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Large Boat Sailing

Coastal Cruising Seamanship – HESPER

A week of cruising the coast of Maine aboard HESPER

July 7 – July 13
Brooklin, Maine
$1,995 (Tuition includes accommodations/meals. Discounts do not apply.)
Tom Hollyday
Experience Level
All Levels
Activity Level

This is a five-day course ending on Friday.

Over the years we’ve learned that the best way to discover the pleasures and develop the skills of cruising under sail is to sail off in the right boat with the right skipper. This season we are again proud to offer an exciting liveaboard course onboard a beautiful classic vessel.

Join the crew of HESPER for a unique 5-day course sailing Penobscot Bay.  This trip offers students a once-in-a-lifetime opportunity to sail aboard a true to form Isle of Scilly Pilot Cutter.  From proper line handling techniques, to sail trim, this promises to be an authentic, hands-on traditional sailing experience. Each day will be filled with sailing, navigation and in the afternoon, a stop at a new anchorage for shoreside activities.  All meals and accommodations are provided onboard.  You will depart the WoodenBoat School Docks Sunday evening, and return Saturday morning.

Pilot Cutter HESPER, a 60′ gaff-rigged Pilot Cutter, was built in 2004 by renowned boat builder Luke Powell, and is the 4th Pilot Cutter build out of 9 (most recent being Pellew, the largest wooden sailing vessel built in the UK in over a century). Based of the lines of the Isles of Scilly Pilot Cutters, she is a faithful recreation of the hardiest of sailing vessels in the 1850’s. Built to be fast, strong and most importantly kind to their crew. The would set off from the Scillys in all weather, racing to the incoming ships and dropping their pilots off. Once empty, they would be sailed back by a boy, often only 15 or 16 years old. These boats are a precursor to the more well known Bristol Channel Cutters- In fact, after the industrial revolution started, charts improved and pilotage rules changed the Bristol Pilots took over, thus bypassing the Isles of Scillys and relegating the pilots and their crew to daffodil farming.

This is a rare opportunity to learn anything and everything you wish to about the complex subject of big-boat cruising, and we’re very pleased to have the chance to offer it to you. Sign up for a truly great adventure under sail!

We ask that all passengers be in good health, and capable of going to and from a dinghy, and traversing a companionway to reach the below decks.

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