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Making a living while cruising...

5547 Views 38 Replies 18 Participants Last post by  travlin-easy
There seems to be a lot of wannabee cruisers on this and other forums, most of which will never become full-time cruisers. The vast majority of those that I have met over the past decade that are full-time cruisers usually had unique and very marketable skills, or had bankrolled lots of money during their working lives and spending the interest while cruising. Living on Social Security is darned near impossible, but I have come across several elderly couples that live aboard quite comfortably using this as their sole source of income. These individuals are usually tied to a dock, or mooring ball, have great, year round dockage rates and rarely spend time at nite clubs or expensive restaurants.

I know one guy in Boot Key Harbor who is a retired engineer. Shortly after he retired, his company called and asked him to return to work. When he turned them down, they said how about just being a consultant, to which he agreed. He works from his boat using a laptop, fax machine and sat phone. He only works two days a week, and often makes more at consulting than he did when he worked full time, plus he no longer has to commute to Boston.

At one time, I was a full-time, freelance writer, but the print media dried up, fishing in the Mid-Atlantic region went to hell, so I decided to go back to playing music and singing for a living, which was one of the smarter things I've done in my life. It's also a lot more fun than writing and meeting deadlines, and I can usually find work everyplace I've sailed in the US. Unfortunately, the pay scale in the warmer southern climates is lousy, but for the most part, the tips are pretty good, which kinda offsets the lousy pay rate.

So, for all you younger wannabees, now is the time to begin making plans for when you raise the sails and point the bow of the boat south for the winter months. Don't wait till you're too old and infirm to man the helm. My only regret is that I didn't do this 30 years ago. ;)


Gary :cool:
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I've read several books on cruising -- memoir types. A few make extra money by: a) writing, b) consulting; c) the occasional barter.

I often wonder about c. It seems like people are getting their motors fixed by other cruisers for free.. a current book there was a guy who had a tool and die set up in his boat... I wondered if that guy would charge.

I don't have a travel profession... but it seems like if you promoted yourself you could do several professions --- like chiropractor or diesel mechanic

but if you are a musician... couple question.. can you always make it to you gigs? are their perks, like can you contract a gig where you also get free docking?
I know I'm gonna kick myself in the end, but I'll probably never be able to afford to retire in the lifestyle that would make me happy.

I'm too busy traveling and drinking good scotch NOW. I take long vacations and live a pretty good life.

I can deal roulette, craps, cards, cook, and bartend. That will keep me in beer money and sailing till I'm too old to walk, but probably never cruising full time.
ahhhh good scotch, I had a blended and water the other day and couldn't believe I ever drank the stuff...

Hopefully you are fit enough to kick yourself. I am in that perspective now... probably not as much sailing as you...but living the good life and education... books and toys.. to the point to pay off my house and student loan I have to work at least until I am 67, most of the men in my family die at that age (albeit they were smokers and I am not).

I toast you tonight with box wine: "May death get to you before poverty, but not a second sooner!"
In many instances, you can get free dockage at locations where you perform. I had a deal worked out with one location in Marathon, but the venue changed hands with new management and is no longer open to the public. Consequently, that particular deal disappeared.

Unfortunately, many music venues book their performers 3 months in advance, therefore you'll have to do some legwork prior to your arrival to get booked. This is not always the case, but during snowbird season, musical entertainers seem to come out of the woodwork. Most are not very good and not professional, but a handful of them are quite talented.

One thing I almost forgot, good musicians are a dime a dozen nationwide. In this instance you must be an entertainer and singer as well or you will not find work. Yep, you must be a one man/woman band, have the ability to read an audience, and able to perform a wide variety of songs ranging from country to rock. You must be able to perform the songs that were popular when your audience members were 15 to 40 years of age, and do them as close to the original song as possible. DJs and Karaoke entertainers will not find a lot of jobs in the islands of the US and other resort areas - live entertainers are in high demand, though.

The average rate of pay ranges $100 to $150 for a 3-hour performance. Some will also provide you with a free dinner and beverages. If you are in the very talented category, you can work as much as you desire. I'm only working two days a week in Marathon, but that's really all I wish to work. I would rather have fun doing nothing more than fishing, riding my bicycle, and finding other ways of pissing away my children's inheritance. ;)

If you love neat day sails, snorkeling, recreational fishing, all in beautifully clear water, this is the best part of the US to cruise. Unfortunately, when tourist season ends sometime around the end of April, most of the jobs down here pretty much cease to exist. Some venues actually close down for the summer and do not reopen till mid November.

There are several web sites that list all the restaurants and nite spots where musical entertainment is available. Put together a contact list, call them, ask for the manager, and send them a quality advertising package, one that includes a cover letter, CD, song list, photo, business card and recommendations if you have them. If you have a web site that portrays your performances, including You Tube videos, by all means include this information as well. All of these things will help you pick up jobs along your cruising route. The only drawback is that you will have to sail on a schedule, which can be quite a challenge when the weather fails to cooperate.

Good luck,

Gary :cool:
I used to book bands for an outdoor concert series... one of the things that was high on my list is what the musicians brought to the table. As an example there was a guy who with his son and another guy played folk/blue grass (His son was an olympic athlete too). I didn't think they were that good, though it wasn't the kind of music I liked.. anyhow I always booked them because when they showed up, the son would have 20-30 friends and family members... just those folks filled the park and made it worth it

Do you play accordion? You could become the pied piper of the cruise docks.. walk through the marina playing and say follow me to fun...:eek:
Be glad to assist you, Mike. Hope to see you later this summer as you slowly make your way south. Let me know when you are in the area and I'll make the Margarettes.

Gary :cool:
Sounds good Gary, but it won't be this summer. Maybe 2016. We've decided to linger in Lake Ontario this year b/c we have waaay too much to do getting out of our house (complicated story). Then we're planning to linger in Newfoundland for a year or so. But I'll get there ... eventually.
Maybe together you could organize little Music Festivals.... I'm doing something like that on land... I have written murder mysteries and in one town when we perform we sell out, so I am getting the town to put on a murder mystery weekend... everyone is buying into it... so far.. :confused:
Understand, but my point isn't so much mini concerts... or even concert....

I was more thinking some kind of music event.

First let me say... it wasn't a design for you or anyone, just thinking out loud

I was thinking more an event of music, not in one bar, but possibly one island.

I don't even have a clue what would sell, but say: "Show Tunes in Sanibel" and you try a weekend where where very you go --- there is a guy or band playing show tunes.. Or Rat Pack in Monserratt (Lots of Sinatra... so on)

I'm not a cruiser, so I don't know how it could happen

Now forget those ideas, my point is to come up with something new, different that would appeal to people, that might get them to drop anchor... The hardest thing is trying to get people to buy into it... and if there is an island with lots of marketing dollars and a need to attract people.. In my case, I try to present even one murder mystery in some towns and I get: "Good idea, but not for us" so we move down the road and make it happen
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