All-inclusive Vacation - Caribbean,
Dreams Playa Mujeres, Cancun, Mexico

All-inclusive vacations can be easy, safe and reasonably priced for families in search of a fun and relaxing escape from the daily routine. My husband and I have been taking our two children to resorts in the Dominican Republic on a regular basis since my daughter was just about one year old and my son was five years old. After nine all-inclusive family vacations to the Caribbean over the past seven years, I have compiled this guide for families unsure of what to expect from an all-inclusive resort. Over the years, we have edited our thought process, corrected our mistakes and maintained realistic expectations. This guide is filled with helpful tips for those interested in an all-inclusive Caribbean vacation.

The online travel market is saturated will all-inclusive deals, ranging from some that disappoint to those that exceed expectations. It takes time and patience to sift through the good and the not-so-good deals, resorts, packages and travel websites. I have noticed from chats with fellow vacationers and through online reviews, that some go into these experiences with unrealistic expectations. Bottom line, these resorts deal in bulk and unless you are able and willing to spend $10,000 or more per night, it is unreasonable to expect top shelf drinks, vintage wine lists, farm-to-table cuisine, round-the-clock V.I.P service catering to your specific preferences and numerous other fantasies projected across social media and reality television. It is a fact that the staff at these resorts work long and hard hours no matter which resort you choose. Service is as good as your attitude when you step onto a resort. A friendly smile paired with a relaxed and respectful attitude goes a long way. Sky’s the limit with an open mind.

It may have taken a couple of tries but we eventually found resorts that meet our desired standard for rooms, food, drinks, and activities without breaking the bank. When we planned our first all-inclusive vacation to the Dominican Republic over the Christmas/New Year’s holiday, our primary concerns were safety, comfort and convenience. Our children were little and at the top of the agenda was to ensure that the flight, airport transfers and stay went smoothly. The first few trips were practice runs that I used to work out the kinks of executing a family vacation that no longer leaves me entirely exhausted before, during or after the fact. Since the pleasure to workload ratio started to work in my favor, leaving the cold of New York City to celebrate New Year’s Eve in the Caribbean has become an annual family tradition that we have come to cherish as a family.

Since we started taking family vacations at Caribbean resorts, we have adjusted our resort of choice, desired location, length of stay and other details in response to our evolving needs and wants. These vacations laid the groundwork for us to eventually expand into Europe with longer flights and more adventure. For families interested in traveling with their kids, all-inclusive travel is one way for kids to become accustomed to the rhythm of traveling by air, staying in a hotel room and frequently eating out. At first glance, an all-inclusive vacation may not seem educational but there are lessons to be learned about relaxing, disconnecting from the rest of the world and re-connecting as a family. This quality time together has enabled an organic family dynamic – at home and away – that is shaped by independent thought and not beholden to tradition.

We were not sponsored by any of the resorts, online travel sites or other businesses mentioned below. We have always paid our own way and all references, good and bad, are based on actual paid-for experiences. I would love to hear your thoughts and questions in the comments section below.

Resort Brands & Travel Web Sites

In the most general terms, the amount paid for an all-inclusive resort covers the room, all meals, snacks and beverages, including alcoholic. In addition, guests are given full access and provided with food and drink service around the pools and on the beach where beach towels, lounge chairs, umbrellas abound. Most resorts offer multiple pools for guests to choose from, different types of seating on the beach, and a selection of restaurants, bars and cafes to dine at throughout the day. Also included is live entertainment and a range of activities for children and adults.

Resort packages can be easily found online through websites such as Apple Vacations, Cheapcaribbean.com and Vacationexpress.com. These are the websites that I have used in the past to book a resort and flight, however, there are numerous websites that offer these vacation bundles. Take the time to shop around and compare prices across the many travel websites when you start looking for a vacation package. After you plug in your desired dates, location, number and ages of the guests, you will find yourself looking at a long list of results. Sort the results with the highest rated resorts at the top and work your way down. After you find a resort that falls within your budget, dig a little deeper into this resort by looking at the resort’s website and reading the reviews on the travel website as well as on TripAdvisor.com. If this resort’s website looks appealing and you find a majority of good reviews, start comparing rates for this resort across other travel websites where you should continue to skim through reviews. Reviews are helpful but should be read with a grain of salt because it is unrealistic to find glowing reviews across the board. A majority of good reviews outweigh a couple bad reviews. Keep in that mind that expectations, attitude and preferences are not universal. What may be a deal-breaker for some may not be so important to others. Years ago when I had little to no experience with the different resorts, I just picked one and hoped for the best.

