Skip to content


Date: Monday, September 23, 2013

Location: passing by Monhegan Island off the coast of Maine

As a result of getting ahead of schedule on this transit from Erie, PA to Boston, it was possible to pull into Rockland, Maine last Thursday and spend Friday dealing with logistics (laundry, groceries, fuel) in preparation for a tightly scheduled visit in Boston. As a result of today’s cold front and attendant fresh northwest breeze, proceeded by fresh southerly breezes Saturday and Sunday, it was prudent to delay heading to Boston until today’s favorable and fresh NW winds.

What do you do with Pride of Baltimore II in Maine waters with the extra time and the essential work is completed?

You sail in company with some of the resident windjammers of Maine. You anchor for the night with them in secure coves sheltered from the fresh southerlies. You take advantage of an invitation to go alongside the town dock at Castine, Maine. Here, friends, instructors and students of Maine Maritime Academy, as well Pride of Baltimore II alumnae crew, can visit the ship. Academy alumnae members, some of whom are now officers aboard the Pride of Baltimore II, can visit their alma matter.

At first light this morning, Pride of Baltimore II‘s crew mustered to ready her for departure by shaking-loose some sail. We maneuvered Pride of Baltimore II clear of the dock and into Penobscot Bay and the fresh northwest breeze. Then she set sail and made way for Boston.

Boston is less than 140 nautical miles away now and at a rate of 6 – 9 knots, we ought to get to Boston near midday Tuesday in plenty of time for her first obligation Tuesday evening at 6 PM; a cocktail party for 180 guests spread across the deck and the adjacent dock. With foresail, staysail, jib and reefed square-topsail set in the fresh northwest breeze, we should arrive in plenty of time.

Penobscot Bay is the central sailing ground for Maine’s long enduring Windjammer Fleet. The windjammers serve a public interest for what might be described as “traditional country lodge” living on the water. Every day the traditional wooden windjammers sail. Every night they anchor or tie up in different locations amid the seemingly infinite choices of coves and harbors spread throughout the inshore waters of Maine east of Portland. The most central activity is from Rockland eastward to Bar Harbor on Mount Desert Island. With the fortune of weather delay and the promise of pretty fast sailing toward Boston come Monday, Pride of Baltimore II‘s crew were able to enjoy a little bit of the wind jamming tradition of Maine.

The windjammer fleet is around two dozen or more vessels with crew that come from all over the country. Regularly Pride of Baltimore II has had crew that got started in Maine windjammers. Also Pride of Baltimore II crew members have gone to the windjammers. As a result there are lots of friendships that exist between current Pride of Baltimore II crew and crews of the windjammers, as well lots of Pride of Baltimore II crew alumnae that reside in Maine just because it is a traditional wooden sailing vessel center. We experienced a lot of friendly visitors to Pride of Baltimore II and also many curious visitors that have heard of her but not visited her. Evening times ashore or at anchor were spent meeting past shipmates or visiting between vessels.

From my perspective it is a high privilege to mingle with the extensively experienced sailing masters of the area. I expect between the windjammer masters and the sailing master instructors of Maine Maritime Academy in Castine, the assembly of highly experienced inshore and offshore sailing masters in this area is the densest in the country – if not the globe. I also expect some one-third of all the sailing masters in this area are highly experienced ocean and international voyaging sailing masters.

Captain Kip Files is owner of Victory Chimes – a wooden three-masted schooner that is over 100 years old and a relic of the Chesapeake Bay. Kip has extensive offshore experience as well years skippering of the large square rigger Elissa of Galveston, Texas.

Captain Chris Flansburg, an alumnae officer to Pride of Baltimore II, is one of the masters with Ocean Classrooms Foundation. He sails that foundation’s schooners along the East Coast of North America between Nova Scotia and the Caribbean, and he instructs high school students.

Captain Andy Chase is a big commercial ship master. He has longtime been a nationally and internationally recognized instructor/author at Maine Maritime Academy; he has extensive international sailing experience. One of his voyages in a schooner was to Greenland.

Captain Dan Parrott is an alumnae crew of both the Pride of Baltimore, as well one of the past Skippers of the 2nd Pride of Baltimore. He too is a nationally and internationally recognized instructor/author at Maine Maritime Academy.

Captain Steve Tarrent is a part-time instructor at Maine Maritime Academy when he is not Chief Mate of the large four mast high-end passenger square-rigger, Sea Cloud. She is located in the Caribbean or the Mediterranean. Previously he was a Captain for Sea Education Association – a university level ocean and maritime sciences semester program with two schooners, one in the Atlantic and one in the Pacific.

A very august group wouldn’t you say? What a privilege to be welcomed by such as these!

Jan C. Miles and the Boston bound crew of Pride of Baltimore II