Watching The River Flow
Looking to retire on the water? Fatty Goodlander shares the best places for sailors to live on a budget—from the Caribbean to Southeast Asia.
Like most Americans, I enjoy going to new restaurants. If I like the food and the vibe, I’ll return. With luck and a great kitchen staff, the new dining spot might even turn into a personal favorite—a place I’ll go as often as whim and wallet allow. The menu is, of course, all important. While I like most food, I’m not fond of liver or cabbage-based meals—nor do I like hearty soups in warm climes.
But every social institution is born, grows, decays, and dies. Some restaurants like Le Dome in Paris take many centuries for this life cycle to complete; other roadside eateries, only a year or two. The head chief leaves. A new owner changes from jasmine rice to Uncle Ben’s—and ditches the more expensive butter for the cheaper margarine.
The place loses its magic.
I drift away.
Towns and cities in America do this as well.
I was born in Chicago. And while I’ve awakened in too many southside ERs to be a fan of the Windy City, its blossoming theater scene in the late 1960s—when I and some friends founded Unity Player on the near-northside (Belmont and Broadway)—was utterly amazing. Goodman Theater. Hull House. John Belushi, Bill Murray, Tina Fey, and Chris Farley of Second City. Bob Sickenger. Playwright David Mamet. Directors John Hughes, Joe Mantegna, Michela Mann. John Candy. Bob Odenkirk. Actor/comedian Robin Williams. Bernie Mac. Gillian Anderson. Terrence Howard. Daryl Hannah. Even Mister T!
But this is a sailing mag, right?
The marine scene of New Orleans was nearly as hot as its music scene. West End not only produced some of the best yacht racers—think OJ Young on Lone Ranger and John Dane III—but also the best smugglers, gun runners, and tomb raiders of its day.
Oh, what fun I had as a young lad tracing all the bullet holes in the 100-foot schooner Jester as Hempi Taylor (of Taylor Diving and Salvage) and his boys raced their XK120 Jags around the harbor as if they owned the place. (They did.) And if Hempi was in a good mood, he’d allow us Goodlanders to help count their stacks of money, their shining bars of gold. Hippy Jim. Bill Seemann of C-flex fame. The infamous schooner Haze. The notorious Lovik the Lazy. Davey Jones’ Locker. And Walter Q, who regularly made runs to Cuba for the CIA or Fidel, depending on the size of purse offered.
Georgetown, South Carolina, also nurtured us wonderfully in a time of great need. Boston too. Saugatuck, Michigan. Fort Liquordale. Key Wasted.
It’s not just a matter of lat/long—it’s timing too. One year a place is Nirvana, the following it sinks back into dreaded mediocrity.
In the Caribbean: St. John, St. Barts, and Bequia all were, at different times, the Very Best Place on This Planet to Be While Young & Wild & Stupid.
I was all three—and still, at 72, am proud of it.
At least I lived while I could.
But times change. Everything decays, dies, and is ultimately reborn. One second Rome conquers the world—the next, its befuddled gladiators can’t even tie their own shoelaces.
There’s a time to stay and time to go.
Of course, I could have found a restaurant or a city that I liked in the 1960s—and stubbornly continued to eat there as the food and culture coagulated… but I wisely chose not to. Life is short—and life is to be kissed full on the lips, not suffered through.
November started off nice enough—then, suddenly, my Inbox was full of frantic messages inquiring how and where a freedom-loving American sailor might retire—on minimum bucks for maximum fun.
If you are pressed for time and want to cut to the chase: the Lesser Antilles is a perfect destination for an American sailor to punish their liver over the long-term. However, as nice as the Eastern Caribbean is, there are numerous other equally-excellent cruising grounds in the Pacific and Indian Oceans as well.
Mexico—on both the Caribbean and Pacific sides—as well as central and south American offer almost endless possibilities.
South America is a fun place to cruise—that is, if you don’t mind all those Nazi doctors with DME degrees (Diabolical Medical Experimentation) that have infiltrated the place.
But—why dwell on the past?
My writer friend Doctor Spock—the baby doctor, not the Star Trek guy—used to live aboard year-round, on a modest 28-footer in Maine to summer aboard and an austere 24-footer named Carapace which he wintered aboard in the Virgins.
That’s right—not many men sitting on a hundred-million-dollar writing fortune would reside aboard such no-frills production craft but Spock was all substance and zero flash.
Yes, he was an Olympic rower in his youth—and well into his 80s he’d regularly row from Peter Island to Road Town for a brewski.
Morgan Freeman kept a liveaboard boat in the Caribbean for years—often within sight of his home on Virgin Gorda.
One of the first questions that must be answered is whether the migrating sailor wants to be internationally mobile (sail from nearby country to country) or remain in one country. Long term visas aren’t easy to come by—which is part of the beauty of living aboard. You can take your home with you as you travel from Visitor’s visa to Visitor’s visa.
This is why we’ve HQ’d out of SE Asia for the last decade—because Myanmar, Thailand, Malaysia, and Indonesia all welcome the cruising sailor for between three and six months automatically upon arrival—longer, perhaps, on application.
SE Asia is dirt cheap, non-violent, and almost crime free. (I do not lock my boat, my dinghy, or my expensive bike in Serangoon Harbour—why waste the time? I’m not kidding! In busy food courts teeming with hundreds of people, my Asian friends leave their iPhone 16 Pro Max to mark their seat!).
Of course, for the more adventurous—a sailor who tires of Southeast Asian can then sail downwind to Sri Lanka, India, the Maldives, Chagos, Seychelles, Madagascar, and Africa—easy-peasy. (We know—we’ve wandered across the Indian Ocean many times, with mainsail safety stowed.)
