Everyone is selling cruises these days and that includes Wal-Mart and your local wholesale warehouse, such as Costco. It pays to comparison shop. Start by doing a few searches on various cruise web sites. Consult a travel agent who specializes in cruises (you can find one in the travel section of your Sunday newspaper). Consider what memberships might give you a discount. Do you belong to AAA or AARP? Talk to friends and find out how they booked their last cruise.
Pay attention to the amount of time you will have in each port
It's important to consider how much time your cruise will spend visiting each island. Have you always dreamed of visiting Jamaica? Well, if your ship is only in Montego Bay from 7 a.m. to 3 p.m., you might be disappointed that you don't have time to see much. If you want to maximize your days in port, ask for the latest dinner seating (if your cruise offers timed sittings). That way, you don't have to rush back to the ship for dinner.
Consider traveling in the Caribbean's off-season
While the Caribbean is a popular destination year-round, there are times that are slower than others. September through mid-December is generally the slowest time for Caribbean cruises. While part of hurricane season (see below) overlaps with these months, the cruise bargains abound and the ships, beaches and island shops will all be less crowded. The first 2 weeks of January and April (except Easter break) through June also present opportunities for bargains as they are generally less popular cruising times as well.
Don't assume you need to take the shore excursions the cruise line offers
The cruise lines really hype up their shore excursions, and for good reason: In addition to selling alcohol onboard, this is one of their main revenue streams. Many of the excursions are overpriced and can be put together on your own. If you're just looking for a day at the beach, hire a cab and ask the driver to take you to the nicest one in the area. You don't need the cruise line to plan this for you. You can also hire your own car or moped in many ports.
In addition, many of the same-day trips can be booked with independent operators as soon as you get off the ship. Do consider the ship's shore excursions if they offer opportunities to see multiple sites or if you have limited time in port. Also, if you are someone who will constantly worry about getting back to the ship in time for departure, go with the ship's group; they will definitely arrive in time.
Do some homework before shopping onboard or on land
Oh, the Caribbean, land of duty-free shopping! You could go broke in one shopping trip! Luxury items such as jewelry, perfume, china and electronics are imported from all over the world and often offered up to 50% off what you would pay for them in the United States. But this is not always the case. It pays to consider what you want to buy before leaving home and checking on the prices in the United States. That way you will know if you are really getting a deal. Remember that you can bargain and should, even in established stores.
Keep the Caribbean hurricane season in mind, but don't let it stop you from going
Hurricane season runs from June through November in the Caribbean, but don't let that scare you from taking a cruise during these months. Cruise ships get plenty of warning when a hurricane is forming and, when necessary (rarely), can change the itinerary or reroute the ship accordingly. The worst you will probably experience if a hurricane is forming is bumpier sailing. Ask your cruise line about its hurricane policy.