Stop planning trips in advance; Trust me on this one
October 19, 2021
In the last four years my family has not planned a single trip in advance.
Read that again.
That means no booked hotel, no planned activities, no pre-bought tickets.
Read that again.
After taking one spontaneous trip to the New England area over New Years Eve 2018-2019, we have never looked back and neither should you.
We have been to Canada, the Carolinas, every major metropolis up and down the East Coast, the border states of Maryland, and many more places to say the least.
But not one of those trips did we plan more than a possible flight in advance.
So what do you do then Jackie, when nothing is planned. I know you are asking me this.
Ask the locals what their favorite spots are.
Like that time we got lost in West Virginia without service, so we stopped at a deserted town to ask what direction to head in. Then we were told about one of the most charming natural parks filled with massive boulders, that was a county secret hidden down a dirt path.
Ask the locals what food the area is known for.
Like that time my dad and I stumbled into the single-greatest restaurant in Michigan. A hole in the wall place where the owner took the time to make us meals catered to our personalities. And on top of that, gave us a free cannoli and told us anytime we would venture into the area again, he would gladly make us another meal for free.
Ask the locals if there are any hidden secrets or treasures about the area.
Like that time the girls in the family, found the hidden haunted wing of the Grove Park Inn in Asheville. And got to explore the vintage untouched decorated hallways, as if we were taken back in time.
Do not flock with the crowd because, who really wants to stand in lines all day.
Like that time my sister and I accidentally wandered into a French fort in Old Quebec and got shooed out by the guards, just because we were trying to avoid the crowds.
Do not fear the weather and let it prevent your plans.
Like that time my dad and I went to Kaaterskill Falls in the pouring rain. Not a single soul around on the miles of slippery trails, a truly magical experience. Not only during the seasonal changing of the leaves, but also during a glistening rainy time.
Do not feel obligated to follow the rules.
Like those times where we’ve snuck into numerous luxury hotels like The Plaza in New York, The Homestead in Hot Springs, The Grand Hotel in Mackinac Island, and Sagamore Pendry in Fells Point. Acting like you belong or fake it til you make it, like I like to say, will become your best friend. Because boy do you deserve to feel like a luxury.
Let me tell you, spontaneity leads you to find the most unexpected gems in the most common of places. You are forced to use your resources to figure out where and what to do next. Just ask more questions, engage in more conversations, and take more risks.
Some of my favorite memories have come from traveling by these principles. Now it is your turn to go make those favorite memories too.