Caribbean Vacation Packages 101: How They Work and What to Expect

by  Laura Motta | Jan 23, 2019
Breathless Punta Cana
Breathless Punta Cana / Laura Motta

With cooler temperatures in play in much of the U.S., January, February, and March are prime months for Caribbean travel. One especially practical way to take a hassle-free trip is to book a vacation package. In most cases, your flights and lodging are included in a single price, and some packages also bundle in airport transfers and excursions. Booking an all-inclusive resort as part of your trip means that you won’t have to worry about meals, drinks (including alcohol), and simple activities such as snorkeling and paddle boarding. In short, a package makes Caribbean travel a breeze.

We recently traveled to popular Punta Cana, Dominican Republic with online travel agency CheapCaribbean, which specializes in travel to the Caribbean and Mexico, to get a sense of how a packaged Caribbean vacation works, and what you can expect. Here’s how it went.  

How It Works

Caribbean packages are designed for travelers who crave ease every step of the way. Plus, they can be fully booked online, often without the assistance of an agent. (Though most tour operators and travel agencies have plenty of customer service agents available if you have questions). Most, and often all extraneous taxes, fees, and gratuities are covered. All you really have to do as a traveler is pick your resort and your departure date, book, and remember to pack your sunglasses. Beyond that, travel agencies — CheapCaribbean included — often pass along significant savings to travelers that they’ve earned through years of working with specific destinations and resorts. A package can save you hundreds of dollars (over booking flights and a resort yourself), and will often include resort credit or other perks. 

The downside? Choosy travelers who need highly customized vacation experiences, lots of hand-holding in the booking process, or those who are traveling with larger or varied groups may need a different solution. After all, it’s the one-size-fits-all nature of Caribbean packages that makes them easy and affordable. Adding customized features will drive up the cost — and the complexity — of both your booking process and your getaway. 

Note, too, that Caribbean vacations are often priced per person, with the assumption that two people will book and stay together. If you’re traveling alone, you’ll pay a significant premium — sometimes as much as 50 percent to 100 percent more than double occupancy rates. 

More on All-Inclusives

When you’re booking your getaway, be sure to carefully consider whether you want or need an all-inclusive option. All-inclusive resorts provide travelers with all of their meals, beverages (alcoholic and non), and select activities (usually non-motorized water sports, entertainment, and classes or tastings). These resorts usually have multiple on-site restaurants offering different cuisines, a combination of buffet-style and à la carte dining, unlimited room service, and an in-room minibar that’s restocked daily with beverages and snacks.

There are plenty of resorts in the Caribbean, however, that do not have all-inclusive options. These properties may have plenty of on-site restaurants and bars, but you’ll need to pay à la carte for meals and drinks. Read the fine print carefully when you book your package, as you want to make sure you’re getting the option that’s right for you. 

Hard and fast rules don’t really apply when it comes to pricing all-inclusive resorts vs. their less-inclusive counterparts, but if you’re looking to make a comparison, try this. Compare the pricing of all-inclusive and non-all-inclusive resorts that are similar in quality, in the same destination and location, and during the same season. You will find that all-inclusive resorts are priced higher per person, per night than non-all-inclusive resorts. 

And, how do you know which option is right for you? It depends on what you value in a vacation. If you’re passionate about patronizing local restaurants, exploring the area on your own, and spending most of your time away from the resort, an all-inclusive option might not be worth the money. If you’re looking to laze away the days by a swimming pool without having to spend another penny on your trip after the initial investment, all-inclusive getaways are a godsend — and can be a major money-saver if you take advantage of all the eating and drinking the resort has to offer. 

Money Matters

What you pay for a Caribbean vacation depends on when you go, where you stay, and how you get there. Here’s a general rule of thumb, though: Popular destinations with lots of all-inclusive resorts and frequent flight connections from the U.S. (Cancun, Punta Cana, Ocho Rios, Los Cabos) will tend to be less expensive than islands with fewer resorts and less frequent connections (Nevis, St. Lucia, St. Croix). 

Additionally, you’ll find lower pricing on packages when the weather is less likely to be perfect (i.e June through November, in Caribbean hurricane season), and when kids are in school — especially when it comes to destinations like Nassau, Bahamas, for example, as well as resorts that cater specifically to families.

Be sure to check the price breakdown of every package element before you book, and make sure nothing is missing. Some packages include airport transfers, for example, but some don’t. You don’t want to find out that your transfers aren’t included when you land alongside thousands of other passengers, all of whom are clamoring for rides to the resort.   

