Gordon Ashcroft · Annapolis, Maryland
Give me one Saturday morning at the dock, and I’ll keep you off the forty-thousand-dollar boat.
Gordon explains it in 90 seconds
Ready to look at boats? This is the one
The Retirement Cruiser’sBuying Guide
Buy the boat you’ll still love at seventy-five. Second edition, expanded.
Three hundred-odd deliveries taught me where a sailboat hides its bills. This is the guide to finding them before you sign — and walking away from the boat that ends the plan.
- Which boats a couple over sixty can really handle — and why length is the wrong number
- The twelve-point dock walk-through, with what each fault costs to put right
- Rig, deck, engine, wiring and gas: what tired looks like before it’s a bill
- The twenty questions brokers don’t enjoy, and every step from offer to keys
- Safety at seventy, the first season, and what she really costs a year
Instant PDF · today $19.99, was $39.99 · Secure checkout by Gumroad · 7-day money-back guarantee
Not ready to look at boats yet? Start here
Before the Boat
The year-before guide for couples thinking about retiring onto a sailboat.
The Buying Guide above is for couples who’ve decided. This one is for the year before that — when you’re still asking whether to do this at all, and whether it’s both of you who want it.
- What the life is really like — a real week, not the brochure week
- Is it both of you? The two-skipper rule, and your body at seventy
- The money nobody puts in the brochure, and owning against chartering
- Health cover, insurance and the paperwork of being away
- A one-year trial plan: seven tests, each with a clear yes or no
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How it works
Three steps. Nothing to wait for.
Pay once
Secure checkout by Gumroad — card, PayPal or Apple Pay. One payment, nothing renews.
Download on the next screen
The guide and the four printables open the moment your payment goes through. Read on a phone, tablet or laptop.
The link lands in your inbox too
Gumroad emails you the download link as well, so you can find it again. Nothing ships, and there’s no account to set up.
The honest math
Five bills a clean survey can miss — and what it costs to see them first
A well-loved thirty-eight footer on the Chesapeake. Clean survey, lovely joinery. The people who bought her spent their first two seasons paying for her instead of sailing her.
The usual way: find out at the yard
| Standing rigging — all new wire and terminals | $8,000 – $15,000 |
| Deck core rot — one side deck, cut and recored | $6,000 – $20,000 |
| Blisters — peel, dry out, barrier coat | $10,000 – $25,000 |
| Repower — 30–40hp diesel, installed | $20,000 – $40,000 |
| Mainsail and headsail, new | $8,000 – $14,000 |
| If she needs the lot | $52,000 – $114,000 |
With the guide: find out at the dock
| The twelve-point dock walk-through — your Saturday morning | $0 |
| This guide 50% OFF | |
| A rigging shop’s opinion, asked at the dock | $0 – $150 |
| Full condition survey, thirty-eight feet | $760 – $1,140 |
| Haul-out so the surveyor can see the bottom | $500 – $900 |
| Knowing before you sign | $1,280 – $2,210 |
One wet side deck you walk away from — six thousand dollars at the low end — pays for this guide three hundred times over.
Ranges quoted by East Coast yards, rigging shops and surveyors in recent years, for a boat of thirty-five to forty feet. Your yard will quote its own numbers. The order of magnitude is the point, not the invoice.
Look inside
Four pages, as they read in the guide
Plain language, in the order you’d actually do things. Tap any page to read it full size.
What’s inside
Each chapter answers a question you’ll have at the dock
Which boat, and why
- “Which boats can I still handle at sixty-five and beyond?”The five boats I’d still buy at sixty-five, what each one asks of you in return, and seven questions for any boat that isn’t on the list.
- “Is forty feet too big?”Why length is the wrong number — and how to judge the companionway, berths and galley you’ll be living with at seventy.
- “The broker says she’s bluewater.”What “bluewater” means, and monohull against catamaran, line by line.
- “She’s twenty-five years old. Is that a problem?”Buy the systems, not the year — how long every major system lasts and what it costs to replace.
- “What does ‘motivated seller’ actually mean?”Reading a listing — the phrases decoded, the photos that are missing, and what she’s really worth.
The walk-through, and every system behind it
- “Is she worth paying a surveyor for?”The twelve-point dock walk-through, with what good looks like, what sends you away, and what each fault costs.
- “How old is that rigging, really?”Standing rigging — the $8,000 question you can answer from the deck in four minutes.
- “The survey came back clean — so we’re fine?”Deck core, blisters, the survey’s blind spots, and how to brief a surveyor so the report is worth the fee.
- “The engine started. Is it any good?”The engine, and the wiring, plumbing and gas — what tired looks like before it becomes a bill or a fire.
- “What should I ask, and what happens after the offer?”The twenty questions brokers don’t enjoy, then offer to keys, with a worked negotiation in real numbers.
Can you run this boat — for years
- “Can I sail her without extra crew?”Short-handed: the six systems that decide it, and what each upgrade costs.
- “What actually hurts sailors our age?”Safety at seventy — falls, staying aboard, calling for help, fire and fatigue.
