Sail Grace Bailey

Sail Grace Bailey We offer 3 to 6 night All-Inclusive, Maine vacations aboard our charming 1882 Schooner.

Get yourself a follower like .He’s not messing around.
10/06/2023

Get yourself a follower like .

He’s not messing around.


It’s official, Sam is famous, meme-famous, but still - that counts.    📸 .bum.memes
10/04/2023

It’s official, Sam is famous, meme-famous, but still - that counts.



📸 .bum.memes

.lbert discovers why having  onboard is so good.Because cat.   📸
10/01/2023

.lbert discovers why having onboard is so good.

Because cat.



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Everlasting Gobstoppers - remember those?A Wonka candy that packed the taste of full meals into a single piece. That’s t...
09/29/2023

Everlasting Gobstoppers - remember those?

A Wonka candy that packed the taste of full meals into a single piece.

That’s the same kind of magic that creates in the galley.

From this wee setup comes BIG flavor and tasty surprises. Every. Day.



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09/29/2023

“Scissors are just two knives, right?”

Not only is Chef Katey great with kitchen knives, she can put two together and cut a dandy hairdo.

Becca volunteered, and it went really well.
Maybe we’ll open up a salon in the aft cabin.



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Floppy hat vacations are the best kind of vacations.   📸
09/27/2023

Floppy hat vacations are the best kind of vacations.



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Chef Katey concocting ‘Bailey Bagels!   📸
09/26/2023

Chef Katey concocting ‘Bailey Bagels!



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Always fun to wave at folks as we leave the harbor.   📸
09/23/2023

Always fun to wave at folks as we leave the harbor.



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Coming out of the fog, looking like a page from a history book. A great shot from an avid local and keen photographer fr...
09/22/2023

Coming out of the fog, looking like a page from a history book.

A great shot from an avid local and keen photographer friend of ours.

This was from this year’s Great Schooner Race. Being aboard, weaving among the fleet - there’s a magic to it, a magic anyone can experience, which is, for lack of a better word, magic.


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“I learned so many new words this week. Everyone should . Thanks for the vocab lessons and the memories  ⚓️🛟⚓️”We agree,...
09/21/2023

“I learned so many new words this week. Everyone should . Thanks for the vocab lessons and the memories ⚓️🛟⚓️”

We agree, everyone should sail Grace Bailey.

A fun repost of a guest’s take on his time aboard.
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You know what you should do if you live in Maine? - *warning: you won’t believe the last one, even though it’s the most ...
09/20/2023

You know what you should do if you live in Maine? - *warning: you won’t believe the last one, even though it’s the most important.

First thing you should do - celebrate every day the fact that you live in Maine;

second: say “wicked” a lot.

The third thing: You should jump on one of our trips!

Why? Other than the obvious?

Two reasons -

The good part of summer starting late this season, is that it’s also ending late this season. The picture is from minutes ago today.

We’re on a streak of wicked good (see, there it is) weather.

The last reason, that should be first, is that - for Maine residents - our trips are discounted 40%!



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You know how, when it snows, your neighbors are more neighborly?The shared experience blooms a certain camaraderie. Mayb...
09/19/2023

You know how, when it snows, your neighbors are more neighborly?

The shared experience blooms a certain camaraderie.

Maybe you help each other shovel out, or at least wave to each other in a way you never do when the weather’s nice.

That’s what the recent tropical storm was like here; sailor-neighbors helping figure out how best to secure all their boats.

Checking your lines and fenders during the storm, always with an eye on your neighbor’s setup too.

Is it a Maine thing? Is it a sailor thing?

Don’t know.

Doesn’t matter, really. It’s our thing. We like it that way. All of us.



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Lena  captures the mood before the storm.   📸 .lbert
09/16/2023

Lena captures the mood before the storm.



📸 .lbert

“Reflections from another time ⚓️”A great shot from a neighbor schooner’s guest.     📸
09/15/2023

“Reflections from another time ⚓️”

A great shot from a neighbor schooner’s guest.



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09/12/2023

Wouldn’t it be great if you could get a degree in Vacation?

You kinda can. Once you take a trip with us, you’ll know how to vacation for the rest of your life.

