Server / Bartender questions.

To really calculate the take home shift money of any waiting job you have to look at your personal section sales possibility for the shift.
Example: If you sold $1500 worth of food and drink and assuming you end up with 15% tip average overall you would start with $225 before you shared out with your backup help - bussers, food runners, Bartenders, Hostess/Host - this is commonly 20-25% of your gross tips, so that shift you might walk with about $165.
Look at the menu prices and P/P check average, section size and overall patron count. At an average of $30 p/p you would need to serve 50 people that shift, at a very high end place with a $60 p/p average only 25.
Lunch patrons of course spend less p/p so day shifts have to be much busier to get a $1500 ring up in your section.
It is fairly easy to estimate how much a server can expect to sell with a few hours of observation at any prospective job and a serious look at the menu prices.

Bartending is somewhat the same idea but harder to estimate - they do not usually have such a high tip sharing percentage however. But it is just as clearly a volume based percentage at the end of your shift. The best bar tipping patrons are off duty restaurant employees - so an establishment that has that kind of clientele base would be considerably more lucrative than a tourist based bar - despite the perceived volume of a bar full of tourists. A late night 10pm -4am bar shift can be a huge money making job but comes with a lifestyle that ages you quickly.
Most of the bills are now being paid with credit cards so the majority of your tips are recorded as taxable income - you may or may not receive that money at shift end - and the much maligned idea that servers and bartenders walk out with pockets of tax free cash each day is a basic falsehood - the $2 - $3 usual hourly wages on your weekly paycheck often does not cover your weekly tax liability and instead you owe the store a good chunk immediately each week to cover your FICA - SS and Medicare deductions - so some of that $165 example might have to go back for taxes each week.
There is a huge variation in business in the Caribbean seasonally!! It may be impossible to pay your bills in Aug Sept Oct Nov without using your savings from the winter season - If the restaurant even stays open during slow season.
There is certainly demand and turnover but the best paying jobs in the highest grossing sales positions are not usually among them - they are usually held by long time professional employees - like yourself - who find a good job, do it well and keep it for years.
It can be done - there are some great restaurant people in the industry here who view it as a career and make a good life for themselves and the families.
But on an overall view most restaurant jobs here are transient and making a viable income doing it is often the reason .

Excellent summation, ExitZero. It's a hard question to answer as the variables are huge but I know of only a few very seasoned longtime servers and bartenders who are able to pull in the kind of money that the OP is hoping for. And they carefully stash plenty away in high season to get them through low season.

You'll find it difficult to get back and forth to a job without a car.
There is no reliable late night transportation unless you wish to spend money on a taxi and even during the daytime, getting around without a car, will be challenging, especially if you plan on being on time for work or doing anything else.

If you plan to arrive in March, be aware that is practically the end of high season, both cruise ship arrivals and tourism drop off dramatically in May, making it difficult to earn what you did during high season during slow summer months.

Most restaurants will be fully staffed in March. The money you make, will also be dependent on where you work. Many restaurants do close for the month of Sept.

Probably better to arrive before season starts to gear up mid November. As OT mentioned, there are many variables.

Plus you have to find furnished housing or roommates, pay, first, sometimes last and a security deposit, set up and pay deposits for utilities if not living with roomates and all the little miscellaneous things that go with a move that are often forgotten about.

It's expensive to live here so you need money to move here, get settled in and find a job and have enough money to see you thru until earnings from a job kick in. Plus something set aside to return home, if things don't work out. Good luck on whatever you decide.

If you have management experience you will find the hours are longer but your income is more stable and less seasonally affected.

Living here without reliable transportation can be done if you find work and living arrangements in close proximity. You will not find public transportation to be convenient or practical in most instances.

You certainly will need to arrive with enough cash available to fund the start up period or you will likely find it to be a frustrating and wasted adventure.
There are jobs available all year - less so in the slowest months but still with a determined effort you can find work.

So many great points you have all made. Thank you for taking the time to answer! Perhaps i should wait until the busy time starts, save a bit more cash, and plan on bringing the car with me.
I always visit the island in October and thought that it seemed relatively busy. Like a bartender job on Magens Bay looked pretty well paying, but i assume it would be hard to get. Duffy's always seemed to do great business as well.
Thanks everyone! I'll keep researching!

Duffy's is looking right now.

http://virgin.craigslist.org/fbh/4833937455.html