AHC: Italian City State colony in the Americas

Your challenge is simple (at-least in understanding what your challenge is, conceptualizing it without dem Alien Space Bats is another thing entirely). Have an Italian City State (Venice, Genoa, Florence etc.) create, populate and hold a colony in the Americas.

Is it even possible? Can it be done? Well, it wouldn't be a challenge if it were easy now would it?
 
Your challenge is simple (at-least in understanding what your challenge is, conceptualizing it without dem Alien Space Bats is another thing entirely). Have an Italian City State (Venice, Genoa, Florence etc.) create, populate and hold a colony in the Americas.
Is it even possible? Can it be done? Well, it wouldn't be a challenge if it were easy now would it?
Well, I'd suppose it'd look something like the Couronian Colonies. But the city-states, in order to have a colonizing motive like Courland, need to have a "expansionist past"- say, something like active participation in the Crusades? For that, maybe the closest thing that can come to colonizing the Americas may be the ITTL "Venetian colony of the West Indies", something of the small islands in the Caribbean.
 
The major obstacle seems to be that the Italian city-states had no real reason to establish American colonies. They were in decline, politically and economically, just as colonization of the new world really took off. Their possessions closer to home were being gobbled up by rivals, and Italy itself was ravaged by repeated wars. That's not the kind of situation where a government decides that starting a colony on the far side of the world is a really awesome idea.

That said: how about a private venture? Suppose: Venetian bankers agree to fund an ambitious plan to establish a trading outpost in the New World. So, sometime well before the 1690's (the point where the French first arrived in the area), a group of Venetian entrepeneur-colonists lands on the North American mainland. They find an area that reminds them of home a little, and start building their outpost. IOTL, the place was called New Orleans, but in this ATL, we call it Nuova Venezia (or something like that). Excellent place for a trading outpost, so it could become a very succesful venture. More investors are found, the Venetian government eventually lends its support to the project.... who knows what might happen? I can see a Venice of the New World emerging where OTL New Orleans is located; a city of canals and gondolas - and where the gondoliers have to fend off the occasional alligator with an oar. ;)
 
Do the Knights of Malta count as "an Italian city-state" for your purposes? They briefly colonised one of the smaller islands IOTL.
 
Do the Knights of Malta count as "an Italian city-state" for your purposes? They briefly colonised one of the smaller islands IOTL.

Unfortunately no, the Knights of Malta don't actually count as an Italian City-State.

And I should stress that i'm not doing this as a way for creating a TL, i'm genuinely curious/challenging you to try and make a stable ICS colony.
 
I have found the idea of a Venetian Cuba always pretty interesting. Tough I have no idea how to achieve that.
 
There are stories that Spain gave Venezuela to Venice as security on a loan - Venezuela means "Little Venice", after all - and I've seen people on here use that as evidence of an Italian colony before, but I don't believe that Venice ever had a chance to take control of the colony, nor do I honestly believe Spain would've allowed them to.

The other major issue you have here is that, to be a colonial power, you need the ability to defend your colonies. Colonies are ripe possessions, prime for plucking by greedy rivals, and essentially colonies are only going to be held in the long term by the more powerful European states. If an Italian city-state founded a colony in the Americas, within 10 years it would've been taken off them by one of England, France, Spain, Portugal or the Netherlands. That's just the way it went. The stories of Courland, the Knights, etc colonising are funny, but at the end of the day if you read into these colonies you see these minor powers with no power projection never manage to keep possession of them for more than a decade.
 
This may sound a bit ASB, but how about-- late 16th century-- a weakened Spain, leading to unhappiness in the Americas, leading to a Protestant revolt and capture of some Caribbean island(s), and a joint Papal-French coalition to violently counter-reform them, resulting finally in a territory of the Papal States in the Caribbean (although perhaps de facto controlled by France).

Or! The very reverse of this, where the Protestant Reformation is particularly violent and successful and the Papacy is overthrown, exiled to the Americas?

Of course, it's pretty unreasonable to think that either of these could last much longer than 50 years or so under purely Papal authority, but just for the sake of using the Papal States as opposed to Venice (which is a rather more likely candidate).
 
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Have Ferdinando I of Tuscany live longer, that could yield a Tuscan Guyana.

Tuscany sent an expedition to explore Northern Brazil and Guyana's for suitable location for a settlement. This settlement would export Brazilian woods back to Italy. Robert Thorton, the leader of the expedition, found a suitable spot for a settlement near Cayenne, but returned to Tuscany to find Ferdinando I dead, and his successor not interested in establishing a colony.
 
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