- “Why do people give up after one season?”The four first-season mistakes, and a first year month by month.
- “What will she cost me every year?”What she costs to own, line by line, and five years start to finish, including selling her.
- “And when we’re done?”When to sell, and how — broker or private, pricing, and the folder that adds thousands.
The clipboard
- “I’ll forget half of this at the dock.”The full inspection checklist, formatted to print — one copy per boat.
- “What do I check on the sea trial?”Sea-trial and survey-day checklists, so the two days that decide the purchase go to plan.
- “I’ve got the keys — now what?”Appendices: the first ten days after you own her, plain words for every term, and who to ask.
- “Can I print it?”Four printables — walk-through, scorecard, broker sheet, first-season list.
Everything you get
The guide, plus four printables for the dock
- The Retirement Cruiser’s Buying Guide — 85 pages, 19 chapters + 3 appendices$39.99
- The 12-Point Dock Walk-Through — printable, clipboard-ready$19
- The “Can We Handle This Boat?” Scorecard — score her before you fall in love$12
- The Broker Question Sheet — 20 questions, and what each answer means$19
- The First-Season Fix List — what to sort in the first six months, in order$19
- Total value
$108.99
$19.99
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Read it for a week.
If it doesn’t save you more than it cost — one boat you walked away from, one question asked at the right moment, one yard bill you didn’t inherit — reply to your receipt and I’ll refund every cent. No forms, no questions. You keep the files. The same goes for Before the Boat and the two-book set.
New · two books
Not looking at boats yet? Start one step earlier.
The Buying Guide is for couples who’ve decided and need to choose well. Before the Boat is for the year before that — when you’re still asking whether to do this at all.
If you’re still deciding
Before the Boat
The year-before guide for couples thinking about retiring onto a sailboat. 49 pages, four worksheets.
- What the life is really like — a real week, not the brochure week
- Is it both of you? The two-skipper rule, and your body at seventy
- The money nobody puts in the brochure — and owning against chartering
- Health cover, insurance and paperwork when you’re away
- A one-year trial plan: seven tests, each with a yes or no
If you’re ready to look at boats
The Retirement Cruiser’s Buying Guide
Second edition, expanded. 85 pages, nineteen chapters, plus four printables for the dock.
- Which boats a couple over sixty can really handle
- The twelve-point dock walk-through, with what each fault costs
- Rig, deck, engine, wiring and gas — what tired looks like
- The twenty broker questions, and offer to keys
- Safety at seventy, the first season, the real yearly cost
If you want the whole road
Both books
From “should we?” to the keys in your hand. Both guides, the four printables and the four worksheets.
- Before the Boat — 49 pages, four worksheets
- The Retirement Cruiser’s Buying Guide — 85 pages
- The four dock printables
- The same yearly cost figures in both, so the numbers line up
- One payment, one download, one seven-day guarantee
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Thirty years of deliveries. Forty-four years in Annapolis. Still cruising at seventy-two.
Why I wrote it
I was the bloke they paid to bring the wrong boats home
I learned to sail on the Derwent in Hobart, in a wooden dinghy that leaked. In 1982 I came across to deliver a boat to the Chesapeake, met a girl in Annapolis, and never went home.
For thirty years I delivered other people’s boats — up and down the East Coast, out to Bermuda, across the Atlantic more times than my wife liked. Whatever was wrong with a boat, I usually found out two hundred miles offshore, in the dark. Then I spent fifteen years teaching people in their fifties and sixties to cruise their own.
I’ve owned the same thirty-eight foot cutter since 1998, and I still live aboard half the year. I wrote this so you get the conversation I’d have with you across a table — before you sign anything.
Not a book about the dream. A book about the boat.
It’s for you if
- You’re getting older and want to retire aboard a cruising sailboat — or simply sail one regularly.
- What worries you isn’t the sailing, it’s buying the wrong boat.
- You’ll often be sailing her short-handed.
- You’ve never had a boat surveyed and don’t know what the report should tell you.
- Not sure you want a boat at all yet? That’s what Before the Boat is for.
It isn’t for you if
- You’re racing. Different boats, different priorities, different book.
- You want a repair manual. This tells you what to walk away from, not how to fix it.
- You want listings. I don’t sell boats and I don’t take a cut from anyone who does.
- You’re buying a powerboat or a trawler. This is sail.
Answered honestly
Questions people ask before they buy
Is it a printed book?
I’ve never owned a boat. Will it go over my head?
Is there a subscription?
What if I lose the file?
What can I read it on?
Which book should I buy?
What if it’s not for me?
Does it replace a survey?
Are the prices in it current?
I’m not on the East Coast. Does it still apply?
I bought the first edition. Do I get the new one?
Is Gordon a real person?
Ready when you are
Buy the boat you’ll still love at seventy-five.
Eighty-five pages, four printables, and a seven-day guarantee. Read it before you look at another boat.
Instant PDF · Secure checkout by Gumroad · Pay once · 7-day money-back guarantee
Or both books — Before the Boat and the Buying Guide — for $24.99