There are always services available, but I would plan ahead. Look on the internet and you will find various guide services that also do transfers. Arrange it in advance and you will probably have better prices and control.

I've only done a cruise line transfer once, on my first cruise. We probably could have done better price-wise by arranging a car service (not knowing then what I know now).

The bigger issue for me was the waiting - we were loaded onto a big tour bus that already had a bunch of people on board, and we sat there and waited some more (presumably for other passengers whose flights were arriving within a certain time frame). I think we waited for almost an hour before we left the airport for the port.

Now I always arrange for my own transportation to the port (whether by car service, taxi, etc.) - it's more a convenience thing for me but I can usually find something cheaper than the cruise line transfer.

That seems like a LOT of money to me. You can get a prepaid taxi for less than $40. I have never cruised into Rio, so I may be missing something, but this seems a particularly egregious cost.

It's farther from Valparaiso to Santiago Airport, and I think you may want to arrange that in advance. It will likely cost more than $100, but I don't think it will cost $200. But check some companies to see what prices are. If you can't get a clear answer here, this is the kind of question that Cruise Critic answers well; you'll no doubt find plenty of people who have done this and will tell you exactly what they paid.

Cruise ship transfers typically charge more than what you can do on your own. However, factors to consider: it's reliable, it is convenient, and it is there at the appointed time.

Many times, I have waited at dock for a cab up to half hour or more. Sometimes, I get lucky and the cab is only a few minutes wait.

With that said, I have never used cruise line transfers myself but I had booked my kids on cruise line transfers as it is easier. If you have time to spare, by all means, save a few bucks.

Thanks so much for your thoughtful suggestions!