IOTL, at the peak of its prosperity and relative power projection, the Duchy of Courland and Semigallia (in the region then known as Livonia, located in present-day Latvia), had a population of 200k, mostly of Latvian and Baltic German ancestry, and was a vassal of what would later become the Polish–Lithuanian Commonwealth. Under Duke Jacob Kettler (ruled 1642-1682), a Baltic German, it established one of the largest merchant fleets in Europe, with its main harbours in Windau (today's Ventspils), and Libau (today's Liepāja). During his travels to Western Europe, Duke Jacob became an eager proponent of mercantilism, and set about greatly developing his relatively small Duchy's metalworking and shipbuilding industries, establishing trading relations not only with nearby countries, but also with England, France, the Netherlands, Portugal and others. Then, he set his sights upon colonial expansion, farther afield. The Duchy's ships had started undertaking trade voyages to the West Indies at least as early as 1637, when a Couronian ship attempted to found a colony on Tobago with 212 settlers; with an earlier European settlement on the island, a Dutch colony named New Walcheren, formed in 1628, having been wiped out a few months earlier by Spain. The first Couronian colony met a similar end, whilst a second attempt was essentially blockaded by Spain and strangled in infancy by 1639. In 1642, two ships under Captain Caroon with about 300 settlers attempted to settle on the north coast near Courland Bay, with this third colony again blockaded, but proving more successful, until Jesuit missionaries among the Carib quickly agitated and armed the tribes to attack the settlement, which was subsequently evacuated to Tortuga and later Jamaica.
Under agreement with other Protestant powers who saw their various individual efforts insufficient to trade and/or colonise the Americas, Africa, and the Indies simultaneously, Courland's attention shifted to Africa. The Duchy established its first colony here in 1651, on St. Andrews Island (today known as Kunta Kinteh Island) in the Gambia River, where the Couronian settlers built Jacob Fort (naming it after the Duke), and used it as a trade base. Major Fock, a Courland soldier, was placed in charge of the first settlement and oversaw the construction of fortifications on St Andrew's Island, which were built following the recognized contemporary rules of military engineering. The main building was in the shape of a rectangle, and was flanked at each corner by a bastion, each of which was triangular. However, the fort had no water supply, and was forced to rely on the good will of the King of Barra in order to stay operational, at least initially- though the Couronians swiftly gained control of additional land, which happened to include Fort Bayona (modern day Banjul, capital of The Gambia) and Fort Jillifree (Jufureh), leasing them from the Kings of Kombo and Barra respectively, and mitigating this to an extent. It was the intention of the Duke of Courland to establish a permanent settlement on St Andrew's Island, and so married couples were sent out to the island as well as a pastor. The first pastor was Gottschalk Eberling, who was replaced in 1655 by Joachim Dannefeld. The island had a small church built out of cane and with a thatched roof, from which Eberling and Dannefeld preached.
There was a supposed deposit of gold along the river, so the Duke of Courland resolved to launch a full expedition to the Gambia; however, as few Courlanders had experience of Africa, he elected to rely upon foreigners, appointing the Dutchman Jacob du Moulin as his Director in the Gambia on 6 September 1652, while a Courlander, Frederick William Trotta von Treyden was appointed as his lieutenant. Three ships, the Crocodile, the Patientia, and the Chur, were placed at Moulin's disposal. There were a number of issues with the expedition, and in December 1652, Treyden wrote to the Duke of Courland describing Moulin as a "light-hearted knave". After setting sail in March 1653, the expedition shortly after ran out of supplies and was forced to return, with Moulin subsequently arrested for his various misdeeds, including embezzling the Duke's money. A second expedition was attempted in 1654, under the command of a Danish (self-proclaimed) explorer, Philip von Seitz, only for Seitz to abandon the expedition in Hamburg, managing to extort 15,000 rix dollars from the Duke.
By this time though, the Protestant powers felt sufficiently organised and prepared to launch several colonial expeditions against Spanish interests in the Caribbean. The alliance between England and the Netherlands against Spain began to dissolve, thanks to England's attempts to break Dutch monopolies. And Courland, having decided to support the English in the growing conflict against the Dutch, had also received permission from its English allies to make still another attempt at a colony on Tobago. On 20 May 1654, the ship Das Wappen der Herzogin von Kurland ("The Arms of the Duchess of Courland") arrived carrying 45 cannon, 25 officers, 124 Couronian soldiers and 80 families of colonists to occupy Tobago, with Captain Willem Mollens declaring the island "New Courland" (Neu-Kurland), and erecting Fort Jacobus on the southwest of the island, with the surrounding town called Jacobsstadt, and other features also given Couronian names, such as Great Courland Bay, Jacobs Bay, Courland Estate, Neu-Mitau, Libau Bay and Little Courland Bay.
