For hitching a ride to and fro you would probably not be able to plan that so much ahead of time but if you can go with the flow, as NC Sailor said, sailors are very welcoming (especially if you come bearing rum or other goodies) and although cabin space might be full, a ride would be within reason for sure, unless you are creepy and throw a serial killer vibe LOL. If you're chill, you will make friends along the way anyway at all of the stops, I would think you would be offered a ride if you told them your situation, island hopping can be expensive because you have to taxi then ferry and that can add up easily and people understand that.