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

Labor Day Leisure Sail

 9a, Sunday, SEP 1–2p, Monday, SEP 2

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SEP 1 - SEP 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

September's Secret

9a, SAT, SEP 7 – 2p, SUN, 8

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SEP 7 - 8

The weekend after Labor Day begins to reveal the Secret of September here in midcoast Maine; the bulk of the summer visitors recede while the weather and winds remain.

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. Watch the sunset dim into dusk and marvel as the stars come out.

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. 


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

Boyd Sheppard schooner cabin
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Maine saling cruise barometer
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 per person

Sweet Spot Sail

9a, Sunday, SEP 15 - 

2p, Monday, SEP 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. 

275 per person

Last Chance

9a, Saturday, SEP 21 -

2p, Sunday, SEP 22

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SEP 21 -22

Like getting the last cookie of the batch, this trip is just sweeter somehow, a bit more of a prize and last indulgence. This is our last overnight of the season. 

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 last sparkle of the midcoast for the season.