How to Plan a Caribbean Vacation

Aerial view of a corner of Barbuda, the Frigate Bird Sanctuary touches a thin strip of sand that separates the Caribbean Sea, Barbuda, Antigua and Barbuda, Leeward Islands, West Indies, Caribbean, Central America
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Planning a trip to the Caribbean should start with a few simple questions:

  • Who's going? Is this a couple's trip? A family vacation? A getaway with friends? Some resorts cater to families, while others are couples-only, for example. Some destinations are far more gay-friendly than others. If you're traveling with someone with limited mobility, it's important to find out whether your destination is handicapped-accessible.
  • What do you want to do when you get there? Some islands are known for their nightlife, while others offer quiet seclusion, great watersports, and diving, rich history and culture, or focus on ecotourism. Some have multiple casinos, while other ban gaming. Duty-free shopping is a big attraction in places like St. Thomas. Choose a destination that has the mix of atmosphere and activities that are right for you.
  • When do you want to go? Mid-winter trips to the tropics are popular, but you can save big by going in the off-season or shoulder season, which actually extends to mid-December in the Caribbean. Hurricane season is also a cheaper time to travel.
  • If you want to get a taste of real Caribbean culture when you're traveling, you also should check out what events are scheduled when you want to visit; the holidays also can be a great time to take a family vacation to the Caribbean.
  • How long will you stay? If you want a weekend getaway or other trip where you need to maximize your time away, look for destinations that are relatively close to the U.S. (such as Bermuda, the Bahamas, and the Cayman Islands) or have frequent, direct flights (like Nassau, San Juan, and Montego Bay). You'll also want to find a hotel that's close to the airport so you don't spend hours in a shuttle van once you arrive. Destinations that get a lot of European visitors, such as the French Caribbean islands, may be better set up for longer stays, offering more efficiency accommodations with full kitchens, for example.
  • How much do you want to spend? Not all Caribbean destinations or resorts are created equal. You can stay in five-star luxury or a beach hut (or even a tent), and places like the Dominican Republic generally appeal more to budget-conscious travelers than, say, St. Barts. An all-inclusive resort may be a better value than a pay-as-you-go hotel -- or at least you'll have a better idea of what your trip will cost upfront.Airfare costs are another huge consideration: it's not unusual for your travel costs to equal or exceed your lodging costs in the Caribbean, and flights to destinations with little competition between airlines can get expensive.
  • How will you get there? For the vast majority of travelers, the answer will be by air or cruise ship. The former is the pure transportation of course, while the latter is an integral part of your vacation experience: you'll be spending more time on the ship than on a Caribbean island with most cruises. Only Grand Bahama Island can be reached by ferry from the U.S. mainland, and only the Florida Keys and the Mexican Caribbean can be reached by car (the latter is a 1,400-mile drive from Brownsville, Texas to Cancun, however, so that's not recommended).
  • Why are you going? Are you celebrating an anniversary, honeymoon, or another special occasion? Some destinations and resorts are better for a romantic getaway than others. Looking for somewhere you can take it all off? Clothing is optional at some Caribbean resorts and beaches.
01 of 07

Planning a Caribbean Vacation: Choosing a Destination

St. Lucia
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What destination should you visit in the Caribbean? There are as many answers to this as there are islands in the Caribbean -- thousands, in other words.

Want romance? Try St. Lucia. Family fun? Aruba. Nightlife? Cancun, or San Juan. Ecotourism? Check out Dominica. For fine dining and sophisticated culture, it's hard to beat Barbados. But no one island has a monopoly on any of these things.

Most Caribbean destinations are safe for travelers, but it's wise to check the latest warnings (if any) about where you are headed and -- as always -- take some prudent steps to protect your loved ones and belongings.

Remember that unless you choose to visit a U.S. Caribbean territory -- Puerto Rico or the U.S. Virgin Islands -- you'll need to have a passport to travel.

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02 of 07

Planning a Caribbean Vacation: Finding a Flight

Air plane flying over a Caribean beach
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The best hotel deal in the Caribbean won't amount to much if you can't get there, or if you have to spend a small fortune to do so. On the one hand, certain Caribbean destinations -- like Puerto Rico and the Dominican Republic -- have a lot of flights and competition among airlines, which tends to keep costs low. But other islands -- particularly smaller ones and those off the beaten path -- have relatively infrequent air service (often only by local, inter-island airlines) and high prices.

Flight duration is another issue: You can find yourself spending a lot of time in the air depending on where you are coming from and where you are headed in the Caribbean. So, if you've got only a little time to vacation, look for a destination with direct flights from the U.S., and check out the approximate flight time from your departure city to your destination. The Bahamas, for example, are right off the coast of Florida, while Aruba is right off the coast of Venezuela. Big difference!

There is relatively little budget airline service to the Caribbean, so it pays to compare prices on flights before you go.

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03 of 07

Planning a Caribbean Vacation: Where to Stay

Cap Cana resort, Punta Cana, Dominican Republic.

Dominican Republic Ministry of Tourism

The hotel, resort, villa, B&B, or cruise line you choose for your Caribbean vacation will play a huge role in how much you enjoy your experience. Invariably, this is where you'll spend most of your time during your trip, especially if you choose an all-inclusive property or take a cruise. Fortunately, the Caribbean offers a huge selection and variety of lodging to fit your budget and interests, from youth hostels to some of the most luxurious accommodations in the world.

