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Small Boats, Big Fun

When we stop for the day, you can keep going. We will always have a few small boats with us for our guests. Below is our full collection. 


If you d not know how to sail or row, our crew will take you out.


Each of our small boats was chosen for its historical significance, just like GRACE BAILEY. 

The culture of traditional sailing thrives in Maine. Our maritime history isn't just about the past, it's the origin story of how things are still done today. As with our ship, knowing the history is part of the experience we offer. It makes the connection stronger.


Meet the fleet, learn their stories, explore. 

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Chesapeake Bay

Crabbing Skiff

This is another “Flattie” type, popular in the Chesapeake for its easy handling, load capacity and shallow draft.  Good qualities for a working skiff and - as it turned out during Prohibition - a darn good resume for running rum.


In a NASCAR style twist, variants of this skiff type are raced in the Chesapeake today.

A small skiff type called a "Hampton flattie."

Hampton Flattie

These flat-bottom boats were very popular on the Chesapeake Bay in the late 1800s. Their shallow draft worked well in the often shallow bay. They were used for oystering and crabbing into the early 1900s. They cruise well and so were also made into small coastal cruising yachts.


This flattie is typical of the smaller working boats you’d have seen in the  Chesapeake.

a dory called a "Lunenberg Dory," popular in the 1880s.

Lunenburg Dory

Lunenburg Dories have been built in the same shop, in the same way, since 1917.


A “Banks Dory” was used as a traditional fishing boat since the 1850s along the Grand Banks of Newfoundland.


By 1880 they were being built up and down the eastern seaboard. Inexpensive to build and stackable by design, they are built to be fully stable when loaded with at least 500 pounds of catch.

A small boat rigged for sailing called a "North Haven Dinghy."

North Haven Dinghy

In the 1880s, summer folks on nearby North Haven island took to racing their yacht's dinghies.


The Weld brothers of Massachusetts had their three tenders beat by a local gaff rigged setup. The next year, 1884, they had a new and faster dinghy. They won against all comers.


By 1919 their dinghy design became the go-to at the races. This led to a “North Haven” becoming the country’s first standardized “racing class” hull design.

A traditional design of row boat called a "Susan Skiff."

Susan Skiff

Each student of the Apprentice Shop, located in our Rockland Harbor, builds a Susan Skiff. It’s a classic, utilitarian design. The lapstrake construction (plank over plank siding) is the foundation of more complex traditional boat designs.


The shop's dedication to tradition resonates with us. It’s why we have two of these skiffs. These skiffs are a rugged, usable pieces of history, just like our ship.

a picture of a small boat type called a "whitehall."


This design is considered one of the most refined rowboats of the 19th century. First made on Whitehall Street in New York City, they were used to ferry provisions and sailors around New York Harbor.


They performed so well that sailors would use them to row out into the open ocean to offer their pilot services to incoming ships. It can be rowed or set up with a "BatWing" sail as seen in the full fleet picture above.

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Meet  the Fleet

Grace Bailey

Small Boats

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