Virgin Islands Sailing Itinerary

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This is a SAMPLE itinerary for Fair Wind Sailing School’s Virgin Islands 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

Welcome to Fair Wind Sailing School! We meet at the yacht Saturday afternoon in Red Hook, St Thomas.   After introductions, we’ll work to fully understand your goals and objectives. Then we jump right in!  Instruction begins with a review of nomenclature and terminology and head operation, followed by a few exercises to help you get to know the boat.   Next, its an introduction to charts and navigation, we get our first weather report and plan the week’s route.  Then we’ll plan meals and provision the boat for our voyage.  You’ll have time to get you settled into your berths and enjoy the evening in Red Hook, the East End’s nightlife capital. Enjoy your first night aboard. 

Day Two - Sunday

Our morning classroom consists of rules of the road and our safety at sea lecture.  Then, you'll complete the final boat preparations and set out on our voyage. We will perform drills under power, raise the sails and do our first trade-wind sailing as we cross Pillsbury Sound and head to the north side of St John.  During the way, we practice our identifying right-0f-way situations through the busy Sound.  After a full day on the water learning the helm and proper sail trim, we’ll do our first mooring ball pick-ups as we get our first taste of working as a team.  We complete the day’s training with a lecture on proper galley procedures and cooking fuel safety.  In the evening there is enough time to enjoy a snorkel or swim off the back of the boat before we eat aboard. 

Day Three - Monday

We’re up early today as we discuss crossing international borders, flag etiquette and customs / immigration requirements.  Then its underway as we head to the BVI.  After clearing in, we have a long upwind challenge in The Narrows as we tack our way into some of the strongest winds in the VI.  By the time we get to Norman Island for our second round of mooring pick-ups, we’ve completed dozens of tacks and have mastered upwind sailing.  Our afternoon classroom session covers communications --, VHF radio operations, distress signals and sound signals.  In the evening, its a snorkel at the legendary Caves off Privateer Point and a celebratory drink at the notorious Willie Tee’s floating bar..

Day Four - Tuesday

An early motor this morning is rewarded with a breakfast snorkel at The Indians – one of the BVI’s top attractions.  Classroom is conducted when we return as we cover emergency situations and responses After breakfast its knot tying practice, Then we set sail for an all day downwind sail.  Along the way we practice reefing, gybing and master the heave-to procedure.  As we make our approach into Jost Van Dyke, we review proper anchor procedures, then successfully drop anchor and spend our first night on the hook. With luck, maybe we'll even meet the Jost's most famous resident, Foxy!

Day Five - Wednesday

This morning’s lectures focus on boat systems, minor engine repairs and advanced anchoring procedures.  Then its off we go!  We don’t sail  far today, so we have plenty of time for man over board drills, reviewing our previous day’s sailing, completing lots of anchor sets at Sandy Cay and even get in a Mediterranean Moor.   We end up in Cane Garden Bay on the hook for a second night and complete knot tying and an evening lecture on navigation. 

Day Six - Thursday

Morning lecture is outboard motor operations and dinghy safety we spend lots of time with the dinghy before heading back out sail.  Then we set sail, performing quick stop man over board drills and more down wind sailing drills on our way back to the USVI.  We clear customs at St John and then set the anchor – without instructor assistance – for yet another night on the hook.  We have time for a final snorkel before a review session as we enjoy our last night aboard anchored at Christmas Cove.  

Day Seven - Friday

We raise anchor and head back to Red Hook for docking practice. Congratulations are in order as you pass your ICSO exam and earn the right to do your own bareboat charter! As we wrap up, it will be difficult to say good-bye to new friends, but you'll leave with the confidence that you have become a capable sailor and the knowledge that your next trip will be as Captain!!


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