Dreams, La Romana, Dominican Republic (now Hilton, La Romana)

We went to Majestic Colonial Punta Cana (booked through Cheapcaribbean.com) the first year and Iberostar Dominicana (booked through Vacationexpress.com) the second year. At Majestic Colonial Punta Cana, the rooms were dated, the bedding and bath towels were rough and uncomfortable, and the bathroom was falling apart. However, the friendly service throughout our stay made up for the room’s shortfalls and below average food. I did fall in love with the coffee at breakfast and every morning looked forward to the breakfast buffet where I savored the rich coffee that was served with warm milk. The New Year’s Eve dinner buffet was also memorable and probably one of the most elaborate ever experienced. The aspects that were less than desirable about this resort did not overshadow our time away. These were observations that I took note of and put to the side for when it was time to plan our vacation the following year.

The next year we tried out Iberostar Dominicana where we paid a little extra at the time of our arrival to upgrade our room to a family suite. This room was certainly an improvement from the previous year but the resort was still lacking in some areas. The service was great, no complaints, but the food was mediocre at best and the property was way too large and spread out for our liking. I do not know if my perception of space was altered because we had toddler and I was suffering from joint and muscle pain at that time but it felt like the distance from our room to anywhere else in the resort required a lot of walking. Once again, I cannot deny that we had a great vacation but I knew I wanted to keep looking and try another resort the following December.

The third year, we went to Dreams Palm Beach Punta Cana (booked through Vacationexpress.com) and this resort was much more to our liking. This Dreams resort excelled where the others had failed. The quality of food was a step up in taste even though this is also a high-volume operation. Their buffets were not overflowing with unappetizing choices. Instead the Dreams buffet showed more restraint with a selection of noticeably tastier dishes. Plus the specialty restaurants that served dinner had a number of stand-out choices on their menus. The condition of our room met our standards with an updated bathroom, comfortable bedding and soft towels. Guests are not required to wear wristbands at any Dreams resort and the service was excellent. We had found ourselves in a resort where the standards came closest to our expectations of an all-inclusive vacation.

Please note that during this stay, we were bamboozled into purchasing a membership with the Unlimited Vacation Club (UVC) which has us committed to staying at the family resorts offered by this brand for the foreseeable future. We have since stayed at Now Larimar Punta Cana, Now Onyx Punta Cana, Dreams La Romana Resort & Spa (sold to Hilton in 2018), Dreams Dominicus, La Romana and Dreams Playa Mujeres, Cancun. As members, I no longer use travel websites to book our stays but do so directly through the UVC website and book flights through our credit card rewards account.

I have mixed feelings about this membership, hence the flippant choice of words, but I can say with certainty that the quality across the Dreams and Now resorts has remained consistently at the high end of the spectrum. We have experienced excellent service everywhere and have felt at home in the clean, comfortable and safe surroundings of these resorts. We appreciate that the Unlimited Vacation Club’s portfolio is comprised of brand new or recently refurbished properties. Thanks to this membership and despite my skepticism, we are even more committed to our holiday tradition of leaving NYC for the Christmas/New Year’s holidays. It took some time and an expensive membership, but we eventually found a resort brand that suits us as a family.

