Find the bottom of the ocean
Oh look! It's right where we left it
Pretty simple, get sunk! This will happen by losing in a raft, or in any ship by losing a naval battle or unsuccessfully crossing a reef.

Nailed it!
...but how did a hat get on a fish?
When fishing, hit a hat off a be-hatted fish. You will lose that harpoon, but you will gain a beautiful (and useless) hat.

Gone but not forgotten
They say a man's last words are his best remembered... They usually just say "Blargh" though
Leave a message in a bottle when you lose.

You are a pirate!
Yar har fiddle-dee-dee
Attack an English ship, arr!


You caught 2000 lbs. of food
but you were only able to carry 200 lbs. back
Catch 1,000 kg (which is about 2,000 pounds) or more of fish. This is 40 turtles, or 200 fish ... if you get a swordfish (worth 50 kg) you can get to 1000 kg faster (10 less fish to catch). Fish spawn more in the rain, so it can be done in about 5 minutes if you have a good spawn rate at your location. If you are going for the whale-catching achievement "The Wanderer and the Whale" you can skip the fish-catching grind here as the whale is much more than 1,000 kg.

Dice Master
Win a game of liars dice without losing any dice



Wealthy Trader
Do you work for the East India Trading company?
You'll need £20,000 in your pocket
How To Accomplish the Traditional Way: Choose Governor or Admiral, buy the raft, go to the pub and win enough rounds of Liars Dice, betting £1,000 (the max) each time.
How To Accomplish the Expansion Way: Earn money by privateering and sailing for profit. Review Yeazzal's Guide for an idea of market prices.

• Fish just before you land at a port or approach a friendly boat
  
• Buy low, sell high
  
• Buy Luxuries in the East, sell them in the West
  
• Sell Oilskins (raincoats) where they are most expensive, in New York / Long Island and Iceland / Reykjavík
  
• Over-power your ship and plunder every ship you encounter!

Reel it back
Catch 100 fish with one harpoon
You need to catch 100 fish in a row in the same fishing session.


Skin that smoke wagon and see what happens
Survive a mutiny without anyone being shot
The description states what needs to occur. Advice to achieve is as follows:

• Start a new profile
  
• Buy food
  
• Set rations to "no portions"
  
• Set sail
  
• Wait for your mutiny!
  
• Point your gun toward the crewmate that started it ... once they no longer have their gun pointed to you, point toward any other crewmate that is pointing their gun at you
  
• Try again if you fail

Courier
I've been looking for you. Got something I'm supposed to deliver...
In a tavern choose "opportunities" (middle right). By chance, you will be offered a quest to deliver a letter to a given port. If it is too far or out of your way, say no and try again at the next tavern.

Artificial Courage
Win a battle while drunk as can be
Win a battle shortly after consuming *4* barrels of rum

• Purchase at least 4 rum from a tavern
  
• Spot a ship you want to attack (use the spyglass as soon as possible)
  
• Go into inventory (i shortcut key) and drink the rum, do this 4 times total
  
• Win the battle (tip: use the keyboard arrows and space bar instead of your mouse)
  
• Pause the game to recover from your nausea

Decked Out
Fully upgrade your ship
Buy all upgrades for a ship at the dock


Master of the Seas
You achieved every achievement in The Caribbean Sail

The Promised Land
wait... This isn't the Willamette Valley
Reach Nassau with at least one survivor. Willamette Valley is a region in Oregon ;)


Survivors all!
That wasn't so bad
Have all of your crew members survive to Nassau.


We're gonna need a bigger boat
Catch a bull shark
After crossing the final (2nd) reef to Nassau, go fishing. Eventually while fishing a shark will jump toward your ship. You'll need to be fast but it's possible with the harpoon. If you aren't fast enough, your will lose a member of your crew, you've been warned!

I and my fleas
Carry the plague to Nassau
Another luck-based achievement. Bring medicine to keep your plagued crew alive. Open any crates and search all abandoned ships (to actually get the plague). Use the clipper for speed and hope for high winds.

