Most people love to travel and take vacations, but not all vacations are created equally.

 As much as it’s hipster to fly by the seed of your pants, in order to truly maximize your dollar and your experience, planning is key to a great vacation.  I’m a very organized and meticulous person by nature, and this has paid dividends for my friends and I when we travel.

For me, I start pretty broad, just conceptualizing what my trip will look like.  This is provided that the time-off aspect of the trip has already been settled.  Depending on what time of year you’re planning to travel, I’d tailor the location to the type of trip you’d like to have.  For instance, I usually take a birthday trip every March.  Because March is the ending of our winter and start of spring, it’s usually cold in many places, so that is something that I keep in mind when planning the trip. 

In 2017 and 2018 I went to Canada and Europe respectively, understanding all the while, that anything I planned on doing would have to be “cold” type of activities.  From snowboarding to simple sightseeing, I was prepared with all the necessary clothing and accessories that I would need to actually enjoy the trip.  After those two trips, my traveling group and I decided we wanted to go somewhere warm so we could just relax on a beach or lay out on the deck of a cruise ship.  We knew that the Caribbean is rather warm during the month of March, so we were quick to book a week-long cruise island hopping throughout the Caribbean. 

Once you’ve locked in the time frame and mapped out the area you want to travel to, you can start to outline exactly what you plan on doing. 

This is the stage where flight routes, train or ship tickets are researched and booked.  This will be the lifeline of the trip.  This is where shit gets real.  What I see people do a lot is talk and plan and talk and stall and never actually move the dial.  This is the point of the planning process where you can’t be reluctant to pull the trigger.  Once you’ve bought a plane ticket or booked a cruise, you’ve really started the countdown to vacation.

And let’s be real, if money is the reason you’re hesitant to make actual moves toward the trip, you shouldn’t be going on a trip to begin with. 

When the first ticket is booked, the trip really takes on a life of its own.  Now that you’ve secured the means to get where you want to travel to, you can start to formulate an itinerary.  The itinerary is the fun part, but it can also be the part where your best judgment needs to come into play. 

If you travel with a group of friends, I’d suggest each of you make a list of “must-do’s” once you’ve arrived at the destination.  For example, when my friends and I traveled to Paris, my list of must-see attractions included the Eiffel Tower, Disneyland Paris and the Louvre.  Once each group member has a list of things they’d like to do, I’d compare notes and see where there is overlap, if any, and see what differences there are.  This is the foundation to creating a successful activity list because you can ensure each person’s points of interest and expecations are, if not fully fulfilled, at least touched on.  You can make sure there is variety throughout the trip and it will aid in the process of mapping out the trip day by day.

If there are multiple points of interest that are in one area of the city, plan to do those activities on the same day so you’re not burning daylight commuting from one activity to the next.  This is what I mean about maximizing your time and dollar.  Instead of wasting money on the transit from one side of a city to another, keep the day’s activities local and maybe you could save money by walking, and have the added benefit of taking in some sights.

Once your activities are chosen, RESEARCH!  Research and compare admission prices, check opening and closing times, currency rates, read reviews and book early if possible.  People literally pay the price for procrastinating when it comes to traveling, so expediting the outlining process will allow you to book things a lot earlier.  This doesn’t only apply to big-ticket items like plane fares or securing your cabin on a cruise.  Sometimes, booking something as routine as a Broadway show early, will save you an arm or a leg.  Sometimes when you wait, you won’t even have a ticket to purchase because guess what people, things sell out! 

I am telling you, do not hesitate to pull the trigger when planning.  If you triage, prioritize and organize your ducks, they will be in a row and you’ll be on a roll.  Failure to prepare for a trip is a costly mistake and will only add stress to traveling, which is inherently stressful.  If you do your homework and do it early, you’ll actually be able to enjoy your trip, instead of coming home in need of a vacation from your vacation. Keep these things in mind, keep calm and carry on with your carry-ons!