I Can Plan Your Vacation - I Can't Plan the Weather


There are a lot of things I can control when I plan your vacation.
I can help you choose the right resort, figure out the best flights, build an itinerary that makes sense for your family, and make sure you know what to expect before you leave.
Unfortunately, I have absolutely no control over the weather.
I was reminded of that this summer when we traveled to Hawaii and found ourselves flying into Tropical Storm Fausto.
That's where good planning comes in. I was ready to pivot if needed, and we did. We switched up the day we planned to drive the Road to Hana and the day we planned to see the sunrise on Haleakalā. (The sunrise turned out AMAZING, by the way!) The actions that led to us being able to pivot happened weeks before our trip, these were not last minute panicked moves.

We're heading into an El Niño winter, and while El Niño can't tell us what the weather will be on your particular vacation, it can shift the odds in ways that are worth considering when deciding where and when to travel.
So, what does El Niño mean for winter travel?
Florida and the Southeast: El Niño winters tend to be cooler and wetter than average. That doesn't mean a Disney or Universal vacation is going to be a washout, but I would pack layers and a poncho. Build in a day where you can pivot as needed.
The Caribbean and Mexico: Winter is still one of my favorite times to travel here. It's typically the dry season, and El Niño doesn't change that recommendation for me. If your priority is escaping winter for reliable warmth, the Caribbean and Mexico – and Caribbean cruises – are still high on my list.
Hawaii: Hawaii can actually trend drier during El Niño winters, although conditions vary quite a bit from island to island. El Niño weather activity is what’s driving fewer hurricanes in the Atlantic right now, and more in the Pacific so Hawaii is on my recommended list for travel after November 30 this year.
Ski country: The southern Rockies and Southwest can benefit from a more active storm track, while parts of the Pacific Northwest and northern Rockies may trend warmer and drier. In the East, conditions are less predictable, so snowmaking capability matters when choosing a resort.
Southern California and Disneyland: El Niño can bring a greater chance of rain to Southern California. That's not a reason to avoid Disneyland, but it is a reason to pack differently and build some flexibility into your plans. Instead of one or two days, consider two or three days so you can pivot and not miss something special that you traveled there for.
Costa Rica: Winter is generally a fantastic time for the Pacific side of Costa Rica as it moves into dry season. The Caribbean side follows a different weather pattern, so let’s talk about where you want to go and what you want to see in Costa Rica first, and then we can examine the weather.
You can't weather-proof a vacation. You can plan for it.
This is the part that sometimes gets lost when we talk about the "best time" to visit somewhere. There is no week I can promise you sunshine. There is no Caribbean island that comes with an absolute hurricane guarantee. And there is definitely no way for me to make it snow in Vermont just because you booked a ski trip.
What I can do is help you stack the odds in your favor.
That means looking beyond average temperatures. It means considering rainy seasons, hurricane seasons, historical patterns, snowmaking, flight schedules, travel insurance, and how much flexibility your particular vacation has if Mother Nature doesn't cooperate.
Sometimes it also means telling you, "Yes, you can go there in March. But here's what I want you to know before you book it." If we have the hard conversation upfront we can spend time later planning for the “what ifs” so that a weather related flight delay or 5 days of steady rain doesn’t completely ruin your vacation.
Thinking about a winter or spring getaway? Send me your dates and what you're hoping for. I'll help you figure out which destinations give your family the best odds of finding it.
Just don't ask me to guarantee sunshine. That's apparently still above my pay grade.
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