Costs – Resorts & Flights

The rates are slightly inflated around the Christmas/New Year’s holiday week but if you start looking early in the year, it is possible to snag some good deals for resorts and flights. Kids’ rates are based on age, so the younger the child(ren), the less you pay. After reviewing what we have paid over the years, the total cost for the resort and flight for a family of four during the Christmas/New Year’s week has ranged from $5,700 to just under $10,000. Since the first three years were booked through travel websites, the amounts for the resort and flight were bundled together. After we became members of the Unlimited Vacation Club and starting booking the stay at the resort directly through this club’s website and flights separately, I have a better sense of how the rates have changed over the years. About 75% of the cost went towards the flights to Punta Cana from New York. However, this past December, we flew to Cancun and I noticed that it cost almost half to fly to Punta Cana yet the cost to stay at the Dreams resort was noticeably higher in Cancun than in the Dominican Republic.

The first two years, we only purchased three seats on the airplane because my daughter was under two years old and sat on my lap. These four-hour flights with her on my lap were manageable because she slept most of the way. This is one way to cut costs if you are traveling with a child under two years old. We discovered during the early years that we preferred to fly with Delta which we used to fly into the Punta Cana airport to access resorts in either Punta Cana or La Romana. There is an airport in La Romana, but no direct flights from New York. It is faster to fly nonstop into Punta Cana airport and take either a pre-arranged car service or taxi to La Romana which is about a 40-50 minute drive. Be mindful of your own flight preferences when booking your flights through a travel website that bundles the resort and flight. After you select the resort, you will be given a selection of flights usually listing the cheapest at the top. Make sure that your selection best reflects your desired airline, time of day to travel, airports, and flight length (nonstop or with stops).

The vacation websites often include with the resort/flight package free transport to and from the airport. This free service is a bus filled with other vacationers going to different resorts which means that when you arrive, your transport will make multiple stops at other resorts to drop off passengers before dropping you at your resort. It is the same system when departing which means leaving for the airport much earlier than necessary to sit on a bus and drive around to other resorts. Even though this service is free, it may not be the best way to start or end a vacation. It is possible to make arrangements ahead of time for a private car service through websites such as Amstar for a price that is dependent on the vehicle class and the distance between the airport and your resort. It is also possible to get a taxi upon arrival but you should be prepared to pay in cash and U.S. dollars are accepted. The benefit of reserving ahead of time allows you to pay by credit card but plan to tip the driver in cash.

Airport Arrival
After you have cleared customs and retrieved your baggage, follow exit signs to ground transportation where you will find your free shuttle, driver for a reserved car service holding a sign with your name or taxis waiting to take you to your resort. Along the way, you will be bombarded by sales representatives trying to sell vacation packages. They will give you the impression that you have to talk to them in order to exit the airport but this is not the case. Simply keep walking and politely decline their requests for you to stop and talk. The goal is to get to the resort and start your vacation as soon as possible.

The length of our stay has increased over the years from 4 nights to 9 nights, which can explain the gradual increase in cost over the years. This combined with the children getting older and a peak season travel have all contributed to the annual increases. We have been able to offset some costs when booking flights through our credit card rewards program and using points to bring down the airfare. It recently came to our attention that resorts charge children ages 13 and above as adults. We have just over a year before our oldest will cross this threshold and we are already preparing ourselves for another rate increase.

Dreams, Punta Cana, Dominican Republic. All-inclusive beach resort. Dinner on the beach.

While your kids are little and if your budget and work schedules permit, take advantage of this small window of time when your family can fly and stay at a resort for less. Families who are not yet tied to a school schedule can also travel during the off season when resorts have fewer guests and offer more better deals. Even though it is a lot of work for parents with babies and small children, the lower price tag can be a worthy incentive.

When, Where & How Long

Our first four Christmas/New Year’s vacations were spent in Punta Cana, Dominican Republic where the beaches face the Atlantic Ocean. The beaches of Punta Cana are lined with resorts one right next to the other. The average daily temperature is around 85 degrees making it pleasantly warm to sit by the pool or on the beach. The ocean is still cold and the water is a little rough. I think my husband was the only one to swim in the ocean the first few years because the kids were little and still learning to swim. Even though the ocean was a little intimidating when they were younger, the kids enjoyed playing in the sand with beach toys purchased from one of the shops at the resort.