Most Caribbean resorts are on a beach somewhere, but the same is not always true for hotels, B&Bs, or villas, so be sure to check first if sun, sand, and surf are high on your priority list.

All-inclusive trips are very popular in the Caribbean and usually offer good value for the money, but probably won't appeal to you if fine dining is a big part of what you want out of a vacation.

Private island resorts offer seclusion and romance aplenty, but maybe not much in the way of nightlife, tours, or excursions.

Cruises allow you to visit multiple islands and always have a place to dine and lay your head at the end of the day. Plus, you'll know up front what it costs, other than your bar tab, which can really add up. Probably the biggest drawback to cruising is that you never seem to get enough time on shore to actually learn much about the places you are visiting.

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04 of 07

Plan Your Caribbean Vacation Activities, Tours, Sightseeing and Other Adventures

A waterfall
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Many people go to the Caribbean with one main activity in mind: laying on a fabulous beach and melting away the stress of their everyday lives. For some, that's enough. But most people want their Caribbean vacation to include at least some sightseeing, activities on the water, and maybe a little soft adventure, like a jungle jeep tour or zip lining.

Hotels and cruise lines have activities desks that make it easy for you to book tours; cruise lines allow you to do so in advance, a must since some popular tours fill up quickly. In both cases, you get the security of knowing that the tour operator has been vetted by the hotel or cruise line. The downside -- especially with cruises -- is that you're often paying a hefty premium for that security.

You can always go online and book tours directly with vendors, but you can also use the Internet to book vetted tours in advance -- often at better prices -- with companies like Kijubi and Viator, both of which work with transportation and tour companies in the Caribbean.

Search for Caribbean Tours with Viator

What kind of activities will you find in the Caribbean? In short, almost anything you can think of, from tours of historic homes and rum factories to river tubing, swimming with dolphins, submarine adventures, party buses -- even a ride on a Jamaican bobsled. Selection varies from destination to destination (places like Aruba and Jamaica, which get the most tourists, naturally have the most offerings), but no matter where you go you'll likely be able to dive, snorkel, take a boat ride, learn some local history, and book a general island tour.

Before you book, however, check to see what comes free with your stay: all-inclusive resorts usually include non-motorized water sports, for example, and some packages include tours, as well. If all you want is a general tour, it's sometimes better to arrange for a car and local driver, who can act as your local guide.

If your vacation plans include sports, be sure to find out whether your favorite activities are available near your hotel. Some destinations are particularly known for their golf, diving, or​ sailing, for example, while certain resorts cater to tennis players far more than others.

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05 of 07

Plan Your Caribbean Vacation: Restaurants and Dining Out

Caribbean meal

One thing you probably don't need to do before you leave home for your Caribbean trip is to make restaurant reservations in advance unless you plan to dine at one of a handful of exclusive restaurants in St. Barts or Barbados. If you're staying at an all-inclusive resort or on a cruise, all of your meals are ostensibly taken care of. However, you may grow a little tired of eating in the same place day after day, so be sure to do a little research in advance on your dining options in your destination of choice.

While you are in the Caribbean, try to be a little adventurous and check out some authentic cuisine, such as the street food that's so popular (and inexpensive) on many islands. Creole and Latin cuisine features a melange of flavors from around the world, using local ingredients like spiny lobster, red snapper, goat, callaloo, and conch. Trying the local beer and rum -- the latter either straight up or in a tropical cocktail -- also is a must if you enjoy a little libation.

Tipping customs are generally the same in the Caribbean as in the U.S. -- 15-20 percent is always appreciated -- and you'll usually find menu prices in U.S. dollars alongside the local currency amount (except in French islands like Guadeloupe and Martinique, where prices are in Euros).

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06 of 07

Plan Your Caribbean Vacation: Transportation and Car Rentals

Cuba, Havana, Revolucion Mural and yellow Coco Taxi
Alan Copson/Getty Images

One expense that sometimes gets overlooked by Caribbean travelers is the cost of getting around, whether it is for getting from the airport to the hotel or getting out of your hotel to do some sightseeing. Public transportation from airports to resort areas is nearly nonexistent (Aruba and Bermuda are among the pleasant exceptions with their excellent bus service), so you're generally faced with the choice of renting a car or paying for a hotel shuttle or cab unless airport transfers are included in the price of your hotel stay (check when you book your room).

Whether you rent a car rather than paying for a cab or shuttle depends of course on how much you expect to travel around once you reach your resort. Keep in mind that the activities desk at your hotel can arrange tours with transportation that leaves right from the lobby. You'll also need to gauge the relative safety of driving around, especially in destinations that have significant crime problems, road signs in different languages, or driving rules that differ from back home (driving is on the left side of the road in many former British territories in the Caribbean for example).

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07 of 07

Plan Your Caribbean Vacation: Packing, Safety and Weather Checks, and More

Luggage on a baggage carousel
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Once you've got your flights, hotel, activities, meals, and local transportation figured out, it's time to pack!

Before you roll the suitcases out the door, however, you also should check the weather report for your destination and see if there are any relevant health alerts where you are going. Finally, make sure your house is secure while you are away, and go have a great time in the Caribbean!