
Cruising to Anegada is not for the weak of stomach. It’s part of the British Virgin Islands, but it’s an outlier, one surrounded by a massive coral reef that has wrecked more than its fair share of props and hulls throughout the years. However, the reward for keeping a careful eye on the depth sounder is magical, with deserted beaches like this one overlooking some of the prettiest water on earth.

On Deck Racing invited me to spend an afternoon taking part in a match race off the coast of Antigua. The intensity of the chase shows in this crewmember’s crouch. We failed to win that day, but we did round the final buoy before the storm clouds opened up—a perfectly good reason, we decided, to celebrate victory at the bar.

I was walking up the dock in Falmouth Harbour, Antigua, at the end of a long day’s boat show with my nose buried in my notebook when I bumped (literally) into a friend. “You’re missing it!” she cried, grabbing the top of my head, tilting it up from my work and twisting it to the right, where I saw this incredible sunset. The “snuggling tenders” between the superyachts Passion and Slipstream made the moment all the more memorable.

Bequia is known as a wealthy island in the Grenadines, and there are always a few large yachts around. But I prefer local hangouts like this one, where the hand-painted boats are colorful and the kids grow up learning that no matter how you find your way into the water, the goal is simply to get there.

Most of us think of luxury boating as limited to the oceans and seas, but in France, the Canal de Bourgogne winds through Burgundy’s farms, vineyards, and historic castle-scapes like a water trail purpose-built for upscale barges. Among the things I learned here: never to call a glass of wine Chardonnay (it’s a Burgundy White); and always monitor the well in the center of an old walled city, because the water supply is where intruders are most likely to create havoc (at least during the 1800s).

The Christmas winds were howling between Sint Maarten and St. Barth’s when I sailed there aboard the 114-foot Sunreef Che. She’s one of the largest sailing catamarans available for charter in the world, with a mast height of 47 metres (154ft). This charter guest, standing awestruck on the side deck, has a posture that says it all.

Calvi, on the northwest coast of Corsica, has this stone-wall overlook that is meant to stop guests from leaning too far over. I succumbed to a bit of vertigo climbing up there to get this shot, but it was worth it, since I’ve never seen another photograph of Calvi like it.

Curaçao is one of the ABC Islands, along with Aruba and Bonaire, at the very bottom of the Caribbean Sea. Few charter yachts go there, and this one, Domicil, was trying to be the first to lure luxury guests on a year-round basis. This photo was shot off Klein Curaçao, a tiny, uninhabited island between Bonaire and Curaçao proper.

I watched this scene unfold from atop the ancient stone wall that surrounds the city of Dubrovnik, Croatia. A single boat had the harbour all to herself when a swarm of kayakers descended en masse. It was hard not to imagine how ancient ships used to arrive by sea, sometimes friendly, sometimes not, and why the giant wall was built in the first place.

Most yacht charters in Greece take place in the Aegean Islands, which are closest to Athens. This scene is much farther afield, in the Dodecanese archipelago, which is right on the border with Turkey. This island, Symi, suffered a great deal of damage during World War II, but today it boasts one of the prettiest harbours in all of Greece.