Five Places to Sail Before You Die

A few years ago author Chris Santella approached my wife for some photos for a book called Fifty Places to Sail Before You Die. He also ended up interviewing me about one of my favourites.

Since this is a post as opposed to a magnum opus, I’ve trimmed my own list of marine must-dos considerably.

Here are five places I think you should sail before you die.

And you don’t even have to know the pointy end of a boat from the other end. Take live-aboard sailing lessons, book a skipper for a day or two to refresh your own sailing skills, just book a skipper and learn as much or as little as you want, or ship a skipper and a cook.

Sunsail and Moorings are the biggest charterers worldwide. Most sailors consider Sunsail boats more on the performance side, while Moorings has a reputation for luxury. Horizon Yacht Charters offer a variety of boats in their fleets as well as great service (they now maintain a base out of St. Vincent, along with several other Caribbean destinations). TMM Yacht Charters offer boats across the Caribbean and, if you want a Canadian connection in the British Virgin Islands, check out Conch Charters.

And now, without further ado, here’s my quintessential quintet of sailing delights.

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One very good reason that you have to sail Croatia before you die: a sunset like this one off Zlarin Island.


1. Croatia

The Dalmatian coast of Croatia is one of the most beautiful spots I’ve ever visited. Dubrovnik is a medieval seaside town decorated by a massive wall and pumpkin-coloured roof tiles. Split, up the coast, boasts, at its core, the palace of a Roman emperor, circa 300 A.D. The land between is gorgeous vistas where the Apennine mountains bow down to the Adriatic Sea.

Cruise here and ply the waters of history. Pine-covered islands, waters in spots are Caribbean green. Pull up for the night and lash to a seawall hard by a fishing village sporting stone buildings that have stood here for fifteen centuries.

Head further out – the Kornati Islands are downright lunaresque. Motorsail to the gorgeous Krka Falls where terraced cascades overlook an emerald river valley.

Stroll cobblestone streets or sail close-hauled in winds that often surpass twenty knots.

If there is one place you have to sail before you die put Croatia’s Dalmatian Coast on your bucket list.

Moorings and Sunsail charters both maintain fleets here. Even if you know how to sail a flotilla – skipper your own boat but sail along with others – is a good option.

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The sheer beauty of granite islands – along with their isolation – makes the North Channel one of the world’s most desirable fresh water cruising grounds.


2. Canada’s North Channel

The minute I get out of the car at Gore Bay on Manitoulin Island and stroll down to the docks at Canadian Yacht Charters, I feel my pulse begin to slow, my blood pressure to drop.

Best yet, as a Canadian, this is my birthright.

Just the name of your starting point says it all. You sail out of Manitoulin Island  – according to First Nations legend, this was actually the home of the Great Spirit, proving that Gitchi Manitou had great taste in real estate.

But get out on the waters and that’s when you’ll be seduced.

Islands of pink granite decorated by wind-crippled pine trees, anchorages you might share with no one, crystal clear waters and some exhilarating conditions.

Three hundred plus islands scattered across this relatively sheltered cruising ground, most completely uninhabited. Anchor here and smell the wood smoke from a campfire, be serenaded by the call of the loon.

I have sailed here roughly five times. It’s not enough.

Bequia to Tobago Cays
Perfect anchorages abound in St. Vincent and the Grenadines. One must-do is inside the reef at Tobago Cays. Sheer paradise.


3. St. Vincent and the Grenadines

Brisk passages over sapphire seas, maybe accompanied by a dolphin or two, heading for a mist-shrouded mountainous island boasting palm trees, amber beaches, sea turtles or pastel-painted shops and eateries.

Sailing here is more challenging than it is in some other destinations, which makes it a must-do for serious charterers. Thrown in a chain of islands, each one unique, each one more gorgeous than the last, and you get the idea.

One night recently we anchored in Tobago Cays. Sea turtles popped their heads above the surface all around the boat, three perfect beaches awaited our pleasure; just outside a vibrant barrier reef we could see one island where they filmed part of “Pirates of the Caribbean”.

Ply the waters of the Grenadines and tonight you’ll be parked in paradise.


4British Virgin Islands

Here is where it all started, ground zero for the inception of Moorings charters.  Sail here and you’ll understand.

If you’re a sailor, chances are you’ve either done the BVI’s or it’s one of your life goals.

A chain of islands like the Grenadines. Unlike the Grenadines, you can achieve almost all of them within a couple of hours of sailing, cruising, within the confines of Drake Passage, with consistent pleasant winds and mostly flat waters.

Hit the Baths, a surreal granite sculptured landmark hard by a tiny perfect beach, stroll through caverns in bathtub waters up to your knees.  Do dinner at Foxy’s on Jost Van Dyke, where the proprietor may well serenade you in song.

Forty-plus islands here. I defy you to find one that’s not so beautiful it’ll make you weep for sheer joy.

The Baths on Virgin Gorda in the BVI's. You don't need another reason to make this archipelago one of the places you have to sail before you die.
The Baths on Virgin Gorda in the BVI’s. You don’t need another reason to make this archipelago one of the places you have to sail before you die.

5. Lake Superior

One day on Lake Superior we are bouncing around like we’re in an aquatic washing machine, a couple of breaking waves twenty feet high, sustained winds well over thirty knots.

A day before we were docked on a secluded forested island we shared with three or four other boats. We strolled down the dock and ducked into a wood-fire sauna. We roared down a rudimentary jetty and jumped into moonlit waters.

At one point I was thanking my lucky stars we had Greg Stroud (from Parks Canada) and our skipper, Greg Heroux, hereinafter referred to as “Greg One” and “Greg Two.” Greg One knew no fear, Greg Two knew both Lake Superior inside out and darn near anything about sailing worth knowing.

It strikes me that this could well be the Mount Everest of freshwater sailing, though for much of our trip seas were pleasant and friendly as well.

And the scenery showed like a Group of Seven landscape.

I am not sure I’d ever want to skipper here. But I’m equally sure I want to sail here again before I die.

2014 09 08 Thompson to Edward (Hook of Horsheshoe Cove)
A perfect day on the waters of Lake Superior – Capt. Greg Heroux checking out conditions; Greg Stroud, from Parks Canada, at the helm. Author Mark Stevens supervises the process from the forward cockpit.





6 Responses

    • Mark Stevens, photos by Sharon Matthews-Stevens

      Let me know if you are interested in sailing on Lake Ontario. We could do that this summer.

  1. Greg 2

    Lake Superior: the Everest of fresh water sailing. I love it. Best concise description I have ever heard. I intend to reuse that phrase. Thank you.

    • Mark Stevens

      Hey Greg – feel free to use the phrase but it might cost you. Might have to take us sailing up there again some day!

    • Mark Stevens

      Hi Brenda. To quote Mark Twain: “Twenty years from now you will be more disappointed by the things that you didn’t do than by the ones you did do. So throw off the bowlines. Sail away from the safe harbor. Catch the trade winds in your sails. Explore. Dream. Discover.” To quote me: “What are you waiting for??”