior

Ladies Sailing Series is a great opportunity for women, children, families, and all, to hone their skills in a comfortable and relaxed sailing setting, all levels are welcome to participate. Encouraging a hands on platform for increasing skills and a chance to ask all those questions you could never ask before. We pledge guidance without arrogance, instruction without condescension; supporting a healthy and fun learning environment.


Captain Molly Eddy:

USCG Licensed 1600 GRT, Master of Steam, Power, Auxiliary Sail and Master of Towing upon Oceans, and co-founder of Saltwater Maritime, a local boating instruction business. 

Captain Kaite McKinlay:


Each session will also feature a female guest presenter, adding to and enriching the curriculum by offering insight to many maritime careers and experiences. 

Also included: Wood fired pizza, fruit and soft drinks.

Snacks to share are highly encouraged, because this is a fun get-together as well as a learning experience.  

7/14: Points of Sail, Sail Theory, basic ship handling (tacking, jibbing, sail trim). Intro to useful hitching and cleating.

7/28: Navigation, Chart Talk, Weather expedition planning.

8/4: Knots, Rigging Basics, Mechanical Advantage

9/29: Helm Time, Anchoring Procedures, Docking Process, Heaving To, Radio usage.  

$50 per person

Viewsday Tuesday


Tuesdays 10 - 12:30

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.

$130 per person

Chef's Choice Dinner Cruise


JUN/ JUL - Tuesdays 4 - 8

AUG / SEP - Tuesdays 3 - 7
Arrive 15-20 mins. prior

The start time differences for JUN/JUL versus AUG/ SEP are to try and include the sunset in your sail. Yes, as if the coastal scenery, our historic schooner and Chef Adam's cooking isn't enough - we try to include a dazzling sunset on your cruise!

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.

  • SPECIAL ENGAGEMENT DATES - Click dates below for details. 

July 16th we have (multiple, multiple) award-winning Chef Melissa Kelly, proprietor of "The Best Restaurant in Maine," - Primo of Rockland. $200 per person. Optional +$65 wine pairing available also. 


August 6th, we are lucky enough to feature the guest gourmet workings of Maine Moonlight Dinners' curated dining events by Eric Petrie. $130 per person. This includes the glorious four-hour sailing tour!

These events are as memorable as they are delicious. Punctuate your time in Maine with these gourmet highlights because, no matter who's cooking, they all serve lifetime memories.

$50 per person

Bay Breezes Day Starter


Wednesdays 10 - 12:30

Arrive 15-20 mins. prior

Put some Weekend in your Wednesday by starting your day with a lovely sail 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.

Seeing our midcoast's sights from the water is a wonderful way to enjoy Maine's rugged coast, and it's a great way to get your Wednesday off to a memorable start. 

$50 per person

Afternoon Sail


Wednesdays 1:30 - 3:30

Arrive 15-20 mins. prior

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.

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. 

$60 per person

Hump Day Happy Hour


Wednesdays 4 - 7

Arrive 15-20 mins. prior

The "Red Lead Drinkery" is open and in full swing Wednesdays,

featuring 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 Wednesday. 

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.


 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.


Bread 1.jpg
Bread 2a.jpg
Bread 3 sprinkle.jpg
Bread 4 wood oven.jpg
Bread 5 pan oven.jpg

$50 per person

Fried? Daysail



Fridays 10 - 12:30

Arrive 15-20 mins. prior 

By the time Friday comes around, you can be a bit fried. Even vacations can get stressful, trying to find the balance between the fun of doing everything and joy of doing nothing.


Why not enjoy both? Let us show you everything while you enjoy doing nothing.

Sailing with us aboard our 1886 schooner, BOYD N SHEPPARD, is a fun combination of sailing adventure and relaxing tour. Exploring Maine's midcoast by sail lets you experience Maine's pristine beauty in a whole new way, and sitting back while you do it will quickly become an old favorite for your vacation To Do lists.

SPECIAL: Windjammer Parade Sail 1- 4:30 

July 12th, for the Maine Windjammer Parade of Sail, we have a special sail from 1:00 - 4:30. We'll be serving a cheese board and Maine oysters on the half shell. $80 per adult. Passengers are fully welcome to otherwise bring their own food for this lovely day aboard amidst the full fleet of historic schooners that ply the scenic waters of Penobscot Bay!

$130 per person

Friday Lobster Dinner: Terre or Mer

Lobster Dinner sail maine_edited.jpg


JUN/JUL Fridays 4 - 8

AUG/SEP Fridays 3 - 7

Arrive 15-20 mins. prior 

The start time differences for JUN/JUL versus AUG/ SEP are to try and include the sunset in your sail. Yes, as if the coastal scenery, our historic schooner and Chef Adam's cooking isn't enough - we try to include a dazzling sunset on your cruise!


The key to a good weekend is a great Friday night and there's no better way to spend a Friday night than enjoying an amazing lobster dinner. If lobster isn't your thing don't worry we have you covered as we offer a "Terre" option too.


Chef Adam adds delicious flourish to the tasty, fresh Maine lobster with oysters, corn on the cob and his choice of prepared potato, slaw and freshly baked bread and dessert, house wine or beer.


Any meal by Chef Adam is special, but prepared and served aboard the BOYD N SHEPPARD, these lavish meals have become renowned and special events that will be the highlight of your time in Maine.


Dockside lodging available at an additional charge.


Not available August 23rd, due to the Marlin Spike Hitch Cruise.

$50 per person

Saturday Magic

sailing rockland tour_edited.jpg



see below for variants

This Saturday sail will have different times and variants throughout the season.

This sail will let you do nothing for the rest of the day and still feel like you've had a wonderfully full day of vacation memories.

You'll be aboard our lovely, historic schooner, touring one of the most beautiful sailing areas in the world. These sails are a wonderful way to launch into the weekend, where every seat is front row to the sights of Maine's maritime magic.

July 24th and 27th daysails 10:00-12:00

August,10,24,31. daysails 10:00-12:00

For all of September, through to October 5th, it'll be every weekend, at its usual time of 10:00 - 12:00.

All of these sails will be $50pp.


To see these sails laid out on the calendar, just hit the button to the left.

$130 per person

Weekend Highlight Lobster Dinner

Lobster Dinner sailing maine_edited.jpg


JUN/JUL Saturdays 4 - 8

AUG/ SEP Saturdays 3 - 7

Arrive 15-20 mins. prior 

The start time differences for JUN/JUL versus AUG/ SEP are to try and include the sunset in your sail. Yes, as if the coastal scenery, our historic schooner and Chef Adam's cooking isn't enough - we try to include a dazzling sunset on your cruise!


Fresh and delicious Maine lobster is a Have To for your time in Maine. And a lobster dinner spent sailing the sights of the bay aboard our charming schooner is a definite Should! If lobster isn't so much your thing but sailing is, Chef Adam has you covered this dinner has a "Terre" option. Popular preparations are cast iron seared Flank Steak or Mustard Rubbed Pork Tenderloin.


As if fresh local lobster with just enough too-much-butter wasn't enough, add to this feast oysters, corn on the cob and Chef Adam's choice of prepared potato, fresh slaw and just baked bread and tempting dessert, house wine or beer - and you've got yourself - not just a sumptuous dinner - but an event you'll remember forever.


If you've never dined aboard a sailboat, then get ready to check if off your bucket list and do it up in grand style. Chef Adam does not disappoint and the scenery always impresses.


These dinners are a wonderful way to set the tone for your Maine trip or cap off a wonderful vacation in style.