Planning a trip? Don’t forget to ask yourself these 5 W’s.

Traveling is definitely in my top five things that I love and I recently realized during my preparing to plan phase of our family vacation   why I love traveling so much. When I travel, and travel includes domestic places not only international, I get to explore an unfamiliar place. It doesn’t matter if I have gone to the same place more than once, it is still new because it’s different than what my senses are used to and what they register as “normal routine.”

As a child, I often times fantasized about what other countries where like. What did it look like? What were the people like? What did their language sound like? Did they wonder the same about my home in DC? This curiosity fed something. Not only did it make me feel connected to a world greater than I could see but it stuck with me until the day I could answer these questions first hand.

When I was a senior in high school, I went on our class trip to Jamaica and got to feed my curiosity. It was more than expected. The culture, the people, the food, the landscape, everything extremely different than back home. What really stuck with me was how I felt. Now I understand that different places have different vibes, and I mean that literally. After that trip, I told myself that I would make traveling a priority.

As much as I love traveling, planning trips can be stressful. It requires a bit of coordination and patience and I get why travel agency’s exist. But for my household, I am the travel agency, me, myself, and I. Every trip I plan, I answer the  these 5 W’s: who, what, when, where and why?

Who? Who is going on this trip. Is it just you? You and your partner? The entire family? Probably the easiest step.

What? What is the purpose of this trip? Maybe this is a girls trip to just chill and catch up, maybe  you need a family vacation or maybe you want to practice you language skills. Whatever your what is, be sure to give it some thought and keep asking yourself, what is the purpose of this trip? There are millions of places to visit so this will help you narrow down your options.

When? When do you want to go? Are you planning this trip for the upcoming year or are you going in the next month or two? Do you need to plan to take off leave from work? Do you need to check the kids school calendar (although I take them on trips during school year if I can, mainly because tickets are less expensive and there’s a lot of us. I also believe the world is a great teacher😊 ). Be sure to check the weather during your desired travel time because different places might have different climates. Also, check to see if there is a low season and high season because the prices are different. Both have their perks. If you are flying, search for flexible dates and see if you get better prices when compared to your exact dates. You’d be surprised how much you can save by altering your dates by a few days.  Some airlines have price matches so before you book them, call the airlines and see if they do. They sometimes offer discounted tickets for children under 11 if you aren’t purchasing a promotional ticket so ask them about that as well. If not book them when you find the price that’s right. I always book tickets before I reserve my accommodations.

Where? Where are you going, where are you going to stay while there and where do you want to visit when you get there? This can be the most stressful and time consuming process. When I was planning our trip to Cuba, I knew that I wanted us to explore the country so this took a lot of planning and patience. I had to coordinate housing and travel arrangements for 2 adults 4 children and 1 baby plus excursions. I recently started using Air B&B and they have what they classify as Super host. These are hosts that really go out of their way to assist with some of this planning, have a certain level of reviews from guest and host a certain amount of times per year. I’m truly grateful for the ones that hosted us in Cuba because they arranged transportation, excursions and meal preparation. The way that this works is that once you book their property, they will assist you with all the planning you need. This assistance is included in the service fee so don’t be shy and ask away.

Research the area on your own and figure out where you’d like to visit and what you can realistically fit in this trip. I actually looked at the map of Cuba and selected places that wouldn’t be too far from the airport but would give us different experiences: city, rural farmland/country, and beachfront. We would have to drive to each location so I figured 2.5 hours in a ’57 Chevrolet with 4 of us in the back (1 baby on my lap) and 3 in the front would be doable.  Figure out what would work for you. Do you need a rental car, is there public transportation or bike rentals? Are you going to explore locally and just walk? Think about the activities (day trips, beaches, hiking, museums, restaurants, etc.) and plan. There are so many options to choose from and this can be overwhelming so the last “W” will assist.

Why? I started off by saying why I love traveling so much. It literally gives my senses new stimulation. Simply put, it energizes me and I feel that I grow. I’m all about growth so it’s important for me to share these experiences with my children. Growth happens outside of your comfort zone. You are taken outside of your comfort when you have to put toilet paper in the trash can when you are used to flushing it down the toilet, when you hear another language 24/7, when you are kissed on the cheek by a stranger and your norm is strangers walking past you, when you eat new food, when you have to take cold showers, when you get out of your everyday normal routine. It can be uncomfortable at times and I’ve heard “I just want to go home” several times as the kids get fed up with something new, but this is what life is about. Facing newness and it takes practice to face it with grace. The more we practice, the easier it will be. I think back to previous travels out of the states when the kids didn’t understand the customs process. As we continue to travel, their lack of knowledge about the customs process turned into “Do we have to wait in that long custom’s line?” Now, they gracefully walk up to the customs counter with passport in hand. Growth. So, why are you going?


These 5 W’s will assist you in what I call the preparing to plan phase. The steps above will create your road map. If your expectations aren’t met, that’s okay, practice using your grace muscle and be grateful for the experience. At the very least, this trip will have contributed to some sort of growth.

Happy Planning!

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