07/27/2016 03:11 EDT | Updated 07/27/2016 03:59 EDT

How To Afford A Private Yachting Vacation

I arrived at St. Maarten's Princess Julia International Airport in the late afternoon, only a compact carry-on in hand. I was advised to pack light: space is limited on a sailboat and realistically passengers don't require anything other than some swimsuits and industrial-strength sunscreen.

Mako photo via Getty Images

I arrived at St. Maarten's Princess Julia International Airport in the late afternoon, only a compact carry-on in hand. I was advised to pack light: space is limited on a sailboat and realistically passengers don't require anything other than some swimsuits and industrial-strength sunscreen.

This was my first time going on a chartered yacht, a vacation I never thought I'd be able to take. "Chartering a private yacht" is just one of those catastrophically pricey travel aspirations that most of us don't even bother putting on our bucket list. I've long assumed that the closest I'd ever come to letting my nautical flag fly would be passing by the J. Crew flagship adjacent to my landlocked condo.

What fundamentally makes private yachting so prohibitive is that a disproportionately small number of travelers must cover the oppressive fixed costs of operating an entire boat. Fiscally, this formula is the equivalent of renting out a whole hotel complex when all you need is one room.

Cue TradeWinds, my yacht in shining armour.

The family-run fleet of "floating hotels" permits guests to book single berths, instead of entire vessels, and subsequently aggregates individual reservations to fill up a boat. Should any initial social lubrication be needed between guests there is an open bar onboard with enough Côtes de Rhône rosé and exotic rum to last an eternity of cocktail hours. Collaborative consumption meets chartered catamaran cruises. Genius.

Compared to the cool five figures it ordinarily costs to charter a luxury yacht, the average week-long trip, which includes a private captain, crew, personal chef, and all food and booze comes in at just US$5,750 per couple (about US$400 per person per day), around the same price as a vacation on terra firma.

Spotting a gregarious group of people gathered around a 'TradeWinds' sign, I deduced that these were my fellow helmsmen. I introduced myself and fell into effortless conversation, as if to prove to any sociologist that might be in earshot - or maybe just to myself - that people can still have social skills. Which is a very fortunate thing, because as we loaded into a pair of dinghies and departed for our yacht, cell service faded, every last signal swallowed by the mighty sea. Let the digital detox begin.

We whizzed through the bustling Simpsons Bay Lagoon toward a 59-foot Monaco-made catamaran. Within seconds of stepping on board, freshly shaken rum cocktails were thrust into our hands, a welcome diversion from the impossible task of trying to comprehend the sorcery that was this sailboat. Not a single person spoke as we slurped down our drinks - not out of shyness but sheer stupefaction.

"Mara...Mara...!" I barely registered the captain calling my name, "Let me show you to your sleeping quarters." In my bewildered state I hadn't noticed that the rest of the group - two couples, a best friend duo, and a solo sailing enthusiast - had already dispersed below deck. I hurried to lay claim to the last remaining cabin, a spacious stateroom with a queen-size bed, en-suite bathroom, and A/C, should the sea air not provide enough breeze come nightfall. I couldn't believe I was in a hull and not a luxury hotel.

Very little time was spent in our rooms, however. The sun-kissed communal dining table was the collective centre of action, a heavenly feast for ten dished up every breakfast, lunch, and dinner by the boat's private chef. Each meal was an artisanal spread of locally-sourced fare, from tuna sashimi caught off the back of the boat to tropical fruit picked up daily from farmers' markets. This locavorism was an act of sustainability I rarely witness in the import-addicted Caribbean travel industry and reflected Tradewinds' commitment to protecting our planet's fragile coral reefs and the oceans that cradle them.

Yet, the vibe onboard was refreshingly way more summer camp than supper club. I had packed three books thinking I'd spend most days in a perpetual state of catnap, but no work of literature or plush chaise could ever compete with the boat's inventory of playthings: snorkel gear, dive equipment, stand up paddle boards, kayaks, windsurf rigs, sport-fishing rods, the list goes on and on. Day after day I manically cycled through this holy grail of activities like a hamster in a wheel.

Or, like a person who spends most waking hours sitting at a desk.

For a week we hopped from isle to Antillean isle, meeting with our captain each morning to create a bespoke itinerary for the day ahead. First stop: Île Fourchue, an island between St. Maarten and St. Barths, regarded as one of the Eastern Caribbean's best scuba spots.

Those of us that were certified divers spent the morning 70 feet below the boat. Godzillian barracudas, dazzling Spotted Eagle Rays, and even a dolphin modelled for us on a catwalk of Seussian sea sponges, a spectacle I've since mulled over many times: Just how much longer will this underwater environment be in tact? The Caribbean has already lost 80% of its coral cover, the waters around St. Maarten among the hardest hit. Will stories of seeing a living reef soon be the stuff of folklore?

