Where to start the Adventure?

[DreaminFred]

Hi all-
I've had boats for 30+ years, I know boats, not looking for boat advice, looking for starting line advice.

I have convinced my SO to do a two month trial of a liveaboard adventure. She's an experienced intermediate sailor, but has no cruising experience. Solid, fabulous, midwestern girl but not a "dreamer."

Got divorced once because of dream incompatabilities (and other bit********), want this to be enjoyable, but realistic. She loves to sail, we've chartered together, but she has a high "security" need. I think that mostly means a pile of money, but don't want to have too many scary bits in this shakedown cruise.

My thought is to buy a 35-40' older cruiser within the next six weeks in the cruising grounds where we want to spend a couple months, cruise, bring the boat back, evaluate the experience, and if all is good, put the boat on the hard for a refit to fix whatever we haven't liked on the two-month shakedown. Then return next winter and cut the docklines. Budget is about 35k for the boat, 10k for the two months.

We live in Phoenix, and if we wanted to sail during the hiatus (between cruises) close would be nice (Sea of Cortez, S. Cal., SF).

I've not sailed the Sea of Cortez, but have read great things, great fishing, lots of places to duck in and not "crowded." Unconcerned about Mexico "safety." Understand not great wind- a negative. (opinions?)

Bahamas- buy the boat in FL, cross, spend two months (Feb-March) in quiet paradise, snorkeling, Hookah-ing, beach-combing, nice shallow protected sailing, then back to FL for the hiatus, then cruise the Caribbean, through the canal, up Mexico, back to San Carlos for retirement sailing. (opinions?)

Caribbean- Buy a boat down the path, sail back, stopping frequently. Better wind, beautiful sailing, more crowded, more "expensive." Leave the boat in FL for the hiatus. (opinions?)

Other options?

Thanks in advance for your wisdom, folk.

DreaminFred

[Cheechako]

I would go the Florida/Bahamas route. I've sailed Mexico too.
-Mexico is great, but it's a 5day-one week offshore trip immediately when you leave San Diego. Not for beginners or someone you want to impress with the cruising life
-It's a 3 week bone jarring bash getting back.
- I love the Sea of Cortez, but anchorages can be 40 miles apart at times too.
-Florida weather will make anyone feel good! (except summer!)
-The Bahamas are just an overnighter. Amazing white sand beaches and sailing in clear protected waters.
-More history and varied cultural experiences in the Caribe to start, if she likes that kind of thing.
Take baby steps... do one or the other, then decide later if you want to do more or not. You dont have to decide now!