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Let's assume I have a ship flagged in a country where certain activities are legal but are not in most of other countries (like, for instance, drug use or prostitution are in Netherlands). Let's assume again that I fullfill every aspect to lawfully carry on with those actions in the country's flag. Can I anchor the ship just outside some other country's territorial waters and provide a mean of transportation from that country to my ship? Would that be illegal?

This is just a theoretical question, so if that helps, answerers may assume any specific country where this ship could be anchored near.

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First: it is a misconception that international waters are "lawless;" many aspects of international maritime law are determined by international treaty.

Second: countries can obtain jurisdiction over criminal acts that took place outside of its own territory under many doctrines: for instance, if you used your boat for human trafficking or child prostitution, the U.S. would likely have jurisdiction over any case in which an American was a victim under the doctrine of passive personalty. See United States v. Roberts, 1 F.Supp. 2d 601 (E.D. La. 1998).

Third: even if the ship was in international waters, any action you took in the United States to obtain customers--advertising, picking up passengers, even storing your earnings in that country's banks--would provide a separate basis for jurisdiction.

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Where I suspect you will run in to your first problem is that in most countries soliciting for illegal activities is also illegal even if those activities are legal where you are planning on hosting them. For instance it was at one time legal in Iowa to gamble at 19. However it was illegal in Illinois unless you were 21. So if you solicit 19 and 20 year old people in Illinois to take a bus trip to Iowa to gamble that is illegal.(There was a case where that exact thing happened though it was pre-interwebs so not finding a link)

Many countries also prohibit enticement. So anchoring just outside territorial waters in order to cater to natives of that territory is likely to fall into that category. Even if you do not provide the transportation. In fact if you work with a third party for the transportation then you could run afoul of conspiracy statutes.

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