Ascending just in time for lunch, I towelled off and chewed over this unpalatable conundrum before joining the group for Niçoise and a midday Chardonnay. After all, it was 5 o'clock in island time, not to mention I had to hydrate somehow before the afternoon hike up to the lookout on Île Fourchue's rocky peak.

It was an incomprehensibly clear evening and from the summit we had a sweeping view of Saba and all the Saints (Maarten, Barths, and Eustatius). Overlooking the cartographic vista, we resolved that the most logical way to pick our next destination was to play a life-size game of spin the bottle: one of us would close our eyes, spin around, and stick out a finger. Whichever piece of land was in its path would be our next port of call.

And that's how we ended up on a custard-tart shopping spree at the century-old Patisserie Choisy on St. Barths. Arteries be damned, we ate enough to bring about the pastry apocalypse, thereupon scurrying into hiding before the world could discover who had ended dessert forever. We sought refuge on the island's most exclusive beach, Anse de Columbier, an untouristed but heavily-Tortoised bay accessible only by boat. Far removed from the intolerable pretense that plagues much of the French protectorate, we sunbathed and snorkelled the day away in solitude before heading back off the beaten path.

The next stop was Sandy Island, a speck of land that quietly exists as if in an altogether different dimension. One of the few atolls in the Atlantic, Sandy Island is perhaps best known (by those lucky few who are in the know) for its little lime-green beach bar, a church of cold beer and crayfish, which large as lobster, sweet as candy, and addictive as The Voice, should be classified as a Schedule 1 crustacean.

I could have stayed on Sandy Island for several days, if not the rest of my days; but, we all know how Lord of the Flies turns out. So, I concluded it would be best to avoid the inevitable and get back on the boat. Which proved to be a very wise decision on my part since Anguilla, our next and final stop, ended up being my favourite of them all.

Prior to visiting I was under the impression that Anguilla was analogous to other overrated Hollywood hideouts like Aspen. After all, it's the getaway of choice for pop cultural royalty and its vacation homes more often than not have helipads. I anticipated arriving on a mutant island, its coastline conquered by other nations' natives and its landscape disfigured by the overbreeding of infinity pools.

However, we arrived to find anything but this Möet-fueled abomination. As we made landfall there wasn't a chlorinated body of water nor pair of satellite dish-sized sunglasses in sight. Instead we beheld a laid-back belt of eclectic beach bars known as Sandy Ground.

We wandered over to the closest cabana, an antique sailboat turned wet bar with a hand drawn driftwood sign that read, 'Elvis's', and ordered a round of the house special, a stiff and spicy potion called Mamajuana, which in addition to being delicious is fabled to work as a holistic remedy for sexual impotence.

It did at least arouse our appetites and we ascended to The Strip, a hilltop boulevard bound by food trucks and roadside eateries. Anguilla is dubbed one of the culinary capitals of the Caribbean, so we spent the late afternoon conducting a very formal investigation into this claim. Not that we had any doubts, but doing things 'in the name of science' is always a good way to rationalize unbridled spending, so we took on this noble cause, virtuously gathering samples of curried conch soup, oxtail stew, blackened snapper, and steaming Johnny cakes to carefully analyze at our picnic table laboratory.

We kicked off our second day of Anguillian-immersion with a kayak trip to top-secret Little Bay beach, a breathtaking cove wedged between towering limestone cliffs. This secluded slice of heaven is easily one of the most picturesque spots on the Caribbean and we spent the morning alone with the sea and sky before embarking on part two of our street food safari.

This time we were on a mission to try the island's best barbecue, trekking to Nat's Place at Junks Hole beach, an Anguillian institution that gives the southern United States a run for its ribs. Reachable only by dirt road, the remote dive is one of the crown jewels of the island's culinary scene, churning out gourmet grub so exceptional it should get its own cooking show.

Satiated and sun-kissed, we boarded our boat and hoisted the sails one last time. After a week of adventure and relaxation, it was time to head home. As Anguilla disappeared from sight, we debated about the next trip we could take as a sandy-footed family. This would undoubtedly be the first of many adventures together since TradeWinds offers trips all over the world.

Next time, we concurred, we would cruise the jewel-like Grenadines and Tobago Cays, a cluster of 32 idyllic islands hidden away in the southeastern Caribbean. Or perhaps we would head overseas to the Aegean and comb the Turkish and Grecian coasts? The year after that, we pinky swore, we'd reunite in French Polynesia, the indisputable pinnacle of nautical pursuits. These discussions went on and on until we docked in St. Maarten, where cell service was now available but no one cared to turn on their phones.

Once strangers, we were now a tribe, TradeWinds our savior and the sea our asylum. And we were heading home with one singular message for all our fellow travelers: take your nautical stripes out of storage and put seafaring (and catching your own sashimi) back on your bucket list. Hotels with two hulls aren't just for telecom tycoons anymore.