The Best Way to Plan a Caribbean Vacation

Candid shot of happy couple entering bright resort

You’ve daydreamed long enough. The time to head to your Caribbean tropical paradise is now. So who’s going with you? Or is this a solo, treat-yourself kind of trip? 

There’s so much to consider when crafting the perfect Caribbean getaway. Here are several key questions to ask as you plan your adventure.

Where Would You Like to Go? 

The Caribbean consists of some 7,000 islands, the southeast shore of Mexico, and northern coast of Venezuela. It’s a massive region with endless hideaways, all of which feature white-sand beaches and crystal blue waters. You can’t go wrong if all you want to do is relax in the sun, jump in the sea, and enjoy a cocktail or two in the tropics. 

Some destinations are more ideal for you than others, and there are a number of factors to help you find them. It starts with how long you plan to be away. If you want to make the most of a long weekend, you might want to select a destination closer to home or with several direct flights. For Americans, this means Puerto Rico (where you can leave those passports at home and skip the currency exchange), the Bahamas, or Jamaica. 

If you have a full week ahead of you (or more), you can be more selective. Mexico’s Yucatan Peninsula offers a great mix of relaxation, jungle and aquatic adventures, and history—with the Mayan ruins a popular tourist attraction. You can find plenty of excellent all-inclusive resorts in Cancun, Tulum, and Playa Del Carmen. 

For a blend of culture, history, and fun, hit the cobblestone streets and white-sand beaches of Puerto Rico. Serious scuba divers might consider the Curaçao Underwater Park, which covers 12.4 miles of shoreline and is famous for its marine life and shipwrecks. 

Families will love Atlantis Paradise Islands Bahamas. Single travelers interested in mingling should book a stay at Sunset at the Palms Resort in Negril, Jamaica. 

Avid golfers should hit the links at Teeth of the Dog Golf Course in the Dominican Republic, designed by famed architect Pete Dye, and noted for its natural beauty and challenging play. 

And if you really can’t decide on a destination and want to explore them all, consider a cruise. It’s often the best way to travel to multiple islands without breaking the bank.


When Should You Go?

You could argue that there’s no bad time to spend a week or so in the Caribbean. You can find worthwhile vacations around the calendar based on your preferences. 

For the best weather, you should aim for the late fall through early spring (roughly November to April). That’s when you’ll get cooler but not too cool temperatures (average highs climb into the 80s), lower humidity, and more sun. 

That’s also the most popular travel period, which means higher rates, not to mention a cavalcade of other tourists. You can, however, score deals in the first few weeks of January once the winter holiday crowd clears. 

You’ll often see significant deals during the off-season, between May and November. That’s because tropical storms and hurricanes threaten the region, so booking ahead is a bit of a gamble. If you are looking for a late spring, early summer getaway, consider the ABC (Aruba, Bonaire and Curaçao) islands, or Trinidad & Tobago. Hurricanes are rare that far south.  


How Far in Advance Should You Book?

It depends! The spontaneous crowd thrives on finding last-minute flight and hotel deals, even if they have to comb through several booking sites to get them. For anyone else, the age-old advice still applies: the earlier, the better. 

One study suggests airfares to the Caribbean from the United State were least expensive, on average, 99 days prior to departure. That’s a little more than three months. Now, when you factor in the time of year (are you headed to your destination in the busy season?) and early booking bonuses all-inclusive resorts often offer, it’s best to lock in that stay as soon as possible. 

Besides, you’ll appreciate the extra time to get every other detail of your vacation just right, from what to pack to excursions to fun for the kids to romantic nights out. 


How Can You Stay Within Your Budget? 

Booking early will certainly help you save money, as will choosing an affordable destination. The Bahamas, Dominican Republic, Puerto Rico, U.S. Virgin Islands, and Jamaica, to name a few, give you the most bang for your buck, according to Travel Pulse

Then it’s all about meticulous planning. Set aside money for nights out on the town or at that fancy seaside restaurant ahead of time. Pack your own snacks before you depart. Choose to boat or ferry places, if applicable, rather than fly. 

Perhaps most importantly, ask what meals, activities, and drinks are covered when you book with an all-inclusive resort. 


Work With a Travel Advisor.

There’s quite a lot that goes into planning a Caribbean vacation, isn’t there? After all the research, sifting through flights, scouring websites, and trying to decipher what activities and tourist traps are worth the hassle, you really will need to escape to the tropics for a while. 

Wouldn’t you rather leave all that work to an expert? 

Of course you would! That’s where an InteleTravel Advisor comes in. Our advisors know the Caribbean inside and out because they’ve traveled there extensively themselves. They can tell you when to go, what to do while you’re there, and get you the lowest price—guaranteed.

Plus, advisors understand the ins and outs of insurance. So if you want to head to Puerto Rico in September, for example, at the height of hurricane season, you can do so knowing your trip is covered properly. 

Here’s the best part about working with an advisor: You don’t pay them! You get access to a true expert without added fees and a wonderfully personal booking experience that no website or app can replicate.

Provide a few details about your trip, let the advisors work their magic, and then sit back and dream about your time in the sun. 

Where would you like to travel?

Select your destination, and we'll pair you with an InteleTravel Advisor based on your travel needs.

Leave a comment

Never miss an update

Subscribe to the InteleTravel blog to receive the latest travel news and updates