You’ll Want To Save Every Penny To Buy One Of These Extraordinary Boats

Say it with us: “I’m on a boat!”

Of course, depending on where you live and what layer of the economic strata you land in, you’ll probably be picturing something different than the person next to you. Some of us think of the humble fisherman bracing against a storm at sea. Others might be taken back to memories of their parents ditching the 9-to-5 and sailing them around the world. Others still may be thinking about the studio yacht party at last year’s Cannes.

Whatever thought or memory is conjured for you, one constant remains — those boats had to be built well, so as not to end up at the bottom of the drink. Last month, Van Dam Custom Boats showed us the mastery that goes into their stunning crafts. Here, take a peek:

In honor of that mastery, we’ve compiled a list of some of our other favorite boats we’d love to spend a day or 70 out on the water with. Some are humble, some are bombastic, some are faraway dreams. All of them are superb.


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#conquest #sunset

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Perhaps it’s best to start out with a little sport and utility before we get into the big hauls. A solid, well-equipped fishing boat is the first step in anyone’s sea-adventuring life. You go out, find some fish, fish those fish, and bring home dinner — all with the added benefit of knowing exactly what that dinner is. It can be a solo journey or a family affair. Either way a fishing boat is where most of us will start our water journeys.

There are so many fishing boat companies to chose from out there. Boston Whalers are always sturdy and reliable. They come completely customizable and tend to last in rough seas or calm.

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A classic runabout or tender can get you from Point A to Point B in sleek style. Or they can help you get away from the Holy Grail henchmen along the canals of Venice. It’s a throwback to the days when people summered on bays and lakes and needed a water-savvy form of transportation to skim speedily across the water. Although these boats aren’t equipped to land a marlin or pull crab pots, they’re going to get you around while looking fly. And that’s worthwhile.

Van Dam is your best bet of getting behind the wheel of one of these throwback beauties — unless you’re a Kennedy or Bush and summer in New England.


Long before Columbus sailed the ocean blue, Polynesians were bobbing around the Pacific on massive outrigger canoes. These canoes got the Polynesians from deep in the South Pacific all the way to the North American coast with nothing more than a couple hauls, sails, and the starry night to guide them.

Although this may be a more advanced form of sailing (outrigger canoes take some serious skills), it’d still be a blast retracing the steps of ancient Hawaiians or Polynesians across the Pacific or around the world in your very own voyaging canoe. After all, an entire culture of people spent millennia perfecting their boats to do exactly that.

Alternately, you can spend a few years, and less dollars, custom building one yourself — there’s space in your garage, right?

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Crossings #hōkūleʻa #rough

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Full disclosure, I sailed one of these boats across an ocean. So my including it on the list isn’t negating the abundance of other great makes of sailboats on the market. I just like this one. I know it. I sailed her blind in the pitch black nights. I slept, cooked, ate, and bathed with this boat for months. And that’s the rub. You can live in this boat and make the world your oyster (also, you’ll be on the sea, so oysters can be your oyster).

For about the same price as a small house ($250,000), you can call this boat your home. Hallberg -Rassey make seriously well constructed and spacious sailing vessels that can handle any of the seven seas. A family of four to six can easily live in the 64-foot sloop. Maybe you’re making the wrong mortgage payment and it’s time to live life at sea? Well, then this is a solid investment in your future and well-being. Adventure literally awaits.


Now we’re getting into speed, class, and design brilliance. A streamlined main hull has two outer floats attached to bring the speed. Overall, this class of sailboat is for someone seeking a side of adventure with their main course of easy cruising.

Dragonfly’s Trimarans are consistently considered some of the best boats in their class for sailing competitively or leisurely. Their compact and sleek design is award-winning. If you’re thinking of getting into racing, this may be your gateway boat.

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Dragonfly 32 #trimaran

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So you’ve decided to become a sailboat racer… You’ll need a boat that is hydrodynamical, built by masters who take the time to design a cruiser that can cut through the water at competitive speeds.

Italia Yachts combine the same devotion to hydrodynamics as they do to classic Italian style. Their boats are sleek. Their decks are clean and designed photo ready. The boats are big enough — and well laid out enough — for your racing team to live comfortably while you cross the sea. And they are fast.


There’s another class of sailing boat that tops all of these. They’re the luxury yachts. And when you win the lottery or invent whatever it is that replaces Facebook this will be your boat. These are for the dreamers whose dreams come true. Lucky bastards.

Sanlorenzo’s yachts are nicer than most 5-star hotels, and they cost about as much as a castle. But you can probably afford that with your lottery winnings too. These boats are for the 1 percent of the 1 percent, and their luxury knows no bounds. Now, where’d I put that lottery ticket…?


Childhood fantasies of buried treasure and adventure on the high seas are always fun to live out. So, why not buy a dang pirate ship? Yes, you can buy a pirate ship (or build one if that’s your thing). Whether or not you’ll find treasure or plunder other ships, well, that’s up to you.

You’ll be hard-pressed to find a pirate ship on the market, but they are out there. Otherwise, you’re going to have to build one yourself. Either way, it’s the most kickass way to sail the world’s seven seas. Let’s face it, who doesn’t want to roll into a new country in a foreboding, badass pirate ship with black sails and a Jolly Rodger flying from the mizzen mast?

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