We hired a car for the transfer from our house to the airport as trying to navigate parking lot shuttles with an infant is not recommended. We arrived 2 hours before the flight and made it through the long security line with minimal hassle. They let the little man remain in his Baby Bjorn through the entire process which was nice. We paid $150/per person to upgrade to first class at the gate. Tip - sometimes paying to upgrade at the airport is less than booking first class in advance. The flight was uneventful, the little man slept and my daughter kept the flight attendants busy in conversation.
We arrived in Jamaica to find only 3 of our 4 bags had made the trip with us. I had mixed emotions when I realized it was the baby's bag. I was thrilled it wasn't mine as my suitcase had considerably more expensive goods and his belongings would be cheaper to replace. Yet, I was panicked because I wouldn't be able to replace his crucial supplies until we were home. (Crucial supplies for babies in the Caribbean = infant sunscreen and bug spray, mosquito nets fitted for the pack 'n play and stroller, baby size sun hats, and swim diapers...) After almost 2 hours tracking down the bag it was deemed lost and we reluctantly left the airport for the villa. We quickly sourced some diapers and formula and I thought I could make it a week with the 5 baby outfits we had in our carry on.
Luckily, I didn't have to wait a week. Air Jamaica located the bag, it didn't make our flight because it was stuck on the belt at the ticket counter. 48 hours later and we had the bag. Crisis averted!
The Caribbean is a great family destination, even for families with infants. The "island time" mentality makes most people you come in contact with extremely patient and understanding of baby's needs.
We were unable to upgrade to First Class on the return flight and thankful to see our bulkhead seats had not been switched. Tip - with babies, try to fly bulkhead, you will be so thankful for the extra space! Overall, it was a great trip even with the littlest one in tow!