If you’re fascinated by boats, chances are you’re also fascinated by the kind of people who’ve guided them. We’re talking real-deal explorers – the bold, curious, and often slightly “crazy” people who loaded up a wooden ship with supplies, pointed it toward uncharted territory, and sailed straight into history.
And while their names are famous, their boats deserve just as much credit. Because let’s face it – without a ship that could survive the storms and stay on course, most of those adventures would have ended a lot sooner (and a lot wetter).
So, at the expense of a bad pun, let’s sail through time together with some of the world’s most legendary explorers and take a closer look at the boats that helped them change the world.
Christopher Columbus and Santa Maria
Let’s start with the one you probably learned about in school. In 1492, Christopher Columbus set out to find a westward route to Asia and ended up bumping into the Americas instead.
But let’s talk about his boat.
The Santa Maria was a nao, a heavier cargo ship that was slower but sturdier than the smaller caravels (the Nina and the Pinta, which also sailed with him). She was about 70 feet long, had a single deck, and carried a crew of around 40 men.
The ship wasn’t exactly built for comfort – crew quarters were cramped, food was basic, and sanitation was nonexistent. But she got the job done and made it across the Atlantic in five weeks, surviving storms and rough seas along the way. It served as Columbus’ flagship until the boat wrecked off the coast of Hispaniola. That wreck actually led to the first European settlement in the New World.
The Santa Maria may not have been glamorous, but she was a workhorse. She’s also a reminder that you don’t always need the fastest or flashiest boat – just one that’s seaworthy and steady.
Ferdinand Magellan and the Victoria
Magellan was the first person to almost circumnavigate the globe. He didn’t make it all the way himself (he was killed in the Philippines), but one of his ships – Victoria – completed the journey, making it the first vessel in history to sail around the world.
Victoria was a carrack, about 85 feet long, with three masts and a high rounded stern. She wasn’t designed for speed but for endurance, cargo space, and survival over long stretches of open ocean. Out of Magellan’s original five ships and 270 crew members, only Victoria returned – three years later – with just 18 men onboard.
If you’ve ever prepped a boat for a long passage, you know how critical endurance is. The Victoria wasn’t built for speed, but she was tough, dependable, and steady over the long haul. (Kind of like the ultimate bluewater cruiser before that was even a thing.)
James Cook and the Endeavour
Fast forward to the 18th century, and you’ll find Captain James Cook sailing into the South Pacific with his ship, the Endeavour. Originally a coal transport vessel, this boat was chosen because of her flat bottom and shallow draft – perfect for navigating coastal waters and unknown harbors.
The Endeavour wasn’t necessarily glamorous, but she was practical. Just under 100 feet long, she carried scientific equipment, artists, naturalists (like Joseph Banks), and a crew of 94. She charted New Zealand and the eastern coast of Australia with so much precision that her maps were used well into the 20th century.
Cook’s Endeavour shows how important versatility is in exploration. She was sturdy enough for ocean crossings and nimble enough for reef-filled shallows. Think of her as the Swiss Army knife of sailing vessels.
Ernest Shackleton and the Endurance
If a boat in history ever lived up to its name, it was this one.
The Endurance was a three-masted barquentine built in 1912, measuring about 144 feet long and reinforced with extra-thick wooden planking to handle icy conditions. Shackleton’s goal was to cross the entire Antarctic continent. Instead, his ship became trapped in pack ice and was eventually crushed by it.
Here’s the wild part: every single member of Shackleton’s crew survived. They lived on the ice for months, then used lifeboats to reach Elephant Island, and from there, Shackleton and five men took a 22-foot open boat across 800 miles of stormy seas to reach help in South Georgia.
The Endurance didn’t finish her mission, but her name became legend. Historians like to point to Shackleton as a lesson in adaptability and leadership. (Also, a lesson in never underestimating Mother Nature.) Now, thanks to a 2022 expedition, the boat has actually been rediscovered, perfectly preserved 10,000 feet below the ice.
Leif Erikson and the Knarr
Long before Columbus, Leif Erikson and his crew were sailing from Greenland to what is now Newfoundland, Canada. This was roughly around 1,000 AD.
Their boat of choice was the Knarr – a Viking cargo ship that was shorter, deeper, and more stable than the more famous longships. Knarrs were built to handle the North Atlantic, with their wide hulls and high freeboards. Leif’s voyage from Greenland to “Vinland” proved that Norse seafarers had both the boats and the guts to explore well beyond Europe.
The Knarr was built for heavy seas, long hauls, and icy winds. If you’ve ever crossed rough channels in a heavy displacement cruiser, you’ve got more in common with the Vikings than you might think.
Thor Heyerdahl and the Kon-Tiki
Let’s move into the 20th century – 1947 to be exact. Norwegian explorer Thor Heyerdahl wanted to prove that ancient South Americans could have crossed the Pacific to populate Polynesia. His method was to build a traditional balsa wood raft using only materials and tools available to pre-Columbian people.
The Kon-Tiki was a 45-foot-long, hand-tied raft with a single sail. There was no engine, no steel, and absolutely no modern navigation. Heyerdahl and his team sailed it 4,300 miles from Peru to the Tuamotu Islands in 101 days.
