The ships of the fleet left in January 1628 from several harbours on the coast of the Dutch Republic and were to sail directly to the Caribbean where they would gather near the Island of Cuba. The ship the Fortuin was the last to leave from its harbour, on th 3rd of March with 63 colonists on board. This ship was accompanied by the Zuidsterre on its voyage across the Atlantic Ocean. On 15 March they had arrived at the Island of St. Vincent near Barbados (North of Tobago). At this island the fleet split up. Immediately the ships set to work, attacking Portuguese and Spanish ships whenever possible. Usually they used the smaller ships and the sloops to scout ahead.
On 8 May 1628 the ship the Eendracht joined the fleet of Ita. They had also been active on their way from the Dutch Republic to towards the Caribbean. En route they had captured a Portuguese ship which was unfortunately lost, because it began to sink rapidly. The last ship to join the fleet in the Caribbean was the Cuba, on 17 May. The Fortuin was the last ship to join the fleet of Ita near Haïti on the 4th of June. With most of his fleet Ita then sailed towards the West Coast of Cuba. On its way the fleet captured several Portuguese vessels the crews of which informed him on the whereabouts of the rich Spanish galleons that sailed regularly with a full cargo from Honduras to Portugal.
The Spanish authorities in the area were aware of the Ita's fleet, however, and the Governor of Honduras advised these vessels to wait a while before leaving the safety of the harbour. The fleet in the harbour, consisting of 2 Spanish galleons and about 10 well provisioned and armoured merchant ships, received extra munitions and armaments. These extra supplies convinced the Admiral Alvaro De la Cerda that they would be able to handle an attack by Ita's fleet and he decided to leave the harbour.
After having sailed round the Cape of San Antonio Ita's fleet went looking for ships in the area North of Havana. On 1 August the fleet spotted two galleons sailing from Honduras. When these two ships saw that Ita's ships were trying to prevent them from sailing into the harbour of Havana they tried to get away. The ship Leeuwinne attacked the Spanish Vice-Admiral ship, but had no entering hooks aboard. When the Spanish galleon tried to escape from the Leeuwinne both ships ran aground on a sandbank. Both ships continued to fire their muskets and cannons on eachother despite this unfortunate incident. During the exchange of fire the Leeuwinne lost her main mast.
While this was happening the ships the Fortuin and the Dolfijn were attacking the other Spanish ship. This ship also ran aground on the same sandbank where the Leeuwinne and the other Spanish vessel were stuck. Both the Fortuin and the Dolfijn were unable to get any closer because of the uncertain location of the sandbank and continued firing on the Spanish vessel from a distance. The Leeuwinne was unfortunately enough sandwiched between both Spanish galleons and was fired upon from both sides. The resulting casualties were high and included the captain Jan Pieterszoon. The Spaniards of Havana tried to relieve both of their ships but Ita was able to prevent most of this. After the Walcheren had joined the fight the battle became fiercer. After several failed attempts to enter one of the Spanish galleons from the Walcheren the Dutchmen were succesful. They used the ship Fortuin as a go-between to get on board the Spanish vessel, which was built considerably higher than the Dutch vessels. The Spanish admiral Alvaro de la Cerda managed to escape with his life and was able to return to Spain. After his report of the battle and the accounts of it from the Governor of Havana, Laurenzo de Cabrera, he was acquitted of all blame for the loss of the ships under his command.
When the Spaniards gave up the vessel half of its crew as well as the reinforcements were dead. Some time after the Dutch ships the Kater, the Eendracht and the Vriessche Jager had joined the battle the second Spanish ship was also abandoned. The names of the captured Spanish ships were the Nossa Senhora de los Remedios and the St. Jago. Of the estimated 600 Spaniards that had battled the Dutchmen only half survived the attack. Only 13 Dutchmen were killed and about 50 were wounded, most of these from the ship the Fortuin. The Leeuwinne and the Nossa Senhora de los Remedios were eventually freed from the sandbank. The St. Jago could not be pulled free. They moved its cargo on board the other ships and set fire to the ship. The fleet left the area rather hurriedly since they knew that the so-called Terra Firma fleet would soon arrive in this area. Ita's fleet would have been no match for it in the condition it was in.
While they were underway to Florida they took the cargo from the Spanish vessel and divided it among the other vessels. The ship was making so much water that they eventually decided that they could not take it with them across the Atlantic. On 15 August they abandoned the ship after having set fire to it one mile off the coast of Florida. The fleet of Ita arrived at the Dutch Republic in September of 1628. In total they had caught two Galleons, twelve bargues and several small ships. These prizes included 2398 chests of Indigo, 6176 dry skins, 266 packets of Salsaparilla, 27 jars of oil, 7000 pounds of Ginger, 12 bronze cannons, 28 iron cannons and 52 pounds of silver. The total amount that it was worth was 1,2 million guilders.
Soon after the fleet had left the Spaniards were aware of this. When this fleet had departed for the Dutch Republic the Spanish authorities in the Caribbean believed that all Dutch privateers had left the area. This is also the reason why the Silver fleet, that sailed regularly from the Caribbean to Spain, was not reinforced. This made the fleet more vulnerable to the privateer fleet of Piet Heyn that was also sailing in the area and which was particularly interested in capturing this fleet.