Please critique my dream.

[BOBSWAY]

Hi, newbie here.
I have a notion about moving someplace warm (Mexico, Caribbean) when I retire in a couple of years, someplace with a sailing tourism industry.
When I get there I'd like to work part time as crew on a sailboat taking snowbirds sailing.
Between now and then I was planning on doing some liveaboard ASA 101 classes, etc.
If anyone has any insight into how better to lay the groundwork for such a move I'd love to hear from you. I have about 3 years to prepare and am currently a Great Lakes small boat sailor.
Many thanks in advance.

[CrispyCringle]

If you are already sailing a small boat on the great lakes thats a great start. Dont know what kind of boat you have, but if you can sleep on it, go "camping" for a weekend. Then go for a week. You will learn a lot about what kind of things you may need and dont need. We took our boat (H24) up to the North Channel for two weeks. Learned a ton about "living" on a boat. Learn how to navigate, read a map, rights of way, etc. If your not already, do all of your own maintenance. At least try. You will save a ton of $$ and wont have to wait to get in line for service calls. This forum can be a huge resource for that. If you jump to a bigger boat and want it insured, and its greater than 10 feet longer than your current boat, plan on the insurance company requiring some kind of check-out with a certified captain that they approve of. That can be a couple of $1000. There are so many subjects to learn about. Almost endless. You can learn a lot just reading forums. But dont let it overwhelm you. Just do it. But do it with knowledge, not ignorance.

EDIT: I see you have a 19 footer. Consider getting a bigger boat- like in the 25' +/- range, so you can sleep on it. A trailer sailor. Even if its just 3 years, it can be worth it.

[BOBSWAY]

Originally Posted by CrispyCringle

If you are already sailing a small boat on the great lakes thats a great start. Dont know what kind of boat you have, but if you can sleep on it, go "camping" for a weekend. Then go for a week. You will learn a lot about what kind of things you may need and dont need. We took our boat (H24) up to the North Channel for two weeks. Learned a ton about "living" on a boat. Learn how to navigate, read a map, rights of way, etc. If your not already, do all of your own maintenance. At least try. You will save a ton of $$ and wont have to wait to get in line for service calls. This forum can be a huge resource for that. If you jump to a bigger boat and want it insured, and its greater than 10 feet longer than your current boat, plan on the insurance company requiring some kind of check-out with a certified captain that they approve of. That can be a couple of $1000. There are so many subjects to learn about. Almost endless. You can learn a lot just reading forums. But dont let it overwhelm you. Just do it. But do it with knowledge, not ignorance.

EDIT: I see you have a 19 footer. Consider getting a bigger boat- like in the 25' +/- range, so you can sleep on it. A trailer sailor. Even if its just 3 years, it can be worth it.

All good ideas, and I've considered getting a larger boat even with my short time horizon, and the short sailing season here.
Ultimately I'm looking to crew on someone else's boat however, not be an owner.

[Sailer_Med]

I don't have direct experience in this, however, a close friend of mine is doing something like it. He did this, not complete CV, but his highlights....

Moved to Barcelona, and first week he had signed up for RYA coastal skipper class. Never sailed before. I meet him in a RYA 1 week practical course Coastal Skipper and Yatchmaster combined. His goal is a circumnav in 2 or 3 years. He came here because of the rich sailing culture.

He immediately started crewing on regatta boats out of BCN and taking more RYA and Spanish (PER) courses where he meet more people.

He also went after powerboat certifications where he meet more people.

His first year in he crewed on 3 deliveries: Swan from wherever to France, a charter move from BCN to Tenerife, and another I can't remember. Spent the summer crewing on a sail charter in Ibiza and thereabouts.

Over the winter he knocked out a couple of more RYA course as well as Spanish sailing courses. He is doing OceanMaster Yacht in November this year. He also obtained a commercial cert from the Spanish.

This summer he skippered in the Balearics a 45 foot charter and crewed a couple of more deliveries. This week he is doing a week long sail with a captain to get familiar with catamaran operations even though Cats aren't really his interest.

Late summer this year he obtained a skipper gig on 20m motor yacht for a French owner. He shuttles the yacht meeting the owner and guests in various places around the western med on a part time basis.

As you can imagine he has very good networking skills and is driven to gain experience as quickly as possible on different boats and in different conditions. Here the certificates are very important as are language skills, he has French, Spanish, English and German.

Watching him move through the process has been super interesting for me. I don't know what the Carib is like but this is one example I know directly from here.

[jt11791]

Need some rain on your parade? Okay, I'm here for you.
Funding even the smallest part of your retirement by sailing is a pipe dream shared by thousands of others, all of whom are more qualified than you and/or willing to work for less than you. The Caribbean is packed with young hustlers who are well networked and able to scoop up any decent jobs, the rest are taken by vagabonds willing to work for beer. With the proper credentials (captains ticket and years of experience), you may get a few delivery gigs, but they will be "bring my boat to the Caribbean" or "bring my boat from the Caribbean" jobs at the start/end of the season. You are unlikely to get any paid crew jobs, and if you do, they won't be sailing clueless urbanites around, they'll be "hurry up with my martini and then scrub the deck" jobs. Not being young and beautiful, you will be the last to be hired, and only by the boats no sensible person wants to crew on. Boats staying in the eastern Caribbean don't need crew. It's Disneyland sailing and with modern amenities, people solo 50+ foot boats all the time, they don't need crew. Even for longer passages, diesel is usually cheaper than crew.

Sorry for the dose of reality, good luck!

[carlosproa]

So if you sail in the Great Lakes where being careless could cost your life, you are in for a pleasant surprise as you transition into somewhere in the Caribbean or Atlantic side of Mexico.

You mention retirement is in 3 years, so I imagine you are not a spring chicken, and probably not viewed as crew material. Most sailor instructions in the resorts are young, well underpaid, and have working visas or are local.

My humble advice is to get the smallest boat you feel comfortable with, and not count in being hired unless you have a special skill not available locally.

Many many years ago, I did a reverse retirement as a traveling salesman for medical devices in the Caribbean. I basically moved my boat from island to island but reality was that it was very 45 days and only being able to sail one week a month at best and always trying to make datelines with the permits. Not sure if it was worth it.

You may have better luck looking to be an English tutor or instructor than compete in the sailing jndustry

[Shrew]

Working inside of a US territory (Puerto Rico, St Thomas, St Croix, St John) will make things significantly easier.

Working outside of the US will be a challenge in many countries.

It would be easier to get a job bartending and sailing in your free time.

[BOBSWAY]

Thank you all for the excellent replies.
They are all on point, and exactly the type of info I was after.
This is my first post, and your replies are indicative of an awesome community here!!!