The "Real" Pirates of the Caribbean

Mar 11, 2026
The Ovens Crew - an Australian live-aboard family - sold everything to pursue their dream of life at sea and a circumnavigation of the globe. Currently island-hopping through the Caribbean - a region well known for its colourful history of swashbuckling pirates - mum Sarah reports on the "pirates" ashore that have caused this cruising family some angst.
Published 2 hours ago

Real-Life Piracy – Ashore

When I think of the Caribbean, pirates are the first thing that come to mind – not just because of the Hollywood blockbuster franchise, but thanks to the swashbuckling history that threads through this island chain. However, I’m discovering that real-life piracy still lurks in these waters, not from cutlass-wielding rogues, but in the form of brazen theft, violence and even (on rare occasion) murder. Yet the kind that’s really got us walking the plank? The relentless swindling every time we step ashore for a meal, provisions or parts.

Pirates of the Caribbean are not always found at sea.  Image (c) the Ovens Family.

Outrageous Prices

Grenada’s prices are the most outrageously hiked we’ve seen since embarking on this circumnavigation – and honestly, I don’t get it. Down Under, amid a cost-of-living crisis, our grocery bills still run a third of what they do here. The gut-punch? Grenada’s billed as one of the cheapest spots in the chain for stocking up. Sailing north means bare-bones basics: fresh-caught fish and rice. Even local fruits and veggies cost an arm and a leg, so we’ll raid the freezer or canned aisles, and I’ll whip up batches of homemade kimchi to fend off scurvy.

Don’t get me started on boat parts. The U.S. is practically next door by sea, yet marine gear is criminally overpriced. A simple propeller anode? Four times Australia’s rate. Locals tipped us to dodge the gouge: order from Amazon via a shipping agent, C14 customs form in hand for tax-free transit. We got played—Ezone’s brokerage fees wiped every saving, leaving us double-charged for every single item.

Dining out is a minefield too: sneaky service fees and VAT tacked on the bill, or a menu that lures in what you expect to be East Caribbean dollars, yet that fine-print reads USD. It stings once the exchange bites, because the Aussie dollar barely floats here. Word from the trenches: never linger as the last at the table, or you’ll foot the bill for dashers. At this rate, it’s beginning to feel like we are taking a pineapple “where the sun doesn’t shine”!

I puzzle why it costs a fortune here – provisioning in remote mid-Indian Ocean atolls, of the Maldives, or St. Helena’s lonely rock was far cheaper. My grim take: this region’s a magnet for deep-pocketed yachties – glossy charters and seasonal yuppies dropping cash like chum. They’ve got stately homes and corner offices waiting to refill the coffers, so they can afford to pay blindly. But for us world sailors? Cruising families on a shoestring, feeding ravenous teens without hawking kidneys? It’s a brutal broadside.

Keeping the Dream Afloat

We’ve learned the hard way that sailing the globe means you can’t chase every siren song and visit every island or country you may be curious about – there are weather windows to consider, visa costs and immigration red tape. Some bite deeper than any kraken*. It’s a brutal calculus, forcing tough cuts just to keep the dream afloat. And we still have to carve out enough for the bare necessities too: that long-overdue boat maintenance, the insurance premiums that could sink a superyacht, and a steady flow of provisions to stave off mutiny from the crew.

Picture Postcard Caribbean anchorage.  Image (c) The Ovens Family.

Yet, amid the plunder, there’s still sweet sailing to savour: warm trades filling the sails, beautiful locals with stories as rich as their smiles, stunning islands begging for barefoot exploration, and adventures aplenty to chase. But we’ll likely blast through this stretch, bound for distant horizons where the prices play fairer. We’ve already struck the Bahamas from the chart – those jacked-up cruising permits and fees make it a port we’d rather admire from afar. It’s a hard sacrifice, no doubt, but one we have to swallow if we’re to keep pressing on – eyes fixed on the Panama Canal and our grand finale: the boundless Pacific.

Sarah Ovens
The Ovens Family
SV Excelsior

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* Mythical Norwegian Sea monster.

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Other Noonsite reports from SV Sailing Excelsior:

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About the Authors:

The Ovens Crew are an Australian live-aboard family who began cruising on their sailing catamaran, Excelsior, in 2020.  Starting out on the east coast of Australia, they have since travelled extensively throughout Indonesia (for 12 months) and then onward to Thailand, Malaysia, Sri Lanka, Maldives.  After crossing the Indian Ocean to explore the African Continent and its cruising grounds, they then crossed the Atlantic Ocean to Brazil and then onto the Caribbean. Find out more about the Ovens family via their:

The Ovens Family with SV Excelsior in the background. (c) SV Excelsior.

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