​Affluent residents of St Barts are accustomed to welcoming ​​mega yachts of the rich and famous.  Unless you happen to know a billionaire, it’s highly unlikely you’d ever get close to one of these vessels, much less find yourself on the most ​beautiful boat in the bay.  It’s a topic that comes up repeatedly among the passengers of the SPV Star Flyer, a striking, 16-sail clipper with four towering masts, polished teak trims, and enormous white sails.  Turning heads from the Mediterranean to the Caribbean, it looks like a pirate ship sailed through an eighteenth-century wormhole.   
 
Sailing with the breeze in high comfort is on many a bucket list, especially romantics with a pinch of salt in their veins.  When I first boarded the Star Flyer late afternoon in St Maarten, it took my breath away. One of three tall ships owned and operated by Sweden’s Star Clippers, my week-long itinerary in the Lesser Antilles promised an adventure both familiar and exotic.   Well-appointed rooms, friendly international staff, and a fine buffet are common on most cruise ships.  Sallying forth under sail, chasing pirate lore, and dropping anchor at small island communities is not.    Born and raised in a landlocked city, salt runs in my blood like integrity in politics. I can’t tell a jib from a top sail, a schooner from a sloop, or the spanker from the anchor.  Regardless of one’s ​prior ​knowledge and appreciation for sailing, everyone goose-bumped when the crew hoisted the sails at sunset.  With speakers booming an epic soundtrack of Vangelis’s Conquest of Paradise, the wind thrust us forward in search of rich Caribbean bounty. 

​The 166-passenger Star Flyer is 115m-long with a 15-metre-wide beam, and it’s not even the biggest ship in the Star Clipper fleet (the 227-passenger, 42-sail Royal Clipper holds the Guinness World Record as the largest square rigger in service).  Both ships rely on the breeze to do the heavy lifting, with low-emission gas used for internal power,  port docking​,​ and maneuvering through idle doldrums.  Fortunately, the wind in the Caribbean from December to April is so reliable you can bank on it, hence, the trade winds. It’s the perfect time to make up the leeway​,​ learn your sailing lingo, ​and ​discover​wild​​ ​legends among the beaches and coconut trees.

​Calling into Anguilla, St Kitts, Virgin Gorda, Jost Van Dyke, and St Barts, I’m sailing into a domain of buried treasure, mythical pirates, and sloop battles.  Borrowing books from the ship’s library, I dove into the Golden Age of Piracy, when motley crews of men – and occasionally women – plundered trade and war ships​, all the ​while swearing impressive oaths of loyalty, democracy, and non-discrimination.  Welcoming all who could be useful and evenly distributing the spoils, the intrigue of pirates has long hijacked ​our ​popular ​imagination. The Black Flag inspired countless legends in the Caribbean, including that of a buried treasure hidden deep inside the coastal caves of the uninhabited Norman Island.  Here, the Star Flyer dropped anchor so ​passengers could snorkel into the same caves that inspired Robert Louis Stevenson’s Treasure Island.  The more I read about Henry Morgan and Calico Jack, Anne Bonny and the infamous Blackbeard, the more I got swept up in the region’s history, and the thrill of sailing under wind.   
 
Operating a tall ship is both an art and a skill.  Experienced passengers on board constantly debated our Polish captain’s decisions, ​analyzing the different sails in use, and the impact of the prevailing winds.  With 3344 square metres of sail, utilizing all four masts could easily blow us halfway around the world.  The captain tells me that he often sails up and down during the night, providing invaluable experience for his navigation and ship crew, and using just fifteen percent of the fuel typically needed for a ship of this size.  Cruising anywhere in modern luxury is a decadent affair, but with its comparatively low carbon footprint, large passenger sailboats like the Star Flyer suggest a more viable and sustainable cruising alternative.   When we dock in St Kitts, I see a line-up of massive cruise ships parked outside a duty-free shopping mall.  It’s the only time our vastly different cruise experiences meet, and it feels like we’re visiting from a different planet.

