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.

Maine sailing sunset.jpg

"The Perfect Time off!"

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See her sailing!

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Overnight Capacity

  • 20 passengers 

  •  9 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.


For less planning and more playing, simply book this Maine weekend Getaway and let us take care of everything: activities, accommodations, meals - done. These outings are wonderful ways to make the most of your time in Maine without having to plan, schedule and scramble to make it happen. 

Exploring the coast of Maine is wonderful by sail. Even better is enjoying that time aboard our charming 1886 schooner with your time punctuated with fine food and, come night, cozy amenities. 


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 Spoil yourself with a wonderful sailing trip through the area's lauded scenery and renowned sailing waters. Avoid the crowds and set sail with us to enjoy the space and beauty of Penobscot Bay.

Ever enjoy a sunset on the water, from a calm and scenic cove as the day ends in a glowing flourish? When's the last time you were gently rocked to sleep under cozy blankets? Do you like waking up to the alluring aroma of a hearty, crafted breakfast?

Wonder no more; book a One Night Wonder. 

One Night Wonder

 9a, Saturday

3p, Sunday

300 per person

one night Wonder

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

The vessel's overnight accommodations for up to 18, 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 9 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

What's better than a night aboard our historic schooner? Two nights - duh. 

Relax deeper, knowing that the whole of your time doesn't depend on just one day and night.  Compare sunsets, sample a larger menu of fine food, stop feeling like you've got to pay full attention every second. Let the ship lull you into a nap. 


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. Twice!

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. Such "traffic" is welcome and wonderful.

The sailing community of this area is unique to few places in the world, dotted with famous ships, able captains and stunning, unspoiled scenery.

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 a wood-fired stove & oven! Our overnight accommodations for up to 18 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 these twice as nice trips. 

9a, Wednesday

3p, Friday

550 per person

two night treat

Two for the Rogue


Schooner Boyd N. Sheppard

11 Front St

Rockland ME 04841


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Custom site design & copy: Q. Donleavy

Contributing Photography: Q. Donleavy

Sonya Siedlaczek