We also offer minors in Bragging, Instagram and graduate level What I Did This Summer essays.



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“fully immersed in the schooner verse.”A wonderful collection from Lena. She spends most of her time in the galley, but ...
09/10/2023

“fully immersed in the schooner verse.”

A wonderful collection from Lena. She spends most of her time in the galley, but when she comes up, she sure has a good eye for Maine treasures.
📸 .lbert

Small, medium, large.That’s us on the left.    📸
09/08/2023

Small, medium, large.

That’s us on the left.



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It’s called “Spark Plug” lighthouse.Exactly why is a mystery…   📸
09/07/2023

It’s called “Spark Plug” lighthouse.

Exactly why is a mystery…



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The official start to every trip is when we pass the     📸
09/07/2023

The official start to every trip is when we pass the



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 We’re all headed to   for the Camden Windjammer Festival.   📸
09/01/2023



We’re all headed to for the Camden Windjammer Festival.



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You wouldn’t even know it rained like crazy earlier. A wonderful, misty pink end to the day. This is what schooner Angel...
08/30/2023

You wouldn’t even know it rained like crazy earlier.

A wonderful, misty pink end to the day.

This is what schooner Angelique saw of us as we headed to Orcutt Harbor for the night.



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This is the last post, post  #3, about our (triumphant) return to  on Swans Island.Following is a really cool perspectiv...
08/30/2023

This is the last post, post #3, about our (triumphant) return to on Swans Island.

Following is a really cool perspective of our outing to Daint’s that night.

It creatively covers the gamut from the windjamming experience, the experience (aka the Marshall) to our outing to Daint’s.

It’s by one of our guests. We have such great guests.

Enjoy -

“Sometimes… without too much thought…you travel to the other side of the country and get on a boat with a famous sailing cat, a Marshall on Mars (who is from Earth), and a few other misfits and sail to an island and you get the secret password to Daint’s Place.

You have a couple drinks, you talk with kind and generous people, and you leave overflowing with gratitude for your hosts and fellow passengers for sharing in the experience.

Just sometimes.

Other times you do laundry.”



Yesterday, we told you that to tell you this.Yesterday was about meeting up with , the invite-only Maine speakeasy on Sw...
08/28/2023

Yesterday, we told you that to tell you this.

Yesterday was about meeting up with , the invite-only Maine speakeasy on Swans Island, two years ago.

Today is about finally getting Captain Sikkema and out there to experience it.

Today is also about the good of change and the charm of staying the same.

Two years ago, we only knew about Marc the way most other people do - through his TV and movies roles.

Today, he’s one of the host/ owners of GRACE BAILEY. Before he ever became a famous actor, he worked aboard Maine windjammers.



Well, he’s back. He’s been aboard on a bunch of trips.

He’s on this week for the Camden Windjammer Festival.

AND

He’s on again for a four nighter starting September 17th. He’s hosting the one after that too, but it’s waitlisted, so - hurry up.

That’s all about change, but what about the “charm of staying the same” we mentioned?

That has to do with Daint’s. The are still - after all the fanfare, notoriety and yes - fame - they are still the nicest, most hospitable folks. .

And so are the people that frequently fill Daint’s. Everyone welcomed Marc, Sam and the gaggle of guests we brought, like they were regulars.

The first pictures shows the wicked fine whiskey they toasted Marc with for the occasion.

The second picture shows our whole merry band of visitors they welcomed from our ship.

Tomorrow, we’ll share a guest’s take on Daint’s



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Nama-staysail.Here’s a question we never thought we’d askWould you do yoga while sailing the coast of Maine?Turns out ye...
08/25/2023

Nama-staysail.

Here’s a question we never thought we’d ask

Would you do yoga while sailing the coast of Maine?

Turns out yes is the answer.

One of our guests is all about yoga. And so -
Yoga broke out, while we were sailing.

How cool is that? To have a bunch of people go - while we’re briskly sailing about - “hey, let’s yoga.”

Everyday magic, that’s the spirit of windjamming.



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Summary of this last trip. 📸
08/24/2023

Summary of this last trip.

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Captain Spear Drive
Rockland, ME
04841

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