Skip to primary navigation Skip to content Skip to footer
Back to Discover Go Sail Virgin Islands Posts

Captain’s Log: Bringing It All Together

diagramThe Basics

The boat: Speculation, a 2018 FP Helia 44’ 

Crew: Captain JT

ASA Students: Mike, Tracey, and Robert

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

Day 1: Coming together

This sailing crew comes together from all walks of life for the first day of their Go Sail Virgin Islands cruise! Tracey lives in Annapolis and is excited to take ASA 104 so she can rent local charter boats on the Chesapeake and get out with friends. Mike is a frequent USVI visitor but has yet to get out on a boat! He’s excited to build sea time and skills so he can take his wife on a chartering adventure on the islands. Robert has the most sailing experience out of the three adventurers and even owns a Hobbie Cat of his own! He’s looking forward to refining his skills so he and his wife can enjoy their dream charter experience in Croatia.  

Day 2: Getting a feel for the water

The first full day on the water gives Captain JT plenty of time to get to know the students strengths and goals for the week. The group starts by mooring to Flamingo Bay for maneuvers under power before setting double-reefed main and single-reefed jib on the way to Water Island. By afternoon, the crew is getting comfortable on the boat and they pick up mooring near Hassel Island to take a break and enjoy lunch. Afterwards, they head to Navy Barges to enjoy some snorkeling and are lucky enough to find a starfish during their adventure to pass around and admire! 

Day 3: Practicing maneuvers 

Raising sails, heaving-to, reefing, jibbing, and anchoring— these are just a few of the maneuvers students get comfortable with during ASA courses! For this crew, the experience of learning and practicing maneuvers is made even more enjoyable by the beautiful surroundings of Buck Island and St. James. They spend the entire day perfecting their skills before picking up mooring in Christmas Cove and celebrating their successes over a pizza dinner! 

Day 4:  Learning logistics 

There is a lot that goes into sailing beyond just raising the sails! On day 4 out at sea, the group works on plotting courses, measuring distances, estimating time, using navigational aids, and learning the rules of the road. These skills come in handy as they power through Current Cut and raise the full main and single-reefed jib out on the open water. The crew also gets in some tacking practice in Pillsbury Sound before picking up mooring in Hawksnest Bay for the night. It’s a full day of adventure that ends with a beautiful sunset beach walk and burgers on the grill!

Day 5: Enjoying the beauty of the U.S. Virgin Islands

Learning to sail is hard work and it’s important to take time to focus on the beauty of the islands as well as the task at hand! On day 5, the group sails over to Maho Bay in the morning and then spends the entire afternoon snorkeling with the turtles, paddle boarding, and enjoying together. He makes his famous jerk chicken and plantains to finish off another fabulous day on the water. 

Day 6: Bringing it all together

Day 6 is the last full day of sailing for the crew and Captain JT works with them to bring all their newly acquired skills together! The crew shows off their skills by working through strong currents in Henley Cay and seamlessly giving-way to traffic in Pillsbury Sound. They practice jibbing west of Buck Island and then head to Honeymoon Beach to moor. However, the day ends with a few bumps in the road. While trying to moor, the crew misses and snags the rudder and then the Captain’s phone goes overboard! However, neither issue dampens their moods (maybe in part because Captain JT’s phone still works!) and they enjoy their last dinner together as a crew– complete with pecan pie cheesecake for dessert! 

Day 7: Hitting the road

It’s time for Tracey to put her skills to the test on the Chesapeake, Robert to take his wife on their dream charter adventure in Croatia, and Mike and his wife to continue their exploration of the Virgin Islands! They group waves their goodbyes and heads out to begin their future sailing adventures.