Depending on the year, you should go to the Med NEVER!!!
I can't remember any way to the Med then through Gilbratar, and believe me, it brings more stress the joy. Even when you manage to enter the Med, it's gonna be hell to pay to return back.
I went on a single mission to the Med and it took me 2 h RL (many more ingame) to get inside Med. And I took the route near the coast and took every single safe was to enter, but in the end, my crew was so tired, they were bererly running the ship. PLus I never met any shipping inside the Med (or it was too far away for me to see).
Work of advice. Never go thorugh the English Channel and through Gibraltar.
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