5 Tips for Care-free Traveling

Whether you’re traveling alone, with a companion or with children, one thing is certain: you’re in for an adventure. Traveling is always memorable. When you travel you experience new places, things and people. As fun as it is to travel, it can also be exhausting, stressful and even frustrating at times.

As with pretty much any undertaking, the best way to make the most of the experience is to plan and organize in advance. Below are 5 tips for traveling which you will hopefully find useful no matter what your circumstance.

1. Leave some wiggle room in your timeline.

Trains get delayed, flights get canceled, vehicles break down, stuff happens. When traveling its best not to plan any major activities for the day of your arrival. This way, if something happens to delay you, you will not miss out on a crucial part of the trip.

My husband and I learned this lesson the hard way on a trip to Chicago a couple of years ago. We decided it would be fun to take the train (and it was). The problem was, the train from Kansas City to Chicago originates in Los Angeles. As is crosses the country it has ample opportunities to be delayed. By the time it got to us it was hours behind schedule, making us hours late to our destination. We had purchased advanced tickets to see Blue Man Group for the night of our arrival. Instead of arriving at 3 pm, we arrived after 8 pm – more than an hour after the concert began. There was nothing to be done about it; we were out the money, not to mention an experience we were both looking forward to.

If you are traveling for a special event such as a wedding, graduation, retirement or reunion, it’s best to plan on being there a day (or more) in advance. Giving yourself that extra cushion will prevent missing out on all or part of the purpose of your visit should you be delayed.

Not planning any specific activities for the day of your arrival doesn’t mean your first day at your destination can’t be a fun part of your vacation.

While living in Israel, my husband and I took a trip to Italy to celebrate our 20th wedding anniversary. We arrived at about 9 am. By the time we cleared customs, collected our luggage, took the train into the city from the airport, walked the few blocks to our hotel and dropped off our bags, it was about 11 am. We had a whole day ahead of us with nothing scheduled. We decided just to explore. We set out on foot from our hotel and wandered the streets of Rome. We had an amazing day experiencing the beauty and culture of the eternal city. Our lack of agenda actually added to our enjoyment because every cool thing we came across felt like an unexpected treat.

By recommending against scheduling anything for your first day at a destination, I’m not suggesting that you do nothing, only that you avoid paying in advance for an event or activity on day one, just in case…

Here are just a couple of the many wonderful sights we stumbled upon as we wandered around Rome on our first day in Italy.

2. Plan for problems.

In addition to unexpected delays in travel, there are a myriad of other unanticipated circumstances which can (and often do) arise while traveling. People get sick, luggage gets lost, you might get lost. The possibilities for potential problems are endless. By expecting the unexpected you make yourself better able to deal with issues if and when they arise.

One useful way to prepare for possible predicaments on your trip is to ‘wargame’ or brainstorm likely issues and develop a game plan for dealing with them. Notice I said 'likely'. I’m not talking about all conceivable conundrums such as accidentally running over someone’s sheep on a winding mountain road in rural Tunisia or mistakenly boarding the wrong ship in Mexico. I’m referring to stuff you don’t necessarily want to deal with but could realistically face.

For instance, what will you do if your baby has a massive diaper breech on the airplane? What happens if you lose your passport or wallet? What if you find yourself debilitated by a dreaded stomach bug?  

Thinking through such scenarios will help you plan and prepare to deal with them should they actually occur. It may even help you to avoid certain problems entirely.

I don't know what it is about Chicago O'Hare Airport, but our family can never seem to get through it without a delay, or worse - a cancellation. We've come to expect it. Here you see my then 11-year-old son taking advantage of a lengthy delay by catching up on some much needed sleep.


3. Talk to someone who has been where you are going.

Talking to someone who has been to the place you’ll be visiting can really enhance your travel experience. It can help you avoid potential problems, know what to pack (as well as what you won’t need), plan your timeline and make the most of the time you have.

Guide books are great, but nothing can replace the practical insights of a real person with whom you can converse and ask questions. This is particularly true when traveling to a different country, but it’s also very useful when traveling within your own country.


4. Keep things in perspective.

A couple of years ago some good friends of ours stopped for a brief visit on their way across country for a family adventure. Our friend shared with us a humorous (but true!) means of categorizing ‘fun’. According to his method, there are three levels of fun.

Level one fun refers to things you expect to enjoy which prove to be truly fun. This might include a trip to Disneyland, for instance. Level two fun accounts for things you think will not be fun which you actually end up enjoying. This often includes things we are afraid to try but end up liking. Level three fun is stuff you don’t expect to be fun, and it’s not fun. What is fun, however, is talking about the experience later. Childbirth, I think, could fall into this category.

When you think about it, fun is relative and objective. What one person finds fun might be extremely unpleasant for another. This is true in our family when it comes to roller coasters. I personally despise them. They terrify me. I hate feeling out of control. My husband and some of my children, however, find them very enjoyable.

To a certain extent, we can decide to have fun, no matter what our situation. To do so, we must learn to put things in perspective. When you are faced with a situation which you did not plan for and are not enjoying, think of it as level three fun. It may not be great to be living without your luggage or snowbound in an airport or seasick in the Caribbean, but it’s going to make a great story. It’s amazing how much embracing that simple notion can change your attitude with regard to unfortunate circumstances.

Our oldest son was ten when he and his dad did their first backpacking trip. His backpack weighed about 35 pounds fully loaded which seems like a lot when you only weigh about 90 pounds yourself. At one point on the first day he fell over in a river. He was certain he would drown. His dad pulled him up and they continued on. When they passed by that same river on their way out a few days later he was amazed to see how shallow it was. Once his confidence was increased by experience things appeared much less daunting to him. 

5. Document your experiences.

Travel often abounds with new and unusual experiences. The best time to capture those memories is while you are making them. Take the time as you sit in an airport, on a train or in a car or bus to write about your journey and the associated adventures. Trying to capture all your thoughts and feelings after the fact often proves challenging once they are behind you. Your narrative will be most colorful and interesting when it occurs in close proximity to the experiences you are documenting.

In today’s world we are fortunate to have numerous methods available to us for documenting our experiences. If a traditional journal doesn’t appeal to you, create an online scrapbook, post images on Facebook or Instagram, blog about your trip, or use another multimedia platform to capture (and share) your memories.

One great way to document a trip is to create a photo book. Here is the cover of a book I did about our trip to Chicago.

Recommended Reading

For more information on preparing for a positive travel experience, check out these additional pages.

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