I’m here to encourage you to get away from the cold and grey Chicagoland skies and jet off to a fabulous vacation WITH kids in tow. Yes, that’s right, you can have an amazingly enjoyable and fun vacation with your kids. It’s not going to be the same as before they were born (I mean, is anything the same since becoming a parent? I think not.), but it will most definitely be a welcome respite from winter. I’ve chatted with numerous Chicago families and have come up with this list of seven family friendly tropical trip locations for Chicagoans.
But before we get to talking about fun in the sun, let’s be sure that you have your expectations in check. Traveling with kids is always an adventure, with them being off their schedules and away from home you really just have to roll with the punches (it helps if you have a rum punch in hand) and just go with the flow.
If possible, try to stick to home base and make it as comfortable as possible. That might mean shelling out a few more dollars for a suite instead of a standard room but trust me, it makes such a great difference. Be sure to look into Airbnb as well as VRBO to expand your options.
Figure out what YOU want to get out of the trip. For me, it doesn’t feel like a vacation unless I have devoured a great book. So my priority is to make sure I have a book and time to read it. If that means that I read on the balcony while my boys are snoozing and encourage my hubby to go out on an adventure, that’s fine with me. If you really want to go to dinner without kids at least once, be sure to look into hotels and resorts that have reputable and highly acclaimed kids’ clubs and other babysitting services. Spoiler alert: All of the resorts and hotels on this list fulfill this need.
Have a willing aunt or grandparent who would love to help out with the kids and have some fun in the sun? Bring them along. It will ease stress (hopefully) and an extra set of hands is always helpful. And it will also ensure that you won’t have to take family selfies all vacation long…if you don’t want to, that is.
Look for trips with the most direct route. Skip layovers whenever possible and be sure to look for hotels and resorts that aren’t a long ride from the airport. Speaking of which, I highly recommend bringing your own car seat. Although it is annoying to lug around the seats, they will come in handy when you cannot rent car seats and will keep everyone as safe as possible so you can focus on having an amazing vacation.
Why moms love it: Travel is a piece of cake with a direct flight and no need for a passport since San Juan is a United States territory. There are tons of beautiful beach front rooms available so this is the perfect place for beach lovers, young and old. And if you can get a break from the kiddos, you can try your luck at the casino.
Why moms love it: You simply can’t go wrong with an Iberostar resort. The Iberostar Lindo is no exception. This all inclusive resort is a hit with families because it is HUGE and boasts so many things that are perfect for everyone in your family. There are many different activities to choose from and you can see many of these first hand on my Instagram feed in a few weeks when my boys and I visit this popular resort. I. Can’t. Wait.
Why moms love it: This all inclusive luxury resort is the only one in Cancun that caters to kids just as much as it caters to adults. There are different kids clubs available depending on ages and specific areas that are just for kids, no adults allowed—how cool is that? There are also family suites with childcare included so that you all can experience every moment of vacation (that means no sitting in the dark after bedtime, parents. Hooray!). This resort is very grand and large so if you are looking for a more intimate yet similar resort, look into Beloved Hotel and Resort.
Why moms love it: This family friendly all inclusive resort has it all. And even better? The kids activities are included in your package price so there is no need to pay additional fees for supervision when you need some time away from the kiddos. There is a waterpark, endless activities featuring Sesame Street characters, and all of this fun is focused around one of the most amazing beaches in the world. It is only a 10 minute ride from the airport to the hotel and there is a quick and easy direct flight from Chicago….basically there is no excuse as to why you aren’t packing your bags right now. Tick tock.
Why moms love it: If you are looking for spacious accommodations to use while at a beautiful white sand beach, the Marriott Aruba Surf Club is the resort for you. There are tons of beautiful villas to choose from, or you can also rent a time share. There are tons of kids’ activities and the nearby town has lots of things to do and explore as a family. Don’t forget that when booking a villa, you will be able to do some of your own cooking, which might serve your picky kids’ appetites much better than restaurant food.
Why moms love it: This highly rated and all inclusive resort caters to both the young and old with a plethora of activities. The food is highly regarded, as are the kids’ pools and amenities. Located on Bavaro Beach, one of the most beautiful beaches in the world, it is truly a great way to get away from mundane parenting tasks and simply enjoy your time together as a family.
Why moms love it: Sandpiper Bay is part of Club Med, so you know that they have delicious food and fantastic activities to keep everyone entertained while on vacation. Kids will love the waterpark while parents enjoy the spa, tennis courts, and more. Sit back and relax knowing that all meals and drinks are included, and that there are highly qualified staff to provide childcare if desired.
And if you want your vacation to actually FEEL like a vacation, book with Mickey and head on a Disney Cruise! You can read all about our amazing experience at sea here.
I hope that these tips from local Chicagoland moms inspire you to book a trip, no matter how anxious you might be about traveling with kids. Once you see that crystal blue water and feel the sand in between your toes, it will be totally and utterly worth it.
Happy and safe travels!
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