River of Insanity

Landfall is the least of their concerns.

In brief: any river voyage (or other journey into the Wild Wilderness) is a doomed expedition in which the characters alternately die, go mad, get lost, go native, or otherwise barely live to tell the tale.

This tends to broadly describe any expedition that involves a hopeless journey along a set path (or path of least resistance) to an unfamiliar (possibly hopeless or nonexistent) destination. Often this involves a boat and a river. This trope explains why Genre Savvy adventurers know to avoid river expeditions at all costs, even though it is usually the fastest way of penetrating the interior.

This trope was popularized in Joseph Conrad's Heart of Darkness. However, this is a more universal feature of wilderness expeditions, and predates Conrad.

River of Insanity more generally describes a doomed voyage "into the wild" (usually focused on the trip itself), since examples show that almost any wilderness voyage in fiction, especially by boat, is doomed from the start, either because of the river itself or the natives or Cabin Fever. The Captain of such an expedition will often be the Determinator, willing to press on regardless of cost, until only he is left. Far from being honored for his perseverance by the reward of a legendary destination, the author himself may mock him for his efforts.

Often there is An Aesop about the supreme power of Mother Nature or, more cynically, the fundamental indifference of Nature to our survival, or merely a metaphor for the triumph of barbarism and the darkness of the human soul. Compare Hungry Jungle.

Contrast Late to the Tragedy (in which the destination is often known because of a Distress Signal). See also Send in the Search Team and Deadly Road Trip, which is the Horror equivalent for vacations. The journey to get there is usually glossed over in that trope. For the exact opposite of this trope, see Walk into Mordor; in which the destination is pre-determined, and there is no set path, such as a river, to follow — only obstacles — such as Climbing the Cliffs of Insanity.

Compare Don't Go in the Woods and Horrible Camping Trip, both of which hold that camping trips in the woods never seem to turn out all that well either (though they turn out worse in the former than the latter...) See also Macho Disaster Expedition and Hungry Jungle. If the destination is merely a MacGuffin, it's Going to See the Elephant.

In this trope, the journey is more psychological than physical, although it can also be both. However, it almost always involves a pre-set route such as a river to an unknown destination.

If their vessel was never seen again, see Ghost Ship. In the worst case, they may become Flying Dutchman, doomed to wander the wilderness forever.

See also Dwindling Party and Inevitable Waterfall. This trope may overlap with Wild Wilderness often with dark results.

Examples:

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Anime & Manga

Spoofed in the Slayers episode "Navigation! Invitation to Sairaag". Lina's gang is traveling on a raft by a river to an unfamiliar destination; they suffer from hunger and are relentlessly pursued by bandits and bounty hunters. Finally Lina has had enough and starts blasting around with her Dragon Slave spell, creating a new lake by the way.

Fan Works

The premise of the "Shadows of the Jungle" sidestory in Pokémon Reset Bloodlines is an expedition to Guyana in search of Mew. As the story is told in an Apocalyptic Log format, you can pretty much guess how it's going to end.

