The Basics

The boat: Jester, a FP Helia 44’ 

Crew: Captain JT (instructor)

ASA Students: Sandy, Chuck, Jon

Courses Completed:  ASA 103 (Basic Coastal Cruising), ASA 104  (Bareboat Cruising), ASA 114 (Cruising Catamaran)

Day 1: Getting to know the crew

Sandy, Chuck, and Jon all eagerly hop aboard the Jester to begin their weeklong journey of sailing and certifications. Sandy is an experienced sailor and is aboard to receive his ASA 114 certification. His wife has also joined on the adventure but doesn’t plan to get any certifications while aboard. Chuck has boating experience as well— but mainly on powerboats. Now, he hopes to gain the experience necessary to charter a catamaran on his own so he can bring his wife on a fun sailing trip. John is new to boating and hopes to add it to his list of retirement activities. It’s a group with a great swath of experience and it’s sure to be an exciting trip!  

Day 2: Casting off

The day starts with boat orientation, terminology, knot tying, and safety protocols. By early morning, the crew is ready to set sail with easterly winds at about 18 mph. It’s a beautiful day of sailing and the crew spots turtles on the open waters. While the group has decided they would like to eat most meals aboard they make an exception for the end of day 2 and head to shore on Secret Harbor, St Thomas for dinner! 

Day 3: Non-stop learning

There is plenty of fun to be had on the Jester— but plenty of work to be completed too! Day 3 is all about drills, practicing, and becoming competent sailors. The day starts with going over rules of the road, sound signals, navigation lights, and points of sail. With light 8mph winds out of the southeast, the conditions are perfect in the midmorning to practice point of sail drills. After lunch, the crew takes some time to relax and even sees a leaping spotted eagle ray near Sprat Bay! 

Day 4: A tour of southeast St. Thomas

What better way to practice sailing skills than with a beautiful tour of southeast St. Thomas! The crew practices maneuvering under power in Nazareth Bay, power maneuvers in Flamingo Bay, and mooring at Honeymoon Beach. Even with a full day of sailing under their wing, the crew still has plenty of energy to finish the day out with some snorkeling! 

Day 5: Island hopping off St. Thomas

With the crew well acquainted with the shores of southeast St. Thomas, the group decides they will now get to know the nearby islands. They start the day with tacking drills on the way to Buck Island. By early afternoon, the crew picks up mooring on Buck Island and decides to do some shipwreck snorkeling! Afterwards, the group proceeds under power to Great St. James Island and later embarks on anchoring practice at Christmas Cove. A full day of island hopping adventure! 

Day 6: St. John bound

The crew is beginning to wrap up their time together. Day 6 is the last full day of learning and sailing! The day starts with man overboard (MOB) drills, distress calling, first aid, knots, and dinghy towing before saying goodbye to St. Thomas. By afternoon, the group finishes up tacking practice and arrives in Leinster Bay in St. John. On their last evening together, the group enjoys snorkeling Waterlemon Cay and hiking up near the Annaberg Estate. 

Day 7: Certified Sailors

The crew has officially wrapped up their ASA sailing courses and feel ready for beginning their bareboating journeys! By late morning the crew arrives at Benner Bay and says their goodbyes— Go Sail Virgin Islands looks forward to seeing the new sailors out on their own boats in the future!