Some Rules of the Road

Rule Number 1

Pick an aircarrier of choice, get a credit card and start buying your groceries, gas and anything else you can find on that card. Log all of your business travel to that one carrier frequent flyer program. There is nothing like low cost travel. You spend more than you think on many things that should be on your card. Miles add up fast. Find and enroll in every associated program you can that helps you accumulate miles to your preferred airline. After some research, I recommend American Airlines. They have consistently more destinations to more of the Caribbean than any other airline, and always seem to have award miles if you book just enough in advance. In addition, American seems to be the only one that offers a true off-peak miles discount.

Update October 2009 - After some changes in the marketplace, from our location of Memphis, Delta Airlines is now our preferred Airline. It also appears that they have many destinations out of Atlanta. Pick carefully based on your preferences.

Rule Number 2

Nothing but Carry on. You are going to the Caribbean. You need a few pairs of shorts and a couple of swimsuits trust me. A good pair of sneakers, some sandals for going out at night and a pair of water shoes for walking the shores. You should have one or two good pair of nicer short pants and a button short sleeve shirt, but unless you have the clear intention of finding the only restaurant on the island (St Barths) that requires coat and tie, then take my advise - Carry on only!

Rule Number 3

Where you stay does not matter, where you go does. We have found over the years that staying in an upscale setting is interesting, but for the 8 hours we sleep there and the couple of hours we shower and drink coffee there or have our light lunch, a ritzy place is taking money out of your pocket that is better spent on adventure. Unless money is no object, we always will recommend spartan but charming and otherwise somehow romantic settings.

Rule Number 4

Despite rule number 3, you must have a kitchenette. You will break the bank on some islands if you plan on eating all of your meals out. Pick your spots and pick your moments. We prefer to eat a great dinner at a great restaurant not just for the food, but because we want to enjoy the romantic evening. Sometimes we want a great lunch, but either way you will find that shopping at a grocery store for breakfast items and some light sandwich meals will give you the flexibility to pick when and where you entertain yourself with some great culinary experience.

Rule Number 5

Always rent a car(except Jamaica). You should have a car plain and simple and we will tell you how to do that best on each island. They all vary as to why and when you need a car, but trust me you do need one. On Jamaica, I do not recommend that first time visitors under any circumstances rent a car. Until you have been stopped by Jamaican Police brandishing machine guns in Duncans you just do not have the experience for it. Call Billy!

Rule Number 6

Don't daytrip islands.

Rule Number 7

Befriend locals and ask serious questions about culture and the economy. Afterall, you are going to live there one day! Find out the prices of real estate and learn who owns the land.

Rule Number 8

I know some of you might disagree, but no matter what you do and no matter what island you are staying on, never ever ever go all-inclusive. You might as well just go to Florida!

Rule Number 9

Make your decisions about an island quickly. If you love it and you know it go back. If you don't love it and you know it don't go back. There is so much to see and you will find your place and you will fall in love with some island and that is what you are looking for.

Rule Number 10

If you have a choice, that is you are paying for your tickets, stage yourself in Miami to fly into St Martin for the rest of the Caribbean. San Juan is just not that great. So if you can connect in St Martin do so.....but if it is your destination or Anguilla or St Barths, then by all means Miami to St Martin is best. Remember the Turks and Caicos is Real Fast from Miami.