California novice planning to (eventually) cruise the Caribbean

[WhichCoast]

Hello all.

Digest: I'm in my mid 50's; 3 years from retirement in California; Learning to sail on other people's boats now; After retirement I plan to buy a boat and cruise the Caribbean for at least a year or two then decide what's next.

I've been "dreaming of the sea" for about 40 years but life has kept it to mostly dreams. I've had a few kayaks and a small trailer sailboat at various times. Sailed a little with friends over the years. Many places in the world I would rather be land-based, but for the Caribbean I want to have a boat.

Working at home during the quarantine, sending my youngest off to college this fall, realizing I can retire in 3 years have all added up to me deciding this is the time to prepare for the next stage of life.

Due to my specific finances I won't be buying a boat until I retire. Beyond finances, since my initial goal is to sail the Caribbean it seems more prudent to to wait until retirement and buy a boat in the correct ocean!

Until then I'm sailing in the LA area with friends in their 33' boat. It's quickly becoming obvious that hanging around the docks one gets invited to join crew on different boats for weeknight races so I'll hopefully start doing that soon. Maybe next year do a seamanship/sailing class. In terms of learning to maintain a boat it turns out if you volunteer to help people clean strainers, change oil, varnish teak they will train you for free!

My "dream boat" is irrelevant today since every different boat I sail on teaches me something about what I like and what I don't. When the time comes my criteria will likely be different than it is today. I imagine something 20-30 years old around 33' or 10 meters length. The probable hard constraints are: Good for solo sailing and living; OK for 3-4 people during a passage or a week at an island; Cost plus upgrades/repairs/provisioning/taxes under $100,000- ideally more like $70k which of course means the boat itself would be under $50k.

That's enough for now...

[LittleWing77]

Welcome aboard, Which!

Your plan sounds solid. Each step building on the next. Amazing how that longing for the sea just never lets go, eh?

As for your crewing opportunities, I found for myself, the more boats I sailed on, the more I was able to isolate essentials that I wanted for my own boat.

Hope you'll be getting out for some race/ crewing nights soon!

Fair winds,
LittleWing77

[Don C L]

Welcome aboard WhichCoast! You clearly have been following a good path to your dream; we should keep this thread handy for other folks pondering a cruising retirement. You have it clearly thought out IMO. I'd say you are close to chartering a boat on your own and doing multi-day trips out to and around Catalina. (I am assuming you are sailing out of somewhere between Marina Del Rey and Dana Point?) Good luck in your adventures!

[WhichCoast]

LittleWing77- Thank you!

Don CL-
Thank you too. My friend and I are trying to figure out a week when our schedules coincide for a trip to Catalina.

I went from thinking and dreaming "some day" to realizing that it makes financial sense for me to retire in 3 to 4 years. I had been assuming I would need to wait another 5 years. So I went from kids at home assuming retirement was 9 years off to pending empty nest and retirement much sooner. I had never made a formal "bucket list". It was more "list of things I wish I could do but probably won't". Now it's serious planning and not just dreaming.

[oslokid]

Originally Posted by WhichCoast

LittleWing77- Thank you!

Don CL-
Thank you too. My friend and I are trying to figure out a week when our schedules coincide for a trip to Catalina.

I went from thinking and dreaming "some day" to realizing that it makes financial sense for me to retire in 3 to 4 years. I had been assuming I would need to wait another 5 years. So I went from kids at home assuming retirement was 9 years off to pending empty nest and retirement much sooner. I had never made a formal "bucket list". It was more "list of things I wish I could do but probably won't". Now it's serious planning and not just dreaming.

Hi WhichCoast,
I think you are on the right track. Sailing on other people's boats is definitely a good idea. I did so too. I ended up choosing a boat that sometimes gets not so positive comments. Oh well. I knew what I was doing and have not regretted it a bit. Its all a compromise. My only advice is whatever you choose, maintain it like you are going to sell it tomorrow.

I retired a few years ago. In hindsight I worked a few more years than I probably should have. My calculations were too conservative. I've seen it happen to a few of my acquaintances. Some financial consultant telling us we needed x dollars in our accounts. I am just a working stiff. Anyway, don't know your situation but time slips by so fast. Don't wait too long. Life is short.

[GordMay]

Greetings and welcome aboard the CF, WhichCoast.

[WhichCoast]

Update-

No major change in plans. As I do a little more sailing, watch more vlogs of people sailing and fixing their boats, and read forums I think I'm getting a more realistic picture of sailboat cruising.

I was able spend the weekend sailing to/fro Catalina Island on a 33 foot boat and had a great time. Broad reach under light winds was great. I like hiking so the idea of taking 5 hours to go 25 miles was no big deal. Slept like a baby at the mooring. Coming home beating against small but steep chop was exhausting but fun.

I'm definitely learning that it's the bits near land that are tricky. Wind shifts, currents, random unlit buoys, kelp, and traffic. I've also learned that backing a boat from a slip is a dark art.

[Don C L]

Great! Where did you go? Avalon?

[WhichCoast]

One night at Avalon and one at the Isthmus.