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 a lot of fun to sail. And after sailing, the interior will feel like a very personalized and upscale hotel. She's even available for charter, so we could try before we buy, and my birthday's coming soon... um, honey? Maybe you should read more: Perini Navi Fidelis: A Ketch Worth Waiting For

Rebecca under sail at Loro Piana regatta

Should I choose Rebecca? Photo: Carlo Bourlenghi/Loro Piana Superyacht Regatta

#2: Rebecca

Okay, now we're getting down to some tough decisions. If I can only choose one... should it be Rebecca?

She's fast, and she's classy. Those teak decks would feel delightful under bare feet. Her varnish is perfect (and there's staff to take care of it). And she's got all the modern bells and whistles, carefully tucked out of plain view.

This might be my top choice. I need to watch the video again, and read over her details a few more times, because maybe it's just the Caribbean sunshine and trade winds that make her look so good.

And besides, there's one more to look at...

Adela bow on under full sail

Adela was originally built in 1903, but a full rebuild brought her back to a life of superyacht racing.

#1: Adela

What a yacht. She's more than a century old—but a significant rebuild in 1995 brought her back to life. She still races hard, and wins her fair share races. And with room for only eight guests, she won't force me to go out and troll for a bunch of new friends.

Okay... I've made my decision. Drumroll, please:

If it came down to it, and I actually had to choose which of these beautiful sailing yachts to buy... Adela would be the one. (Um, honey, you can cancel the order for Fidelis.)

But that's just me. Which one would you buy? Let me know if I'm making the wrong choice, and why, in the comments below...

And now... back to sandpaper, scraper, and reality.