We're Jesse and Jenny, and we're shopping for real now. The homework comes before the checkbook. This page is our actual search: every boat we look at gets the same treatment a member's boat gets, scored by the same engine, written up honestly, wins and mistakes included.
Who we are
I'm a Navy pilot turned airline pilot. We moved to the Memphis area from Hawaii a couple of years ago and found our new paradise on Pickwick, which is how a surf boat ended up in the family. Over the years we've owned a Sea Ray 200BR, a Scarab 255, and now the Heyday, and we've boated Kaneohe Bay in Hawaii, the Jacksonville area in Florida, Fort Worth, and now Pickwick. A Loop boat is a big step up from anything we've handled. I go into that the way I go into anything with a cockpit: assume the thing that bites you is the thing you didn't check. This whole product came out of that habit. The Hunt is where we apply it to our own money. More on why I built the tool is on the about page.
Five Seats · the board
| 1987 DeFever 49 Raised Pilothouse | |
|---|---|
| Asking price | $199,900 |
| Matches what we asked for | 71% |
| How much is actually answered | 3 of 20 |
| The honest range | 10–96% |
| Price at or under $250,000 | CLEARS |
The board holds five seats, and 4 are open. Think a boat deserves one? Nominate a real listing and it gets a real read against our written requirements. Beat the lowest boat on the board and your challenger takes its seat, with the write-up to show for it. A score here is about fit for our search. It is never a verdict on anyone's boat, and sellers get no shade from us.
The episodes
A pilothouse at the top of our price
First, we've cleared the board. As our list got more specific about what we want to live on, the four boats from the first three episodes came off it. This one starts the new board.
She's a 1987 DeFever 49 Raised Pilothouse in Orange Beach, Alabama, listed at $249,990. We've also raised our ceiling to $250,000, so she sits just under it.
She's the most boat we've looked at so far. The listing describes Naiad stabilizers with the seals and system refurbished in 2020, a Portuguese bridge, twin Ford Lehmans and 800 gallons of fuel. The Loop's fuel gate is 250 miles, and on the listing's own numbers she carries several times that. The stabilizers are for the open-water days, the Gulf crossing most of all. For the two of us living aboard, the listing has a full-size washer and dryer, and the photos show a queen with a nightstand on each side.
She also comes with homework, same as every boat on this page. The listing gives a 17-foot bridge clearance without saying what was folded down. On our DeFever pilothouse page, one owner of this model reported about 22 feet with the antennas down, mostly from a fixed anchor light, and about 15'5" to 16' once the radar arch and Bimini were folded. The Loop's one unavoidable bridge is 19'6", so what's fixed above her arch decides it. That's a tape-measure question. The other big one is the fuel tanks: four of them on a 1987 boat, and the listing doesn't say what they're made of or whether they've been replaced.
We've sent the broker our questions. The answers get written up here, including any that take her off the board.
Two boats we haven't stood on yet
The board just got two more boats, and neither one has been toured yet. Both came out of our teardown series, where I work a listing on paper before anybody drives anywhere.
The first is a 1999 Sea Ray 480 Sedan Bridge, listed at $199,500 on Pickwick. That's $500 under our ceiling, close to home, with twin Caterpillar diesels and three staterooms. She also comes with homework. The listing shows a big rebuild on the port engine with no dates attached, two different fuel figures, and no height at all, on a model where one owner reports about 22 feet with everything up.
The second is a 1988 Tollycraft 44 Cockpit Motor Yacht in Daytona Beach Shores, Florida, at $119,500. On her listing's own numbers she clears every hard gate. Her twin Cat 3208s have about 6,500 hours on them, so her paper trail is where the work is.
Watch the teardowns: the Tollycraft 44 and the Sea Ray 480.
The 480 is close enough to go see, so she's next. That visit gets written up here like the others.
The 84% that's really a 44 to 92
Second showing: a 2007 Meridian 368 Motoryacht, twin Cummins QSB 5.9s, listed at $224,730 on Boat Trader. On the headline it scores close to the Sea Ray. The honest range tells the real story: only 10 of 20 questions are answered, so that tidy 84% is actually a 44 to 92. A quiet listing isn't a better boat. It's a mystery wearing a flattering headline.
The price sits over our ceiling, and price is the one gate you can negotiate, which is why it reads amber instead of red. And a detail worth showing you: the listing states a 13'7" bridge clearance and a 13'7" beam. The identical number in two unrelated fields is what catalog data looks like when somebody's software filled in the blanks. Which number is real? That's a question for a tape measure, not a spec sheet.
Since our visit the ask has moved $60. We logged every move. The record remembers so we don't have to.
And a genuine thank you to the owner, who drove four hours to show us his boat himself and made the afternoon a pleasure. Great boat, honestly kept. Our hesitation is nothing the boat did wrong: at 36 feet she may simply be a bit small for two people living aboard for a year. That's a fit question about us, not a knock on her.
The day our Loop technically started
Our usual run is up past Grand Harbor and along the main river toward J.P. Coleman. The evening before the Meridian showing we went the other way, past Goat Island, and into the top of the Tennessee-Tombigbee Waterway. The Tenn-Tom happens to be part of the Great Loop route. So, technically, in a surf boat built for exactly none of this, our Loop has officially started. We did about a mile of it. Only six thousand to go.
How to get your wife to a boat showing
You don't lead with the boat. You promise her a surf session first. We run a Heyday on Pickwick, and Jenny will say yes to just about anything with a wake session attached. So that was the deal: she got her morning on the water, then I dragged her through a 1996 Sea Ray 420 Aft Cabin, twin Cat 3126 diesels, $119,900, listed basically in our backyard.
On paper it checked every box we care about: the walkaround queen aft, two heads with real showers, the washer and dryer, diesel power. But paper is paper. That's why we went. Jenny walked in expecting a glorified camper.
"Two bathrooms? For a boat from the '90s?"
The surf session got her in the door. The boat kept her there. And the honest next move on this one isn't a checkbook. The Cat 3126s of this generation use the HEUI fuel system, and that's the one spot where a survey can turn up a big expensive surprise. As much as we liked her, the next step is a proper survey and sea trial, eyes wide open. That's how you avoid becoming the person who lost thirty grand on their dream boat.
Since we first logged it in July, the ask hasn't moved a dollar. The board above knows.
A genuine thank you to Captain Ron at Captain's Choice of Pickwick, who walked two strangers through a boat on Father's Day. And yes, his name is really Captain Ron. If you know, you know.
The road ahead
- June Started the captain's license course with Mariners Learning System.
- Father's Day First showing: the Sea Ray 420 on Pickwick. Episode 1.
- September 6 The Meridian 368, and the honest-range lesson. Episode 2.
- September Through the license training. Now the studying starts. The exam doesn't care how the training went.
- October Two more boats on the board: the Sea Ray 480 and the Tollycraft 44. Episode 3.
- October Cleared the board. A DeFever 49 pilothouse takes the first new seat. Episode 4.
- Fall & winter More showings and more research, hopefully, while the southbound fleet passes our door.
- After that Until the right boat clears the gates, the record, and Jenny.
Between now and the right boat: more showings, more questions, and the board above quietly doing its job.
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Work up your first boat free →How we write these: listings linked, facts from the listings and published sources, our reactions our own. No verdicts on anyone's boat, no condition claims, and nothing about a seller beyond gratitude. When we pass on a boat we'll say so and say why. Episode 1's showing was in June; this page went up in September with the story told the way it happened.
You still need a survey. We just keep you from wasting one on a boat that was never going to fit.