“There is something about a mass-market Luxury Cruise that’s unbearably sad,” wrote author David Foster Wallace in his book, A Supposedly Fun Thing I’ll Never Do Again: Essays and Arguments. And I—like many of you, I suspect—am inclined to agree with this statement.

The idea of a cruise is not something that has ever much appealed to me. I have no problem with sailing or the ocean itself, in fact, I love being near water, I grew up beside it; it’s more the prepackaged/drifting dinner theatre idea that the majority of such giant floating vessels conjure, that I find less than enticing.

For those who share a similar aversion to this type of prefab vacation, the thought of enjoying a holiday at sea, may not be something you would much consider, apart from suddenly gaining the means to become a yachtsman yourself.

Now there’s an idea…a yacht.

Turns out, as I recently discovered firsthand, you do not need to be liquid, own your own 70-foot boat, or count a personal chef amongst your staff to reap the benefits of a VIP seafarer’s life; all you need, is to set sail with TradeWinds.

Luxury-Travel-Guide-Sailing-St-Barts-St-Maarten-St-Martin-TradeWinds-5

Picture this, a fleet of spacious catamarans—ranging from Cruising Class (luxury) to Luxury Class (super luxury) to Flagship Class (ultra luxury)—a plush cabin with a double bed and private en-suite bathroom, including a shower (each vessel is outfitted with anywhere between three to six rooms) and a choice of crewed, all-inclusive sailing expeditions to over ten destinations in the Caribbean, Europe and Central America. Only slightly more alluring than the thought of being one of a couple thousand packed onto a big-box cruise ship, no?

What makes these impressive catamarans even better is the possibility to reserve the entire boat for a private trip. New Year’s Eve sailing around French Polynesia? Yes, please!

My own experience with TradeWinds took me to the Caribbean, through and around the islands of St. Maarten, Anguilla and St. Barths.

Luxury-Travel-Guide-Sailing-St-Barts-St-Maarten-St-Martin-TradeWinds-3

The sail started in St. Maarten, with a sunset dinner of deliciously grilled mahi-mahi on deck, and a chance to mingle with the eight other guests aboard. By the second night, I was already looking forward to sitting down to an evening meal with my fellow shipmates. With only three to ten guests and two to four crew members on each trip, bonding is as inevitable as the ability to find privacy.

By day three of your holiday, soaking in solitude while watching the sunrise with a freshly brewed cup of coffee (always awaiting you, no matter how early you wake) will be as routine as reading a book stretched out in the sun lounge, with the day’s cocktail hour concoction, chilling by your side.

Freedom is another inevitability when traveling with TradeWinds, and here’s where the major difference between a crewed yacht charter and a cruise ship comes into play. There are many differences between the two experiences. On the not-especially-important side of the spectrum, there is the fact that no shoes are permitted on deck (standard boating etiquette), so, thankfully, loafers worn without socks are not a trend. (FYI: In general, haughty resort wear is not something TradeWind guests need to pack i.e. leave the beaded boho tunic and wedged sandals at home; there are too many water activities and actual relaxing to partake in for all of that.) The significant variances though, weight hard on the critical-to-enjoyment end of the spectrum and concentrate on leisure elements, which comes in plenty and are genuine in form.

Luxury-Travel-Guide-Sailing-St-Barts-St-Maarten-St-Martin-TradeWinds-Filler-Magazine-1Luxury-Travel-Guide-Sailing-St-Barts-St-Maarten-St-Martin-TradeWinds-2

Traveling with TradeWinds is a nomadic and invigorating dose of luxury. Every day the sights are new (pristine desolate islands with secluded beaches are not uncommon to happen upon) and every few hours, the activities are different: swim, scuba, snorkel, whale watch or be escorted to shore by the captain in a dingy and hit the trails for a hike. Unlike other all-inclusive vacations, TradeWinds does not try to sell you a manufactured idea of entertainment and R&R. While the captain and his crew are there to guide you, finding your own relaxation and pleasure is at the top of the official daily [un]schedule. Rumour has it, mischievous mariners can even get in on some friendly pirating amongst sister TradeWinds yachts (yes, seriously…think Jonny Knoxville on a boat), while lucky sailors might receive an invite to get-down like a local at a full moon party, should the lunar calendar cooperate.

Unfortunately, the full moon wasn’t out when I cruised around the Caribbean (no comment regarding the pirating), but I did kickback like a local at beach bars.  (Kudos to my ship’s captain for his tips.) The standout moments  in this category go to an afternoon spent at Elvis’, in a small village in Anguilla (the house-made Mama Juana—a bark and herb infused mix of rum and red wine—here is a must-try) and an evening at Calmos Café in Grand-Case, on the French side of the island of Saint Martin, where happiness was delivered via steak frites, an ice-cold bottle of Presidente and a seaside view.

Luxury-Travel-Guide-Sailing-St-Barts-St-Maarten-St-Martin-TradeWinds-4

Immersing myself in local Caribbean life, also included—of course—shopping in fashionable Gustavia, Saint Barthélemy. For earnest travelers that need a souvenir to complete a vacation, skip the tourist traps on the main drag and head straight to Free in St Barth for some quality tees that will remind you of life sailing the Caribbean Sea. While exploring the island’s capital, be sure to stop by the Longchamp boutique. A bliss-induced swoon is guaranteed when you spot the difference in price here, compared to Fifth Avenue.

In the world of all-inclusive travel, tailored fit freedom and fun is a rarity. Ride the unicorn and book with TradeWinds. It’s the difference between having the identical cookie cutter vacation millions of cruise enthusiasts buy every year and experiencing a spectacular adventure, exclusively your own and never exactly the same twice.

Recent Stories

  • michael-mosley-for-filler-magazine-photography-by-danielsahlberg

Inside LBJ’s Washington

  • thumb-blue-crush

Fashion, Meet Romance