Jamaica Family Travel Diary // Traveling With A Baby


Our Family Travel Diary: Jamaica

So excited to finally share our family travel diary from Jamaica with you guys! We planned this trip right after was Easton born not knowing that it would actually be the most perfect time for a family getaway. We have been nonstop since our world got flipped upside down with a newborn and a new business and this trip was exactly what we needed.

Easton was not a fan of the sand ocean! Ha!

Easton was not a fan of the sand ocean! Ha!

We travelled to Jamaica with four of our friends, and one of the couples has a son one month older than Easton so it was a perfect crew! We flew into Montego Bay early Friday morning… I highly recommend planning your flights around your baby’s naps! It makes it so much easier to travel when they are asleep on the plane! I will leave a bunch of my Travel Tips below but that one just popped into my head!

At the airport we rented a van that came with two carseats for the babies and that made our travel day so much easier because we didn’t have to lug a carseat to the gate! If you are renting a car when you travel, definitely call ahead and see if you can rent a carseat as well!


We stayed at a VRBO house that our friends found and it was amazing! It had a full staff the entire week and felt like our own private hotel. It was oceanfront with a pool, tons of shade, and lots of outside seats… which was great for the babies! You can see the house here (this is by no means sponsored and the home owners have no idea I’m sharing this!). It was actually SO refreshing to go on a trip without having to post any content and just BE! We LOVE working with brands and hotels but it was really nice to not worry about ‘work’ or getting the perfect shots for a few days.

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David and I stayed at our own little AirBNB house in Tulum, Mexico a couple of years ago and that was one of our favorite trips we have ever been on! We were really excited to see what it was like “living as a local” in Jamaica. That’s the fun part about staying at a house as opposed to a hotel- you have your own car and can really make an adventure out of it! We drove to local Jamaican restaurants for dinner a couple of nights and even ventured out to a beautiful beach close by… all you need is a phone (maps) and some street smarts!

We loved seeing Easton with all of the locals, he has really never met a stranger. He adapts really well to new places and people but he does NOT adapt well to sleeping in new places! We brought a pack & play and put it in the bathroom with a sound machine so it would be a dark, quiet and cool place for him… but he was not having it. We are still paying for those long nights!


Baby Travel Tips:

How do you fly with a baby?

Flying with Easton has been awesome (so far). I always nurse him or give him a bottle at takeoff (they say it helps their ears) and he normally instantly falls asleep. He has been a good sleeper on planes but I know it won’t always be like that! We bring snacks (puffs, teething cookies, etc) to keep him occupied. It definitely helps having an extra set of hands if you need to go to the bathroom!

Do you bring a carseat/stroller while traveling?

I ended up NOT bringing our carseat or stroller to Jamaica with us because we rented a van that came with a carseat! But while traveling in the states I always check our carseat and stroller at the gate! It really makes airport travel easier when you have a stroller (a place for baby and your giant diaper bag!!). I have never traveled with our carseat base because our carseat can be used with just a seatbelt as well!

Make sure you travel with a SIMPLE travel stroller if you are traveling alone with your baby. It can really be a pain to fold it up and put it on the x-ray machine while also holding your baby! I recommend one of these:

What does Easton sleep in when you travel?

I ordered this pack&play along with this mattress pad and these soft sheets off of amazon for our trip. They turned out to be a lifesaver! We kept his pack&play in the bathroom connected to our room. Easton doesn’t sleep well when he’s in new places, so we just try to go with it and not get too stressed out about his schedule. We keep the routine the same (bottle, bath, book, bed) but we keep his schedule pretty go-with-the-flow… if we were out to dinner, we didn’t stress about getting him to bed on time!

We also brought his Magic Sleep Suit (he loves that thing and I swear it helps), his sound machine, and his baby monitor. This helped me relax by the pool while he was inside taking a nap! I could still keep my eyes on him ;).

What snacks/food/milk did you pack? How?

I totally UNDERPACKED in the food department!! I am still breastfeeding (trying to ween) so I ended up only bringing a small thing of formula. We ran out and purchased some at the grocery store there (you can always get baby food wherever you go!!). I packed a large zip-lock of puree pouches (2 per day) and we used all of them. I also packed puffs and a few of his other favorite snacks.

If you are pumping, you can travel on a plane with breastmilk! Be sure to check your specific airline rules, but most of the time you can carry it on and they may end up checking it at TSA. I recommend packing frozen breasmilk if you are flying with it!

Is it better to fly with a baby during the day or the night?

I find it best to travel with Easton during his naps! We try to schedule our flights around his “sleeping” times so that he can get a good nap in and be ready to go when we land! We really try to keep him on his normal schedule the first day if there is a time change.

Whatever it that your baby LOVES… make sure you bring a bunch. We knew we couldn’t survive without a Paci, so we brought A TON of pacis!!!! If it’s a type of food, or a brand of formula, or a toy, a show…. whatever makes your life easier, be prepared with it!!

Baby Packing List

Beach Trip

Baby Toiletries:

-Diapers (5/day)

-Wipes (1 pack/2 days)

-Swim Diapers (2/day)

-Night Time Diapers (1/day)

-Baby Wash

-Baby Lotion

-Infant Tylenol

-Infant Motrin

-Pedialyte packets (add to water)


-Baby Sunscreen

-Bug Spray

(That sounds like a lot for a baby but we ended up using all of it!)

Baby Sleeping Essentials:

-Pack & Play (we checked this as a piece of luggage, you can NOT check a pack&play at the gate.)

-Mattress Pad **this made the pack&play a lot more comfortable and a definitely recommend it!!

-Pack & Play Sheets (2)

-Magic Sleep Suit

-Sound Machine

-Baby Monitor (and charger)

-Baby Stroller Fan (I clipped this on to the pack & play!)


-Play clothes (1 outfit/day)

-Dinner outfits (however many nights you plan on going out!)

-Pajamas (1/night)

-Bathing suits

-Sun Hat (we love George Hats! You can use HEYMADI for a coupon!)

-Comfy travel clothes (we ALWAYS travel in Baby Breez!!)

-An extra outfit or pajamas to keep in your diaper bag while traveling!!! You will need it!


-TOYS! (We packed these stacking cups and they were his favorite!!)

-I purchased extra large zip lock bags at Dollar Tree and just shoved as many plastic toys in there as I could fit! Make sure they are toys that can get wet.

-Water Float

-Beach Tent (we didn’t use this much!)

-Our friends packed this Joovy Walker and it was a lifesaver! It folds up and super easy to travel with!


-Baby Formula

-Puree Packs/Baby Food your baby likes! (make sure you pack MORE than enough just in case you aren’t near a grocery store!)

-Bottles (we packed 4 and it was plenty! They take up a lot of space.)

-Snacks (puffs, whatever you like!)

Here are a few of our favorite things we traveled with!

Please leave any other travel questions below!!!

Hope y’all enjoyed these pics as much as we enjoyed our trip!