Traveling with a Baby to the Caribbean

Having a baby turns your world upside down and one of the last things you may be thinking about is traveling.  That said, if your an avid traveler like Samantha and I, once you emerge from the twilight zone and no longer feel like a walking zombie, you'll start to think about how you can make it happen so you can emerge your little one into one of your biggest passions.  While you may not be able to go elephant trekking in Thailand or scuba diving in the Indian Ocean with your 5 month old, you also don't need to be beholden to two hour road trips either.  And a great destination with a lot to offer that's perfect to bring a baby is the Caribbean.

August soaking up the Caribbean 
We took off twice for the Caribbean this winter and our first stop was St. Martin.  The first tip I'd give to you if traveling with an infant is try to make the travel part as seamless as possible aka aim for direct flights.   It was pretty easy to see which islands offered direct flights using Google Flight's map view so once you filter on that, you can start to narrow it down.  One of the reasons we chose St. Martin was given it had the French and the Dutch side, it felt like it had a little more to offer from a cultural perspective than just a nice sandy beach (even though that's all we would really be doing).

The beach at the Belmond where staff would help you get all set up and serve you meals and drinks 

The second thing that was important for us was having everything at our finger tips, especially since it was just Samantha and I.  We didn't want to have to travel for the beach, food, pool etc... and we also wanted a nicer place that would have a good staff to help us out.  We ended up at the Belmond La Samanna, which is one of the nicer resorts in the Caribbean and also one of the reasons I also chose St. Martin.   It was perfect for us, it had everything we needed and the staff was incredible making it very easy to to enjoy ourselves despite having a four month old.  Here are a few tips I would share for anyone going to a beach destination with an infant that we learned while in St. Martin:

The view from our balcony 

  • Bring a sun tent for the beach, it was extremely handy as August was able to take most of his naps on the beach in there 
  • Even more important, bring a portable fan; not only for the tent but for all parts of the vacation as he was way less irritable with it 
  • Make sure you have the mosquito net accessory and the sub block accessory for the stroller; good for day time walks and dinner at night 
  • As for the stroller, I couldn't recommend the Doona more as it's a stroller that easily converts into a car seat and perfect for taking on a plane 
  • If you are willing to splurge and it's available, try to get a room on the beach; it will make it easier for naps because you can easily put your infant down in the crib and have the monitor on the beach.  We were lucky that he was able to fall asleep most days on the beach but there was one nap he wouldn't go down so we trekked back to our room where we stayed for his nap  
  • At the very least, get a balcony with a good view; for his morning naps we would sip iced coffee over looking the ocean and the one time we did have to leave the beach, it wasn't too bad because we ordered wine and cheese while soaking up the the afternoon sun; it made it feel like we weren't holed up in our room when we had to be there because of him 
  • We opted for dinner on the early end so we didn't have to pay for babysitters or eat in our room and we would time his bottle for when we ate as allowed us to get a good table and fit his stroller next to our seats while he was in a decent mood 
August passed out in the tent as me and Samantha enjoy tropical cocktails 

All in all a higher end beach resort is a great spot to head to for 4 - 5 days to feel like you are on some semblance of a vacation with an infant.  I would highly recommend this option if it's just you and your partner along with the baby.  It will me much better than say an AirBnB because you are going to want the few extra hands there to help you relax.  And while there are a number of options out there, I can guarantee there probably aren't many better options than the Belmond.

The beach at the Belmond where we spent most of our time 
If you are going to be with a bigger group, especially with multiple babies, you may want to opt for something a little different.  The great thing about the Caribbean is there are a number of private villas that can host up to 3 - 4 families which can be a great option pending what comes with it.

The whole gang at our villa 

We went away with my entire wife's family which included four infants and a toddler.  That sounds like it could be extremely chaotic but the set up we had was perfect and made for a very relaxing vacation.  The keys for us was truly did not have to leave our property which is what you should be looking for if you find youself in a similar situation.

The private cove at our villa
For one, the house was private and we had enough space for all of us.  It also had a private little cove/beach along with a pool, a small gym, a private tennis court, as well as some water sports like kayaks and paddle boards.  However the best part of it all was that there was a full time staff including a chef so you truly didn't have to lift a finger.  When you have an infant, the last thing you want to do on vacation is have to cook or clean up after yourself so this made all the difference.

Fishermen would come up to our villa for our chef to buy fresh fish 
The other reason why this set up is so great, is that you can easily do everything on the property while not having to worry about any logistics.  If you were schelping to a beach, you would have to ensure you had a enough diapers, bottles, worry if they had a melt down, etc, etc... But here, we didn't need to worry about any of it which made it a whole lot nicer.  We could be lounging out by the beach and when it was time for our son to take a nap, we just went and put him in the bedroom and then went right back outside.  Also for dinners, we would put all the kids to bed first and then the chef would serve us a meal by the water, kid free.  It at times, almost made us feel like our pre-kid life, almost.

The three of us enjoying the pool in Jamaica 

If you are traveling with a big group, especially with multiple kids, I can't recommend this option enough.  We enjoyed it so much we are already thinking about going back next year.  I think the thing to keep an eye out for when you do book a private villa is ensuring you have private beach access, some activities on site and most importantly, a staff.   The villa we went too was called Keela Wee in Discovery Bay, Jamaica.  I was a huge fan of the villa but also really like Jamaica for the culture and the people so it's another great island option to go with an infant, especially with the flight time from NYC.

Discovery bay in Jamaica 
All in all, you don't need to not travel once you have kids.  You should have them start to adapt to your lifestyle and get them on the road as soon as possible.  Just be prepared and do you research and while your first trips may not be as exotic as you were once taking, the Caribbean is not a bad option and has plenty of different options.  Plus, if you are on the East Coast, you can be a number of the islands in under four hours.  I have a feeling we will be seeing a lot more of the Caribbean in the coming years.

The Caribbean 


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