The remainder of our days were spent in the pools where the kids had plenty of time to practice swimming, jumping, floating and more. We treasure our pool time during these vacations because we have limited pool options around our home in NYC. Both kids have become proficient swimmers thanks to the cumulative time spent in pools during all of these vacations. This was a major milestone that I could officially check off as completed with relief last year when we retired my daughter’s swim vest.

Around four years into our all-inclusive research, we decided to try out a resort in La Romana, Dominican Republic because it faces the calmer and warmer Caribbean Sea. This was a dramatic improvement that I wish we had done earlier because swimming in the ocean on that side of the island is far more relaxing, fun and refreshing with the kids. The pools are always a focal point for the kids but we fell in love with the calmer conditions of the beach in La Romana. Our days are almost evenly split between the beach and the pools but I could easily bypass the pools and spend all day on the beach because it is just heavenly.

This past Christmas/New Year’s week was spent in Cancun at Dreams Playa Mujeres where it was slightly cooler than the Dominican Republic when we first arrived. The ocean was cold on first try but thankfully, it eventually warmed up and we were able to swim in the ocean. The slightly cooler temperatures left the beach wide open because the majority of guests preferred to spend their days around the heated pools of which there were several. This was our first Caribbean resort to have heated pools and it was an improvement, especially on the cooler days. This resort also has two very large water slides that we worked into our daily beach and pool schedule. The water park was well-timed because if we had stayed at this resort any sooner, our youngest would have been too young to go down on her own.

Our Unlimited Vacation Club membership came with 28 free nights that we used to visit Now Larimar Punta Cana for a seven-night stay late in June one year and another seven-night stay at Dreams Dominicus in La Romana for spring break last year. In comparison to our December stays, it is progressively hotter during these months and this weather ensured that taking refuge in the ocean and the pools was even more refreshing. By June, the sun gets pretty intense and it was necessary to take a couple of breaks from the sun and rest inside our room to avoid overexposure.

The length of our vacation has gradually grown from four nights to nine nights. Extending the length of our stay was possible after our youngest was potty trained and eating a wider variety of foods. I was no longer concerned that we would run out of diapers, baby wipes, baby food and snacks. These items took up a considerable amount of space and packing was quite the balancing act. With these restrictions behind us, we can take full advantage of the time when schools are closed between Christmas and New Years.

Food and Drinks

When one hears all-inclusive, some think all you can eat and drink with no limitations. Yes, this is true but setting our own limits within this environment of excess has been our go-to strategy to avoid glutinous behavior. We trained ourselves to eat reasonably-sized portions at mealtimes and to limit the number of alcoholic drinks, especially during the day when it is hot and dehydration is likely. Our kids’ safety is priority and we accept that nothing good can come from day drinking. We wait until the early evening to relax with a couple drinks before, during and after dinner. Rather than throw out all rules and restraint, we try to eat and drink in a manner that does not deviate too far from our habits at home. Honestly, my husband and I are in our mid-forties and it is brutal to wake up with a hangover and a belly full of poor choices. Everything in moderation is the way to go.

Dreams, Punta Cana, Dominican Republic. All-inclusive vacation. Children on the beach.

When the kids were little, I was faced with some of the biggest challenges trying to find healthy vegetarian options for my son as well as basic yet nutritious options for my toddler. I brought jars of baby food as backup the first year when my daughter was eleven months old. However, every year after and through to today, I continue to find more ways to balance out the many sugary treats with healthy options over the course of the day. I rely heavily on the availability of fresh fruit and sneak in vegetables to supplement endless plates of plain pasta or pizza.

Once we started going to the Dreams and Now resorts, I was thrilled to find even more healthy options for all four of us. Their fresh juice bars at the morning buffet include green juices which I look forward to every morning. My son has graduated to the omelet station and requests his with spinach (yes!) and we have finally directed my daughter away from sugary cereals (not permitted at home) to more substantial choices. At lunch or dinner time, we have discovered the benefits of sticking to the basics – Spanish rice and beans with some type of stewed or roasted chicken. These are just a few examples of how we have exercised restraint teaching the kids that they can indulge here and there as long as they balance it out with healthy choices.

