Ten practical tips for planning a Caribbean vacation

When you say you’re planning a Caribbean vacation, does that mean you’re dreaming about warm sun and sand or that you’re diligently gathering information and researching options? If you just book the first cheap package you see, you may be disappointed when your dream vacation isn’t as dreamy as you’d anticipated.

Luckily, it’s not too hard to plan the perfect island getaway. If you take a little time to follow our 10 travel-planning tips and do some pre-trip thinking and research, your Caribbean vacation can quickly go from mediocre to amazing.

1. Choose your travel dates wisely

One of the most important decisions you’ll make when planning your Caribbean vacation is when to go. How far in advance you need to plan, how much you’ll pay for airfare and accommodations, how crowded the island is, and what kind of weather you’ll experience are all dependent on the dates you choose for your vacation.

The Caribbean high season runs from mid-December to mid-April. During this time, the weather is superb but prices are at their highest and the islands are full of vacationers. (Like almost everything, however, there are some exceptions to this rule.) During the off season, you’ll find hotel discounts of 20 to 60 percent and you can plan a relatively last-minute vacation, but you may encounter less-than-perfect weather or find construction at your resort. The hurricane season runs between June and November and can affect any island except for Aruba, Bonaire, and Curacao. During this time, prices are at their absolute lowest, but you would be wise to invest in travel insurance just in case a storm comes your way.

The key is determining your priorities. If you must stick to a budget, you can still have a wonderful vacation in the off season as long as you don’t get too upset by the occasional rain shower. If you can only travel during winter school vacation, you’ll want to book as early as possible and understand you’ll be charged premium prices. If you absolutely must plan a winter trip but don’t want to plan in advance or pay high prices, the first few weeks of January often see a slump in tourism after the holiday crowds go home.

2. Not all Caribbean islands are the same

The Caribbean islands stretch over 1,700 miles in the Caribbean Sea. Some islands are composed of volcanic rocks, others of coral and sand. Some are independent countries, while others belong to the U.S., U.K., Netherlands, or France. It’s not hard to imagine, then, that each island has a unique personality with different cultures, popular activities, and tourist offerings.

When you plan your Caribbean vacation, you’ll be most satisfied if you match your island’s personality to your own. For example, if you’re looking for nightlife, you should consider Aruba, Puerto Rico, or the Bahamas. If you prefer active pursuits such as hiking up mountains, you won’t be very happy in flat, sandy Aruba; you’ll find what you’re looking for on more rugged islands like Dominica and Grenada. So before you choose your island destination, you should decide which activities you most want to do on your vacation, be it snorkeling, shopping, beaching, or sightseeing. Then research which islands are best for your preferred vacation style and select your destination from among them. For help on this topic, read our can’t-miss Caribbean picks.

Another factor to keep in mind is the difference in airfare and air accessibility. “Because of frequency of flights, plus low-cost fares, Puerto Rico is the easiest to reach of the Caribbean islands from the U.S. mainland,” say Darwin Porter and Danforth Prince, authors of Frommer’s Caribbean 2006. Other islands with low fares and frequent flights include St. Maarten, St. Thomas, Jamaica, and parts of the Bahamas. Some islands may require several air connections and only offer infrequent flights midweek. If you only have a few days for your trip or want to keep costs at a minimum, you might prefer an island that offers many nonstop flights to the U.S.

3. Know the entry and exit rules

Nothing can ruin your vacation like being told you can’t board the plane because you don’t have the correct documentation. And as much as we all dream about packing it in and relocating to a tropical island, you don’t want to discover at the airport that you can’t return to the U.S. with just a driver’s license. Once you’ve chosen your vacation itinerary, you should read up on the entry and exit requirements of each country you plan to visit.

As of January 1, 2007, all travelers to the Caribbean will need to carry a valid passport. Until then, some islands will allow you to enter with a birth certificate and a photo I.D.; just make sure the U.S. government will let you back in the country with those forms of identification. In addition, a passport that expires within six months is not considered valid by certain countries.

Technically, the U.S. Virgin Islands and Puerto Rico are part of the U.S., so a driver’s license should be sufficient. However, David Downing, columnist and editor of Fodor’s Travel Publications, reports being hassled on a trip to the USVI because he was not carrying a passport.

4. Pick your accommodations based on your travel style

All-inclusive resorts, independent hotels, villas—accommodations in the Caribbean aren’t just a place to stay; they’re a way of life. Therefore, you should choose your accommodations (like you choose your island) based on your travel style.

Porter and Prince suggest “good candidates for all-inclusive resorts are honeymooners, families, inexperienced travelers, the budget conscious, and the super stressed.” All-inclusives include all meals, drinks, and most on-site activities in the cost of your accommodations. They are good for travelers who don’t want to spend a lot of time planning their trip, want kid-friendly activities, prefer to lounge around by the pool or beach all day, and who eat and drink a lot but don’t need much diversity in their restaurant choices.

All-inclusives are not recommended for travelers who want to really experience local culture and who want to spend a lot of time away from their resort exploring the island. These travelers may be better off staying at an independent hotel. The downside is they may spend more on food and won’t experience as much hand holding, but they will have a more authentic experience.

For a truly different and cost-effective option, many travel experts rave about renting a villa. Porter and Prince recommend villas for “families, groups of friends, honeymooners or couples craving privacy, and independent travelers who want to connect with the island.” Many properties cost less than $1,000 per week and some come with housekeepers and cooks. Instead of feeling isolated, Downing says you’ll find “a built-in network of the people who rent you the house and the people who work there,” and they can help you plan day trips and excursions. There are many websites that can help you plan a villa vacation, such as unusualvillarentals.com, islanddestinations.com, hideaways.com, and rentavilla.com.

