Caribbean is a tough place to do it.

Basically you pick a country first, then look at their work laws. Most islands in Caribbean have basically the same laws

You must possess a trade that locals can't do or don't have. They have a right to all jobs first

Most islands require an island permit for each specific job. Must be renewed annually and costs between $7000 to $9000 a year depending on island.

Most islands require you leave every couple of months due to visa requirements

Most require some type of commitment, they are not going to hire you if in 3 months you want to move on to explore another country.

A couple of ideas:

Get a job first that will send you somewhere, they also tend to pay the work pmits and give living allowance. For example, a place like Club Med, they get to move around the different places usually in 6-12 month clumps and are worldwide. Or a worldwide resort. Some do require a work history in that field before they send you off the rest of the world.

Consider a cruise ship

Maybe a teacher teaching English (which of course reqires another language)

Dive master

When you get sent because of work, keep in mind they work you. For example, CM works you long days with very few off, so while you will see a place, you will be working all the time.

In bad economies it's even harder to get jobs where you're not from, tough enough to have locals survive.

What you propose is extremely difficult (near impossible?). And definitely not in the Caribbean islands.

If it's truly your dream I would have and your boyfriend both get 2-3 jobs right now where you are and save every penny until you have enough to take a year off. That is a more do-able and realistic plan imo.

Also realize the pay scale is going to be a lot lower in poorer countries even if you can find work. You can make a lot more money in way less time in the US/Canada (assuming that's where you are now).

You might want to take a look at this website: http://www.transitionsabroad.com/

While it is not easy, I have known people who have worked teaching English as a foreign language legally in Mexico, Japan and China, and I'm sure there are many other opportunities.

Long term, you might consider a career in the State Department Foreign Service (entry by competitive exam). Or you might consider a stint in the Peace Corps.

You could apply for a job on a cruise ship but odds that the both of you will be assigned to the same ship are small. keep in mind that most positions are low level jobs (housekeepers, wait staff, etc.) but there are some higher level jobs similar to hotel management but they normally require prior experience.

Other suggestions would be to apply for land based positions in hotel management with international companies then once you are established apply for transfers to a hotel in a foreign country.

Keep in mind that regardless of the position any job in a travel related business will require you TO BE WORKING while those around you will be on vacation.

Have you thought of being a Freelance Travel Writer - you'll have to pay for your own travel but if you are a good writer you can sell your travel articles to magazines and guide books, etc. The thing is very few people can earn a full time living by writing.

Honestly, what you are contemplating is a very difficult way to earn a living.

Lastly, I know quite a few people who work for international companies and travel a great deal as part of their job. Almost all say business travel gets old pretty art and they never get time for sightseeing. The fly someplace, attend meetings, make deals, get a night's sleep in a hotel then it's back on the plane to go the next city for more meetings. The process keeps repeating itself.

OOPS! That should say "business travel gets old pretty fast".

Thank you everyone, there is some good stuff there. have a great weekend. :0)

In short, learn to sail.

It will take a couple of years but couples who offer a Yachtmaster and Catering service ie one sails, the other one cooks, can earn well into 6 figures for "looking after" other peoples boats. There are also lots of opportunities to deliver boats.

These are lifelong skills.

I'm a freelance writer as a second job, trust me you can't live off of it! Plus, most foreign countries have higher costs of living.

Sailing is a good idea, except if you're working for someone, while they're exploring you have to stay back and clean the boat, still won't see much.

You have a better chance at having a regular job and vacation places. Then when me established maybe spend longer in places?

Another thing to consider, if not married, very few couples make it in that life, the lifestyle leads to straying. One person always loves one place better than the other, it's really hard to agree when on the go all the time. Come to think of it, many married couples don't make it in that lifestyle. Just too carefree and different cultures. None of my business, but worth mentioning.

In my travels I've met many couples who move around from place to place, and just like the lifestyle, the relationship is never " grounded". I've heard nothing but complaints.

Something else to consider.

Blamona

I will never be in a position to do this but would love to have done earlier in life.

Last year, we chartered in Greece.

The lead couple working for the charter company had veiled a transfer to the BVIs. Hey didn't want to go but the money was so good as the company could not find anyone to actually do the job.

I have no idea of the real position but I have the impression that even in the depths of this recession, there is a deficiency of commercial sailing skills.

Do you speak other languages fluently in addition to English? That would be a huge help.

I have met several people who have successfully worked short term in different countries. They are either excercise professionals or aestheticians. They work (and work it is, lots of hours) at spas and resorts for three to six months at a time.

We met some Americans who befriended a man who owns a small sail boat excursion co. They were in their late 20s and took people out on snorkeling adventures/ they captained the boat and cooked our lunch. There were 3 of them and they had all worked for this man for over a year.

This was in St Thomas = (US) They said it was hard work but a dream job.