Pirates with speedboats full of cash is a romantic but pointless idea. This is a country that already has at least some internet (if only satellite based) and international wire transfer infrastructure in place that was working fine for transfers up until two weeks ago.
Use of the international banking network requires support of the international community which is something Somolia is lacking. Given current legal situation and the one sidedness of cashflow to Somalia you need some mechanism to bring currency into the country.
Speedboats was kinda tongue in cheek but it would involve some transfer of physical currency into the country against the wishes if not intent of international community. Using the banking network is a non-starter.
i.e. (fees excluded and exchange rates kept constant to keep it simple)
1) Person in US deposits $100 USD to Mt. Gox (or some other international exchange). Mt. Gox now has $100 USD.
2) Person buys Bitcoins on exchange (exchange still has the $100 USD).
3) Person sends Bitcoins to resident of Somolia.
4) Resident of Somolia uses local exchange (bitcoin-changer) to receive $100 USD cash.
At this point the local money changer is UP $100 USD equiv in Bitcoins but DOWN $100 USD in cash.
To keep it simple say the money changer also uses Mt. Gox. He sells the Bitcoins he just got and gains $100 USD.
The Somolia resident got money but it was only a local transfer from money changer to resident. The same $100 USD is still outside the country. Now the money changer has more resources to move money into the country BUT it requires physically moving currency into the country.
Given this is something the international community is trying to prevent it will require some "smuggling". Maybe not James bondish w/ speedboats filled with millions in shrink wrapped pallets but you need to move the fiat.
Bitcoin is useful for handling the value transfer (US resident -> Mt. Gox -> Somolia Resident -> Money Changer) but it doesn't eliminate the need to move the currency.
Given the one sided nature of currency flows that money changer needs to be able to sell those Bitcoins. If he has an exchange account he could sell the Bitcoins for USD but the USD are now outside Somolia.
So the original issue remains.... how to bring USD into Somolia in bulk against the wishes of international banking community. Using their international wire network is a non-starter. Some for of physical money transfer will be necessary.