Film — Live-Action

The main characters of The Abominable Snowman trek up into the Himalayas in search of the yeti, but find their infighting and bad decisions causing them at least as much trouble as the beasts.
Ad Astra uses something of an outer space version of this as Brad Pitt's character is aware of his slowly deteriorating sanity while he travels between Mars and Neptune.
The African Queen is an amusing example — the actual film has the characters not going mad, and instead falling in love and defeating the Germans (what, you expected a spoiler for that? It was during The Hays Code, there was literally no legal way to have a Downer Ending, given the premise), but according to Katharine Hepburn's book, the making of the film took its cast and crew through the sort of arc this trope normally describes.
Aguirre, the Wrath of God: the conquistadors ride several rafts expecting to find cities of gold to conquer. Instead, they slowly turn on each other, get picked off by hostile natives, and go insane. It ends with Aguirre giving a delusional diatribe to a colony of monkeys, the only things left to hear him.
In the original Anaconda, a documentary crew travelling up the Amazon gets shanghaied into hunting a giant killer snake, and all but two of them die (along with the poacher who shanghaied them).
The 1983 movie Antarctica is based on a 1958 Japanese expedition: two dogs really survived by themselves for one full year in Antarctica and recognized their master when he came back: tough dogs.
Apocalypse Now (which Francis Ford Coppola based on Conrad's Heart of Darkness). The characters encounter increasingly primitive conditions the further upriver they go, to some extent becoming more primitive themselves. The river is also one of metaphorical time travel in later cuts of the film, as the soldiers experience the history of Vietnam backward, encountering a French colonial farm still protected by former French soldiers.
There isn't a river but there is an Amazonian jungle and some really misguided and disturbed people in the film and novel At Play in the Fields of the Lord.
Black Robe: It's no spoiler to say the Jesuit priest goes native. Portrayed as a good thing.
The canoe trip in The Burning, where Todd and Michelle take the 15 oldest campers downriver to camp out. Not all of them make it back, and those who do are traumatized by the end of it.
Dead Man: The eponymous title character is taken to the "river made of waters".
"I wouldn't trust no words written on no piece of paper from no Dickinson in the town of Machine. You're just as likely to meet your own grave."
Deliverance (1972) is about four suburbanites who go on a canoe trip in rural Georgia that goes from bad to nightmarish. One of them is raped by hillbillies; then they end up killing said hillbillies, hiding their bodies, and evading local law enforcement; one of them get his leg broken; and another one is killed or possibly commits suicide.
Fitzcarraldo. Kinski plays Peruvian rubber baron Carlos Fitzcarraldo, who dragged a steamship overland just so he could build a new rubber plantation (not to mention an opera house!) on a previously unreachable river, regardless of the cost. Oh, and he was one of the founders of Manaus, Brazil, where you can still visit the opera house, still used for shows and cultural events today.
Force of Nature: The Dry 2: Five women take part in a corporate hiking retreat deep in the Victorian mountain ranges. Over the course of the hike, the group gets lost, loses the map in a flooded creek, suffers several injuries, and—before they can find their way out—one of the group disappears.
The Conquistador story arc of The Fountain (probably inspired by Aguirre).
Guyana: Crime of the Century: What seems to be a peaceful travel to Guyana to find answers about Johnsontown and the people living in it, ends in tragedy when O'Brien and some of the people who accompany him (reporters and people from the commune wanting to leave with him) are killed in Port Kaituma by Johnson's henchmen.
John Carter: John Carter's, Dejah's, and Sola's river journey leads them to an important revelation, but also gets them ambushed by Warhoons.
