One big problem with a cruise ship timeshare is the ongoing costs. If we used the migration route and kite power, the ongoing costs could be reduced. It would still use engines to get in/out of port, just when out at sea use a big kite. Much of the travel market is retired people who have plenty of time for long trips.
EasyCruise charges for food and does not use so many staff, so they can operate at $50/day per person double-occupancy. With kite power we should be able to do better than this for regular customers (less again for timeshare). Another thing that EasyCruise does is let people get on/off at any port. Since they passed by Anguilla my wife and I chose this line for a trip (saves air fare). We had a good time (stayed in larger room than the minimal rate). Nice part is you can eat on the islands without feeling like you are wasting money. Also you don't pig out as much since it is not "free food".
http://ezinearticles.com/?You-Can-Be-a-Cruise-Ship-Owner-Even-If-You-Are...
Article on cruise ship timeshare. Has some prices on used cruise ships. Even mentions using kites. Says it would be easy for ships propellers and generators to make electricity as the kite pulled the ship through the water, even slowly. Even if the ship is all timeshare the regular customer market is important because many times timeshare people don't use their slots. Can also rent out restaurant space, store spaces, gym, etc to help a bit in the funding of the operation of the ship. I would even charge for tender rides to/from the pier if the ship was at anchor.
http://wiki.seasteading.org/index.php/User:Vincecate/Migration
There really are a lot of islands that could be visited on this route. Probably could spend nearly half the time in port with a kite powered cruise ship (since it will move much faster than 1 MPH it can spend a lot of time stopped). Also, if there were a storm this could use the engines to get out of the way (seems like low chance on this route).
http://wiki.seasteading.org/index.php/User:Vincecate/KiteAndSeaAnchor
Kite powered cruise ship could also count on a lot of free publicity. Kite power could be a good selling point for tourists who want to be "green".
Where do I sign up?
This looks like a no-brainer - what's the catch?
Some of the problems
Here are some of the problems:
If we spend half our time in port, then we are not generating electricity by having the kite pull the propellers through the water at least half the time.
If we want to spend half the time in port, we are probably staying at each stop like 5 days. Most cruise ships would only stop for 1 day at each location. Personally I think most islands are interesting enough to spend 5 days on, so I think the market for a more relaxed pace could be a big enough niche to be interesting. But any untested market has great uncertainty.
Most people are ok in a small cruise ship room for 6 days. But to live on a ship for a long time they would need more space. So if it is $100,000 for a small room and a family wants to have 5 rooms or more, then we are looking at $500,000+ and this is still small compared to the house the family had before.
Islands can charge boats just to anchor in their harbor. And if you are there 5 days they might even want to charge you hotel tax.
Getting lots of people to each put up lots of money in a new venture that has no operational history yet is hard. Most people with money are just not that foolish.