In their first year on the island, the colony was rapidly successful, with the Couronians building an Evangelical Lutheran church, and the goods exported to Europe including sugar, tobacco, coffee, cotton, ginger, indigo, rum, cocoa, tortoise shells, tropical birds and their feathers. However, the Netherlands was not willing to accede to losing their claim, and replied by establishing its own colony nearby a few months later. Thus, the small Couronian colony soon became overshadowed by a second Dutch colony, which grew far more rapidly- still more so, after the Duchy of Courland became a focus of strategic interest for both Sweden and Poland–Lithuania, with the Swedish army entering the territory of the Duchy in late 1655, and the Second Northern War (1655-1660), aka the 'Swedish Deluge' commencing. Prior to this though, after the failure of two successive Gambian expeditions due solely to betrayal, the Duke had finally stopped outsourcing, and turned to his own people in the hopes that they'd be more loyal; with Captain Otto Stiel, a Courlander who had previously visited the Gambia, leaving the first full Couronian expedition there in 1655, and being appointed as its Governor and as Commandant of St Andrew's Island. And both colonies continued to thrive, Duke Jacob Kettler had also reportedly already gained the blessing of Pope Innocent X to colonize Australia, which had at that time been discovered and claimed in its entirety by the Dutch, and was preparing an expedition to do so.
However, the Duchy itself fell under Swedish occupation when the Swedes invaded in 1857; the Duke's wife, Louise Charlotte of Brandenburg, managed to receive a promise from the Swedish general in charge to spare her manors and peasants, but in the spring of 1658, the Duke of Courland and his family were taken captive by the Swedish Army, in the process of their forced withdrawal northwards from Royal Prussia, with the Swedish destroying the Couronian merchant fleet and factories in abandoning the region, to deny them to the advancing Polish and Austrian Hapsburg armies. Imprisoned, first in the city of Riga, then in Ivangorod, communication between Courland and St Andrew's Island was cut off for around two years. And the Dutch West India Company capitalized upon this to come to an agreement with the Duke's representative in Holland, Henry Momber, by which Momber agreed to allow them to take over Courlander Africa, so long as they'd resupply it (rather than killing the garrison and all the settlers there). The Dutch sent a ship of soldiers to the island to seize it, and Stiel objected, attempting to rally his men to repulse the invasion force; but upon learning that the Dutch West India Company would guarantee them their pay, the garrison mutinied against him, and returned to Holland on the ship that had brought out the new Dutch replacement garrison. And on the island of Tobago, the more numerous Dutch settlers surrounded Fort James and forced Hubert de Beveren, Governor of the Couronians, to surrender, with Courland officially yielding New Courland on 11 December 1659.
This war finally ended with the Treaty of Oliwa (signed near Gdańsk) of 1660, with the Duke and his family released from Swedish custody. And after heated negotiations with the Amsterdam chamber of the Dutch West India Company, Tobago was returned to Courland, in exchange for ceding its claim over the Gambia and its ivory, gold, furs and spices exports to them. Courland's venture into Africa wasn't done yet though- only a couple of months later, the Dutch lost control of St Andrew's Island, after a French privateer in Swedish service surprised the fort by attacking under the cover of darkness, expelling the Dutch garrison and plundering the island. The privateer subsequently met a merchant ship of the Groningen chamber of the Dutch West India Company, who, in a breakdown of communications, refused to buy back the island and insisted that it still belonged to the Duke of Courland; hearing of this, Henry Momber got in touch with Otto Stiel, who had been living in Holland since the mutiny, and Stiel traveled back to St Andrew's Island in a ship provided by the Groningen chamber, together with a handful of members from the original garrison who he still deemed trustworthy.
