Sail into the Extraordinary

Overnight Trips

For further sailing exploration of the Maine Coast, and a deeper enjoyment of our historic schooner, these overnight Schooner Cruises are pampered gems of time in Penobscot Bay.


"The best night away ever. 

The schooner is wonderful, very well restored, the food was amazing, beautifully cooked on a wood fire. Presentation was fabulous and everything was fresh and homemade.


The cabin was small but very comfortable and well appointed, we had everything we needed for a night out. The mattress was very comfortable and we slept well.


Everything was very well thought out and even going up to the head at night was well lit with lanterns. The crew were fun and very welcoming. This was a bucket list trip and worth every penny, make sure you try out this schooner."

When you want more

Stay overnight

Click choice below or scroll to explore your options.

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"The Perfect Time off!"

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See her sailing!

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One Day Wonder Capacity

  • 20 passengers 

  • 11 Cabins


Children's Fares:​

5 and under: sail free with 2 adult fares* 

6 -13: 25% off with 2 full Adult fares*

14 and over: Adult Fare

*based on cabin availability

Some restrictions apply.

275 per person

One Day Wonder - Season Premiere

9a, Sunday, June 9 - 

2p, Monday, June 10

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JUNE 9 - 10

Turn a sail into an adventure - spend the night aboard! Watch the sunset dim into dusk and marvel as the stars come out.

Relax deeper, knowing that the sail doesn't end, just the sailing. We know the best local spots to anchor for the night and the charm of our 1886 schooner makes for a wonderful setting to dine and unwind.

You'll see farther sights than any daysail can reach and you'll love our inviting and tastefully furnished cabins. And you'll get to have meals prepared by Chef Adam, masterfully cooked on a wood fired stove and oven! Not for the novice, such cooking is a trick and a treat. He's been at it for 18 years and his meals feature influences and flavors from his far flung world travels and regional adventures. 

Always the highlight of your time in Maine, these trips easily fit into any length vacation. 

275 per person

One Day Wonder - Slice of Summer

9a, Sunday, June 23 -

2p, Monday, June 24

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JUNE 23 -24

The best way to get more of Maine's scenery, Katie's drinks or Chef Adam's cooking, is more time aboard the Boyd N Sheppard! Book this One Day Wonder to put the most of Maine's summer into the least amount of time.

A full day aboard, 28hrs actually, is a complete and transforming experience. You'll go from walking the historic wooden decks of our great schooner with curious fascination, to feeling right at home and waving to passing ships like an old salt.

Knowing that you don't have to leave, and having a cozy cabin to retreat to for a nap or to grab a sweater really makes you feel welcome and comfortable. And, with more time sailing, you can casually soak up the ambiance of the vessel and the beauty of Maine without feeling rushed.

Just sit back for a day of wonder and feel like crew and family. 

419 per person

The Great Schooner Race

9a, Thursday, July 4 -

10a, Saturday, July 6

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July 4 - 6

Join one of the largest annual gatherings of wooden schooners in America, and  race down the Penobscot Bay. What a spectacular way to spend 4th of July weekend, on board a historic US vessel, joining in the fun. We will try to anchor somewhere to watch the local fireworks displays, weather provided.


The Great Schooner Race is hosted by Maine Windjammer Association and is in its 43rd year. This will be BOYD N. SHEPPARD's first race under her new masters, we are not in it to win it but it sure would be a good way to say hi to the competition. 


Boarding is early so we can get underway early to find and meet up with the fleet. Bring your racing best, holiday vest and let's get sporty.


That great vintage picture is from when she first sailed and raced!     

275 per person

One Day Wonder - Jewel of July

9a, Sunday July 7 -

2p Monday, July 8

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July 7 - 8

Another great thing about midcoast Maine, you should know more than a few things by now, is that "hot summer days" are never that hot, and - even if a few slip by the angels that bless Maine's weather - it's always cooler on the water and cozy at night.

We'll likely see other historic schooners that ply these waters. It's an amazing sight to see such regal and historic vessels off the pages of history books and out sailing with gusto among the timeless beauty of Maine's evergreen coast.

They are as enamored of us as we are of them. We cross paths with waves, hellos and lots of picture taking to share back and forth. The sailing community of this area is unique to few places in the world, dotted with famous ships, able captains and stunning, unspoiled scenery.