Jungle: The trip into Bolivia's jungle initially goes well, but cracks quickly begin to show. Eventually the group splits in two: with Marcus and Kurt attempting to hike back to civilization, while Kevin and Yossi plan to raft down river. Neither group fares well. Marcus and Kurt are never heard from again, while the raft is wrecked and Yossi is lost in the jungle for weeks, nearly starving and going insane in the process.
In Mohawk, Colonel Holt and his men are trying to get to Fort George through the wilderness of northern New York, but Holt's slipping sanity and bloodlust keep diverting them from their path and the Dwindling Party is picked off one by one. Eventually Private Allsopp looks at the setting sun and realises that Holt has been leading them in a completely wrong direction. On hearing this, Holt howls that when the war is over, he is going to have this forest cut down and turned into fields so a man can see where he is going.
In The Mosquito Coast, based on the novel of the same title by Paul Theroux, Harrison Ford is a Yankee inventor who takes his family to live in the jungle on the coast of Honduras. Their misfortunes culminate in a perilous river journey during which the inventor grows increasingly paranoid and finally winds up completely insane.
Subverted in Pirates of the Caribbean: Dead Man's Chest, when Capt. Sparrow flees upriver into the jungle in order to escape the Kraken. Sure, he encounters cannibals and dangerous voodoo gods, but he seems to be in his element nonetheless.
Gibbs: Let's put some distance between us and this island, and head out to open sea.
Sparrow: Yes to the first, yes to the second, but only insofar as we keep to the shallows as much as possible.
Gibbs: That seems a mite... contradictory, Cap'n.
In Rambo IV (the fourth movie), Christian missionaries hire/convince Rambo to take them up the river into Burma where they can help villagers with medical supplies, dental exams, and religion, but their journey is doomed from the start, beginning with Rambo killing a gunboat full of soldiers and ending with the village being raided and the missionaries being taken prisoner.
Werner Herzog's Rescue Dawn, after Dieter Dengler escapes. Dengler and Martin head towards the Mekong River with a plan to cross over into Thailand by fashioning a crude raft. but they run afoul of rapids and a waterfall. After losing their raft, Dengler and Martin are soon found by a mob of angry villagers, who kill Martin. Dengler escapes and flees back into the jungle, hiding from the pursuing villagers.
The River Wild is about a family whitewater rafting trip that becomes an increasingly desperate fight for survival against a criminal who takes them hostage and becomes more and more unhinged.
The 1996 documentary Seven Go Mad In Peru is a non-lethal version. No-one actually goes insane; they start off believing that Misery Builds Character but instead of becoming Fire-Forged Friends get plagued by insects, divided by Testosterone Poisoning, and disillusioned when the Closer to Earth tribes of the Amazon turn out to be walking around in jeans and trainers.
Shackleton dramatizes Sir Ernest Shackleton's Real Life expedition to the Antarctic. However, everyone survived and Shackleton was forced to travel the last leg by himself, over sheer cliffs because they landed on the wrong side of the island of South Georgia, the only source of possible help for 5,000 miles in any direction.
In Valhalla Rising the characters arrive in a mysterious land (The Americas apparently) via boat and subsequently fall to each and every one of these tropes ultimately leaving the now orphaned child standing on the edge of said river. Presumably wondering why he decided to get out of bed at all. This film is the purest incarnation of this trope.
Wings Of Hope, about Juliane Koepcke, who was the sole survivor of a plane crash in the Amazon and walked for ten days out of the jungle - and then 30 years later, Werner Herzog brings her back to retrace her steps.
In Without a Paddle, the characters get lost, lose their boat and supplies, and are attacked and pursued by a bear and violent locals.