Several weeks later, three ships of the Amsterdam chamber anchored off the island and demanded that Stiel surrender. He stubbornly refused (yet again), and the Dutch effected a landing, bringing a large amount of firepower to bear on the fort, forcing Stiel's surrender to save the lives of his handful of men. However, when the King of Barra saw Stiel evicted yet again, he decided to come to his aid by capturing a party of Dutchmen who had landed at Juffure for fresh water, before demanding that Stiel be re-instated, joined by a large number of other native kingdoms, including the King of Kombo. A four-week stand-off ensued, before the Dutch caved in to their demands, with the Dutch commander partially destroying Fort Jacob and taking all of its provisions out of spite before turning it back over to Stiel and the Courlanders. And over the next eight months, the garrison was reduced to just seven Europeans, before Stiel handed it over to the English Royal African Company in 1661 (who renamed the island James Island and the fort Fort James after James, the Duke of York, later King James II of England, and used it first for the gold and ivory trade as the Couronians had, before expanding its operations to the slave trade 2 years after its acquisition), with the Dutch formally ceding the fort to the English 3 years later, in 1664.
And across the Atlantic, following several attacks by buccaneers seeking new harbours, and an expeditionary fleet of Spanish vessels, the Couronians left Tobago in 1666, with a Couronian ship attempting to reoccupy Fort Jacobus in 1668 only to be driven off by the Dutch. Tobago was regained again just for a short period at the end of Duke Jacob's rule, who'd begun to restore the fleet and factories, with an attempt in July 1680 at a new colony (which also involved a settlement near modern Toco on the neighboring island of Trinidad), but this also later failed, and the Duchy never again reached its previous level of prosperity. The island was abandoned except for visiting buccaneers from March 1683 to June 1686, before again being occupied by a collection of scattered Couronians from throughout the Dutch, French, and English West Indies, as well as by fresh settlers from the home country. And in May 1690, the Couronian government permanently left Tobago, with those who remained essentially joined the buccaneers or other Anglo-Dutch colonies; the island was sold to the British in 1693, by Duke Jacob's son and successor Frederick Casimir, to fund his glamourous celebrations and over-indulgences, with Courland losing its geopolitical position under his rule to become Sweden, Prussia and Russia's territorial subject of interests. Though absentee governors of Neu-Kurland would continue to be appointed until 1795, thereby facilitating the continued use of covert privateering Letters of Marque and Reprisal in the region.
So, that's the long and not-so-short of how the Duchy of Courland's colonial empire panned out IOTL. Anyway, how much better could it have potentially have panned out for them in a different TL, particularly given all of those setbacks and betrayals that they came up against IOTL (including the ill-fated war against the Dutch, which they only entered into on the behalf of the English, only for their supposed English 'allies' to lend them no support or assistance whatsoever, and then scavenge the remnants of Courland's colonies for themselves later), and all of those potential PODs which could've gone far more favorably for them than they did? And even in spite of the wars and turmoil in the Baltic taking precedence, and having every chance of wiping it out regardless- if its colonial efforts had been successful and secure enough, might Duke Jacob Kettler, his family, and the Court of the Duchy have conceivably been in a position to escape by relocating to one of the Duchy's (presumably larger, more populated and more developed) Couronian colonies in a strategic retreat from the Swedish Deluge, in a manner akin to the transfer of the Portuguese Court to Brazil during the Napoleonic invasion of Portugal over a century later IOTL, until the wars' end?
Under agreement with other Protestant powers who saw their various individual efforts insufficient to trade and/or colonise the Americas, Africa, and the Indies simultaneously, Courland's attention shifted to Africa. The Duchy established its first colony here in 1651, on St. Andrews Island (today known as Kunta Kinteh Island) in the Gambia River, where the Couronian settlers built Jacob Fort (naming it after the Duke), and used it as a trade base. Major Fock, a Courland soldier, was placed in charge of the first settlement and oversaw the construction of fortifications on St Andrew's Island, which were built following the recognized contemporary rules of military engineering. The main building was in the shape of a rectangle, and was flanked at each corner by a bastion, each of which was triangular. However, the fort had no water supply, and was forced to rely on the good will of the King of Barra in order to stay operational, at least initially- though the Couronians swiftly gained control of additional land, which happened to include Fort Bayona (modern day Banjul, capital of The Gambia) and Fort Jillifree (Jufureh), leasing them from the Kings of Kombo and Barra respectively, and mitigating this to an extent. It was the intention of the Duke of Courland to establish a permanent settlement on St Andrew's Island, and so married couples were sent out to the island as well as a pastor. The first pastor was Gottschalk Eberling, who was replaced in 1655 by Joachim Dannefeld. The island had a small church built out of cane and with a thatched roof, from which Eberling and Dannefeld preached.