Bring the gospel to pirates
I never said it would be easy
"Beat the game" - Reach Nassau as a Missionary

How To Accomplish: Fish patiently & get lucky. With the new updates, it is easier since you can approach French or Spanish ships (with the correct flag) to pickup more harpoons and see if pirates are coming soon (so you don't fish unnecessarily). Additionally, you do not have to sail direct so you can spend a lot of time fishing to work on earning money for supplies (or a new ship if you are really adventurous).
Tips:

• Check the shop - if there are apples continue - if not, start a new game
  
• Purchase a luxury item so you have something left after being raided by pirates
  
• BE PATIENT, only try to catch fish on the closest 1/4 - 1/2 of the screen
  
• Fish in the rain when you can, fish spawn more in the rain
  
• Around day 10 eat your apples (they tend to rot around 11-14 days)
  
• Use the spyglass and "approach" any ship you can (when you have their flag) to pickup more harpoons if needed
  
• Since you can't avoid pirates, if they are coming close (again use spyglass), don't fish until after they leave
  
• After pirates have taken all your food and money, trade your luxury item when you can for more harpoons
  
• Get lucky ... but with these tips you should accomplish this in a few tries

A doubloon saved
isn't worth very much, but you're too good for shopping
Hint 1: Re-read the Achievement sub-text
Hint 2: You have to get to Nassau for it to trigger
Answer: You have to get to Nassau without purchasing anything throughout the entire trip - do a speed run!
How To Accomplish: You'll need to be lucky so it may take a few tries. Choose Governor or Admiral as your occupation and purchase the Clipper. Keep your portions "pathetic". When you encounter your first ship, ram it with "full sail" if it's a small ship, you'll win the battle. Hopefully, you'll get harpoons or food. Flee all other battles against large ships since you don't have any cannons or cannon balls. The Clipper's speed should keep you as safe as you can be considering you are a cheap monster!
Additional Tip: If you come across apples, use them to help with hunger

A great guide for the next 2 achievements listed below is available here

A round on us
Defend Nassau from the Spanish fleet
After arriving at Nassau for the first time, choose "yes" to the offer. This will send you on the Pirate Questline: Collect £10,000 and then go back to Nassau. Prepare for a 3-part battle. I recommend purchasing and upgrading the "Turtle" ship prior to battle, it should make the battle easier. It may be worth also going for Wealthy Trader when following this path

Nobility
"Sir" is it?
After arriving at Nassau for the first time, choose "no" to the offer. This will send you on the Royal Navy Questline: Defeat increasingly difficult ships, returning to London after each one

Shantyman
Collect every shanty
You will be short on inventory space when going for this achievement (20 slots totals). Make sure you have completed any current quests so you have the inventory space! The letter of marque is the only one which cannot be "dropped." Once you have a decently upgraded ship, this makes sense to try when also working toward the Explorer achievement.
There are 20 total shanties to collect and they all look a little different:


The long haul
Should have crossed the pacific
As the achievement image implies, sail from Shanghai to New York (17,130 miles). An upgraded clipper and highly skilled captain will make this trip less painful. Fantasy mode and the unlocked faster ships make this nearly trivial.
Some items for your inventory should include:

• Net (in case you are a bad fisherman and run out of harpoons)
  
• Recently purchased apples
  
• Sextant
  
• Compass
  
• French and/or Spanish Flag

The Transatlantic Sail
Sail from New York to London in under 5 days and 14 hours beating the current world record - Purist mode only
Difficult but not impossible. With a highly skilled captain, an upgraded clipper, and a bit of luck you can do cross the Atlantic in about 5 days. Purist mode means no fantasy toggle - this needs to be done sailing - no steamships (or faster)!

The Wanderer and the Whale
Catch a gentle giant of the sea
In your journeys, you will sometimes see a whale surface. When you see this, go fishing and hit it with a harpoon. The fun is not over until you click enough times at exactly the right time (just before the the red line) to reel it in.
If you want to grind your attempts, whale spawns are much more probable in a new game when traveling from London to Nassau (spawn can occur after the halfway point normally around 2000-500 miles remaining). Do not use a fully upgraded clipper as it moves too quickly for the whale to spawn on screen.

Achievement Unlocked
Unlock everything
Finish a whole lot of sailing - 200,000 experience (this many successfully completed miles sailed across all play-throughs).

