Our guests Katy Stewart, Jeff Oakleaf, and Jake Beattie have lots of sailing experience, but nothing is quite like sailing in the Race to Alaska! It’s a tough and quirky race with just one rule — you cannot have an engine aboard your vessel. It’s nicknamed the America’s Cup For Dirt Bags. Listen to this for some great insight into … Read More
Ep 17: Earning A Living While Sailing & Cruising
We’re talking with Patrick Schulte and Cindy Wallach both veteran liveaboards and cruising sailors who make a living while sailing and travelling. A lovely chat about the life of living, cruising and working. The struggles, the rewards and the freedom.Pat has been on the go for decades! He runs http://wandererfinancial.com — you can sign up and work with him to … Read More
Sept 27–Oct 4: Newport – Annapolis
This near coastal, offshore jump will start in one sailing capital, Newport, and make its way to the other sailing capital, Annapolis. After a night anchored in Block Island, we’ll head offshore and cross some of the busiest shipping lanes on the East Coast. Our course will be towards the mouth of Delaware Bay. Once inside the Bay, we’ll head … Read More
Sept 18–25: Rockland –Newport
A classic fall passage! This near coastal/offshore leg from Rockland ME to Newport RI will give you a good idea of what “heading south” is like. Depending on the forecast, we may spend a night anchored in Penobscot Bay to give us time to get to know the boat and go over some safety protocol. But if the forecast looks … Read More
September 20–26: Rugged Maine Coast
Join us for this 7 day near coastal sail among the islands of Maine. These are some of our favorite cruising grounds, and challenges are aplenty. September is one of the best times to sail in Maine. There is usually less fog, stronger breezes, beautiful blue skies and crisp cool nights. These courses are designed to challenge you while at … Read More
September 6–12: Down East & Bay of Fundy
Join us for this 7 day near coastal sail along the remote Down East Coast of Maine and Canada. The goal is to sail as far down east as we can. East of Bar Harbor, the coast really changes and the population thin out significantly. It’s truly rugged. Hopefully we’ll make it to Grand Manan Island or Campobello Island. The … Read More
August 16–21: Rugged Maine Coast
Join us for this 6 day near coastal sail amongst the islands of Maine. These are some of our favorite cruising grounds, and challenges are aplenty. These courses are designed to challenge you while at the same time, offer the opportunity to really work on skills and drills. Maine’s rugged coast is full of rocks, fog, variable winds, schooners and … Read More
Aug 2–8: Halifax – Rockland
Join us for the return trip from Halifax NS to Rockland ME. Last time we made this passage, we ran into the most intense lightening storm we have ever seen! We’ll probably head west along the Nova Scotia coast towards Mahone Bay, and find an anchorage, perhaps Lunenburg. We’ll check the forecast and make our plan to jump across The … Read More
July 26–Aug 1: Rockland – Halifax
Join us for this coastal and offshore passage from Rockland ME to Halifax NS! We haven’t made this passage since 2011, when we sailed to Newfoundland and filmed One Simple Question. We’ll probably head east through the islands of Penobscot Bay the first day and drop the hook somewhere cozy for the night. We’ll check the forecast and make our … Read More
July 11–18 Cape Cod Circumnavigation
Join us for this exciting new offshore loop that circumnavigates Cape Cod! What?! How can you circumnavigate a cape? Via the Cape Cod Canal of course! Thanks to modern technology, Cape Cod is now an island. We’ll set sail from Rockland and point the bow south against the prevailing sou’westerlies til we get to the canal entrance. We’ll sail directly … Read More
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