Don't Spend All of Your Time at Your Resort
Caribbean culture is rich and diverse, but you won’t necessarily find it at your hotel pool or buffet line. Get out of your perceived comfort zone, go into town, meet some people, have a drink, eat some street food, explore!
One or two nice outfits for evening should be more than sufficient for more Caribbean vacations. The rest should consist mostly of light shirts, shorts, and bathing suits. Especially with checked-bag fees, you’ll want to err on the side of packing light. Plus, you’ll need to save some room for souvenirs, right?
Don't Forget the Sunscreen
Skin cancer is one Caribbean souvenir you don’t want. You can easily get a sunburn in less than half an hour down here, so never leave you skin unprotected – that means you, people who "only tan" and "never burn"!
Don't Wear Camouflage Clothing
Don't Expect Beach Weather Year-Round in Bermuda and the Bahamas
Despite their Caribbean vibe, these Atlantic (yes, Atlantic) islands are subject to cooler temperatures in the summer, not to mention that the water can get chilly in the off-season. (Ditto for the Florida Keys.) Of course, the weather in Bermuda and the Bahamas is likely to be milder and more pleasant than up north in January or February, but you should at least have a “plan B” as an alternative to the beach if you visit these destinations in the winter, whether that’s playing golf or tennis, getting pampered at a spa, shopping, going on hikes or tours, or visiting local museums or historic sites.
Don't Make a Beeline for the Most Familiar Foods on the Hotel Buffet or Menu
From ackee and salt cod for breakfast to mofongo for lunch and conch ceviche at dinnertime (not to mention a bountiful selection of fresh, local tropical fruit), the Caribbean has a rich culinary heritage to explore. You can get plenty of scrambled eggs and bacon at home -- be adventurous!
Don't Wear Your Bathing Suit into Town, or Worse, to Church
Believe it or not, the Caribbean can a pretty conservative place, which you’ll see on Sunday mornings when local residents dress to the max to attend church services. It varies from island to island, but generally speaking it is frowned upon to wear revealing beach gear when you aren’t on the beach. At least throw on a cover-up or a t-shirt, and if you do plan to attend church, long pants (or skirts) plus a button-down shirt or modest top are most appropriate. Also, it should go without saying, but ... ditto for topless or bottomless!
Don't Expect Everyone to Party with You
Again, don’t mistake the party atmosphere at your resort or at the bar as the norm everywhere. Caribbean residents don’t all have a perpetual rum buzz, and not everyone is getting high and listening to reggae. Most are hard-working and -- while warm and fun-loving by nature -- save their partying for weekends or after work ... just like you do back home.
Don't Assume Everyone in the Caribbean Speaks English
Don't Be Shy about Haggling with Beach Merchants and in Local Markets
The initial price on those souvenir t-shirts and crafts at the Straw Market in Nassau and elsewhere is always set higher than vendors expect to receive, and frankly the tourist who pays full price is looked at as a bit of a rube. Look to pay at least 20 percent less than the asking price.
Don't Buy Marijuana
First of all, marijuana is illegal most places in the Caribbean. Second, you could be in big trouble is you forget your “leftovers” in your bags or try to bring some herb back home with you. And third: most crime in the Caribbean involves locals and drugs, not tourists. So why would you potentially involve yourself in danger while you are on vacation?
Don't Leave Valuables in Your Rental Car, Room, or Unattended on the Beach
Don’t make a thief’s job so easy but leaving money, jewelry, or other property in plain sight. Carry them with you, lock them in the room safe, or put them in the trunk.
Don't Assume That You Drive on the Right Side of the Road
Don't Spend Your Last Dollar Before You Get to the Airport
In some countries, you’ll need to pay a departure tax before you can board your flight home -- up to $40 in cash in some places. It sucks to have to beg your travel companions for cash or fork over a fee at the airport ATM, so plan ahead.
Don't Forget to Relax!
The Caribbean is no place for an over-planned vacation. Be sure to build plenty of beach or pool time into whatever itinerary you put together!