I got the time, now where to go?

I think your goal should be to complete a course progression up to ASA 104 / US Sailing Bareboat Cruising AND rent / crew on your own 3 times per week during your time off. Classes are important. But there’s also no substitute to hours on the water, starting in a small boat, making mistakes and learning from them. You need classes AND a lot of charter time. Finally, ending with a stint as crew on a costal or offshore passage would be great. Make sure you actually enjoy ocean sailing. That’s a lot to make happen in 3 months, but if you’re taking time off work and just doing this, I think you should aim big. I’d start looking at where you can take the classes and charter boats with other people. There are “zero to hero” classes that claim to teach to ASA 104 in a single week (mostly in exotic locations). I’m skeptical of these, however. It just take most people a lot more time and practice to internalize the skills you need (learning the vocabulary, the feel for docking large boat in windy conditions, the feel when a boat is overpowered). What if there are no strong winds during your 1-week course? In any case, also look if the credential will allow you to charter boats where you’re taking the course, what that costs, and how hard it will be to find friends to sail with and split costs. I’m familiar with the San Francisco Bay Area. There are 3 schools here that would work for you (but prices are high). Club Nautique focuses in off-shore sailing and cruising, and has new / nice boats and an active email list where you’d be able to find people to sail with most days. Tradewinds Sailing School is cheaper and also has a nice community, but is mostly focused on day sailing (less ocean sailing / cruising) and has older / smaller / less well maintained boats. Modern Sailing is racing focused. In all three cases, you could come to SF, pay ~$4k in tuition plus maybe another ~$3k in charter fees (don’t forget living expenses) and basically do what you’re looking to do. SF is probably one of the most expensive places to do this. However, you would get trained in the strong currents and winds here (SF gets 25-knot sea breezes in the summer) As for offshore crewing, that’ll be harder without experience. There are paid (expensive) options. Your best bet might be just to continually ask everyone as you’re going through the classes. Good luck!