About Boston

With a rich sailing history, scenic vistas, and a wealth of popular sailing destinations, Boston is an amazing place to sail in luxury. This week, we’re excited to profile SailTime Boston and its owners, Brian Moseley and Paul Sullivan.

What is the history of sailing in Boston?

Boston has a long history as a seafaring city. It was a crucial port during the American Revolutionary War, and was heavily fortified during the Spanish-American War. The USS Constitution, a wooden-hulled 3-mast frigate also known as “Old Ironsides” was built in Boston in 1797; and is renowned as the world’s oldest commissioned and fully operational naval vessel. With such a rich history, it should be no surprise that Boston’s Harbor is home to six sailing schools and seven sailing clubs to meet the demand.

Why do people like sailing in Boston?

Boston Harbor provides a unique venue for sailing. The city skyline offers a magnificent background for sailing in the inner harbor, especially for sunset cruises as the sun sets behind the cityscape. There are 34 large harbor-islands and dozens of ships, tugs and barges in the harbor, offering exciting navigation and anchorages with access to beaches, hiking, and camping for overnight sails.

Boston is a great jump-off point to get to the North Shore (Marblehead, Gloucester, etc.). It’s only a 6 to 7-hour sail to some of our countries most picturesque and historic ports with excellent sightseeing, shopping, and dining. To the south, you have access to the Cape Cod area, the Cape Cod Islands, Nantucket, Martha’s Vineyard, and Plymouth Rock. All are excellent excursions for overnight sails.

About SailTime Boston's Team

Brenton, a well-known captain and sailing instructor, became familiar with SailTime Boston in 2005 and kept regular tabs on the business at boat shows each year. Upon hearing of a need to improve the sailing training for SailTime Boston members, he launched Blackrock Sailing School with the previous SailTime Boston owner in 2008. One of Brenton’s students, Paul Sullivan, joined the Blackrock team in 2009, first as a staff member but later a co-owner. In 2015, Brian Mosely became a student and SailTime member, giving all three men a chance to become acquainted.

With Brian having a business background, and Paul’s sailing background, it was a natural fit when they decided to join forces to purchase SailTime Boston in 2019. Collectively, they have more than 50 years of sailing experience, featuring exotic excursions to the Great Barrier Reef in Australia, the Dalmatian Islands of Croatia, and regular tips through Bermuda and the Virgin Islands.

Feature Member and Owner Member

Owner-Members Chris and Martha Kristian own a Beneteau 38.1 named Defiance, which sells out every year since entering the fleet in 2018. Part of its popularity is attributed to the regular invitations they offer their boat’s members to the annual Figawi Charity Race in Nantucket. As avid supporters of America’s Warrior Partnership, Chris enters Defiance in the race each year to raise money for their mission to support communities helping veterans succeed. A veteran of the United States Army himself, Chris makes sure to have other veterans join him on the racing crew. He also donates hours of his time getting veterans out on the water to learn the therapeutic benefits of sailing.

Michael Kaye is beginning his 10th season as a member. He also serves the U.S. Coast Guard Auxiliary, a volunteer organization that promotes boat safety and awareness. He’s helped several members advance their sailing skills with his extensive knowledge of Boston’s Harbor.

What boats are in the SailTime Boston Fleet?

For more information, contact [email protected] or call 888-607-SAIL (7245) or visit them at SailTime Boston. Also, follow them on Facebook for exciting updates at

Adventure Awaits

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