There was a supposed deposit of gold along the river, so the Duke of Courland resolved to launch a full expedition to the Gambia; however, as few Courlanders had experience of Africa, he elected to rely upon foreigners, appointing the Dutchman Jacob du Moulin as his Director in the Gambia on 6 September 1652, while a Courlander, Frederick William Trotta von Treyden was appointed as his lieutenant. Three ships, the Crocodile, the Patientia, and the Chur, were placed at Moulin's disposal. There were a number of issues with the expedition, and in December 1652, Treyden wrote to the Duke of Courland describing Moulin as a "light-hearted knave". After setting sail in March 1653, the expedition shortly after ran out of supplies and was forced to return, with Moulin subsequently arrested for his various misdeeds, including embezzling the Duke's money. A second expedition was attempted in 1654, under the command of a Danish (self-proclaimed) explorer, Philip von Seitz, only for Seitz to abandon the expedition in Hamburg, managing to extort 15,000 rix dollars from the Duke.
By this time though, the Protestant powers felt sufficiently organised and prepared to launch several colonial expeditions against Spanish interests in the Caribbean. The alliance between England and the Netherlands against Spain began to dissolve, thanks to England's attempts to break Dutch monopolies. And Courland, having decided to support the English in the growing conflict against the Dutch, had also received permission from its English allies to make still another attempt at a colony on Tobago. On 20 May 1654, the ship Das Wappen der Herzogin von Kurland ("The Arms of the Duchess of Courland") arrived carrying 45 cannon, 25 officers, 124 Couronian soldiers and 80 families of colonists to occupy Tobago, with Captain Willem Mollens declaring the island "New Courland" (Neu-Kurland), and erecting Fort Jacobus on the southwest of the island, with the surrounding town called Jacobsstadt, and other features also given Couronian names, such as Great Courland Bay, Jacobs Bay, Courland Estate, Neu-Mitau, Libau Bay and Little Courland Bay.
In their first year on the island, the colony was rapidly successful, with the Couronians building an Evangelical Lutheran church, and the goods exported to Europe including sugar, tobacco, coffee, cotton, ginger, indigo, rum, cocoa, tortoise shells, tropical birds and their feathers. However, the Netherlands was not willing to accede to losing their claim, and replied by establishing its own colony nearby a few months later. Thus, the small Couronian colony soon became overshadowed by a second Dutch colony, which grew far more rapidly- still more so, after the Duchy of Courland became a focus of strategic interest for both Sweden and Poland–Lithuania, with the Swedish army entering the territory of the Duchy in late 1655, and the Second Northern War (1655-1660), aka the 'Swedish Deluge' commencing. Prior to this though, after the failure of two successive Gambian expeditions due solely to betrayal, the Duke had finally stopped outsourcing, and turned to his own people in the hopes that they'd be more loyal; with Captain Otto Stiel, a Courlander who had previously visited the Gambia, leaving the first full Couronian expedition there in 1655, and being appointed as its Governor and as Commandant of St Andrew's Island. And both colonies continued to thrive, Duke Jacob Kettler had also reportedly already gained the blessing of Pope Innocent X to colonize Australia, which had at that time been discovered and claimed in its entirety by the Dutch, and was preparing an expedition to do so.
However, the Duchy itself fell under Swedish occupation when the Swedes invaded in 1857; the Duke's wife, Louise Charlotte of Brandenburg, managed to receive a promise from the Swedish general in charge to spare her manors and peasants, but in the spring of 1658, the Duke of Courland and his family were taken captive by the Swedish Army, in the process of their forced withdrawal northwards from Royal Prussia, with the Swedish destroying the Couronian merchant fleet and factories in abandoning the region, to deny them to the advancing Polish and Austrian Hapsburg armies. Imprisoned, first in the city of Riga, then in Ivangorod, communication between Courland and St Andrew's Island was cut off for around two years. And the Dutch West India Company capitalized upon this to come to an agreement with the Duke's representative in Holland, Henry Momber, by which Momber agreed to allow them to take over Courlander Africa, so long as they'd resupply it (rather than killing the garrison and all the settlers there). The Dutch sent a ship of soldiers to the island to seize it, and Stiel objected, attempting to rally his men to repulse the invasion force; but upon learning that the Dutch West India Company would guarantee them their pay, the garrison mutinied against him, and returned to Holland on the ship that had brought out the new Dutch replacement garrison. And on the island of Tobago, the more numerous Dutch settlers surrounded Fort James and forced Hubert de Beveren, Governor of the Couronians, to surrender, with Courland officially yielding New Courland on 11 December 1659.