​Occasionally, the wind howls over twenty-five knots, creating large swells that rock and roll the ship, stabilizers be damned.  Sometimes, I reach for the Gravol, or need to retreat to my comfortable cabin on the Commodore Deck, watching sea water rinse my cabin window.  More often the​​ sea is as calm as a mirror, but sailing will always be an adventure, especially for landlubbers lacking​ ​sea legs.  Seventy-three international staff and crew operate efficiently under any conditions, spotlessly cleaning our rooms, preparing fantastic meals, cocktails, and typical evening entertainment.  There’s pirate parties and trivia nights, disco dancing and interpretive talks.  Daily activities include swimming and snorkelling, various watersports, an onboard spa, and opportunities to explore the history and culture of different islands.  Tenders deposit us on quiet beaches that are home to some of the Caribbean’s legendary sailing bars, like Soper’s Hole on Tortola, and the Soggy Dollar on Jost Van Dyke.   My personal highlight is a visit to The Baths on Virgin Gorda, a series of rock pools, beaches and cave swims in the turquoise water of ​your ​dreams.  ​Being on a smaller ​vessel with a minimal footprint means we can visit and interact with beaches and communities beyond the reach of​ giant ​cruise ships.   My dining mates, a couple from Toronto, are cruise veterans with dozens of voyages under their belt.  Both agree the tall ship had exceeded their expectations, with just the right combination of adventure and comfort.   

Embracing the warm sea breeze, I stretch my arms towards a pod of dolphins cresting a few metres beneath me.   I’m lying on the netted bowsprit at the fore of the ship, my favourite spot on the Flyer to soak it all in.  It’s a giant hammock, of sorts, meeting the sea breeze and ocean spray head-on.  I often lie back on the thick net to admire the clouds, or zone out staring at the waves.  That’s when the dolphins appeared, gliding playfully in front of the bow, providing another singular moment of joy in a week of many. Admittedly, not all passengers have the nerve to hang out at the bowsprit, much less take up ​the ship's offer to scale the mainmast.  Securely kitted with a safety harness, I climbed the rope ladder to a viewing platform eighteen metres above the ​sparking ​water. It provided a priceless and occasionally knee-shaking birds-eye view of the ship,​ sea, islands​,​ and sparkling horizon.  Although travelling alone, I quickly found my crew of fellow bowspritters and mast-climbers. Spanning six decades of age, I gathered with my group to enjoy fine cocktails, fun company, and tall tales at the Tropical Bar.  No matter what boat you sail in, it’s the people you meet who create the paradise you find.  

​Reliably gorgeous sunsets​ and epic sailaways​ are greeted each evening with champagne, cocktails and quirky maritime toasts suggested in the daily program. “To our wives and girlfriends… may they never meet!”    An unannounced wedding takes place on the Sun Deck one evening, and the entire ship celebrates.  Small ships just have that kind of vibe.   Later, we’re invited to follow the cruise tradition of dressing in white to sail the warm breeze under the spotlight of a full moon.  Naturally recalibrating my balance with one hand steadied on the ship, I’d found my sea legs at last.   

Everything moves a little slower under sail.   Although internet is available at the bar, it is pricey and limited. Most passengers agree that screens can wait. Sailing on a tall ship is about reading and resting, conversations and stargazing, staring into the distance, and wondering why it took you so long.    ​When we anchored ​in St Barts, ​it was a thrill to find ​ourselves on the most impressive ship in the harbour, and nobody need​ed​ a personal invitation from a billionaire either. Any way the wind blows, it’s reassuring to know we can all find our own swashbuckling sailing adventure.

​T’was a time when chasing a bucket list did not necessitate cracking an Enigma code of shifting Covid tests and requirements, juggling what’s needed to board a plane, to enter a country, to embark on a boat, to disembark, to return in transit. T’was a time recently where nobody was allowed to travel at all, but it looks like we’re finally done with that bit.  There’s still too much friction when it comes to global travel, the legacy of Covid lingering like a suds stain around a student’s bathtub.  The good news is that much of the world has collectively decided to move on, focusing efforts on protecting the vulnerable while living with Covid the way we live with other problematic viruses.  It just took time and money, which tends to solve most problems. The better news:  last month I returned to both my Canadian and Global Bucket List after too long a hiatus, and I returned in style.   I’ve always wanted to sail in the Caribbean, and I’ve waited over a decade to once again experience to the deep virgin snow of backcountry skiing.  March presented the opportunities, and so I grasped them, tightly, with the wind at my sails, and a smooth path from peak to gully.

​Part One: The Caribbean
 
It started with a thought about sailing as an eco-friendlier form of cruising.  Then I got lost in the fascinating real-life history of pirates, and distracted by the pool-clear waters of the Caribbean.  Putting it altogether, I found the perfect itinerary on board one of the world’s largest passenger sail boats, a towering old-world tall ship operated by Swedish-owned, Malta-flagged Star Clippers.  My experience will get its full due in an upcoming issue of the Vancouver Sun, but I will say this:  Star Flyer – a 4-masted tall ship that swivels the head of even the saltiest sailor – is out of this world.  It carries up to 166 passengers served by 74 crew, sailing the trade winds and ocean currents in the Caribbean, Mediterranean, Central America and across the Atlantic. Unlike cruising, you feel the ocean (sometimes a little more than you’d like, but that’s part of the adventure), visiting bays, islands and beaches beyond reach of the cruise ships.  It’s a luxury sailing adventure for those who don’t know anyone with a luxury sailboat, which I’m assuming describes most of us. 

