When is the best time to book a beach trip?
It’s a trick question.
The answer is any time.
As has been well documented in this space, our family takes a beach trip each summer. For 20 of the past 21 years we’ve been to Santa Rosa Beach on 30A along the Gulf Coast of Florida between Destin and Panama City. We have settled on the week of the Fourth of July as the timing for this trip even though it is literally the most crowded and most expensive week of the year to go to 30A. Family schedules forced us into the date. Nostalgia draws us back to the location.
We have also tended to book this vacation in the immediate aftermath of the Christmas holidays. Maybe it’s because we have a moment to catch our breath and do the planning. Maybe it’s because it’s cold outside, and we want to think of warmer destinations. Maybe it’s because we need to book a rental because 30A fills up. Maybe it’s all of the above.
Just like moms make the magic of Christmas happen for most families, they also make beach vacations materialize out of thin air. I give my dates of availability, pack the car, wake everyone up WAY too early, and drive to the beach. That’s about the extent of my involvement.
But I have noticed this year’s planning is somewhat different than in years past. For one, it’s the last day of January and we still don’t have our vacation booked. It feels very dangerous. The delays are understandable given the current life stuff we’re dealing with, but instead of letting the thoughts of sun, sand and surf transport me to stress-relieving daydreams, I worry that we’re missing out on the best condo with the best view and best beach access.
Another way our planning is different this year is that it has become protracted. We used to pick a date, my Darling Beloved would pick the place, and voila, done. Anyone we would be taking with us was already subject to our dominion and their scheduling conflicts were already factored in. This year, planning our beach trip has been trying to solve the world’s most complicated logic puzzle factoring in persons, availability, locations, rooming arrangements and non-human companions. When my Darling Beloved pulls this off, she will have attained new levels of necromancy.
This year we have also seriously opened the discussion of location in a way we haven’t before. We go to Santa Rosa Beach. That’s the one place in the entire world with the beach. At least that’s the way we treated it. SRB is where we’ve made the family memories and begat the traditions that we must re-enact every year.
Only, the last few trips to SRB have seen an increase in cost and congestion. We’ve had a great time, but we’ve found ourselves daring to ask the question on the way home, “Is there a beach somewhere else in the entire world we could go and still have a good time?”
Lastly, one of the biggest differences in our planning this year has been the juxtaposition with repeated winter storms, casting a bleakness and isolation not experienced since pandemic lockdown. Last weekend it was Winter Storm Fern. This weekend, we’re looking at 1-3 inches of snow here in the thriving metropolis of Thrillburn. We get it. Baby, it’s cold outside. The threat of winter precipitation out here keeps canceling all of the activities that take our minds off of beaches and such leaving us to sit in our homes and contemplate, nay, even covet time on the beach.
The travel industry knows this. I defy you to turn on your television (no, not one of the thousands of streaming services you subscribe to when you “cut the cord” in order to pay more while “saving money.”) I’m talking regular, old cable TV. The commercials are all cruise lines, inclusive beach resorts, hotels, VRBO, AirBnB, and exotic destinations like Panama City Beach. I don’t know who these travel marketing people are, but they are making data-driven decisions on ad buys, that’s for sure.
Here’s what I know about our 2026 beach vacation: some time between June 1 and August 1 some number of our family members and their significant others numbering between two and eight will spend five to 10 nights on or near a beach with one to four rooms overlooking either a resort swimming pool or the Gulf, and I will pay an exorbitant amount of money for the privilege.
That’s what I know.
For now, it will have to be enough to get me through this winter, or at least the 57 days of January. And I am pledging publicly to do all the chores to give my Darling Beloved time to do all the mysterious things she does to make our beach vacation wonderful.
New South Essays 