The quality of the alcoholic beverages leave much to be desired but that is okay because this makes it easier to adhere to our own self-imposed limitations. My drink of choice is wine and the house options are not great but every now and then, I do come across a decent wine. If the wine is truly bad, I turn to champagne mixed with a range of fresh juices. My husband likes to throw back a few cocktails and beer but the liquor is premium by international standards, not top shelf. There is the option to purchase bottles of wine when dining at the specialty restaurants. These wines are of an acceptable quality but slightly overpriced, however we have purchased a bottle here and there as a treat.

Activities, Entertainment & Excursions

Our days follow a lazy rhythm of beach, pools and meals. Common to all of these resorts is the kids’ club that provides daily babysitting services for parents who prefer to drop off their kids for part or most of the day. This is a service that we have never used because we want to spend our days with the kids. These kids’ clubs do a number of activities with the kids throughout the day around the resort. There are some kids’ club activities that our kids have taken part in without us dropping them off and leaving them in the care of strangers.

There are also performances around the pool as well as games in the pools and on the beach that are open to everyone. In recent years, our kids have gotten into the habit in the mornings of reviewing the daily schedule to see which activities they would like to partake in that day. Even though we are relaxing, our days have become a little busier catching games of basketball in the pool, soccer on the beach or foam parties.

We have celebrated New Year’s Eve at a resort the past seven years and have come to eagerly anticipate this evening when the resort transforms itself and throws the biggest party. We have had some of our best nights at the Dreams in Dominican Republic where the buffet became a magnificent presentation of festive dishes and elaborate dessert displays. On these evenings, we reserved our table and pre-purchased a bottle of wine to enjoy with dinner. As per usual, there were plenty of options to accommodate the kids’ eating preferences as well as a number of culinary delights for the adults. Afterward, there was dancing, live music and performances throughout the resort. It was not long before both kids were able to stay up until midnight and we could conclude our night watching the fireworks on the beach.

We look forward to and count on the New Year’s Eve party at the Dreams resorts every year. Unfortunately, this past year at Dreams Playa Mujeres in Cancun did not live up to our previous New Year’s Eve celebrations in the Dominican Republic. It rained the entire evening putting an end to all of the outdoor festivities that we had watched the staff prepare for over the days leading up to NYE. We found it peculiar that the resort did not transform the central buffet as we had experienced previous years at other Dreams resorts. Instead, this resort organized a banquet-style event where for an additional amount, guests would be seated at tables, given a prix fixe menu and entertained by live performances. This wedding/formal party event did not sound or look appealing. We were approached multiple times in advance of this evening to reserve a table but we did not like the idea of a fixed menu because the options were limited for the kids. Plus, we were under the incorrect impression that the buffet would be just as we had experienced in previous years. I am unsure if this something that has changed across the brand affecting all Dreams resorts or if the Dreams vary in how they celebrate New Year’s Eve in the different countries. We will just have to wait and see when we celebrate at Dreams Tulum.

Two years ago, we expanded our vacation to include Christmas day. At Dreams La Romana (which is now owned by Hilton), it was quite the event when Santa Claus arrived on a helicopter and handed out gifts to the children. This past Christmas when we were in Cancun and we went on our first excursion to the archeological site of Chichen Itza. I booked the private tour to Chichen Itza with Amstar prior to our vacation and with the UVC member discount, paid about $800 for a full day excursion. There are plenty of opportunities to plan an excursion after arriving at a resort but I was informed that the rates are better if you book ahead of time. We had considered excursions in the past but chose not to because the kids were too young for some of the activities and length of time away from the resort. Back then, it had not occurred to explore private excursions but just looked at the group packages and was mainly turned off by the itineraries. For the private tour to Chichen Itza, we could have paid half or even a quarter of the amount and joined different sized groups but that would have meant a much longer and drawn out day. Booking a private van allowed us to bypass driving around to other resorts to pick up and drop off other guests, stopping for multiple bathroom breaks along the way and following the tour’s itinerary. Our day trip in a private van with a driver and tour guide gave us complete flexibility over the structure and length of our day trip.