Literature

The Adventures of Huckleberry Finn: Subverted in that the river voyage appears indeed to be heading towards disaster, as Huck and Jim miss their turn towards freedom and are carried helplessly down the Big Muddy towards the slave markets of the Mississippi Delta, only to turn into a farce at the end.
Anna Pigeon: A small scale version happens to the crooks in Destroyer Angel. After they lose their map, their trek through the forest with their hostages to the rendezvous point takes days longer than it should, as none of them have any survival or navigation skills. They start to fall prey to paranoia and infighting, which is exacerbated by Anna who is following them and playing mind games to keep them off-balance.
The first and third book of The Dark Tower series: although Roland is following The Path of the Beam instead of a river. The latter book is called The Waste Lands, and the path of the beam takes them down along a river that empties into a vast radioactive rift in the earth. Nuff said.
Downriver is a young adult novel by Will Hobbs that follows a group of teens who go whitewater rafting in the Grand Canyon but stray off from the main group. Eventually, tensions within the group leads to all sorts of problems.
Gone to See the River Man by Kristopher Triana is a horror novel about Lori, a woman corresponding with, and occasionally visiting, an imprisoned serial killer named Edmund Cox. She hopes to gain his trust, with a vague goal of writing a book or doing a true-crime podcast about him. He asks her to do him a favor: go to a cabin he owns by a river, find a key there, and take it upriver to "the River Man." She unfortunately has to take along her sister, Abby, who is mentally and physically disabled and can't stand to be apart from Lori for long periods. They manage to reach the cabin, where Lori realizes the "chest" where she was supposed to find the key is actually the rotting corpse of one of Cox's undiscovered victims. Things get worse from there.
Heart of Darkness: The deeper that Marlowe gets into Africa, the closer he comes to the darkness inside of the heart of man.
The Priest's Tale from Hyperion is a lot like this: the journals of a man hiking out into the most deserted wilderness of an alien planet, only for things to get progressively more insane.
Into the Wild is a partial example. The river is more of an obstacle than anything, and the kid is a Wide-Eyed Idealist who wants to go as far away from humanity as possible and is doomed from the outset. Instead of being trapped on a boat, he ends up trapped in a bus.
The journey of the City in The Inverted World. For over two hundred years, the massive mobile City has been pulling itself in pursuit of the optimum. It is a truly Sisyphean effort: even if the City reaches optimum, they cannot rest, because optimum is always moving. The City is doomed to struggle to move 1/10 a mile a day, every day, forever; an unending pursuit of the unattainable.
The Lord of the Rings: The longer the Fellowship travels with the One Ring, the more its seductive evil weighs on them, first turning Boromir temporarily against the party and then slowly draining the will of Frodo.
Midnight's Children: has one down the Brahmaputra in Bangladesh, in which all the characters go mad, and everyone but the main character die or kill themselves; the main character eventually recovers.
Moby-Dick: Despite being set on the high seas, the story gradually becomes this as everything seems to conspire against them, which only makes Ahab more determined to push on.
The Mosquito Coast by Paul Theroux is about a Yankee inventor who relocates to the coast of Honduras, taking his wife and children along. Their experience in the jungle is a series of misfortunes and disasters, culminating in a perilous river journey during which the inventor grows increasingly paranoid and finally goes completely insane.
In Jasper Fforde's One of Our Thursdays Is Missing, Thursday gets to go on a Genre Savvy one of these.
The second half of the Conan story Queen of the Black Coast involves Conan and the pirate queen Bêlit sailing up a jungle river inland to find and loot an abandoned city. The journey there goes smoothly (minus one crew member being eaten by a snake), but dealing with what still lived in the ruins leaves everyone but Conan dead.
In The Red Tent, Jacob crosses a fast river ahead of his family and servants, and has his famed vision of angels ascending and descending a ladder or staircase, as well as an alleged fight with one (which results in his thigh being dislocated.) He is shown to have a fever, and the other characters take his visions as delirium. This is an important point, as it is essentially where Jacob (fearful from his unexpected Vision Quest, and later jealous of his wealthy twin brother Esau) starts to listen to Simon and Levi's influence and become corrupt and greedy.
In the Shirl Henke novel The River Nymph, the male protagonist grows darker and darker in character as the titular riverboat goes ever farther up the Missouri River and into the wilderness of the American frontier.
The horror novel The Ruins by Scott Smith starts out with a group of twenty-somethings on vacation at the beach who decide to explore some old ruins inland. In The Movie, all but one of them die thanks to a sadistic, man-eating vine. In the book, they all die.
In the Seventh Sword trilogy, there is only one river and this river connects all the cities of the world. Because the river symbolizes the power of the goddess that controls the planet, the river can flow in either direction and ships that travel on her waters may drop anchor in one location at night and mysteriously re-appear elsewhere by morning. Not only that, but the river is inhabited by flesh-eating fish that appear within seconds of someone entering the water.
In The Swans War trilogy the heroes travel down the river and to adventure the whole first book. They actually do much good in the standard epic fantasy way, but a river spirit influences one of them and he never really recovers and dies one year later by what is implied to be suicide.
The second expedition in the novel Water Music by T.C. Boyle about real-life Scottish adventurer Mungo Park and his search for the Niger. He found the river on his first expedition, but he came back for another expedition to find out where it ends.
There is a book called Who Is the River that is about two guys going up a river in South America. The point of the trip was to find a set of ruins and make their careers. It didn't work.
In Algernon Blackwood's "The Willows", two men on a canoe trip down the Danube find themselves in the middle of a willow-infested swamp with a thin wall between them and Another Dimension.
The seven Telmarine lords whom Caspian and his crew are seeking in The Voyage of the Dawn Treader were sent to explore the seas, losing members to various enemies, traps, and temptations, until the last three fell into an enchanted sleep. An invoked example, as the usurper Miraz intentionally sent them on a doomed expedition to get rid of his brother's staunchest political supporters.

