Caribbean boat life - /out/ (#2821511) [Archived: 937 hours ago]

Anonymous
5/28/2025, 6:19:47 AM No.2821511
a24-lighthouse
a24-lighthouse
md5: 142f38c6c44bac9547ccfa588ae8679a🔍
What's up my bros - was wondering if people with similar experiences or insight could chime in on some of the mad schemes I'm going to try to pull off

I grew up in and live in the Canadian Maritimes. 30 years old. I have a good buddy who makes great money as a pilot who is in the process of buying a good comfortable long range blue water cruiser and the dream is to live aboard and sail south for the fall, winter, and early spring. We have both had enough of Canadian winters and his work will fly him back and forth. I have a pretty crazy good bartending, hospitality, service management resume with a couple of years experience sailing tall ships. What is the feasibility of finding work in the Caribbean or even the Florida Keys? I've been doing a lot of research on how difficult it can be to find legit work in the islands but a lot of Caribbean bros I'm friends with up here seem to think it won't be that hard for a fit young white dude to find something. Any recommendations for places to go - businesses to contact - things to start working on, etc. I've started reaching out to major players like club med and other resorts as that seems like the easiest way to get legit work
Anonymous
5/28/2025, 6:45:44 AM No.2821513
If you lived with your buddy and it got lonely on the long days (and nights) at sea would you blow each other?
Replies: >>2821514
Anonymous
5/28/2025, 6:56:33 AM No.2821514
>>2821513
No we'd have starlink but would probably share what we were busting to on long nights under the stars
Replies: >>2821691
Anonymous
5/29/2025, 3:17:27 AM No.2821691
>>2821514
what about giving each other a helping hand while you jack it to straight porn and your eyes are definitely on the straight porn the whole time and not each others' throbbing cocks?
Anonymous
5/29/2025, 10:35:23 AM No.2821753
Islandbro here... Finding work should be the least of your troubles. I'm not sure how well paying or available the jobs are in the large all inclusive resorts but the ones I know of have half a dozen or more restaurants. A gig like that would shield you from a lot of the pains that come with living in the islands but freedom and other things would suffer. Finding work with private entities who run their own enterprise should be very easy, someone like you would immediately be the most qualified person to possibly ever grace their eyes, at least on a smaller island like mine. I could offer you a job myself but a fair wage down here is a slave wage where you're from and typically it's a day rate not hourly and you wouldn't be shielded from any of the 3rd world bullshit that goes on here.Long hours, poor facilities, poor quality of workers, poorer quality of locals, natural disasters, with a yacht or boat you'd need to worry about break-ins. With all that said there is room in many of these islands for someone like yourself to build something great but not on a part time type of deal. If you were operating your own establishment you could accumulate the kind of money you would be satisfied with but not without work and struggle. Most foreigners who try usually end up leaving with less money than when they came and a sour taste in their mouth but these types are naive and weren't prepared to deal with the lazy, dishonest and self-interested people they encountered. This applies to women especially. 1/2
Replies: >>2821857
Anonymous
5/29/2025, 10:36:25 AM No.2821754
. Sorry if this is black pilling but it's my experience having grown up here and while it could be different on other islands I wouldn't expect it to be. Islands with more established tourism industries and likely better opportunities: Grenada, large University with lots of US students, Barbados, long established with hundreds of hotels, resorts, Antigua, St Kitts and Nevis, Barbuda). So I'm mostly speaking of the Lesser Antilles, don't know much at all about Greater Antilles, Virgin Islands, etc.
Replies: >>2821857
Anonymous
5/29/2025, 9:32:22 PM No.2821857
>>2821753
>>2821754
Appreciate the feedback hugely big dawg. I've lived adjacent to poverty and shit people often in my life. I'm probably sheltered enough to think i'm not going to be naive about things but I'm definitely leaning towards working somewhere large and reputable that makes most of their money off people wealthy enough to be sheltered from raw humanity

The places you listed are what we had identified as places to go and to focus on blanketing with work applications and inquiries. Do you have any method of communication I could ask you more questions on? Snapchat, email, w/e. I can provide mine or give you my discord. Discord name should be : spankfurt
Anonymous
6/5/2025, 2:51:51 AM No.2822952
bumpy poo's