(360) 281-6495 john@BoatDollars.com

Do you find yourself lurking on sailing and cruising forums? I do. I always get a little chuckle when someone posts a question about “the best cruising sailboat.”

I chuckle because there is absolutely no way to answer that question. There are too many variables. How are you going to use it? How many people will be aboard? Where are you planning to go? What is your experience? What is your budget? The perfect cruising sailboat for one person or couple or family, might be an abomination to another.

The boat you ultimately end up cruising aboard will be a compromise based on your unique situation, plans, wants, needs and budget. It’s a very personal thing!

My search for a cruising sailboat began probably like most with hours upon hours surfing Yachtworld.com and similar sites, looking at pictures, evaluating specs and, of course, looking at asking prices. At some point though, pictures just don’t cut it anymore.

One of my favorite waterfront restaurants in Portland, Oregon is Island Café. It’s a really cool floating restaurant on Hayden Island with a Caribbean flair, great food and strong drinks. It also floats adjacent to the docks of the premier sailboat brokerage in Portland, Passion Yachts. After a basket of coconut shrimp and a strong margarita or two, I would often stroll through Passion’s docks ogling at sailboats.

It was on one of these excursions that she caught my eye. She had a Sleek hull, smallish cockpit, and beautiful teak decks. I whipped out my smart phone and pulled up Passion’s website, clicked on inventory and scanned through the listings till I found it.

S/V Mysterycruising sailboat. 1986 CT38 Princess Fast Cruiser.

“Taiwan built, Alan Warwick designed for fast passages and for the challenging Tasman sea conditions.” The pictures of the interior teak work were stunning! I clicked on “full specs.” 16,775 pounds displacement, Yanmar engine, 2400 hours, 50 gallons of fuel, 95 gallons of water, electronics, sail inventory, etc., etc. Asking price, $98,000.

“Hmmm, a bit above my price range.” Maybe someday I could afford a beautiful cruising sailboat like this… Back to Yachtworld…

Over the next year, I surfed many sites, strolled many docks and ogled at many boats, but for some reason this sailboat, Mystery, stayed in the back of my mind. In retrospect I think I understand why.

When Shelly (my other, and decidedly better, half) and I started sailing we were attracted by the looks of the classic old cruisers with all their wood trim and deep gunnels and so forth. But now that we were several years into the journey and had spent considerable time racing and cruising on a number of different types of boats, there were other features that were important to us as well.

I think Mystery stuck in my mind because, with her teak decks and rich teak interior, she was a good compromise between the classic vessel look we were attracted to and the more modern design and performance features we had come to appreciate.

Our plans do not necessarily involve crossing oceans. We plan to sail down the Pacific coast. We may never get past MexCruising Sailboatico – or we may keep going down to Panama, transit the canal, cruise the Caribbean, Bahamas, Gulf Coast and end up on the East coast of the U.S. That’s thousands of miles and years of adventure and nearly all of it is considered “coastal cruising.”

So it is no “mystery” that when I noticed her asking price drop from $98,000 to $89,000 and then to $84,000 that she hit our radar. Mystery was the best compromise for our unique situation, wants, needs, plans and budget. She’s an ideal cruising sailboat for a couple, coastal cruising, under $100,000 and she’s unique, she has some classic character that’s all her own.

Of course, there’s a lot more to consider than just these things when acquiring a cruising sailboat. In part 2 I will share our experiences with the actual offer, negotiation and purchase of Mystery.

John Ensley
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John Ensley

A Dad, a Grandpa, an entrepreneur, a veteran, an adventurer and a consummate lover of life and liberty. My mission is to help you experience more financial security, confidence, safety, privacy and peace of mind.
John Ensley
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