5. Consider alternative vacations

Where there’s an island, there’s water, so if you’re planning a Caribbean getaway, you shouldn’t forget to think about a sea vacation. Cruising is a popular way to see the Caribbean islands, and you can find a cruise itinerary to fit any budget. Cruises are like all-inclusive resorts, but you can see several islands and only unpack once. However, with some of the larger ships that can hold thousands of passengers, you’ll be descending on the island in a big pack and everywhere you go will be crowded. Downing recommends Windjammer Barefoot Cruises for a more intimate cruise experience. The smaller ships go where the larger boats can’t, and he believes that Windjammer passengers are treated better by the locals than the hordes of guests on the big ships.

The more adventurous mariners might want to consider chartering a yacht with a captain and cook or bareboating (renting a boat that you sail yourself). Porter and Prince report that “chartering your own boat—even a yacht—may not be as budget-breaking as you think. A seven-night combined hotel-and-crewed yacht package starts at $1,472 per person in Tortola or at $1,450 on the island of Grenada.” If you’re interested in finding your Caribbean sea legs, they recommend The Moorings, an outfitter that operates the largest charter yacht fleet in the Caribbean.

6. Research activities in advance

In an area with lots of tourists, you’re sure to find just as many tourist traps. Whether you’re looking for an operator to take you snorkeling or a vendor to sell you local spices or crafts, you want to be sure you’re dealing with someone reliable, honest, and legitimate. The best way to find reputable agents for all of your island activities is to do your research in advance.

And, there are many sources of reliable information available to you both on and off the island. Richard Kahn, spokesperson for the Caribbean Tourism Organization, recommends utilizing the service of the local tourist office. “Tourist offices are the best reliable sources because they are there to protect the destination. Most have outlets in the U.S. as well as local information services on the islands.” Tourism office staff will be sure to research their recommended operators carefully because they don’t want you to have a bad experience and then repeat your negative impression to other would-be travelers.

Guidebooks are another helpful resource because the authors only include legitimate operators in their books. Many guidebook publishers now post updates and corrections to guidebooks that aren’t updated every year, as well as host message boards on their websites where travelers will give you candid opinions about their trips, favorite operators, and worst experiences. After you’ve gotten a sense of the island from a guidebook or tourism board brochure, you can get another perspective by posting specific questions and reading the responses of fellow travelers.

Doing your homework will also prevent you from overspending. When you book an excursion through a resort or cruise line, you’re often paying inflated prices because the booking agent is taking a cut of the profit. If you can book directly with the tour or activity company, you can often find a better deal.

7. Immerse yourself in the local culture

Many travelers never see the outside of their resort except on the drive to and from the airport. But you’re more likely to have a memorable and unique experience if you get even the smallest taste of local culture.

Where do you find local culture? Usually where the tourists are not. “Away from the resorts, the clubs and eateries attract more locals than visitors,” say Porter and Prince. If you venture away from big tourist destinations, you’re almost guaranteed a more authentic experience. And if you’re not sure where those places are, just ask a local. On many islands, the local people are friendly and willing to show you the places they like.

Another way to avoid the crowds and fraternize with islanders is to hide from the cruise ships. Downing illustrates this point with a story about St. Thomas. “In St. Thomas, Megan’s Bay is a gorgeous public beach,” he says. “But the cruises bring guests in between 11:00 a.m. and 3:00 p.m., and the beach is overrun with tourists. Everyone on the island knows when the cruise ships leave, and that before 10:00 a.m. or after 4:30 p.m., Megan’s Bay will be empty.” If you’re looking for locals, you’ll find them after the cruise ships have gone.

8. Think twice about renting a car

Renting a car in the Caribbean can be a great way to see parts of an island you wouldn’t see otherwise. It can also be a recipe for disaster if you’re not comfortable driving on the left side of the road or navigating areas with no street signs. Kahn reports that Aruba and St. Thomas are easy to drive in, Barbados is quite difficult, and Bermuda doesn’t allow cars at all. If you’re considering renting a car, just be sure to find out in advance what side of the road people drive on and whether the roads and driving style on the island are tourist-friendly.

You may also be tempted to rent a motorcycle or moped. Unless you’re an experienced biker, both Downing and Kahn advise against renting motorcycles because of the dangers involved.

9. Do not believe you’re Superman after two rum punches

A vacation can be the time to finally try an activity you’ve always wanted to attempt, such as SCUBA diving. But as Downing notes, “People get some sun and after a few beers, they think they’re 18 again and can do everything.” When you’re deciding which activities to try, think seriously about your physical abilities and limitations. “A guy who hasn’t waterskied in 25 years could very likely throw his back out when he tries it in the Caribbean,” Downing says. “You have to be judicious. Try a jetski instead of waterskiing. Don’t go hang gliding but try parasailing instead.” Of course, if you’re in great physical shape, it’s fine to be a thrill-seeker. But all travelers could benefit by tailoring their activities to their abilities.

10. Be prepared

The Caribbean islands are modern countries with all the amenities, but that doesn’t mean you shouldn’t be prepared. A smart traveler packs a few practical items along with the bikinis and dancing shoes.

Mosquitoes are prevalent in the Caribbean, so bug spray is a must. Sunblock is also a necessity. Even in the dry season, a rain jacket can come in handy for passing storms. A small first-aid kit can be useful for unexpected cuts and bruises, and if you have a chronic condition, don’t forget to throw in your back brace, painkillers, or any other items you may need. Also, if you don’t want to pay island prices or get caught with hunger pains on a tour, it can be helpful to bring some snacks from home, just in case. While you can purchase all of these items on the island, you’ll find better prices at home. Plus, it’s just easier to have provisions with you rather than having to hunt them down in a foreign city when you discover you need them.