Chesapeake Bay School Itinerary

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This is a typical itinerary for Fair Wind Sailing School’s Chesapeake Bay week-long Instant Bareboat sailing lessons.  While destinations are subject to change based on weather, student preferences or Captain’s prerogative, this is representative of our week-long journey.

Day One - Saturday

Welcome! We meet at the yacht Saturday afternoon at Green Pointe Marina in Worton, Maryland.  After introductions, we’ll work to fully understand your goals and objectives. Then we'll begin teaching trip preparation, route planning and conduct a few fun exercises to introduce you to the boat and its safety gear. Finally, we’ll provision the boat for our voyage and still have time to enjoy a quiet evening on the bay and your first night aboard..

Day Two - Sunday

After our morning safety at sea lecture, we'll complete our final boat checks and set out on our first voyage.  We will perform drills under power, raise the sails and do our first sailing as we sail through the bay and head to a quiet anchorage, such as Fairlee Creek, Still Pond or the Worton Mooring Field.  After a full day on the water learning the helm and proper sail trim, we’ll pick up our first mooring ball or spend our first night "on the hook". Now we're cruising!

Day Three - Monday

Today we head to the wonderful town of Rock Hall. On the way, we’ll sail through all the points of sail, begin our tacking practice, hold lectures on rules of the road, the lateral buoy systeml and sail trim. We'll also cover the "sailor's safety valve", the heave-to maneuver.   As we approach, we put our lessons into pactice as we read the buoyscoming into the channel. Once there, we'll get a chance to practice our docking skills. Finally, we head out on the town to explore one of the Eastern Shore's best anchorages.

Day Four - Tuesday

We sail the Kent Narrows and learn how to go through drawbridges on the intercoastal..  Lots of tacking practice, man-over-board drills and navigation lessons fill the day as we head to St Michael's.  If conditions are right, this is the perfect time to practice putting reefs in the sails and shaking them out.  We’ll pick up another mooring ball – a skill that you'll know well by now.  Our nice long sail will be followed by a relaxing night with an evening lecture on plumbing and electrcial systems. There's still time for the thing that makes the bay the bay -- Crabs!!

Day Five - Wednesday

Today’s lectures focus on preparing for and preventing sea sickness, minor engine repairs and anchoring challenges.  Then we set off on a through the East Bay and that out into the open Chesapeake. Next, its across the Bay to Annapolis and then some down-wind sailing with practice reaching, running and gybing.  We’ll heave-to for lunch outside and finish the with more anchoring practice.  

Day Six - Thursday

We'll begin with an early lecture on VHF radio operation, weather and dinghy safety. Then we set sail, performing quick stop man over board drills and more down wind sailing. Then it's more sailing drills on the way to Great St James Island and Christmas Cove.  Yet off to yet another anchorage where our anchor set is rewarded by some Eagles, Osprey, Hawks and more of nature's beauty.   We'll enjoy a relaxing night onboard, practice some knot tying, and review for the final exam as we count shooting stars and enjoy the seclusion that can only be acheived by a night on the water.

Day Seven - Friday

We begin day seven with final sailing drills followed by docking practice as we head back to Worton Creek for the final review and exam.  Congratulations are in order as you pass your bareboat charter 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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