I get asked, “Are there different ways to sail?” Yes, here are eight ways.8 Little-Known Ways to Sail
1. Caribbean Day Sail—The common expectation for a trip on a yacht rental in St. Thomas or St. John is to fly in and take a bareboat out for a week with another couple or two. That’s fine, but pricey and tricky unless everyone is a competent sailor or crew. The easier alternative is to take a half-day or full-day charter sail on a sloop, fetch or schooner. They leave in the morning and come back in the afternoon. They usually offer snorkeling at an anchored spot. Make sure they sail the damn thing, though. My wife and went aboard a 60-footer in Grand Cayman Islands where the captain never raised the sails, preferring to motor instead. Once under sail and having insinuated yourself with the captain, he or she will likely give you a turn at the helm. It’s exhilerating to sail at that level and perhaps the best of 8 little-known ways to sail.
  1. Substitute Crew—Everyone says they want to crew, but they can’t always make the Wednesday night or Saturday races. You can endear yourself to the racing set by serving short notice to crew. This assumes your schedule is clear and that you can move quickly. Let the racing team know that you’re available on two hours’ notice, and watch how frequently you get called.
  2. 8 Little-Known Ways to Sail
    Ice Sailing—Here is a unique, fast and dangerous adventure that is limited by geography and weather. Ice sailing clubs are active in New Jersey and New York, notably on the upper Hudson River. It’s hard to say how to insinuate one onto a boat. First, go there and make yourself known, perhaps helping with the equipment. For more on the history of the sport, check out my blog here. It is perhaps the most obscure elemenet among 8 little-known ways to sail.
  3. Lunch Hour—If you work downtown near a harbor, chances are you can find a rental boat to latch onto for 90 minutes. Check out com for what’s near you. Once you make the first arrangement, you’ll be able to go back more easily the next time. If you’re ASA qualified by 101 or 103, you can take out sailboats of 22 feet and 36 feet. The smaller is more suited to lunch hour. Don’t worry about the time required to set up the boat. Advancement in boating technology has made today’s new sloops virtually ready to go. Make sure the engine is working well, though. This is without a doubt the fastest among 8 little-known ways to sail.
  4. Videos—Hundreds of videos are out there on You Tube to show all manner of sailing, from how-to to harrowing races. Sailing Anarchy has excellent clips of races. The beauty of videos is that you see them quickly and bookmark sections that may be useful for further study. ASA has the best set of how-to videos. Review them before attending class. ASA also developed a nifty app through Brainrush that has keen challenges for points of sail, apparent wind, trimming, tacking/jibing, right of way and docking.
  5. 8 Little-Known Ways to SailVirtually—Better than videos because they’re more lifelike. Virtual Regatta claims to be the world’s largest such community. These are video games for grown-ups, providing a rush without getting wet. Many other sites offer virtual sailing as well. You’re not likely to qualify for extreme sailing in the America’s Cup, but you can get your thrills with these games.
  6. Mentally—While stuck in traffic, instead of checking your email start thinking about making a turn on a port tack. Consider easing the main as the wind builds. Sit off to one side to work the jib sheets toward better aerodynamics. Are all three sets of telltales flat and horizontal? Perfect! Time yourself to see if you can keep them flat and horizontal for 10 seconds. That’s longer than a cowboy can stay on a bucking bronco. Congratulations. HONK!! HONK! Oops, the light turned green.
  7. Alone—The video above shows sailing around the world alone, which is a surprisingly popular idea. Children as young as 16 have done it. But it’s sufficient to sail a few hours alone. Commentator/explorer Lowell Thomas once said, “Separately there was only wind, water, sail and hull, but at my hand the four had been given purpose and direction.” Without interruption from crew, the skipper can relish every movement and moment on the water. Time flies with purpose and direction.

Imagine Sailing Every Weekend

Given these eight ways to sail, now imagine sailing every weekend. The plan requires carving out time on a given Saturday or Sunday, even if it’s only a few hours at first to watch videos or virtual sailing. Before long, the day gets filled and then another. The mind boggles.

Let’s Go Sail    

Scroll down Rates and pick a day for a sailboat charter. Scroll down Reviews on Trip Advisor. Go back to the Home Page of Williamsburg Charter Sails.  

8 little-known ways to sail 8 little-known ways to sail

More from the Captain...

Police Sail

Police Sail recounts dispatcher’s account of two bad accidents on the Rappahannock and James Rivers. Let’s go sail.

Full Story >

Wedding

Bonnie and I went to Gainesville for the wedding of our daughter Robin Ann O’Donovan to Christopher Chase Tucker. They’ve known each other for five years, and he has endeared himself to her children Remy and Ivan. It was a solemn yet festive occasion on a beautiful day, followed by

Full Story >