Explorer
Visit every port
14 total ports to visit in one play-through (15 if you including your starting port of London). Make sure to upgrade your ship prior to heading to India (Kozhikode / Calicut) or China (Shanghai). It is worth going for the Shantyman achievement while doing all that traveling. You will experience about 6 reefs from India to China - so use some skill points toward Navigation. Some of the Fantasy ports are hidden so you will need to follow other Fantasy quests. The Explorer career will show some additional ports without starting certain quests.

Performing man
You impressed the great Walrus
Go fishing near Iceland, you may get a random encounter (higher chance with greater luck). Hit every ring. Sail back and forth to/from Iceland to try again (once per trip).

1. Aim slightly up
   
2. Aim up
   
3. Aim down
   
4. Aim up (just 1 ring)

I am the Captain now
Give pirates the power of flight
Attack 2 ships, a pigeon will stop by with a message a little later, go to Libertalia and return after completing the quest

Hypocrite.
You did the Devils bidding, priest.
As Pope (or missionary if you are also a masochist), play tarot cards (in a tavern under "opportunities") eventually you will get the Devil quest, accept and complete the quest

Divine Intervention
Defeat a ship using the Raft
Play tarot cards until you get "An unstoppable force protects you" then buy the raft and attack the first ship (non-ghost variety) you come across

HARK!
Receive the boon of Poseidon
Use the net, catch a mermaid, check your inventory and use the conch, drop bait near Iceland, defeat the Kraken, return to Atlantis

• Carry as many harpoons as possible, at least 40-60 depending on how good you are
  
• Upgrade throwing with your skill points
  
• Choose the Monster Hunter career for an additional boost
  
• Seek inner peace and do not let the music inspire you to rush the fight

Treasure Hunter
Good to know you can follow simple instructions
Buy a treasure map in a tavern (under "opportunities"), go to the location indicated on this new item in your inventory, and well, follow simple instructions

Oh well
I guess you've done the impossible
Complete the main fantasy quest

Get **** on
It's probably a sign
This one is hidden but fairly obvious. When you see birds flying, every once in a while you'll see some ... droppings. This will trigger when one eventually hits your ship.

Pfft, we don't need this
Maybe the fish can use it
Another hidden but fairly obvious one ... go into your inventory and drop (then confirm) your spyglass.

The stuff of legend
You found an Easter Egg!
Hint: Name your captain after a legendary pirate
Answer: Choose one of the following (capitalization matters!):
Blackbeard, Captain Butterjugs, Edward Teach, Solaire, Frisk, Drunken Sailor, Captain Flint, Jack Sparrow, Guybrush, Captain Kidd, Long John Silver, Captain Ahab, Edward Kenway, Colonel Mendoza, Baron Raymondo, Captain Crunch

Into the Unknown
Go beyond the known.
Follow the main quest. You will know it when the time is right.




You made a fish tower
Because that matters.
Catch at least 20 fish (and a hat for good measure).

Spoilers:
Hint 1: Stack them!
Hint 2: On the screen after you finish fishing...
How to: On the screen that shows you all the fish you caught, don't leave that screen,
click and drag your fish into a large tower - once you have stacked ~20 high to the top border this achievement will trigger (place a hat on top if you wish, you don't need to) ... be gentle with those slippery fish!

Congrats.
I hope you're proud.
This is a combination of 2 other achievements.

Spoilers:
Hint 1: Look at the image and think about We're gonna need a bigger boat
Hint 2: Hint 1 + You made a fish tower
WARNING: Narwhals can take out a crewmember just like the bullshark!
How to: Catch a narwhal (typically within about 500 miles of Iceland / Reykjavík). On the screen that shows you all the fish you caught, balance the narwhal on its tusk. Click and drag the narwhal and change its angle by "pushing" against other fish. Once the tusk is straight down, drop it (let go of Left-Mouse). To see the end result, check out VC's screenshot

Thanks to Uriah for assistance with some of the original achievements.
Thanks to Yeazzal for the Merchants Guide.
Thanks to Olek3381 for the Quests Guide.
Thanks to CzechKronner for the whale spawning tip.
Thanks to Carotid Pulse for the legendary Captain Crunch
Thanks to you for reading this guide and enjoying The Caribbean Sail.

And a big thanks to Victorian Clambake for making, continuing to expand, and supporting The Caribbean Sail