Who doesn’t love escaping the cold long winters and heading to the warmth of the Caribbean. With so many islands, each offering something different, the travel possibilities are endless. From luxury resorts, to eco-lodges, to vacation rentals, there are accommodations for every families needs and price point. We always choose a smaller resort, with a more local vibe, over a large commercialized resort. We travel, explore and immerse ourselves in local culture.

The Caribbean boasts about 700 Caribbean islands, but only 28 of them are deemed sovereign states and dependent territories. Starting with the Bahamas and Cuba, located off the tip of Florida, the string of Caribbean countries arc down towards Venezuela.

Covid Restrictions: Check the most recent Covid requirements of the island you are wishing to visit, every island has different requirements. And remember getting back into the USA (or your home country) there are also Covid requirements. This makes Island hoping difficult, and the logistics of travel a bit more of a pain. But in the end it is always worth it.

Airport Security with toddlers: Be organized, I can’t stress this enough. Have your fluids in a Ziploc bag and let the agents know if you have water or milk for the baby. Have your laptop & any tablets together, so you don’t have to remove one from everyone bag. Shoes have to removed for adults, but children don’t, I found the most amazing shoes by Kizik, while a little pricey they are hands down a necessity.

Waiting in the airport with toddlers: Let them get all of their energy out. Take them out f the baby carrier, or stroller and let them walk, jump, & run. My 4 year old loves the moving walkways, so we do those a bunch, that is, if they are close to our terminal. I always feed my kids snacks and offer drinks while waiting, refill their water bottles and then as boarding starts everyone (including myself) tries to go potty. If you have a kid in diapers, this is your opportunity to do one last diaper change before boarding. I do not rush onto the plane, we always board towards the end regardless of our boarding status, otherwise you just are sitting waiting on the plane.

Flying with toddlers: I have never bought a seat for my kids under the age of 2, lap infants fly free (just pay taxes) till 2, so we are taking full advantage. At the gate you can check with the agent if there are any empty seats on the plane, if there is, they can usually arrange it so your lap infant has their own seat! It is important to know on shorter flights, under 3 hours, there is no food service, just a snack, usually pretzels, and beverage service. So make sure to bring food or snacks on board. Each of my kids gets their own backpack as a carry on, and I fill it with toys, activities and snacks to keep them occupied. If your kids are going to have their own carry on, keep them light!

Jet lag with toddlers: My rule of thumb is to power through day one. I find babies very easy to travel with, my kids have always napped anywhere and so we didn’t have to worry about a routine, or bedtime.

Naps on the go: I’m lucky that my kids literally nap anywhere, whenever they are tired. My daughter has grown out of a routine nap, but my son still is napping in the middle of the day.

Tips for travelling the Caribbean with toddlers: The sun gets very hot in the middle of the day. This works for us because my youngest naps in the heat of the day, and my oldest and I take a little relax or swim in the pool and have a mommy daughter lunch date. I highly recommend bringing sun hats, SPF sun-shirts and SPF 50. We pack light no matter where we go, so I bring TIDE laundry detergent powder so I can wash the swim suits and any clothes, and hang them out to dry.

Getting around the Caribbean islands: It really all depends on your trip, sometimes rental cars are not necessary. Your resort or hotel usually can arrange ground transportation for you from the airport, and usually can arrange tours or day trips. However if you want to see more of the island, and head out from your resort or hotel, a rental car is the most cost efficient and reliable way to get around. Island hopping used to be much easier, but because of Covid it is more expensive, logistically more complicated, and not always possible, as flight routes have been cut.

Click the links below to explore the Caribbean with us!


St. Kitts & Nevis

US Virgin Islands

British Virgin Islands

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