Kon-Tiki was an incredibly powerful statement to the world at that time (and even one in the 21st century). It proved that the ocean wasn’t a barrier in ancient times, but actually a bridge of sorts. And it showed that you don’t need cutting-edge tech to cross oceans – just the right boat and the right knowledge.
Francis Drake and the Golden Hind
Sir Francis Drake circumnavigated the globe between 1577 and 1580 aboard his galleon, the Golden Hind. She was about 100 feet long and armed to the teeth – with cannons on both sides and a reinforced hull for long-range raids.
Drake’s voyage was part exploration, part piracy. He charted new territories and looted Spanish ships along the way. The Golden Hind became one of the most feared ships of her time, and a symbol of England’s rising naval power.
Interestingly, Drake’s Golden Hind shows how boats served multiple roles in the Age of Exploration. She was a warship, a trading vessel, and a floating base of operations. The modern equivalent might be a tough-as-nails trawler with long-range capabilities and the ability to defend itself in rough conditions.
Robert Falcon Scott and the Terra Nova
Robert Falcon Scott’s Terra Nova was built as a whaling and sealing ship, so she was already tough before she ever headed to Antarctica. About 187 feet long with reinforced hull plating and a strong steam engine, she was used during Scott’s ill-fated expedition to reach the South Pole in 1910–1913.
Scott and his men made it to the Pole, only to discover they’d been beaten there by Norwegian Roald Amundsen. Tragically, Scott and his entire party died on the return journey.
Despite the tragedy, Terra Nova represents a pretty big turning point in historical exploration. It was the merging of traditional sailing ships with early industrial technology. Steam-assisted sailing gave ships more reliability, especially in harsh climates, and paved the way for today’s hybrid propulsion systems.
Jacques-Yves Cousteau and the Calypso
You can’t talk about modern ocean exploration without tipping your hat to Jacques Cousteau. His ship, the Calypso, was a converted U.S. Navy minesweeper – 126 feet long, with a shallow draft that let her sneak into lagoons and river mouths.
Cousteau turned her into a floating laboratory, complete with diving equipment, film gear, and even a mini submarine. With Calypso, he brought the underwater world to millions of people for the first time.
Calypso was basically a hybrid of a mobile science lab and a boat. For anyone who’s ever dreamed of living aboard a boat and making discoveries at sea, she’s pretty much the gold standard.
Roald Amundsen and the Gjøa
Before he became the first person to reach the South Pole, Roald Amundsen made history by becoming the first to successfully navigate the Northwest Passage – the icy, treacherous sea route through the Arctic connecting the Atlantic and Pacific Oceans.
His vessel was a modest 70-foot sloop named Gjøa, a former herring fishing boat. Amundsen refitted Gjøa for polar travel, reinforcing her hull and equipping her for extreme cold and isolation.
From 1903 to 1906, he and his small crew lived aboard her while slowly picking their way through the ice-choked waterways of northern Canada. They spent two winters frozen in place, relying on the knowledge of local Inuit to survive and learn Arctic living techniques.
Like a lot of the boats we’ve covered in this guide, Gjøa wasn’t a flashy expedition ship. She was actually a pretty humble fishing boat. Her story is a perfect example of how thoughtful outfitting and respect for local knowledge can make for powerful expeditions and discovery.
Sir Robin Knox-Johnston and the Suhaili
In 1969, Sir Robin Knox-Johnston became the first person to sail solo, non-stop around the world. His boat was a 32-foot teak ketch named Suhaili, built in India and modeled after traditional Colin Archer designs (which are known for their toughness, not speed).
Suhaili was small, slow, and had no modern navigation equipment – not even a GPS (this was the 1960s, after all). Knox-Johnston navigated by sextant, battled massive storms, faced equipment failures, and spent 312 days at sea alone. When he crossed the finish line, he was the only competitor in the Sunday Times Golden Globe Race to actually complete the journey.
Abel Tasman and the Heemskerck
In the 1640s, Dutch explorer Abel Tasman set out to map uncharted parts of the Southern Hemisphere and ended up becoming the first European to reach Tasmania, New Zealand, and parts of Fiji.
His flagship was the Heemskerck, a Dutch war yacht rigged for both speed and firepower. About 110 feet long, she was built for exploration and defense, which were critical during voyages into the unknown, where encounters with hostile ships or unfamiliar shores were always a possibility.
Tasman sailed alongside a smaller ship, the Zeehaen, and together they reportedly covered thousands of miles of uncharted waters. Despite limited instruments and often poor weather, Tasman’s journey expanded what was the known world at the time and gave his name to the Tasman Sea, Tasmania, and numerous landmarks across Oceania.
Tasman’s journey isn’t the most famous in history, but it certainly highlights how crucial a well-equipped and well-defended ship could be in an era where “exploration” often meant risking everything. It’s a pretty interesting – albeit quiet – part of history that’s wroth studying.
Laura Dekker and the Guppy
Let’s end with a modern-day adventurer. At just 14 years old, Dutch sailor Laura Dekker set out solo aboard her 38-foot ketch, Guppy, and became the youngest person to sail around the world alone.
Her boat was actually a pretty simple sailboat, refitted for safety and durability. Dekker navigated storms, crossed oceans, and handled everything from repairs to provisioning on her own.
Guppy shows what’s possible with a smart setup and a little grit. It’s not the most impressive boat on this list, but it does speak to the power of knowing how to pick the right boat for the right situation.
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