If you have long dreamed of swapping your polished leather Oxfords for a pair of Topsiders, take heart. Regardless of weather, now is the right time of the year to think about buying a sailboat. New boats are built over the winter and delivered in the spring. Meanwhile, used boats are often put up for sale after one last season of sailing.

The first step in buying a sailboat is to decide what type of sailboat you want. There are big boats and small boats, shallow-water boats and open ocean boats, day boats and cruising boats. You can get to know some of the different types of boats at discoverboating.com.

Boat shows are another great resource for deciding on what is right for you, whether you go to a show stateside or take a trip abroad. Boating magazines are also useful.

Buy a Boat, Save On Your Taxes

New or Used?

Once you know what type of boat you want, the next important question is whether to buy new or used. Like cars, boats depreciate in value during their first few years off the lot, although higher quality boats tend to hold their value longer.

For many would-be sailors, the question of whether to buy used or new comes down to price. Among new boats, a modest 18-foot day sailer such as the Nomad from Vanguard costs around $16,000. The same Vanguard slightly used might sell for only $11,000 or so.

Likewise, a new top-of-the-line 42-foot day sailer from The Hinckley Company can cost $800,000, while the same boat used but still in good condition might fetch around $600,000 or so.

Cruisers, which are larger sailboats built with live-aboard accommodations, range from about 22 feet to 70 feet in length. Cruisers tend to be more expensive than day sailers because of the size difference and the sleeping accommodations. A 40-foot cruiser, like a J/42, can cost around $400,000, but you could buy a used model from 1996 for much less -- from about $215,000 to $275,000.

There are also more expensive cruiser options. A 40-foot J/122 can cost about $500,000 new and about $400,000 used, depending upon its condition.

Then there are the luxury cruisers like the 70-foot Sou'wester 70 from Hinckley, which can cost upwards of $7 million. A used 2002 70-foot Hinckley cruiser carries a hefty price tag of $5.3 million.

One rule of thumb suggests that you should buy new if you are confident that you will keep the boat for more than the industry average of four years. If you think you might have to resell the boat, or you might only want it for a few years, then a used boat could be your best bet.

Before You Buy

A used boat with a price tag that seems too good to be true could in fact be a floating money pit. If you're buying used, enlist the aid of a marine surveyor to inspect the boat. A surveyor can help avoid any nasty surprises by identifying problem areas before you buy the boat. You should also request a sea trial where the seller takes you and your broker out to demonstrate how the boat handles in the open water.

Use a broker if you are buying a boat over 20 feet in length. For smaller boats, the price tag is often not big enough to interest brokers, who work on commission. A broker can help save time by researching dealers and builders, and can keep tabs on the national and international listings for used boats (such as Sailboatlistings.com, Sailboattrader.com and others). The Yacht Brokers Association of America has a list of members who, in theory at least, adhere to its standards of ethics and professionalism.

If you buy used, the broker can help manage the negotiation between you and the seller. As with real estate, the buyer's and seller's brokers will often share a pre-established commission paid by the seller. If the seller has no broker, you may have to pay your broker yourself or have your broker negotiate with the seller.

Whether you are buying new or used, be sure to check with the Coast Guard to see if the make and model you are about to buy has a decent track record with maritime accidents. And if this is your first boat, know the specific regulations and accreditation required by your state before you set sail for the first time. A couple of boating safety courses, also offered by the Coast Guard, might help you stay out of trouble on the high seas.

Peter McDougall is a freelance writer who lives in Freeport, Maine, with his wife and their dog.

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