Cruising and the Caribbean go hand in hand, and boomers are the yin to the cruising yang. Cruising is a perfect fit for many boomers, with warm tropical breezes, turquoise blue-green waters, pearlescent white-sand beaches, lush floral landscapes, sunny days, star-filled nights, and cocktails that are refreshingly festive and fruity.
As a seasoned cruiser, I have experienced a variety of ships, many seasons, and plenty of islands, so I can honestly say that when it comes to a holiday at sea, there is a near-perfect match for every cruiser. With a little bit of planning beforehand, cruising the Caribbean can be an enjoyable, effortless escape.
You’ll need to decide how long you want to cruise for. If you’re just looking for a quick weekend getaway, your options will be a little more limited, but these short cruises are a great way to test the waters. I’ve found that the passengers on the shorter cruises skew a little younger, and they tend to pack as much party into a short trip as they can. With that said, today’s ships are so big that you can always find a place to squirrel away and find your Zen.
Cruise itineraries are segmented into eastern, southern, and western Caribbean ports of call. Whether you want to experience Aruba, “the happy island” as it is known to locals, take a leisurely stroll through the cobblestone streets of old San Juan and taste the local fare, or go to Honduras and check “explore the rain forest in Roatan” off your bucket list, there are dozens of ports of call, and they are as similar as they are different. Most have a plethora of shopping, both local and touristy dining options, beaches, and bars.
Choosing your cruise line and ship is like picking a date on Match.com. Every cruise line and ship has its own unique personality, and you want to find the one that is most compatible with yours. You wouldn’t want to find yourself on a bad date a minute longer than you had to, nor would you want to be stranded on a week-long cruise that didn’t match your expectations. If you booked a cruise to relax and get away from it all only to find yourself surrounded by a raucous crowd cheering on the latest contestant in the hairy-chest contest, you might be second-guessing your decision.
Outline what your expectations are in advance as well as those of your travel companions. If you don’t think bigger is better, then you might try Holland America Line, whose midsize ships feature museum-quality art, fresh florals, chef demonstrations, and classes. If top-flight entertainment, international cuisine, and movies under the stars float your boat, then Princess Cruises might just be your perfect match.
For a more personal experience, then perhaps Viking Ocean Cruises, with newer, smaller ships, handpicked itineraries for cultural immersion, fresh local ingredients, and regional specialties might be your dreamboat. If you want to combine your love of travel with your desire to make a difference, then Fathom could bring you harmony with itineraries in Cuba and the Dominican Republic. Or tap into your youthful exuberance and playful side on a Disney cruise—with or without kids. The only things that limit you when it comes to cruising are your budget and your imagination.
Viewfinder Tip: If you can be flexible with travel dates, you can often snag a great last-minute cruise deal.
What I’ve learned from experience:
1. Take half of what you think you need. The Caribbean is very casual. The worst way to start off a cruise is with an aching back from schlepping a bag that weighs half a ton.
2. If there is something on the shore excursions list that you really want to do, book it in advance. There are a limited number offered, and when they’re gone, they’re gone. That also goes for making reservations in specialty restaurants and spas. As soon as you know where you want to dine, or that you want to schedule a massage, book it. It is far easier to cancel a reservation than get one at the 11th hour.
3. Location, location, location! If you’re prone to motion sickness, select a cabin mid ship. While you may want a penthouse experience, the lower you are on the ship, the less motion you will feel. Because of the way ships are designed these days, I find that most of the time, you don’t even realize you’re moving.
4. Speaking of location, I think a balcony brings added value to your cruise experience. While they cost a premium, not only do you have a skosh more room, but also some fantastic views.
5. Check out the floor plan before securing a cabin. Find out what is next to, above, and below your desired stateroom. If you’re a light sleeper, you want to make sure that your stateroom isn’t right below the disco or the casino.
6. Hurricane season runs June through November. I have cruised many times during hurricane season without incident. However, weather happens. There are things you just can’t control and weather is one of them. You may be really looking forward to one particular port, only to hear an announcement that due to high winds or inclement weather, you won’t be able to go to that port. Cruise lines prepare as best they can for a “plan B at sea.” Copping an attitude isn’t going to change the weather, nor will it make your trip more enjoyable.
7. Travel insurance, especially during hurricane season, might not be a bad idea. This will also come in handy if your flight to the port city is delayed or canceled and sets your once perfectly planned trip into a tailspin. To avoid extra stress associated with delays, plan on arriving a day or two in advance.
What do you love most about a Caribbean cruise?