Sail Cheap

Our charter company Let’s Go Sail offers a special Boat-Buyer Cruise for those inclined toward acquisition. The three-hour cruise is a challenge because the prospective buyer is often a fellow whose wife isn’t all that crazy about the idea. In fact, some women remain hell bent against it.

For both of them, I suggest and as alternatives to ownership. You get to rent a boat near you and take it out for the day or half-day. Kick the tires, rev it up, sail till you drop, maybe sleep on board overnight, and generally get the urge out of your system. Try different sizes of boat to see which is more appealing. If you plan to cruise for a week at a time, think 36 feet and up. On the other hand, if you just want to daysail, think 25-32 feet. In any event, you get to walk away after the trip without any of the hassles of repair and maintenance.

Then if you’re still interested in buying a boat, I offer them five paths to sail cheap.

Location, location

Determine where you’re going to sail, because unless the boat is trailerable you’re pretty much stuck at a given marina or mooring. The distinction between trailer boats and mid-size boats is the keel. If you can crank it up to slide the boat onto the trailer, fine. All others have fixed keels and are known as keel boats. They require large steel trailers driven by semi-trucks, a considerable expense withheld until moving day to another home marina.

Trailer sailboats are less expensive and can go anywhere on land. Not so much on the water. The small size (up to 21 feet) limits the speed and therefore the range to a few miles at a time, maybe ten miles tops in a day. We sailed our trailerable 16-footer for 11 years on the James River before moving to the York River with keel boats. The 32-footer used for Let’s Go Sail can crusie the entire Chesapeake Bay, which is fantastic range. 

  1. Boats anchored in Sarasota Bay
    Sarasota Bay, Florida.

    Anchor out

Consider the illustration above of anchoring the boat in a cove vs. a marina slip. A mid-size slip at York River Yacht Haven runs $3,000 a year. But during the spring and summer, people come into Sarah Creek and simply drop anchor for days or weeks at a time. It’s free! Others tie off to a well-anchored mooring ball, which avoids the danger of fouling the anchor. Of all the scenarios to sail cheap, this is the best.

The scene is picturesque, as shown in photos of Catalina Island, Sarasota Bay or Monte Carlo. But you have to climb into a dinghy to get back and forth to shore. Marina life is much more enjoyable if you have a slip because you get to enjoy the people and the amenities. And if there’s a storm coming, you definitely want to be in a slip.

Bow got stuck on the pierSlips are safer than moorings because some protection is offered with the surrounding land mass and fellow boats. But not always. This winter we had an old 30 Hunter sink in its slip because it was tied too loosely. During a big windstorm, the bow pulpit got stuck on the finger pier at low tide. As the tide rose, it ran into a topside scupper and sank the boat quickly. The engine is a goner and a fellow at the yard put it succinctly. “It’s totaled.” He didn’t quite learn how to sail cheap correctly.

Go partners

Storm approaching
Storm approaching.

Compatible couples and friends find nice arrangements by throwing in together. One group I know agreed to every other weekend schedules, with a third weekend together. The permutations are endless, the savings considerable. Try to bring a mechanical guy in the mix, since he’ll prove invaluable.

Some sort of contract has to cover contingencies for moving away or otherwise backing out. It can be hard to find a replacement member. The aggravation is worth it for the immense cost savings. A variation of partners is to own a boat in the Caribbean for leasing by companies. Moorings is the leader. They sell new and newis yachts, but brace yourself for damage by renters.

Buy used

Sailboats depreciate just like cars. After a few years the declining value tends to stabilize. I’m on my sixth boat, five of them used. You get the benefit of a lower price along with knowing the engine is sufficiently broken in. Look for key features: overall cleanliness, no fiberglass cracks or spider cracks, crisp and clean sails, bright and clean running lines, tight rigging, clean head, minimum odor, no mold inside the cabin, dry bilge and clean engine. If the boat lies in a slip, get the buyer to throw that in free for the rest of the season. He already paid for it and won’t get a refund anyway.

Got time?

If you’re serious about buying a boat, give some thought to usage and timing. If you plan to sail at least three times a month, fine. Anything less, stick to renting. If you plan on DIY tinkering and have a yen for it, fine. Otherwise, stick to gardening. If you play a lot of golf or tennis, figure out how you’re going to fit sailing into the equation. And if you have kids, consider their age and interests before lashing them to a boat they may hate. Sailing is a fabulous bonding experience with children, but they have to be willing. Finally, if all this is confusing, talk to other couples to learn their experiences and disappointments. And take a look at YouTube videos that depict the sailing life. “Sailboat Life” is a popular sailing video (below) that shows the pros and cons of cruising.

Let’s Go Sail Cheap

Check rates and then pick a day for a sailboat charter. See reviews on Trip Advisor. 

Sail cheap
York River Yacht Haven


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