Live-Action TV

The 100: The expedition to the City of Light in season 2 is confronted to several obstacles, including landmines, giant mutant creatures, a sandstorm, brigands stealing their supplies and members considering abandoning the party. Eventually only Jaha and Murphy survive to the end.
Parodied in The Goodies episode "The Lost Tribe", where they set out to find the Lost Tribe of the Orinoco and experience many of the misfortunes expected on a River of Insanity expedition, but only make it as far as Sevenoaks.
I Shouldn't Be Alive had "Escape from the Amazon". Only two of the explorers were found.
The series The River follows the expedition of a crew as they search for an explorer who has been gone missing along the Amazon River. They encounter many strange and, at times, haunting challenges along the way in their increasingly desperate attempt to locate him..
The Terror centers on an arctic expedition with both ships stuck in the ice. Forced to live on canned food, the crews slowly succumb to a combination of lead poisoning, botulism, scurvy, hostile weather, and an even more hostile monster that seems to be preying on them.

Roleplay

In The Gamer's Alliance, Alent's infamous Threshold district is an urban version of this trope. Most people who enter it go gradually insane the longer they spend in there (and the deeper they walk into it), eventually ending up mad or dead. The very air, ground, buildings and narrow, labyrinthine and twisting alleys seem to be alive and hostile to any non-native, and the shadows play with trespassers' minds with sometimes fatal consequences. It later turns out that the people living in Threshold are in fact disguised demons whose chaotic powers have warped the district to suit their needs. The horrible visions which trespassers experience turn out to be manifestations of their own inner darkness and emotions which have been triggered by the demonic auras in the area.
Javan: The truth is that the only real darkness in this place is the darkness you bring in it yourself. Every sin, every repressed memory, every stray fear and blind rage. Everything people want to ignore about themselves. What's in here was always there, it's just a bit more... insistent in its existence in Threshold.

Tabletop Games

Rocket Age: A number of expeditions have gone to Saturn, Uranus and Neptune, but most have not returned. One expedition to Uranus sent out a radio signal warning that "something" grabbed a hold of the ship, before all contact was lost.

Video Games

The Fallout: New Vegas - Honest Hearts expansion pack involves traveling to Zion National Park with a caravan company. Your party gets slaughtered by raiders immediately after entering the canyon, leading to your character getting caught in a war between native tribes and vicious invaders. At the same time, there's a philosophical struggle between two different missionaries, one an idealist who wants to preserve the peaceful natives' innocence by leading them out of Zion, the other a cold pragmatist preparing for war against the invaders. There's no Golden Ending, so the player has to decide what compromises they're willing to make as they escape the valley and return to civilization.
Metal Gear Solid 3: Snake Eater has the River of Sorrow, where the protagonist Naked Snake has to walk up a stream and meets the dead Cobra Unit member The Sorrow, who summons ghosts of the soldiers he has killed throughout the game, provided the player actually killed them.
The Oregon Trail is the PC game version of this trope, where you can easily run out of food and starve, freeze to death due to taking the wrong route at the wrong time of year, or randomly catch dysentery and die, especially if you're doing a Let's Play and you leave decisions to popular vote. There's also a literal raft ride at the end.
"That's how I learned what it means to be an American. To embrace the pioneer spirit, shoot everything that moves, drown my family in a river, and die of starvation somewhere in the Midwest."
- Its tropical twin The Amazon Trail also counts. And yes, you travel up the Amazon river. In a canoe. Along the way, the encounter with Lope de Aguirre (see below) plays kind of like a brief, kid-friendly version of Apocalypse Now.
Subnautica has a set of Apocalyptic Logs detailing the fate of the Degasi, whose crew fell victim to this trope. A mining executive decided to take a detour to the unexplored Planet 4546B, which resulted in the loss of the Degasi, leaving only the executive, his son and their bodyguard. They were able to settle on an island for a time, but the need for mineral resources led them to set up an undersea base, then another one even deeper. Their group also fell into infighting, to the point that the bodyguard was stealing resources from the others to force them to relocate deeper underwater, since she became convinced that the answer to their problems was down there somewhere. By the time the Player Character arrives on 4546B, all that's left of the Degasi survivors are their data logs and several derelict habitats.

