Ocean Passage Itinerary

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This is a SAMPLE itinerary for Fair Wind Sailing School’s week-long Instant Bareboat® sailing lessons.  The exact trip varies week by week and destinations are subject to change based on weather, student skills or Captain’s prerogative. This is REPRESENTATIVE of our week-long journey however trips vary and itineraries are not guaranteed..

Day One - Saturday

Our trip starts as we meet in St Thomas. For many, this is a return visit to our yacht Island Retreat and we recollect on our last class, the places we visited and things we learned. For others, this is the first voyage with Fair Wind and its time to get started. We begin with meal planning, provisioning and a boat safety check. When our days work is complete, its off to dinner in Red Hook to get acquainted and enjoy some island fun before we set sail.

Day Two - Sunday

We start with a weather briefing, then, its on to trip planning. We check the tide tables, cruising guides and charts. Next, we choose our destination, plot our course and determine our ETA. Finally, we fill the tanks and set sail around mid-day. Our first leg is a short hop over to the BVI. Along the way, we all take turns at the wheel and get back in the swing of Caribbean sailing. After clearing customs on Jost Van Dyke we have time to enjoy the entertainment at Foxy’s before resting up for our journey down island.

Day Three - Monday

Its early to rise as we weigh anchor and head out for St. Martin. Jack lines are secured, harnessed donned and tethers connected as we head north and away from the familiar protection of the Drake Channel. The swells are bigger than we saw on our last trip as we round the far side of Guana Island and Virgin Gorda. With 100 nm dead upwind and into the current, our progress is slow but steady. We get a quick peak at the luxury on Necker Island before we head off into open water.

As both daylight and the BVI fade off into the western horizon, our first night at sea begins. The watch schedule is reviewed, the sea berths rigged and dinner is complete, time for our shifts to begin. The Caribbean night sky is gorgeous with too many stars to count! But attention must be kept at the horizon anyway as our evening is also lit by the cruise ships passing. We progress toward the middle of the Sombrero Passage, and are rewarded by the glow from St Croix to the South. Its hard work sailing this far upwind, but it sure is fun!

Day Four - Tuesday

Land Ho!! Sunrise at sea and we see our destination, St Martin. While still hours away and while tired form our first night as sea, we are encouraged by the island rising out of the water, growing larger by the minute. After what seems like all day, we finally make the approach into Marigot Harbor, the adrenaline is flowing now -- we’ve done it! We drop anchor, raise our “Q” Flag and head to shore to clear customs. We’re rewarded on island with a wonderful French meal and some great wine. We’ll all sleep well tonight.

Day Five - Wednesday

We stay on the hook today and tonight in Marigot. As we rest up from our all night sail, we realize we have work to do. The day is spent completing the lessons for our navigation class and we all happily pass our Celestial Navigation exam. Time to celebrate with another delicious meal on St Martin, some island exploration and a restful night at anchor.

Day Six - Thursday

One last site-seeing trip ashore on this beautiful island before clearing out of customs. We plot our trip back to the USVI and after a nice lunch weigh anchor for home. Soon, we realize how much easier it is sailing downwind and with the current. The wind builds from behind as we clear the lee of the island and we make great time heading back to St Thomas. We’ve grown accustomed to the rhythmical rocking of the downwind sail and already feel much more comfortable then we did just a few days ago. As the sun sets and we prepare for our second night at sea, it is relaxing and we’re having fun.

Day Seven - Friday

A little before dawn we awake to the cries of “Man Over Board!” Its time for the last of our practical tests – the night time man over board drill. As the boat circles around to get our MOB pole, we realize why this is the advanced class – much tougher to spot the pole and strobe at night then it was during the daytime.

After completing are MOB drills, we rest and discuss the experience in the cockpit. The sun begins rising over Norman Island, we are back in the friendly and comfortable confines of the Drake Channel. There’s time for a new pot of coffee and fresh baked pound cake for breakfast before we clear back into customs on St Johns. Welcome Home!

Our journey sadly ends as we tie up to the dock in Red Hook. We complete our final review and then our Advanced Sailing exam. More success! We depart having made new friends, further developed our sailing skills and expanded our horizons to new lands. We leave confidently knowing we’re sailors!!

 
 
 
 

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