It was about a two-hour drive to the archeological site where we were taken around the Mayan ruins by our tour guide who provided an engaging and informative tour. When we had finished walking through the ruins, we deviated from the itinerary and requested to eat lunch at one of the restaurants around the entrance to the site. After lunch, we were taken to a nearby cenote, as known as a sinkhole, a feature common to the landscape in this region. I had no idea what to expect going in but I was relieved that all swimmers are required to wear life jackets. Swimming in a cenote as a family was a unique and very cold experience that I almost skipped because due to the water’s temperature. There was another stop planned in a town after the cenote but we were content with everything we had seen and done and asked to return to the resort. It was a perfect day.

Extra Costs

I have already mentioned some additional costs such as a private airport transfer, the purchase of a premium bottle of wine with dinner or an excursion, all of which are not mandatory to have a good time. Most resorts offer a full menu of spa services and those fees vary. Furthermore, some resorts offer special dinners out on the beach or in romantic/private locations around the resort, also for an extra fee. These are all optional and at one time or another we have paid extra to try some of these extras but have never felt obligated or committed to spending more with the exception of us always preferring to pay the extra cost for private airport transfers to save time. Depending on preferences and priorities, paying a little extra here and there can make all the difference.

Do not forget to tip the resort staff!

The staff at these resorts work long and hard hours and we have learned that it is not uncommon for many these workers to live several hours away from their families. These staff members are responsible for making the guests’ experiences memorable and it is our duty as guests to show our appreciation through tips. We arrive with an ample supply of $1, $5, $10 & $20 bills that we hand out to staff members throughout our days. Not only does generous tipping show our appreciation but it guarantees exceptional service. After all of these years, we have never had any complaints about service. As I stated at the beginning of this post, service is as good the guest’s attitude and it is within the guest’s power to easily upgrade the quality of service through tips.

Vacation Clubs

For better or for worse, we are members of the Unlimited Vacation Club and will be staying at the Dreams family resorts for years to come. This membership includes a range of resort brands, some that are adults only and others that cater exclusively to families. We tried out a couple of the Now resorts but they do not have as many activities for the kids and carve out a prominent areas of the resort as adults-only, a feature we resented because they were off-limits to us. The benefits of membership include “preferred treatment” meaning that we are treated as V.I.P.’s upon arrival. Some perks include automatic room upgrade if available (which we have received every stay), access to preferred pools, beach areas and restaurants, and upgraded room amenities such as nicer toiletries and, my favorite, a pillow menu. I love the pillow menu and take full advantage every time by choosing pillows of different fillings and firmness. My family does not share my enthusiasm but the shabby pillows at our first all-inclusive resort left their mark and I cherish a plush pillow every time.

Our membership also came with 28 free nights that we have six years to use. These nights cannot be used during days set aside for holidays which means that we cannot use these nights for our Christmas/NewYear’s vacations. We have managed to use 14 of these night for two separate vacations during other times of the year when the kids’ schools are closed and the days are not off-limits. We plan to use the remaining nights for two more vacations which means that this membership came with four vacations. That is how I rationalize what I felt was an exorbitant membership fee. They claim that we get better rates as members but I have not thoroughly researched this claim and cannot state whether or not this is the case.

I have foggy memories from the day when we were approached by a charismatic salesman who reminded us of Pitbull (yes, the rapper). I remember telling him that our goal was to travel the world with our kids and he sold us this membership with promises that it would fulfill our dreams. After we woke up from the haze and I read the fine print in the sales documents, it became clear that this membership is great for the Caribbean but nowhere else. However, we recently learned that UVC has opened Dreams resorts in Spain and they are waiting for all-inclusive permits from the European Union. Supposedly, once this happens, as members we will have access to these resorts in Spain.

At the time of sale, we paid for half of the membership up front with a credit card and the second half was paid in monthly installments over four years and was completed this past January. As mentioned above, we do appreciate that UVC is continually adding to its portfolio with brand new or refurbished properties. The fact that the company continues to expand around the Caribbean and into Europe is also encouraging.