Web Videos

The topic of the Counter Monkey episode Never Get On The Boat. Spoony advises player characters to never get on the boat, or if they absolutely have to, then at least prepare for the inevitable ambush.

Real Life

When Robert Scott and Roald Amundsen raced to be the first expedition to reach the south pole, Scott's expedition found the Norwegian flag waiting for them. Then Scott's entire team died from exposure on the way back.
Several Real Life expeditions into Darkest Africa inspired this trope, most notably Emin Bey's expedition to Equatoria, a vast and inaccessible swamp on the headwaters of the Nile. (A German-Jewish geographer who had been appointed Bey of the Turkish Empire, he claimed the region for either England, Egypt, or Germany, it's not clear which.)
- Averted with the 1913-1914 Roosevelt-Rondon Expedition along the River of Doubt^note (a then-unknown tributary of the Amazon), but just barely. Out of nineteen expedition members, three died^note, but if the tribes along the river had decided not to let the expedition pass by quietly, if they hadn't been able to buy supplies from rubber tappers on the lower reaches of the river, or if one of Rondon's colleagues hadn't pushed upriver from Manaus with more supplies and medical aid, it's unlikely that any would have survived.
In November 1978, Congressman Leo Ryan led a delegation of aides, journalists, and concerned relatives to investigate conditions at the Peoples Temple's "Jonestown" settlement in Guyana. It ended with members of the Temple murdering Ryan and about a dozen of his party on an airstrip shortly before the mass poisonings at Jonestown.
Donald Crowhurst was a British businessman who entered the 1968 Sunday Times Golden Globe Race, in which he was expected to complete a non-stop circumnavigation of the world single-handedly. Crowhurst, who was in deep financial trouble, entered the race in hopes of winning the cash prize. Unfortunately, he encountered difficulty early in the voyage and began reporting false positions. The pressure between completing the race and solving his financial woes, or letting his deception be exposed, gradually eroded his mental state as evidenced by his increasingly rambling logbooks. It is believed that he eventually committed suicide by throwing himself in the ocean.
After "discovering" Dr. Livingstone (who was doing just fine without him), the "journalist" Henry M. Stanley made a name for himself penetrating the headwaters of the Congo in the service of King Leopold of Belgium, executing uncooperative natives along the way, and claiming the Congo basin for Leopold's personal rubber fiefdom. His expedition is what inspired Conrad to write his book, after it came out what Leopold's men were actually doing in Stanleyville.
- Also Stanley's expedition to rescue the above-mentioned Emin.
There were many, many doomed voyages into the interior of Australia, filled with some of the harshest desert known to man and landscape utterly foreign to Europeans. One notable mention was Charles Sturt, who nearly died multiple times and even took a boat with him to settle the debate about whether Australia had an inland sea. Many Australian explorers barely came back alive and others died miserable lonely deaths. Surviving comfortably in the outback is perfectly possible, but they were too proud to ask survival tips from the natives (didn't help that Europeans and native Australians were prone to not understanding each other even when they had words in common- their worldviews were impossibly mismatched on many points). Ironically, there was an inland sea... once. Stuart and his fellows were just about 100 million years too late. (Or possibly too high up, depending on your definition of "sea". There is indeed an enormous body of water in inland Australia, over 9000 feet deep in some places and covering roughly 22% of the continent...but it's underground).
The first white explorers to take a boat down the Grand Canyon: Half of them died.
- Lampshaded in the case of a honeymoon couple that attempted to go down the canyon in a two-ton scow, with much buildup by Ken Burns in The National Parks documentary. They were never seen again, but the boat was found sitting with all their belongings (and lunch) intact.
Deliverance was based on the author's real-life experiences rafting in Appalachia. Massively inverted in that the locals were incredibly helpful, and were excited to hear he was writing a book about the area!
Apropos of a related trope, the Donner Party is worth mentioning. Basically, a group of pioneers set out for California, ended up snowbound in the Sierra Nevada, and resorted to cannibalism, eating the corpses of those who died.
