- 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's 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 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 other 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.