The Mistake That Costs My Clients Double Every Time
I almost made it myself last Tuesday.
I have been telling clients for years. Book early. The best properties, the best rooms, the best experiences fill up faster than you think. And when they are gone, what is left will cost you significantly more or simply will not exist.
Dan and I have been talking about a luxury cabin getaway for our November anniversary for longer than I care to admit. It kept landing on the "we should do that soon" list without ever making it to the calendar.
Last Tuesday I finally sat down to look at Blackberry Farm in Tennessee. Two cabins left at the entire resort.
I did not close the tab. I did not sleep on it. I booked it right then, at 10pm on a Tuesday, and Dan was very happy about it. 😉
Here is what I want you to understand. Booking early is not about being impulsive. It is about being intentional. No pressure, no full commitment upfront. Just a smart, intentional first step that keeps your options open while securing the best of what is still available.
Annnd I have a system for it. (surprise, surprise)
Start with your bucket list.
I keep mine in the notes app on my phone. Destinations I am dreaming about, with weather notes throughout the year so I know the ideal time to visit each one. It sounds simple because it is. But having it written down means I am never starting from scratch when it is time to plan.
Look ahead and pick one or two.
Every year I look at the following year and choose one or two trips I really want to make happen. I pull up my calendar and space them out intentionally so travel feels like something to look forward to, not something that snuck up on me.
Do your research early.
What is that beautiful little luxury boutique property that is difficult to get into? What does it cost at a refundable rate versus nonrefundable? I research both. And I set a calendar reminder for when the refundable window closes so I am never caught off guard. Sometimes I even go back and compare the nonrefundable rate to what I originally booked. If the savings are significant enough and it’s still available, it is worth making the switch.
Get your people excited before you book.
I talk to Dan or my girlfriends early. I share what I am thinking, get a feel for who is in, and confirm schedules before I commit. Nothing worse than booking something wonderful and then discovering nobody can make it work.
Book it. Even if it is just a deposit.
I would rather secure that luxury boutique room at a refundable rate than deal with spiked pricing and last pickings three months from now. A refundable booking is not a full commitment. It is a placeholder that keeps your options open while everyone else waits and loses.
I have a client who books last minute every single year.
She knows she does it. We have talked about it. And this year she decided to book a cruise the month before departure. She paid significantly more than she would have if she had booked even six months earlier. She almost didn’t book it. The pricing from months prior had more than tripled. In the end, she grabbed the trip. But she paid for the procrastination.
This October I am taking my daughter on a mother/ daughter glamping trip with Under Canvas.
She just started her first job after years of law school and studying for the bar. Time is limited and precious. So instead of our usual road trip and backcountry adventure, we are meeting in the middle. All the outdoor magic, none of the logistics, with a real bed waiting at the end of the day.
I booked the perfect spot with plenty of time. And I cannot wait.
That trip would not exist if I had waited until she had a free weekend and then started looking.
The best experiences do not wait for you to feel ready. They fill up while you are thinking about it.
Start your list tonight. Even just one destination. Look at your calendar. See when the window opens. And when you find the right property at a refundable rate, do not close the tab.
Book it.
Speaking of glamping, I have been dreaming up something special for next year. Stay tuned!
And if you want help building out your future travel calendar, I would love to do that with you. I even love suggesting some little known special corners of the world. That is exactly what I do for my clients and it is one of my favorite parts of this work.