The first Western voyage up the Mekong River in Southeast Asia was pretty difficult, partly because the river isn't actually navigable up most of its length, and partly because most of the crew repeatedly caught tropical diseases.
The ill-fated Narvaez expedition of would-be Spanish conquistadors in the 1520s. Despite suffering from serious food and supply shortages and a near shipwreck prior to even leaving their base on the island of Cuba, and drifting over a thousand miles away from their intended destination, the expedition's leaders decided to go a-conquering anyway - with predictable results. Amazingly, after being stranded in the wilderness of what is now western Florida, enduring another series of shipwrecks on a few homemade rafts and being captured by a dozen or so successive groups of Native Americans, 4 of the expedition's original 300 members managed to wash up on the Texas shore and walk over 1700 miles to Spanish-occupied Mexico. Almost too surreal to be believed, but check out the whole story on That Other Wiki
The real life Lope de Aguirre who mutinied against his leaders during an expedition to find Eldorado (in itself a goal that fulfills this trope), and then led the soldiers and Native American slaves left alive on a hundred day march through the jungle to capture the main Spanish settlements in Venezuela, Panama, and Peru. At first relatively successful, the Spanish army offered free pardons to any of Aguirre's soldiers who would desert, at which they all did, leaving him to die.
Yermak Timofeevich, the Russian Cossack ataman and the first Russian to conquer Siberia, found it somewhat less than welcoming. He died escaping a clash with the natives, falling off a boat (into a river, yeah) and drowning due to his heavy plate armor. However, Yermak's quest was followed on by other Cossack atamans, and in the middle of the 17th century Russians reached the Pacific coast.
Quite along the lines of Lope de Aguirre in terms of tough luck (not so much in insanity) is Juan Díaz de Solís. He discovered the "Fresh Sea": Río de la Plata, an estuary so big it looks like a sea. They thought that it may be a good idea to go upriver, set their feet on the land and see if that pesky Eldorado was there. He didn't find it, and what he did find instead were hostile natives who killed him and his escort in full view of all the men aboard. Taking good notice, his second-in-command decided that it was about time to go back to Spain.
Remember Werner Herzog, from the Film section? While filming Fitzcarraldo (mentioned above), he decided that the best way to capture the madness of moving a 300-ton steamship overland from one river to another in the middle of the jungle... was to actually move a 300-ton steamship overland from one river to another. There's a reason that film is also listed under the Troubled Production trope.
Captain Sir John Franklin's Arctic expedition in 1845. All Arctic voyages are hazardous, but Franklin's crew had an additional problem; several of the men developed lead poisoning, which impaired their judgement and made them more susceptible to disease.
Another arctic example: Andree's attempt to fly a balloon to the North Pole in 1897. Not only did they underestimate the difficulties of flying a balloon across a sub-zero wasteland, but they had virtually no knowledge of how to survive in the Arctic after crashing and having to walk back to dry land - on ice that floated northwards. Somehow they managed to survive for three months, despite almost walking in place, before they succumbed just as they reached a remote island; they weren't found until 33 years later.
In 1291, the Vivaldi brothers set out from Genoa in two galleys filled with provisions, trade goods, and a missionary or two. Their intent was to bypass the Venetian monopoly on the overland trade with India and China; it's unclear whether they planned to circumnavigate Africa like the Portuguese would in the mid-1400s, or head west and pull a Christopher Columbus two centuries early. What is known is that after passing Cape Nun on the southern coast of Morocco, they were never seen again (although rumors persisted up to Columbus's time that they made it to the tropics before being captured by one of the local West African kingdoms).
The Burke and Wills Expedition into the Australian interior during 1860-61. While the party's trek to the north coast of modern-day Queensland was uneventful, their return journey was plagued by delays and monsoon rains, eventually resulting in the deaths of all seven members in the bush.

Examples:

Alternative Title(s): River Of Madness, Doomed Expedition, Doomed River Expedition

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