In the midst of the dog days of summer, it might be hard to even think about planning your winter break vacation when you're still soaking up the sun and heat and sipping that rosé all day everyday. Not to mention the thought of going back into the carpool drop-off lane gives you the heebie jeebies.
Yet the reality is that most resorts and hotels quickly sell out over what the travel industry calls, “Festive Season.” This is the period of time that begins around a week before Christmas and goes through a few days after the New Year. And not only is availability limited, but the rates increase drastically, especially in September and October as more people begin to plan their winter break fun.
Which is why if you've got a specific resort or destination on your mind—especially if it's somewhere in the Caribbean—it's time to start looking and booking now. Like, right now.
So where to start?
First, and this is a no-brainer but bear with me, find out your school break dates. Then work with your partner, kids and maybe grandparents, over which dates could work for a getaway. Keep in mind that Christmas and New Year's Eve will have higher rates than the other dates.
Third, and this is the fun part, pick two destinations for where you want to go. One tip to remember is that flights get expensive over this time of year as well, especially to popular destinations like Florida and Mexico, so that cost might impact your destination choice. Lastly, start looking at hotels and resorts in both destinations for the best type of spot for your family.
Think about this carefully. Do you want to drop the kids off at the kids club and hang out with your lover during the day? Then a full-service hotel is for you. Or maybe you want quality family time which means a vacation rental could be a better option. If you want something in between, then maybe you'd splurge for a suite at a not-as-fancy hotel. If you've got a big crew and want to keep costs reasonable, consider an all-inclusive resort.
THE EASY BUTTON: One last option is to hit me up for planning and booking help. In addition to being a travel journalist, I'm also a travel agent with Elite Travel International, a Virtuoso-affiliated travel agency that's powered by Cadence Travel. What this means is that I can tap into access, contacts, and perks from a variety of hotels, resorts, cruises, and tours.
Below are a few of the luxury hotels and programs that offer my clients special benefits. However, the range of perks and personal attention goes well beyond these brands.

Typically, these perks include resort credits, upgrades (if available), welcome amenities for you and your brood, and more. You'll pay the same rates but you'll get personalized service than if you booked through some giant travel supplier. And as your trusty travel agent, I'll give you honest feedback about properties and cruises, based on my own first-hand knowledge and that of my fellow agents. (Seriously, the agents all talk to each other all day long about places to see and places to skip.) So send me an email!
OTHER STORIES YOU MIGHT LIKE:
Living La Vida All-Inclusive at the Grand Velas Los Cabos Resort
Kids Get Merits While Parents Get Mai Tais at Montage Kapalua Bay Resort
You Take The Good, You Take the Bad With The Moon Palace Jamaica Resort