Book this trip to experience the sparkle of the midcoast in July. 


Enjoy the comfort of our ship and the beauty of our area.

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Cabins dressed. Thanks to stewardess _so

The vessel's overnight accommodations for up to 20, and all wares, were designed for comfort and warmth for our cruising area, sustainability and protection of our environment and a commitment to support locally or ethically made and manufactured products.

The interiors of the 11 cabins have a boutique camp vibe and we showcase local art and interior products in many of our cabins. We provide locally made goat milk soap, facial tissues, ear plugs and many other complimentary products.

Nobody Does it Boyder


275 pp

One Day Wonder - Midsummer Night's Dream

9a, Sunday July 21 -

2p Monday, July 22

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JULY 21 - 22

Some of the best scenery on our One Night Wonder sails is right on the plate in front of you.

The delightful food that Chef Adam prepares is one of the few things that can make a sail with us even better. These longer sails, these potent, overnight adventures, have the tasty advantage of enjoying multiple meals crafted and presented by Chef Adam. 

You'll really get to appreciate the kismet of Adam and Katie pairing their passions to create the sailing experience of extended time aboard this charming, historic schooner. 


Sailing the sights of Maine, dining on gourmet meals aboard a charming schooner built in 1886, and getting to stay the night is about as bucket list as it gets! The really neat part is that this is something that's not hard to do and it isn't even expensive. 


Booking this trip is a midsummer night's dream come true. 

275 per person

One Day Wonder - Summer's Brass Ring

9a, Sunday, AUG11 - 

2p, Monday, AUG 12

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AUG 11 - 12

August is the brass ring of summer. It is the peak and prize of the season. The greenery will be at its most verdant and bright. The warm days of August, always cooler on the water, sigh into a velvet dusk that will keep you on deck far past the late sunset. Enjoy lingering in the sparkling calm to savor the magic, star-filled quiet of being at anchor just off the rugged coast.

Maine sailing cruises, in the renowned waters of Penobscot Bay, crisscross some of the world's most sought and storied sailing territories. Being aboard a schooner built in1886, among other fine ships drawn to these waters, is a wonderful experience.


The comaraderie of midcoast Maine's sailing community means a lot of smiling, waving, picture taking and arcing lines of closer greeting to hail a kind "hello." That it's August just sweetens the experience, shining that brass ring 'til it shines like a wave top's glisten.

Sailing on the BOYD N SHEPPARD is always a pleasure. Sailing with us in August is a peak Summer treat. Spending the night aboard, deepening the spoil and getting to have meals by Chef Adam; that is truly Summer's Brass Ring.

275 per person

One Day Wonder - Labor Day Leisure Sail

 9a, Sunday, SEP1–

2p, Monday, SEP 2

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SEP 1 - 2

This trip is a memorable way to punctuate a Maine summer. As everyone tries to eek out a last hurrah of the summer, avoid the crowds and set sail with us to enjoy the space and beauty of Penobscot Bay.

Sailing midcoast Maine is one of the few times where more really is merrier. This area is such a renowned area to sail that the waters are often freckled with amazing sailboats from all over the world - and Labor Day Weekend is the unofficial "Parade of Sail" when such "traffic" is welcome and wonderful.


While the roads can be packed, the bay and regional island byways are only made more scenic and friendly with vintage, historic and modern craft, all out-and-about enjoying the spoils of Maine's wide spaces, clean air and blue water.

Spoil yourself with a wonderful sailing trip through the area's unspoiled scenery and renowned sailing waters. 

275 per person

One Day Wonder - Sweet Spot Sail

9a, Sunday, September 15 –

2p, Monday, September 16

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SEP 15 - 16

An open secret among local sailors is that September has some of the best sailing winds and weather of the season here in midcoast Maine.

The winds pick up, the crowds die down, and the weather stays in the sweet spot of warm days and cozy nights.

As if the sight, sounds, smells and scenery of a sailing trip aboard our charming schooner weren't enough, Chef Adam will spoil you with his savory creations. He cooks all meals on wood-fired stove / oven! Our overnight accommodations for up to 20 are comfortable, cozy and inviting, but his cooking is what makes people love our ship like home. 

Food is love, so come be cared for and spoiled by Maine's beauty and our kind hospitality. We are proud of our ship and happy to share the best of Maine with you on this trip.