Taking two young children to another country on your own might sound like a wild idea — and I totally get it. But recently, I packed up the essentials, embraced the adventure, and flew to Jamaica with my two little ones… solo. And you know what? It turned out to be one of the most rewarding experiences of my life.
Yes, there were challenges (hello, 5 a.m. flight delays and surprise flat tires), but there were also unforgettable moments, new discoveries, and plenty of laughter. Whether you’re a seasoned traveler or a first-timer, I’m sharing what worked, what didn’t, and what I’ll absolutely do again on our next family trip — because moms deserve vacations too.
1. Pack Kid-Friendly Snacks Like Your Sanity Depends on It
Let’s start with one of the biggest lessons: never underestimate the power of snacks. Our 5 a.m. flight was delayed, and we had a tight connection, which led to me literally picking up my youngest and sprinting through the airport to catch our next flight. We were one of the last families to board, with no time for food or restroom breaks. Having kid-approved snacks on hand was the difference between a smooth(ish) journey and a full-blown toddler meltdown at 30,000 feet.
2. Pull-Ups Are a Smart Backup
Even if your child is potty-trained, long travel days don’t always go as planned. Between flight delays, airport transfers, and customs lines, bathroom access isn’t always guaranteed. I opted to use a pull-up for my youngest just in case — and I’m so glad I did. It gave me peace of mind, and there were zero accidents.
3. Carry Cash — Especially in Local Currency
This may not be a popular opinion in today’s tap-and-go world, but I always recommend traveling with cash. And in this case, it saved us. While driving in a rural area, I ended up with not one but two flat tires. Although I contacted the rental car company (a major brand), they said it would be hours before help arrived. With two small kids in tow, waiting wasn’t an option.
Thankfully, a local tire shop nearby was able to patch one tire and replace the other. They didn’t take cards — only cash. Having Jamaican currency on hand meant I could take care of the issue quickly and get us safely to our destination. The extra out-of-pocket expense? Totally worth it.
4. Use the Family Line at Immigration
Not many travelers know this, but some international airports offer special immigration lines for families — and they are a lifesaver. We were able to breeze through customs while others waited in longer lines. If you’re traveling with kids, always ask about this perk!
5. Don’t Be Afraid to Rent a Car
This might surprise you, but renting a car was one of the best decisions I made. It gave us the freedom to explore, stop for snacks, take bathroom breaks, and visit places off the beaten path. Plus, I got to challenge myself — I now confidently drive on the left side of the road, roundabouts and all!
When traveling with kids, convenience is key. Renting a car saved us both time and money and made everything from excursions to mealtime so much easier.
6. Plan Ahead, But Leave Room for Spontaneity
As a travel concierge, I’m all about having a solid plan, especially when kids are involved. But I also believe in leaving space for spontaneous fun. One day, we made an impromptu stop at some nearby caves — and my youngest hasn’t stopped talking about the bats since! It wasn’t on our itinerary, but it turned out to be one of the highlights of the trip.
Final Thoughts: Moms Deserve Joyful Travel Too
Traveling solo with kids can be challenging — but it doesn’t have to be stressful. With the right preparation, mindset, and support, it can be one of the most empowering and joy-filled experiences of your motherhood journey.
As a certified travel concierge specializing in Caribbean travel for families, groups, and first-time visitors, I’m here to make the process smoother, safer, and more enjoyable. From kid-friendly accommodations and local guides to transportation and emergency tips (like where to find the nearest tire shop!), I’ve got you covered.
Ready to Plan Your Own Island Adventure With the Kids?
Whether you’re dreaming of sandy beaches, vibrant festivals, or a relaxing reset with your little ones, I’d love to help you make it happen — stress-free.
📩 Let’s talk about your next Caribbean escape!
[info@caribbeanislandfestivals.com] or follow along on Instagram [@caribbeanislandfestivals for more tips, stories, and travel inspiration.
