Sail into

the Extraordinary

Descriptions of our Overnight Trips

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"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 TRIPS BELOW OR SCROLL TO EXPLORE

One Night Wonders......................SAT -SUN

Two Night Treats

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"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.

 

 9a SAT - 3p SUN   Click HERE for trip dates      300 per person

One Night Wonder

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. Click HERE for dates. 

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

THU  July 2 -  SAT July 4             650 per person

The GReat Schooner race

Imagine sailing in a whole fleet of gorgeous, old wooden sailboats! The fun, fellowship and seamanship of such a great idea is exactly what has made Rockland's Great Schooner Race one of the bigger draws of the summer.

 

First run in 1953, it's a spirited race from Gilkey Harbor in Islesboro, Maine down to the natural finish line of the Rockland Breakwater.

 

Sometimes, between tacking maneuvers, guest are offered the helm. Wheel in hand, looking out at the other boats is exhilarating. We like to share the excitement when we can. It's a once in a lifetime experience.

 

To be aboard our charming1886 schooner is always a time of adventure, sightseeing, relaxation, and radiant ambiance. To be surrounded by a whole fleet of like-minded captains and sailors, all proudly sailing their fine ships is a sporting experience you don't want to miss out on. 

 

Because the ships are ripe with enthusiastic guests, there's cheering, jeering, raising sails and a special feeling of camaraderie. We all know just how lucky we are to be together, doing what we love, in the renowned waters off the very special place we call home.

 

To top it off, The Great Schooner Race is part of Maine's Bicentennial celebrations. This means the Breakwater finish line will be full of admiring - and jealous - crowds. We really like feeling like celebrities in a parade as we glide by to cheers. You will too!

We'll dock back at the Rockland Public Landing on the 4th.  Book now to save your spot aboard!

july 2 - 4

WED August 5 - FRI August 7      600 per person

ALL CAPS TITLE

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, enjoy more of Chef Adam's wood-fired creations, and stop feeling like you've got to pay full attention every second. Imagine just relaxing as we glide along in Penobscot Bay. 

 

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 wood-fired 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. 

two night treat

THU  September 3 -  SAT September 5           650 per person

Camden windjammer festival

No other place in the country is as steeped in the history and  preservation of classic sailing ships. No wonder Lonely Planet chose Maine as the only U.S. top destination for 2020.

 

The Camden Windjammer Festival is a celebration of Maine’s maritime community and culture. 

 

First, there’s the Parade of Sail; this is where all the local, classic wooden sailing ships gather to promenade along the Rockland Breakwater. We all loop about in the bay to skim the Owl’s Head lighthouse and glide by the breakwater and its lighthouse. Imagine being in the middle of all the ships!

 

There’s a proud camaraderie and cheery fellowship as we spoil each other with the sight of our ship’s passing each other. Guests get wonderful photo-opportunities as we pass, tack and sail about the bay in celebration of tall ship history and the many ships that still sailing locally, every season.

 

Then it’s onto the cozy and picturesque harbor of nearby Camden. All the ships gather to celebrate sailing the Maine coast.

 

Ashore, there’s a local festival with vendors, artists and live bands. At night, the Blaine House Orchestra plays and there’s a Talent Show put on by the ship’s crews  - and sometimes guests too! There's a lovely sloping harborside park that fills with spectators. The show’s backdrop is the quaint harbor filled with ships. It’s a wonderful small town event with a big heart and amazing scenery.

 

To top off the event, in the evening, there’s a fireworks display over the water! Any one part of this would make for a nice trip, all together - it's a bucket list trip that you don't want to miss. 

september 3 - 5

WED  September 23 -  FRI September 25    600 per person

season finale

The joy of late September sailing is no secret among Maine sailors. Many vacationers have retreated south for the return to school, but the days are still comfortable and the wind is encouraging.

 

For further sailing exploration of the Maine coast, and a deeper enjoyment of our historic schooner, these two-night treats are pampered gems of time explore, relax and be spoiled - and this is the last of them. 

 

Being the last trip of the season, this one is that much more special. The September winds are lively and the nights are a bit crisper. Fine blankets and a potbelly stove keep things cozy, our schooner keeps things charming and Chef Adam keeps things delicious.

 

Imagine gourmet meals, ripe with the ambiance of being aboard our 1886 schooner; the feel of old wood, the patina of the long-trodden decks and the wafting scents of the wood-fired stove in the galley. Our sailing trips are filled with such wonderful moments that fill the senses.

 

We love sailing the Maine coast. We enjoy sharing the unique experience of combining the pride of sailing a historic schooner, with the care and innovation of the latest cooking, and the timeless pristine scenery of Penobscot Bay. We’ve struck upon a winning combination. You will have a wonderful time sailing with us.

september 23 - 25

Two for the Rogue

 
 
 
 

Schooner Boyd N. Sheppard

11 Front St

Rockland ME 04841

1-877-238-1325

© 2020

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Custom site design & copy: Q. Donleavy

Contributing Photography: Q. Donleavy

Sonya Siedlaczek