Navigating Through the Airport

Disembarking at a Caribbean airport can feel chaotic. Many flights from the United States (and elsewhere) arrive at the same time, sometimes making for long lines at immigration (if you have to pass through it) and at baggage claim. Add to this a heady dose of humid Caribbean heat and less assertive air conditioning than you’re probably used to, and nerves can fray quickly. To avoid the overheated scramble, look over the airport map before you arrive, take off your sweater or your coat before you get off the plane, and keep your transfer information handy. After you clear immigration, keep an eye peeled. Some resorts, tour operators, and transport companies have their own airport desks. Depending on the desk, you can confirm or book a transfer, collect resort information, get directions, or, sometimes, even check-in to your resort. CheapCaribbean partners with transportation company Amstar, which has a desk at the Punta Cana and Cancun airports, among others. 


Your transfer may be private or shared, depending on what you booked, and can be as short as ten minutes or as long as two hours. The trip from Punta Cana’s airport to its central resort area takes about 40 minutes, while a trip to the resorts at La Romana, a quieter area on the south cost of the Dominican Republic, takes about an hour each way. From Cancun, Mexico, to the city’s central hotel zone, expect a 20- to 25-minute transfer, and a 45-minute transfer, minimum, if you’re heading out to the Riviera Maya. 

Though gratuities at all-inclusive resorts are typically included, transfers — which usually occur off the resort — present a bit of a gray area; we leave the equivalent of $5 to $10 USD per trip. 

With limited places to park, roads of varying quality, and the general inconvenience associated with renting and wrangling one, we don’t recommend renting a car on this kind of vacation. 

Checking In

Upon arrival at your resort’s check-in desk or welcome area, you’ll learn about the resort and what’s available, and you’ll likely be given information about on-site restaurants and activities, including meal timing, room service hours, reservation requirements, and more. Don’t assume you can ignore this speech and easily get the information elsewhere. It’s a good rule of thumb to write it down or take a photo of any printed information that you can’t take with you. Many resorts will offer you a complimentary welcome drink, and a staff member may walk you directly to your room to show you around. 

At Dreams Dominicus La Romana, on the less-visited southeast coast of the Dominican Republic, we were given a brief resort tour, and, when we got to the room, an explanation of how elements in the room worked — lighting and air conditioning, the minibar process, and more. 

What to Expect During Your Stay

Relaxation is the name of the game at most Caribbean resorts. Experienced travelers stake out the best spots by the pool early in the day, especially during busy periods. (You likely won’t need to do this in shoulder and low season.) From your chosen spot, you can order drinks, snacks, and sometimes even meals from waiters who cater to poolside guests. The same can be done on the beach, where there’s usually additional seating, umbrellas, towel stands, and more — provided the weather is cooperating and the sea is safe for swimming. 

Restaurants at all-inclusive resorts open and close at set times, so you won’t be able to wander into any venue at any time of day and grab a meal. Ask to see a schedule at check-in. In many cases, all of the resort’s restaurants won’t be open every night, and you’ll want to make reservations or arrive early at any must-try spots. Buffet restaurants are often open longer hours, offer a wide variety of foods, and often have a casual ambience. Make sure you check the dress code for dinner; some resort restaurants will have guidelines in the evening. In our experience, the best meals at all-inclusive resorts can be be found at dinner time in à la carte restaurants with fewer tables than you’ll see at the sprawling buffet. Also, if you find that you have a favorite waiter or bartender, additional tipping in cash is often welcome and appreciated — and will likely earn you premium service. 

Look out for special events during your stay. Concert-style entertainment, nighttime barbecues on the beach, pool parties, and poolside games are the norm at many Caribbean resorts. Now Onyx Punta Cana, which caters to families, hosts an evening concert with singers performing well-known hits with a live band, while Breathless Punta Cana, which caters mostly to adults and honeymooners, hosts blacklight pool parties. All of these are included in your stay. 

Note that some kinds of activities aren’t included in your stay. Spa treatments, upgraded activities such as boat trips,  fishing, or excursions into town will incur an additional cost.  

At Checkout

Checking out of your resort and catching your transfer van or car back to the airport is usually a straightforward process. Hotel staff will assist with your bags and may whiz you back to the hotel entrance on a golf cart to speed up the process. Check your bill for any additional or unexpected charges, and return anything you borrowed (resort cell phones, iPads, adapters, etc.). Some resorts offer you snacks, water, or a small parting gift to see you on your way — and encourage you to return. 

Find The Best Cruises
Find a cruise

Find the best deals!

Click on multiple sites to get the lowest prices

Click on multiple sites to get the lowest prices