From The White-Knucklers File

The benefits of going this route are several: “Certification is a confidence builder and shows that you have the skills to keep a boat safe in Greece, Turkey, and in the B.V.I.,” he says. “If you don’t have formal training, a company will seldom charter you a boat substantially larger than the one you’re already sailing at home. If you own a 32-footer and get certified, they’ll feel comfortable giving you the larger boat. Having it is a great way to bridge the gap in a sailing résumé, especially for the white knucklers who want a 40- to 45-foot boat in the Caribbean when the résumé doesn’t support The Moorings giving them that boat.”

But don’t assume that a piece of paper is your passport to palm trees and white-sand beaches. “Nobody ever learned to operate a boat in a classroom,” Jepsen says. “Doing the maneuvers and refining your ability to do the maneuvers over a period of time takes training and practice. Instructors take time to run through drills in sufficient numbers so folks feel like they can recall those skills in an emergency. The key is to do the maneuver enough times with an instructor so that there’s enough muscle and brain memory to launch through the procedure with enough confidence,” Jepsen says. “We love certification, but the skills are critical.”
By combining the core points of key courses with onboard instruction, the Colgates’ Fast Track program in one week puts students through enough drills to prepare them for their own sailing vacation. First, sailors spend two daylong sessions learning aboard the tiller-driven Colgate 26. On Day Three, they move to a bareboat in the 30- to 40-foot range and continue the learning process while living aboard. On Day Five, the crew drops off the instructor and takes off on its own overnight. “It’s intense,” says Doris Colgate. “Students tell me, ‘If you told me I was going to take this 49-footer off the dock when I started, I would’ve told you that you were crazy.’ But it happens.”

Following the Fleet
OK. You sail a 32-footer at home. You’ve taken some courses. But you still haven’t booked that first bareboat charter. And you still want the sun and the fun of a sailing adventure. And you want it now—but you’re still a little anxious. How on earth do you make it happen?
Relax: You join a flotilla!

This group of bareboats organized by a qualified individual or group, charter company, or school follows an itinerary to a specific destination. In other words, it’s a trip whose organizers match and place more experienced sailors with less experienced sailors aboard the same boat.

“We have about five flotillas a year in different locations,” says Charlie Nobles, the executive director of the American Sailing Association. “We provide everything from the beginning to the end, and it becomes a mentoring process. Getting students out with those who’ve chartered before is the best way to get students over that hump.

“Some skills and experiences are impossible to teach, and some students may have technical skills but they may not be confident, especially in unfamiliar waters. There’s customs, local winds, provisioning, navigating. People can tell you about these things, but there’s nothing like going out there and seeing it for yourself,” he says.

“Flotillas have consistently been a huge part of chartering,” adds US Sailing’s Jepsen. “How can we get newer sailors without the certification excited about the Caribbean? We’ll put them on boats with our certified skippers. We’re confident enough in our program and our certified skippers. Experienced sailors do it because it’s a bigger party. Inexperienced sailors do it for security. Flotilla sailing helps you meet new people. There are always people to go with to see ruins or to go shopping with.”