International Harbors

Timeshares

We're fans of timeshares, although increasingly less so.

Downsides include:

You can't always get reservations in cities that you would like
Sometimes timeshare trades are inconveniently located
Sometimes you have too book so far in advance that is just isn't possible, i.e. we were told that we have to book a year out for Greece or Italy and because we never plan that far ahead, we opted to trade our timeshare for a cruise along Mediterranean coastlines
A "discount" that isn't a discount. Our Mediterranean cruise was purportedly $1500 off of rack rate because of the timeshare affiliation. That turned out to be untrue and we paid rack or more.
We stayed in a timeshare in Phuket, Thailand that was miles away from anything, the resort did not provide transportation to/from the center of town, and I don't like driving on vacation, so we moved to a Holiday Inn on the beach.

Upsides include:

You won't ever have to sleep in a broom closet, which I did once in London when nothing else was available. (As broom closets go, it was nice—it actually had a huge window overlooking a square and as it was snowing and I was cold, I remained in bed reading Tolkien's "The Hobbit" until I acclimated)
We recently returned from a week in a one bedroom condo in Cabo San Lucas which cost us nothing other than the food we purchased (photos left).
After the initial timeshare payments, travel is actually free for the next one-hundred years, with the exception of airfare, food and entertainment, and annual maintenance fees which are around $600/year depending on the resort.
Rack rates on the deluxe accommodations provided by a timeshare of the caliber of where we stay would easily exceed $1500 per week.

Cautionary Notes:

Be careful of timeshare sales people. It's worth a google search on any you are consdering. We were thinking of a new resort in Mexico and were stunned to read online nightmarish reports of untruths told by that timeshare's staff.
Never never pay their first asking price. Timeshare sales prices are amazingly negotiable.
Most timeshare sales people will tell you it's easy to sell your timeshare outright or sell your weeks to others if you don't need them in any given year, both have proved to be untrue.
If you don't think you will be able to use a given week, consider giving it as a gift to family, friends or clients.