Besides it being well-overdue, it was everything Aiden and Mommy needed. The second we landed in Jamaica, whatever sinus pressure we were feeling was GONE! I mean, let’s face it, we were thrilled to escape the bitter cold. This was not Aiden’s first time out of the country or his first time to Jamaica, rather our first time traveling alone (flying that is)–without family. I was excited, whilst my mother was a nervous wreck about EVERYTHING.

Needless to say, I over-prepared and I’m glad I did. The last time Aiden and I went to Jamaica, his father was with us. He was a lap baby at the time, traveling only at 6 months of age. Jamaica–my father’s island home, gave me a slight hard time leaving with my child. Not that they were holding me there, but they took a copy of his passport without real explanation and attempted to make me pay additional fees for Aiden despite him having a roundtrip ticket booked attached to my airline ticket. But guess what, none of this happened this go around. So let me tell you!

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Planning our trip: The airfare to Jamaica was ridiculously overpriced. I’ve been accustomed to round trip tickets in the $300 range; however, these round trip tickets were nearing $500 and up! This was also the first international flight that I had to pay for Aiden’s flight full price–courtesy of 2 year old Aiden P. (holds head in turmoil). I waited and waited and waited, then finally purchased our airfare in December for our January trip for my brother’s wedding (don’t tell him I waited that long–the ring bearer was there and that’s all that matters).

The plan was pretty solid. My brother chose the resort that he wanted the wedding to take place: Sunscape Sunsplash and Cove Resort in Montego Bay. The resort was cute and purposeful. Our family normally stays in Ochi (Ocho Rios), but the proximity to the airport and decreased travel time for everyone was appreciated.

My intention for this trip was to rest, relax and soak in every little bit of the sun that I possibly could. I did just that. Let’s not forget enjoying time with family and the wedding itself!

Departing NYC: The ride to JFK in the wee hours of the morning was still a lengthy hour and some change trip, but it was smooth. We had to arrive at the airport sometime in the 4 o’clock AM hour, so we left home around 3:00 AM. Aiden woke up curious of where we were going, which was absolutely fine and tied right into my plan. We were dropped off by his dad, so it worked out well. I do think; however, I won’t inconvenience anyone else and will make sure to find a Groupon for airport parking for future trips.

I was concerned that there would be issues with getting through security due to the government shutdown, but it was SMOOTH. I tend to book the first flight out because I want to spend as much time in our destination as possible. At this point, there were only 10 people in the line for TSA. The workers were pleasant and still took their jobs seriously–I didn’t experience any of those other neglectful behaviors being mentioned on social media.

Through the airport: After clearing security, we ventured through the airport while Aiden rode his chariot (the suitcase). Then there was the most important part for a peaceful and successful flight. I let Aiden walk. I let Aiden run. I let Aiden have all of the fun. This is the reason why I was okay with him having been awake at the time that we left home and for the duration of the ride. He would be tired once we boarded the plane–and that he was. We ate our chocolate chip muffins for breakfast that I pre-packed. However, for my hungry child, that was not enough and I did have to buy something small from McDonalds. It was a really big muffin though, y’all.

Eventually Aiden grew tired and we slowed our steps. I pulled out his flashcards and kept him entertained for about 10 more minutes until it was time to board. One of my favorite parts about traveling with him is being one of the first to board the plane. It allows us to take our time in settling on the plane. Specifically, I use this time to allow him to walk up and down the aisle to see the plane, stand in the chair and then finally buckle his seatbelt. I had a child safety harness to attach to his seat since I wasn’t traveling with a carseat, but the flight attendant on Caribbean Airlines was looking at me like I was crazy, as she had never seen the FAA approved contraption before. Best believe I kindly put it away and planned for its return to Amazon.

To our surprise, we had the entire row to ourselves. I laid out Aiden’s blanket prior to takeoff, as I knew the time would come where he would be ready and willing to sleep. We were barely in the air when I noticed my little man SNORING! (Huge mom win!)

I was pleasantly surprised by Caribbean Airlines–a breakfast meal included in the airfare. Anyone who knows me, knows I love food. You also know I don’t eat eggs; however, I ate the breakfast frittata and it was delicious. Our flight from JFK landed early, around 3 hours (should have been 3.5 or a little more) and I was THRILLED! My uncle awaited our arrival and on to the resort we were. My mom was beyond excited to hear that we landed and I was ready to touch down, unwind and eat. Aiden behaved as if he had been there before, like he owned the place and as if he was home. He was the big man on campus.

Our Resort: Sunscape Splash and Cove was a cute resort. It served its purpose. The property was clean and fun. It was definitely tailored to families. The lazy river sealed the deal for me and the beach was functional. It was a low-key resort that did everything we needed to do. I personally won’t make any plans to stay in Montego Bay anymore, but that’s also because I have my preferences and familiarity to Ocho Rios. Furthermore, I’d like to stay in my family’s parish more often–Portland.

What Did We Do: Besides the wedding, we had a beach day and a pool day. Both were amazing. We were able to maximize on relaxation time before we planned for our excursion to Jamwest where we rode on ATVs, zip lined and then ventured to Rick’s Cafe in Negril for the sunset. We had people who attended the wedding who were traveling to Jamaica for the first time and needed the tourist experience. We also made a stop to Scotchies that provided some satisfaction to our tastebuds.

For Aiden: His priority was the water. Whether he was on the beach or in the pool, he wanted to be in the water until he dropped. Each day, the sun and water knocked him out for a nap. This allowed me to rest and listen to my audiobook uninterrupted. Room service made this process all the more easier.

Returning Home: We had a later flight, around 5:00 PM that returned us back to NY some time after 9:00 PM. Surprisingly enough, we did not experience any issues in Jamaica or in JFK when we returned. I sailed through the check in process at the airline’s counter, then proceeded to check into Club Mobay. Club Mobay is a must-do lounge that allows you to await your flight’s departure comfortably. They had a play area that was optimal for the time spent in the airport, especially since you should arrive 3 hours before your flight. Aiden played freely and ate the food provided in the lounge.

Unfortunately, on our return flight, Aiden did not want to sleep. I was bummed because I had to (1) keep him still and keep him entertained. He had his shows pre-loaded on Netflix, but Mr. Particular wanted to watch specific things that I did not download. He wasn’t fussy or anything, but this flight did not have any open seats like the previous flight and I just wanted to sleep myself. I felt badly for the woman sitting next to us because she was trying to sleep and he was somewhat fidgety.

Once we landed in JFK, I completed the Mobile Passport form, zoomed through customs and we were on our way to my friend’s car and returning home.

The trip was so necessary for both of us to get away from the day to day of New Jersey living. The adjustment on the return side was a little difficult. He had some trouble continuing potty training and quite frankly I’ve seen a decent amount of regression ’til this day. We’re working on it though.

Here are some tips to take away for traveling with your toddler:

Travel during the times your child would otherwise be sleeping
Pack your child’s clothing in the carry on (I’m a little on the paranoid side and would hate to lose his clothes)
Move around the airport as much as you can
Board before everyone else
Be prepared with books, flashcards, videos or whatever else keeps your child entertained
Pack snacks to minimize cost
You can bring bottled water and/or juice if you have your accompanying toddler (I don’t know of the maximum age)
Keep extra clothing accessible (personal item or book bag)
Have a portable charger/external battery