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Aye sailing be tough.. but like Jason and Toanuju22 said before me, A strong crew makes all the difference. Perhaps there are also friends that own wars that could help you? It never hurts to ask.. but keep in mind not to ask more then once. Many a pirate be busy and one must always respect that. But if your lucky you'll catch someone looking for a good sail who might just need to work on cannons (which would earn you even more rep)! If ye ever catch Maria in game I'd be more than happy to lend ye my war galleon and come along for the ride! (Juliana doesn't have herself a war yet but she be close!)
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