While sanding the varnished coaming on our Herreshoff Marlin yesterday afternoon, I found myself imagining what it would be like to have someone else do all the brightwork next spring. No more tender fingertips, no more varnish-stained blue jeans... I could sit back with a sparkling beverage in hand and watch the work get done.

But then I realized that if was going to dream, I might as well dream big... superyacht big. I mean, why fantasize about paying someone to do the varnish on a twenty footer when you can fantasize about owning a really big sailing yacht?

So if I could only buy one superyacht... which one would it be?

I like to race. I like to go fast. And I like classic yachts. So I narrowed it down to five yachts that would all (in very different ways) meet my high standards for superyacht-ness.

Pendennis catamaran Hemisphere under sail

The Pendennis catamaran Hemisphere would be the best buy if calculated by the acre.

#5: Hemisphere

I've never owned a catamaran, but for combining space and sailing this one takes the cake. At 144 feet long and 54 feet wide, Hemisphere would definitely provide the biggest acreage for me and all my friends—of both deck and sail. The mainsail and gennaker together exceed 12,000 square feet. Top speed: 20 knots. Wow.

And in the climate to which I wish to become accustomed (read: Caribbean), that forward trampoline would definitely be the first choice hangout spot. "Oh cabin boy, bring me another sparkling wine..."

Velsheda Photo-by-Marc-Heupers

Velsheda is a refurbished J Class yacht that was first launched in 1933.

#4: Velsheda

Rupert Holmes chose Velsheda to top his list of 10 Sexiest Sailing Yachts, and with good reason. A refurbished America's Cup J Class yacht, she won a lot of races in her day (the 1930s), though she never vied for The Auld Mug. I think if this was my chosen one, I would race her in a tropical climate... and then have a very comfortable tender with a hot shower awaiting at the end of each wet day.

Perini Navi Fidelis underway

Fidelis has two cockpits and acres of sail area.

#3 Fidelis

Two cockpits (his and hers?), fold-down transom steps, and 16,000 square feet of sail... Fidelis could definitely improve my image at the local yacht club. She also looks like