Then what? Simple! You just wait for the monsoon to reverse—and toddle back to Thailand dead-down-wind once again. Far out, right?
…imagine how cool the Caribbean would be if the Trades reversed every six months!
Once in the Med, it is easy to kick around Turkey and Greece without paying much attention to the Schengen Regulations—but westward towards France and Spain, outright lying and some minor forgery skills are required.
If you’re well-heeled you can leave your boat in French Polynesia half the year—and explore the Societies and the Cooks undersail, then have a change of scenery ashore in NZ, India or Africa.
When I first started cruising Thailand, you could stay in a beach hut for a buck—now, sadly, it’s between $4 and $6 a day.
If you like a ‘capful of wind,’ then summer in New Zealand and when the area clears of hurricanes, meander northward to Tonga, Fiji, and Vanuatu for the other half of the year. (Don’t worry about running out of tropical isles as there are thousands of ‘em in this area—tens of thousands if you include Micronesia.)
Well, obviously, sailing to a distant paradise takes time, talent, money, and seamanship. However, any idiot can buy a boat in Australia, overnight to Indonesia, and then learn the ropes there in flat seas and light airs before reaching Borneo and/or Southeast Asia.
Too many choices? Wanna leave the US of A today or even sooner?
…just fly into KL and take a bus to the west coast, then a ferry to Langkawi.
Langkawi is one of the nicest, safest places in Malaysia—and chockablock with yachts for sale, many at bargain prices. (You can peruse them first on the WWW if you want.) Have the yacht broker pick you up at the airport. You should be able to find yourself a yacht in a day or two—there’s even a deaf, dumb, and blind yacht surveyor who will ‘guarantee’ that the vessel he may (or may not) be standing in front of is in 100% Lloyds shape (whatever that means).
The beauty of this is that Malaysia is a very stunning, very benign cruising ground. And, once your new vessel is ‘shipshape & Bristol’—which usually takes between one week and two decades of work—you can cruise thousands of coastal miles of Malaysia, Thailand, Singapore, and Indonesia without overnighting. Hell, you can almost sail from Langkawi to Darwin with only a night or two at sea.
Don’t worry about boat bits—both Thailand and Singapore have more boat parts than NYC. Cheap labor, too!
Why are there so many good boats selling for so cheap in Langkawi? Because mom-and-pop cruisers often get this far—then panic about the high winds, large seas, and blood-thirsty pirates of the Indian Ocean.
Pshaw! I say.
What—you’re going to allow a few YouTube beheadings to discourage you? Tsk-tsk!
If you’re really feeling your oats, you can sail Singapore, Cocos Keeling, Rodrigues, Reunion, Madagascar before tying one on in Cape Town. (On passage between Cocos Keeling and Reunion, we experienced gale force winds each-and-every afternoon! FUN, FUN STUFF!)
I do not recommend the Hawaiian isles—even as a place to buy-and-depart from.
Forget the North Sea—let the few remaining cod fish have it.
Brazil can be fun—just make sure to wear two pairs of shorts during carnival—one pair with your wallet & money—and another pair on top of that… so that, when those ‘big fellas’ come up behind you, jam their fat, muscular hands in your (exterior) pockets… they don’t get anything (other than, perhaps, the fleeting pleasure of killing you).
The Philippines are a fun place—especially if criminality is your cup of tea. Anything goes—but, hey, that might be what you’re attempting to escape from, not run towards.
…fickle, sailors can be so fickle!
Some other factors: make sure your passport has a lot of years left on it.
Forget American-only banks—you’ll want your money stashed in a wide variety of truly international banks. E-trade is one that I use. Barclay’s, in certain locales. Ditto, OCBC—the Oversea Chinese Banking Corporation.
Don’t rely on social security to continue—that might not last for more than a few nano-seconds, dudes!
Avoid Papua New Guinea if possible—since the Aussie’s stopped paying for their drugs with money and began trading AK-47s for the ganja… Well, it’s a wee hot, hot, hot in that section of the world.
I’ve been up the Red Sea and don’t recommend it. For example, young starving men enlist in the Sudanese army in hopes of being fed—but aren’t. Instead, they’re armed and sent out to ‘hustle up’ dinner amongst the populace and stray passers-by. Worse, are the Naval vessels on patrol at sea. Each time they request food, they receive a case of WD-40 and the non-compassionate instructions on how-to maintain their weapons in case they need to murder someone.
Yes, the world can be a tad tricky—and you thought riding the subway in NYC was chancy!
And, sure, catamarans (pronounced cattle-ma-rans) are continuing to be sought after cruising vessels. I mean, I frowned on all those ‘glued in’ windows in the hull that weren’t mechanically fastened… now I see the wisdom… those sheets of Lexan are sooooooooooo easy to kick out in order to fire our AK-47s through!
…totally convenient (if not overly watertight).
The bottom line is this—as a sailor, the entire world is on your menu. You can still, for a limited-time-only, pick and choose our course as wealth, wind, and whim desire.
Once upon a time, a literary hero of mine used to say, “When the going gets weird, the weird turn pro.”
We’re beyond that now.
Thus, I offer a gentle historical reminder: should the barb wire begin to be gleefully strung around you, you won’t have much time—all weather windows, no matter how benign or long-lived, eventually slam shut. Just ask Anne Frank’s father or any passing gypsy reading the news of the Kristallnacht with disbelief, And don’t forget, with the proper seamanship skills, there’s no better get-away vehicle than a boat.
Cap'n Fatty Goodlander has written for ALL AT SEA since 2005.
Worth your time?
Thanks — noted.