​Staff and service is fantastic, the meals top notch, the cocktails smooth and the onboard amenities (two pools, a massage therapist, deck chairs, an open bridge, stocked library, water sports etc) most accommodating.  Time slows down, and people read books, not feeds.  You can do bucket list things like hang out on the bowsprit, sprawled on the netting as it dips over rolling waves above playful dolphins (yep, that happened). You can climb up the rope ladder to an 18m-high viewing platform, gazing over islands and ocean. You can bake in the sun like those fried European passengers who don’t seem to know about skin cancer. You can dance at night, request tunes from the pianist, dress like a pirate, or ask a thousand questions of the patient crew as they pull ropes and release topsails with special names that I forgot the moment I heard them.   Pop into the Caribbean’s most legendary beach bars (the Soggy Dollar, Foxy’s etc) for a souvenir headache, nap in your cabin, listen to stories of fellow passengers, snorkel into sea caves, paddle-board, ogle at super yachts parking in St Barts.  It’s everything one would expect the good life to be, and a very different kind of cruise experience. The more I travel on a small ship – a luxury river barge in the Amazon, a catamaran in the Galapagos, an expedition ship in the Antarctica – the more I fall in love with boats as a bucket list form of travel.  If you can burn just 15% of the fuel of a regular ship, as the Star Flyer does under sail, it feels like the future of cruising, and the responsible way to go.  As time progresses, I hope to add more small ships to my growing, curated bucket list cruise collection.

​Part Two: Catskiing in the Skeena
 
The last and only time I cat-skied was on a private mountain in Chile.  We were filming an episode of Word Travels, and my single biggest memory of that adventure is nervously watching our cameraman Sean ski backwards while he filmed my descent with a large six-figure camera on his shoulder.  It was the only true bluebird ski day I’ve ever had, when the sky is crystal clear after a big dump of white snow.   Skeena Cat Skiing in BC would be my second, and this time I wouldn’t have to worry about my TV show crashing with a wipeout (I can do that all by myself, thank you). 

I had one day to switch my Caribbean bag for my snow gear, catching a prop flight north from Vancouver to the town of Smithers BC.  Here I met a group of elite ski journalists, gathering at the helipad for our memorable ride into base camp.   Any day you get to ride a helicopter is a good day.  Skeena Cat Skiing is a family-run affair and clearly a passion project of immense love and hard work.  Many hours away from anything, guests stay in heated dome tents buried in snow, which is a cool experience unto itself.  The comfy, wood-fired heated lodge tent is loaded with fine beer, snacks, worn couches, and a friendly chef who prepared outstanding hearty dinners and desserts.  We’re surrounded by the Thomlinson and Gail Creek mountains, 30,000 hectares of fresh powder and skiable glades in every direction.  Our ski chair is a customized Piston Bully snow grader, with a large heated cabin for 14 passengers on the back.  This ‘cat’ can go anywhere and everywhere it pleases, and it does.  Skirting a steep ride, it deposited us at the top of runs that funnel into valleys where we would be collected by the cat for another ascent.   Backcountry safety is taken seriously:  we’re all equipped with avalanche kits, air bags, walkie-talkies, and given a tutorial in rescue.   Veteran guides know what they’re doing and accidents are rare to non-existent.  Any nerves dissipate after the first run, replaced with elation and joy and wowzers because this is the skiing you dream about, every time you strap in, and every time you head up a mountain.  I was easily the weakest boarder of the group, and I’m no slopestyle expert (especially in the company of Olympic skier Yuki Tsubota).    But even at my own pace, I was able to keep up, sharing the pinnacle of what snow sport can deliver.   Cat skiing is more affordable than heli-skiing, and you can read more about both in my Bucket Listed column for Can Geo Travel.  Suffice to say:  it’s going to be hard going up a local ski hill again, but there’s always something to aspire to, and something to look forward to next time.