After becoming members, we continued to be pursued by sales representatives every time we went to one of the resorts until we finally made it clear that we were not going to pay anything further to upgrade our membership. Thankfully, it was put into our record that we did not want to sit through anymore sales pitches. When we arrived at Dreams Playa Mujeres, Cancun this past December, the Unlimited Vacation Club representative reassured us that we would not be disturbed during our stay. He was true to his word and this made all the difference because no one approached us to discuss our membership. I hope that this trend continues.

New Year's Eve, 2018, Dreams, La Romana, Dominican Republic

Healthcare & Travel Insurance

When planning a family vacation, the inevitable is unavoidable. Illness will rear its ugly head at the most inconvenient of times. Our son was running a fever when we arrived at the resort two years in a row. In both instances, he received the necessary medical attention on location at each resort. Should the situation arise, these on-site facilities are equipped to handle unexpected and minor medical problems without taking up too much time. Each one of our visits were quick and effective. We did not wait long before doctor examined our son, diagnosed that he had strep throat, prescribed antibiotics and arranged for the medication to be delivered to the resort from a local pharmacy.

We paid out of pocket for the prescription and could have been reimbursed by either our own health insurance or the travel insurance that we purchased for these trips. I never had the chance to explore either option but do recommend that those who find themselves in a similar situation pursue reimbursement after the vacation.

I have been inconsistent about purchasing travel insurance over the years and do not feel passionately about in either way. It is at your own discretion to do so and in most cases it is inexpensive. Keep in mind that most credit card automatically offer a travel insurance and coverage for unexpected cancellation, lost baggage or other issues that could arise before or during travel. Check with your credit card company used to pay for your vacation before purchasing additional travel insurance to see what type of coverage is already in place.

How to Pack

The years of packing diapers, swim diapers, baby wipes, baby food, and snacks are behind me but I did it and although these items take up space, it was not terribly difficult. During this period, we had no choice but to check our luggage because of all the extras needed when traveling with a toddler. There are small shops on location that sell some of these items, but the prices are ridiculously inflated and probably not the brand or type you are used to at home. With this in mind, it is best to pack just a tad bit more than enough diapers to cover your child from the moment of leaving your home to the moment of returning walking back through your front door. Luckily the clothing and shoes for toddlers and little kids take up very little space leaving room for the diapers.

Other items to remember for little kids are swim vests, goggles, sunscreen and maybe some small toys to play with in the pool if you have the room. For new walkers, a pair of crocs or other type of water shoe is good for getting around the resort during the day. You can purchase beach toys to dig around in the sand and inflatables floats for the pools and ocean at the stores that are reasonably priced. In more recent years, since the kids are older and we can travel much lighter, I did pack our own floats that we had inflated when we arrived. I wanted to leave these behind but my kids insisted on bringing them home. This was a one-time experiment that we will not do again because they did not use the floats as much as we had anticipated. We do have a small ball that we toss around in the pool that has been an endless source of entertainment. The kids also bring along their iPads to watch only when we are the room and mainly in the evenings.

As for clothing, bring plenty of bathing suits, cover ups, t-shirts and tanks to wear during the days. These are the items that will get the most use and it is better to have several suits per person because the majority of your days will be spent wearing a bathing suit. Bring some nice clothing to wear in the evenings but no need to go overboard as these items can be re-worn. Some of the resorts require men to wear trousers and some type of loafer when dining at some of the restaurants.

We currently pack everything into four carry-on suitcases, a backpack and a couple of other bags that are permitted as carry-on. We transitioned to carry-on only after my youngest was potty trained. Skipping the baggage claim has cut down on our time exiting airports and eliminated the possibility of lost luggage. Although it is difficult to travel light with babies and toddlers, cherish these years because in a blink of an eye, these babies will be helping with their luggage.

It has seven years and we have not lost interest in the Caribbean as place to relax, reconnect and appreciate the change of scenery from NYC to tropical paradise.

For more about family travel click here.

Click here if you are looking for a little guidance planning your next vacation.

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