Before considering any trip, it’s important to work through as many details as possible. Of course what we’ve assembled is not an all-encompassing list of things to consider, just something to get you in the right mindset:
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What is the reason for your journey?
There are numerous reasons people travel to other places. It can be to sight-see (nature, historic, etc.), shopping (jewelry, clothing, wine, etc.), combined with work because work is sending you there anyway, food/wine, attractions, music/festivals, pottery/china/crystal, rest/relaxation, scenic (mountains, grand canyon, etc.) and sometimes even airline points (yep).
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Is it to experience something specific?
Are you considering a historic site (Cherry Blossom Festival, Boston’s Freedom Trail, The Historic American Revolution Trail of Philadelphia, Mt. Rushmore, Cliffs of Moher, Great Wall of China, La Sagrada Familia, Colosseum, Vatican, etc.)? Do you want to go Hiking in Hawaii on the Kuli’ou’ou Ridge Trail, or among the Armstrong Redwoods in California? While similar to number 1 above, this drills further down into what you want or need to accomplish. If the whole point of the trip is to tour Alcatraz Island off in the San Francisco Bay in California, you don’t necessarily want to settle for eating at a restaurant with a view of Alcatraz because you didn’t book the tickets before you left (lead times for some things are months in advance). So you want to plan your journey around the goal, not squeeze it in.
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When or what time of year is the travel anticipated?
Weather is important. Are you traveling to Cancun during the hurricane season? Is there a possibility of a snow/ice storm which could affect my flight? You may be able to book a cheap vacation, but only if you’re ok with the risk. Weather can also drive the clothing we need to wear while traveling. Will it be cold when I leave, but warm at my destination?
Timing can be extremely critical. Oktoberfest in Germany is typically the end of September to the beginning of October (not all in October). Sometimes it’s not to attend an event, but rather avoid one. More than once we have modified our vacation plans to avoid an event that we were not intending to participate in. -
What’s the best method to travel, both to get to the destination and while at the destination?
Is it best to drive, take the train or bus, or fly to get to the ultimate destination. If you’re flying, is it best drive to the airport/train station and park, have someone I know drop me off, or use a shuttle service? Once there, should I use public transportation, rent a car, or rely on friends?
If we’re traveling local, depending on location, we either drive or take the train. You can take the bus if you like, two of the more well known are Boltbus and Megabus. What’s crazy, is that you can honestly pay as little as $1 one way from Washington, DC to New York, NY.
Normally each way ranges from $10-$15 (plus nominal taxes), which is still way cheaper than gas and highway/bridge tolls. The Holland Tunnel alone is now the most expensive water crossing toll in the US. Plus they offer free wifi, individual power outlets, and tons of leg room. -
Do I want/need someone else to plan out my trip?
If you are a complete novice and fall apart considering planning out your own trip, you may want to do your first larger one via travel agent, find a stock rail/cruise vacation, purchase an all-inclusive at a resort (that comes with airfare), etc. to take some of the guess work out of the picture. If your journey is with someone who has experience, you can learn a lot from how they set the trip up. Believe it or not, the challenge of putting together a journey to another country can be quite fun!
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Is there a need, or is it desired to combine personal travel with a work event?
This is a little more complicated, as working around work may be complicated. The answer depends on whether your employer even allows this type of arrangement. Most do, but require all travel partner(s) and non-work expenses to be paid by the employee. Therefore, if your whole family is going, anything above what’s required for you to travel is on you.
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Will my travel be out of my country or the region I live in?
This will affect how much you need to research and prepare for your trip. Some day trips can easily done by public transportation. When we went to the Cherry Blossom Festival, we took the MARC train into Washington, DC.
If more than a day trip, should air, train, or car be the preferred method of transportation?
If traveling to another country, air is usually preferred, but depending on your country of origin, train may be better (from Madrid, Spain to Paris, France for example). A ferry might even be the most practical option. In many cases, you’ll at the least need a passport, sometimes a visa, and in yet other cases working papers (if there for work). There have been times when officials have asked us for all three. -
Am I traveling with family or friends?
Family traveling is always interesting, one has to make sure that the travel is catered to everyone (at least to some degree). If there are young children involved, this also changes the dynamic on what, where, when, how, the travel occurs. Traveling with friends? Be sure to read the link provided as there’s an art to having a great vacation with friends.
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How much time will be required to plan?
For this one, we just have to verify we have enough vacation time stacked when we plan to go. We also need to plan enough time to travel and experience everything.
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How much money will be required?
The budget. Figure out how much you need and add 25%. For most of us, we need to set the budget to avoid “budget creep” where we end up spending more than we actually have and pay dearly on the back end with interest charges on the credit card. Not advisable. Note that saving up in advance may determine when you go. Travel Points & Programs can be quite helpful in paying for at least part if not all of your trip.
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Based on my journey, how far in advance will I have to start planning?
Different journeys and locations have different requirements. There are some items (train tickets, tours, etc.) where timing is critical to purchase early to avoid a crisis, or not being able to secure the item.
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Do I have any physical or medical accommodations that require special needs?
Most people think of ADA – Special Accommodations, in other words someone in a wheel chair or arriving with an oxygen tank. It’s surprising how even the smallest of limitations can hold us back if we don’t plan ahead. We had to work through a double knee surgery while in Ireland that modified our course and gave us two of the best overseas stories ever, Small World and the Cliffs of Moher.
While planning consider things like; do I get short of breath walking? (Diamond Head in Oahu, Hawaii has some 555 steps) are there specific required meds I’m taking that may not be available at my destination? (other countries don’t have similar drug stores) have I recently had a condition (rotator cuff surgery, knee surgery, heart surgery, etc.) that may affect may ability to travel? It’s good to work through where you are and where you’re going so that you can maximize your journey. -
Is there some sort of global “thing” happening, like a pandemic?
Seriously. When we started this blog, no one was even considering this possibility. However, now? It’s an actual scenario to deal with. This requires checking wherever it is you’d like to travel to understand what is required before you go and when you get there. Even travel within your own country can have specific restrictions.
Even if you’re planning is through a travel agent, you’re going to need to have answers to many of the questions above (and then some) as your travel agent works you through the process prior to booking your arrangements.
Once your basic questions have been answered, you’re ready to start formulating your implementation plan, which is fancy terminology for you’ll know the purpose of your journey, where you’re going, when you’re traveling, which accommodations to book, and how you’ll spend your time there.