10 Quintessential Steps to Planning your Next Vacation

After days, weeks, and months of the hustle and bustle of everyday life, most of us can’t wait for that joyous opportunity to get away and escape the daily grind. Whether you are a seasoned jet-setter or someone who plans all year for one big family vacay, the way and time in which you invest in planning will ultimately make everything worthwhile.

Step 1 – Set a Date

The first thing you want to determine is when you want to go and for how long. In many cases the time of year can greatly affect the weather, cost, and overall experience. You wouldn’t want your tropical escape to be ruined by a hurricane, nor accidentally schedule your trip on the same weekend as a major sporting event if you’re not a fan of crowds. (Trust me, you only make that mistake once.)

Step 2 – Determine Who You’re Traveling With

This is one of those things that a lot of people find out the hard way. Just because you have a great time with cousin Tina at the family reunion every summer, it doesn’t necessarily mean the two of you would make compatible travel mates. Active people probably shouldn’t travel with the more leisurely crowd, just like foodies should  avoid the disappointment of exploring new restaurants with super picky eaters. In a best case scenario, everyone can meet in the middle or expose each other to a new experience that they end up enjoying, but the alternative could easily ruin your vacation.  Different people value different aspects of travel, so choose wisely.

Step 3 – Figure Out What Sort of Experience You Want to Have

Now this is the fun part. Before you decide where you are going, it’s important to establish the sort of experience you’re looking for. This is usually dependent on who you’re traveling with and the occasion. A vacation with your family might lead you in a very different direction than a bachelor/bachelorette weekend and it is important to try and accommodate the needs and desires of all those included. If you’re in need of some serious relaxation, tropical destinations tend to be more ideal, whereas adventure-seekers may want to consider camping in a national forest or something of that nature. (no pun intended) The larger the group, the more thought should be put into this, but thankfully there are lots of options out there that incorporate a little something for everybody, including children. Cruises are always a great option for large groups to ensure everyone can find something that appeals to them, and most cruise lines have programs for kids on board that can keep the little ones entertained while you sip Pina Coladas by the pool.


With all the different methods of booking travel these days, it is VITAL that you do at least a small bit of research on the most important aspects of your vacation, which are generally flights and hotels. I recommend focusing on cost comparison, location, and hotel reviews. It may surprise you to find that many hotels are guilty of posting outdated photos, so try to read reviews from people who have stayed recently. (I suggest reading at least a handful for each, as prospective can vary greatly from person to person)

* The most reliable reviews tend to be found on sites like Tripadvisor and booking sources such as Expedia, Travelocity, etc.

Step 5: Reserve Flights, Hotels, and Shuttles

Once you have done enough research to make an educated decision, its’s a good idea to go ahead and secure your flights and hotels as far out as possible. Prices tend to go up the longer you wait, so book early to avoid paying more than you should. Rental cars can typically be reserved close to your arrival date or even at the airport on the day of, but shuttles to/from the airport or for events and excursions should be booked ahead of time, if possible.

Step 6: Study the Map

It’s always good practice to familiarize yourself with the lay of the land before arriving at your destination. What I normally do is make a “hit list” of all of the places I want to go during the trip, and then sort them into groups based on the area they’re in. This is super efficient if you really want to maximize your time and see and do as much as possible. Whether physical or mental, sorting all of your must-see sites will allow you to see and do more, which will make your trip even more fulfilling.

Step 7: Book Excursions, Make Restaurant Reservations, Purchase Show Tickets, Etc.

This is one of those things that can somewhat be a double-edge sword. Where you DO want to give yourself enough freedom to move plans around based on how you’re feeling each day, you DON’T want to miss out on something you really want to experience due to sold out tickets, over-booked restaurants, etc. Needless to say, if it’s something high on your bucket list, you might want to think about nailing it down ahead of time.

Step 8: Familiarize Yourself with Local Transportation, Currency, and Dress Code

This is something you mainly want to do when traveling to foreign countries. When going abroad, you definitely don’t want to wait until you have reached your destination to start learning about the local customs and such. Even an elementary understanding of how things work will give you a leg up and prevent precious time being wasted or unnecessary frustration and confusion. This will also help you identify certain things you may need to pack, such as foreign plug adapters, weather-related gear, etc.

Step 9: Establish an Itinerary

This is by no means mandatory, but highly suggested. Some people prefer to simply “wing it” while on vacation, and there is nothing wrong with that. If you have a pretty hefty hit list however, an itinerary is the best way to ensure you and any travel mates stay on-track. You can put together anything from a simple list of places you would like to see and things you would like to do, or go all-in with a regimented day-by-day schedule. Even the simplest of itineraries can help you experience everything the way you imagined it, so do what works best for you and keep a copy of it on your phone or in your email so you can reference it at any time.

Step 10: Pack Early and Smartly

I will admit, this is something I am working on being better at myself. For years, I have made the terrible mistake of waiting until the last-minute to pack, and I can tell you from experience, this is a huge mistake. I always feel like I have plenty of time, and the next thing I know, it’s the night before and I’m up at 2:00am doing last-minute laundry and searching for the packing list I made two weeks prior. If you start at least a week in advanced, you will allow plenty of time to pack carefully and thoughtfully, and purchase anything you may find you’re missing. Packing lists are ALWAYS a good idea to keep you on track and ensure you’re not missing anything vital such as chargers, tickets, etc. Be sure to leave a little space in your suitcase for any souvenirs you might want to bring back as well.


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