Buy a sailboat, charter a sailboat, or fractional ownership?

[Dr. Moreau]

My wife and I have big dreams, we are putting our eye on hitting the open ocean in May 2010 for a circumnavigation. We both are on a very intensive training plan, however after our first week in a US Sailing Course (Basic Keelboat) we realize that we need as much on-the-boat experience as possible.

We are not planning on buying our ocean-going sailboat until October 2009; this gives us ~9 months to get familiar with the ins and outs of our new ship before we hit the open ocean. However, we need on-the-boat experience first, which leaves use with three options.

1) Buy a "nice" used sailboat, we see plenty of boats in the $3000 - $5000 range (even a few $1000 sailboats). Most of the boats are pretty much ready to sail the SF Bay, however they all need a little bit of work. This is a advantage to us, because we need to learn the innerworkings of boats too before our big sail. These boats are 25' - 29'.

This option would also need a ~$200 a month slip rental as well as regular upkeep.

2) We belong to OCSC, a sailing club who also provides US Sailing instruction. They also allow members to bareboat charter boats. Once we complete Basic Cruising in June, we can charter sailboats up to 30 feet. The daily rate is $155 or $280 for a weekend.

Once we complete the Bareboat Chartering course, we can bareboat charter 30+ feet sailboats. The daily rate on a Catalina 36' is $370 or $665 for a weekend.

3) Join a fractional ownership 'club' like Windpath, for a initial investment of $3500 ($2500 of which is a security deposit) and $575 a month we can sail up to 7 days a month on a Catalina 34' sailboat.

So, what do I choose?

I am leaning towards buying a good used boat, keeping it maintained over the next year and hopefully sell in right before we buy the 'ocean-going' boat for a small loss at most. However the Windpath option seems appealing to me because the 'class' of boat is similar to what we need to get used to sailing for our circumnavigation.

I feel OCSC is a bit expensive for the two of us to charter, however they offer a great service where they can pair you with other students to help split the total charter cost.

Is there any options I should consider? Which option is the most appealing to you, if you were a beginning sailor?

Thanks