This war finally ended with the Treaty of Oliwa (signed near Gdańsk) of 1660, with the Duke and his family released from Swedish custody. And after heated negotiations with the Amsterdam chamber of the Dutch West India Company, Tobago was returned to Courland, in exchange for ceding its claim over the Gambia and its ivory, gold, furs and spices exports to them. Courland's venture into Africa wasn't done yet though- only a couple of months later, the Dutch lost control of St Andrew's Island, after a French privateer in Swedish service surprised the fort by attacking under the cover of darkness, expelling the Dutch garrison and plundering the island. The privateer subsequently met a merchant ship of the Groningen chamber of the Dutch West India Company, who, in a breakdown of communications, refused to buy back the island and insisted that it still belonged to the Duke of Courland; hearing of this, Henry Momber got in touch with Otto Stiel, who had been living in Holland since the mutiny, and Stiel traveled back to St Andrew's Island in a ship provided by the Groningen chamber, together with a handful of members from the original garrison who he still deemed trustworthy.
Several weeks later, three ships of the Amsterdam chamber anchored off the island and demanded that Stiel surrender. He stubbornly refused (yet again), and the Dutch effected a landing, bringing a large amount of firepower to bear on the fort, forcing Stiel's surrender to save the lives of his handful of men. However, when the King of Barra saw Stiel evicted yet again, he decided to come to his aid by capturing a party of Dutchmen who had landed at Juffure for fresh water, before demanding that Stiel be re-instated, joined by a large number of other native kingdoms, including the King of Kombo. A four-week stand-off ensued, before the Dutch caved in to their demands, with the Dutch commander partially destroying Fort Jacob and taking all of its provisions out of spite before turning it back over to Stiel and the Courlanders. And over the next eight months, the garrison was reduced to just seven Europeans, before Stiel handed it over to the English Royal African Company in 1661 (who renamed the island James Island and the fort Fort James after James, the Duke of York, later King James II of England, and used it first for the gold and ivory trade as the Couronians had, before expanding its operations to the slave trade 2 years after its acquisition), with the Dutch formally ceding the fort to the English 3 years later, in 1664.
And across the Atlantic, following several attacks by buccaneers seeking new harbours, and an expeditionary fleet of Spanish vessels, the Couronians left Tobago in 1666, with a Couronian ship attempting to reoccupy Fort Jacobus in 1668 only to be driven off by the Dutch. Tobago was regained again just for a short period at the end of Duke Jacob's rule, who'd begun to restore the fleet and factories, with an attempt in July 1680 at a new colony (which also involved a settlement near modern Toco on the neighboring island of Trinidad), but this also later failed, and the Duchy never again reached its previous level of prosperity. The island was abandoned except for visiting buccaneers from March 1683 to June 1686, before again being occupied by a collection of scattered Couronians from throughout the Dutch, French, and English West Indies, as well as by fresh settlers from the home country. And in May 1690, the Couronian government permanently left Tobago, with those who remained essentially joined the buccaneers or other Anglo-Dutch colonies; the island was sold to the British in 1693, by Duke Jacob's son and successor Frederick Casimir, to fund his glamourous celebrations and over-indulgences, with Courland losing its geopolitical position under his rule to become Sweden, Prussia and Russia's territorial subject of interests. Though absentee governors of Neu-Kurland would continue to be appointed until 1795, thereby facilitating the continued use of covert privateering Letters of Marque and Reprisal in the region.
So, that's the long and not-so-short of how the Duchy of Courland's colonial empire panned out IOTL. Anyway, how much better could it have potentially have panned out for them in a different TL, particularly given all of those setbacks and betrayals that they came up against IOTL (including the ill-fated war against the Dutch, which they only entered into on the behalf of the English, only for their supposed English 'allies' to lend them no support or assistance whatsoever, and then scavenge the remnants of Courland's colonies for themselves later), and all of those potential PODs which could've gone far more favorably for them than they did? And even in spite of the wars and turmoil in the Baltic taking precedence, and having every chance of wiping it out regardless- if its colonial efforts had been successful and secure enough, might Duke Jacob Kettler, his family, and the Court of the Duchy have conceivably been in a position to escape by relocating to one of the Duchy's (presumably larger, more populated and more developed) Couronian colonies in a strategic retreat from the Swedish Deluge, in a manner akin to the transfer of the Portuguese Court to Brazil during the Napoleonic invasion of Portugal over a century later IOTL, until the wars' end?