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Vacation Under Sail

I MUST go down to the seas again, to the lonely sea and the sky,

And all I ask is a tall ship and a star to steer her by,

And the wheel’s kick and the wind’s song and the white sail’s shaking,

And a gray mist on the sea’s face, and a gray dawn breaking.

-John Masefield

For thousands of years mankind has obeyed the urge to return to the sea, so why shouldn’t it be my turn?  The feel of a boat moving through the water under sail is a thrilling sensation.  And this time of year, its exactly the kind of sensation that I yearn for when the weather has turned cold and I find myself dreaming of warm waters and sea breezes.  To be honest, owning my own sailboat just isn’t feasible, but that should not stop me from “borrowing” one for a week or two and then giving it back when I remember that I truly belong back on terra firma.

If you think you might enjoy a sailing vacation this winter, now is the time to think about making reservations.  These three ideas offer various options that might work for even the most landlubber-ish:

Luxury Under Sail

If you’re looking for a gentle way to transition to the sailing lifestyle, this just might be the trip for you.  This 6-night itinerary on a sailing cruise ship means you don’t miss a single luxury, but still can experience the magic sensation of a boat harnessing the wind.  The crew will encourage you to get as involved with the sailing of the ship as you are comfortable with and on occasion will even allow passengers to step into a safety harness and make the climb into the rigging.  The itinerary starts on the Pacific side of Costa Rica, transits the Panama Canal (how cool is that?) and finishes in Balboa, Panama.   More info

Getting a Taste for Chartering

Take seven days in the British Virgin Islands (BVI), add a top of the line sailboat from The Moorings Fleet and mix with an experienced captain to get you where you want to go safely.  Voila, you might just have the ultimate vacation cocktail.  The Moorings provides you with the boat, someone to drive it and a few sample itineraries and then allows you to shape the where and when of how you spend your time.  If you’re new to sailing and spending time afloat, this may be the best opportunity to get your (a’hem) feet wet.  This is a great opportunity to become familiar with the basic mechanics of sailing and navigation.  More info


Dare to be the captain of your own destiny?  Obtaining your “Bareboat Certification” from a sailing school is the best way to get there.  With this certification you should be able to charter sailboats from most major charterers, without the expense of hiring a captain.  The Colgate’s Offshore Sailing School offers a 7-day course that teaches you the basics of sailing on a small 26’ sailboat and then challenges you to apply those lessons by skippering a larger cruising sloop.  On the final day of the course, you take the sloop out for a short cruise without an instructor.  Students who successfully pass the course are allowed to test for a “Bareboat Certification”.  That certification is the key to being able to charter boats on your own, without the expense of a captain.   More info

Had any amazing experiences on a sailing vacation?  Share your favorite voyages in the comments.

This Post Has 2 Comments

  1. Very interesting. I’ve always wanted to do this; chartering and sailing on a luxury boat. AND I’ve wanted to learn how to drive a boat, preferably a small yacht. Would love to get a boating licence one day.

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Samantha Brown - Sailing Vacations
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