Get over Jaws.  Sharks rarely attack humans, are vital to the marine eco-system, and as any diver will tell you, a thrill to meet in their natural habitat.   With rampant shark finning, the entire species is at risk.   Encounter them underwater, and you’ll quickly realize just how beautiful, and harmless sharks really are.  ​

Mossel Bay, South Africa, Great White
​
The coast of South Africa’s Eastern Cape is full of Great White Sharks, the most feared predator in the ocean.  Cage diving is popular and while thrilling, is completely safe.   Years later, I can still see that Great White coming towards me, literally rattling my cage. ​

Malapascua Island, Philippines, Threshers
​
A stunning tropical island, Malapascua is the only place where you can dive with thresher sharks every day, due to “cleaning stations” that attract the sharks in nearby Monad Shoal.  Shy around divers, threshers are known for their distinctive tail. ​

Shark Reef, Fiji
​
For those looking for variety, Fiji’s Shark Reef Marine Reserve has a regular shark population of 8 different species: Whitetip Reef, Blacktip Reef,  Grey Reef, Tawny Nurse, Sicklefin Lemon, Silvertip, Bull and Tiger sharks are all found in the reserve. ​

Galapagos Islands,, Hammerheads
​
During the December to May season, divers on live-aboards yachts around Darwin and Wolf Islands can find themselves in the water with thousands of hammerheads. Aggressive predators for marine life , hammerheads do not attack humans unless provoked. ​

Palau – Reef sharks
​
With 50 metre plus visibility clear Palau is renowned as one of the best diving locations in the world. Since establishing the world’s first shark sanctuary in 2001, it’s also one of the best places to dive with sharks. ​

Instagram needs a new filter to turn any picture into a Caribbean island paradise.   They should call it "Anguilla."   I'm here for a few days to explore its dive sites, and learn a little about this understated, off-radar island that attracts celebrities, honeymooners and urban escapees with opulent villas, lavish resorts, and 13,500 inhabitants who are so laid back even their trigger fish are uncoiled.  
Westjet flies direct from Toronto to San Maarten, and it's a short 20-minute boat ride to the British Overseas Territory of Anguilla.  The tax haven is only 26km long by 5km wide, with one main road running through the middle.  There are no mountains, and hardly any traffic.  What it does have is 33 mind blowing beaches, dreamy tropical weather, fat mangos and proudly, no chain hotels, burger joints or coffee shops. 
"This is what everyone wants the Caribbean to be," says Patrick Lynch, who owns Roy's Bayside Grill.  "White sands with nobody on it."    
The sentiment is echoed by Jim, a television director who's been visiting the island with his family for 15 years.   Celebrities love the island's lack of pretentiousness and relative privacy, which explains why actress Annie Potts gave me her sunscreen.  A strong summer sun was baking my back onboard Dougie's boat, returning from our incredible couple dive at Dog Island.  Every dive delivered the goods, be it the 200ft wreck of the MV Sarah, the dozen turtles who played with us on the 75ft Oosterdiep wreck, or the lobster, barracuda and countless fish feeding off the MV Commerce. The island's three dive companies - Shoal Bay Scuba, Special D and Vigilint - were knowledgeable, professional and fun to hang out with. Like other locals  I met, these guys love what they do, and love where they live.   Dive sites, including a half dozen amazing wrecks, were easy to get to, and ideal for recreational divers like me.  
Anguilla has three, pricey five-star resorts that are extraordinary:  The Viceroy, Cap Juluca, and the sprawling CuisinArt, owned by the same chap behind the appliances.  Picture infinity pools, white brushed villas, expensive cocktails and swept powder beaches.  I stayed at the more affordable Anacoana Boutique Hotel, centrally located, comfortable and rather less flashy.   Their packages are worth checking out. 
I'm not exactly sure how Anguilla came to be a foodie island because I spent too much time eating to find out.  Standout meals were at the Straw Hut, Jacala (my new friend and fabulous underwater photographer Nadia Aly swears their mahi-mahi is the best thing she's ever had), CuisinArt's Le Bistro (the lobster was sensational) Roy's Bayside Grill, Smokey's and the Firefly.  Deep fried Johnny cakes,  fresh fish, peas and rice and that sweet hot Caribbean sauce...no wonder locals are always smiling.  
I found myself swimming under the stars, and scuba diving with bioluminescence under a bright supermoon. At the exotic Birds of Paradise villa, I lived like the 1%, for a couple hours at least. I also found great companionship, true local characters, a new appreciation for air conditioning, and late night fun with banana rum.   Each photo I posted to Twitter or Instagram screamed:  Don't you wish you were here?   No photoshopping, just a little something I call the Anguilla filter.  ​

Find out more about visiting Anguilla here.  ​