I came close to doing something similar almost 20 years ago but in a trawler
vs sail. My model was to be the trawler
version of John and Amanda Neal on Mahina Tiare (www.mahina.com
). Had my other half been willing, would have done it. Her concern was the lack of privacy and the amount of work
from being "on" 24x7. I have to admit, she was correct in her assessment. About that time we did a crewed sail charter with two other couples in the BVI
and the couple who ran the boat
did not exactly look like they were having fun trying to create a mini Below Decks experience. Sailing all day and making sure everyone is fed and is having a good time is a lot of work
. Heck, provisioning
a boat for six in the tropics is tough duty once let alone multiple times per month. You cannot have a bad day or take a day off.
I can add that insurance
was very expensive. Thinking back to the crewed charter, they had some sort of dual insurance
and AVI and was limited to a certain number of days in US waters. Also, I think there is quite a bit of competition for crewed charters in the Caribbean
. There's also a lot of competition for YouTube and Patreon funded sites - there doesn't seem to be a lot of rhyme or reason why some breakout while others languish. The breakouts usually have attractive, young females and above average video editing skills, though that doesn't seem to guarantee success. Heck, there's one sailing channel that unabashedly hawks some sort of adult content option with a $99/month subscription.
My other concern was how to deal with mechanical failures. I used to drive a 74 passenger dinner cruise
boat in SF Bay
. Keeping it running wasn't too bad but was really stressful sometimes when something broke at the wrong time.
I can tell you that some people are simply not reasonable - we own a very nice condo in Mexico
that we also rent VRBO. We are very clear this is our planned retirement
home vs some sort of property management business, and very clear they are coming to a place where the infrastructure is less reliable. We had one person become positively irate and want a full refund because one of three AC units in the condo failed and we didn't have another condo to move them to while it was fixed. Another complained that the driver they hired (yes, they hired) from the airport
was 30-mins late picking them up and it spoiled their trip. Another complained about loss of power even though it was caused by the power grid for the entire town was out for an afternoon. My point being that you can move heaven and earth and be crystal clear you are providing a liveaboard
sailing experience but will have people with different expectations. In short, living at the mercy of avoiding a bad review sucks.
If I were you, I'd book a leg on Mahina Tiare and see how they are holding up. They've been doing sail charters for 25 years and seem to have a full boat. They must be doing something right. I'm guessing by the end of the passage
, you and your wife would know whether this was for you, and what it takes to be successful. Plus you'd have a great time. I do not know the Neal's but have attended a couple of their presentations many years ago. They seem like very nice people. They certainly get good reviews