Planning Your Way to Paradise: 8 Questions to Ask When Arranging a Vacation

October 5, 2021

Everybody loves to go on a vacation. However, before you can enjoy your holiday, you need to plan it. While some people love the organizational aspect of planning the perfect holiday, others find it daunting to iron out the details. If you fall into the latter camp, asking yourself these eight questions can help your ideal getaway. 

Will I Need a Housesitter?

Before you go away, think of what you’ll have to take care of at home. For example, you can hire a housesitter to keep an eye on your place, water your plants, and feed your pets. Depending on their rates and the duration of your trip, a house sitter can also handle home maintenance tasks, like minor repairs or cleaning.

Alternatively, you might use technology like a smart doorbell or remotely operated thermostat to ensure your home is secure while you’re gone. Lastly, consider subscribing to a virtual mailbox if you’re worried about thieves stealing packages or paper mail while you’re out of town. Virtual mailboxes are staffed locations that receive your mail and upload pictures to an app, so you won’t spend your beach day worrying about that scheduled delivery. 

Do I know Where You Want to Go?

Some people have a bucket list of destinations they want to visit. Others just want to escape anything familiar for a while. If you aren’t sure where you want to go, start by considering some foundational points, such as whether you prefer traveling internationally or staying in the country.


That alone might not narrow it down enough, so ask yourself some more detailed questions. Do you prefer a city trip, or do you want to venture into nature? If you like natural scenery, would you choose to go to the mountains or the beach? Keep exploring your preferences until you arrive at a few places that make sense for your goals and budget. 

What Type of Trip Do I Want to Take?

When determining your location preference, you should also think about what kind of trip you want to take. Some people prefer to spend their vacation relaxing. For example, if you don’t want any hassle, a beachside resort-stay might be for you.


Other people want more action during their holidays. A city trip allows you to scope out museums, restaurants, and architecture. Alternatively, a wilderness adventure gives you the chance to participate in activities like rafting, horseback riding, and more.

How Exotic am I Willing to Go?

Exotic, far-flung locales can be exciting, offering you the opportunity to explore new cultures. However, these experience-packed trips also tend to be more challenging. Be honest with yourself about how exotic you’re willing to go.


Are you okay going somewhere where others don’t speak your language? How comfortable are you trying cuisines you aren’t familiar with?  Are you willing to learn about and adapt to other cultural norms and customs? If you don’t feel like dealing with these features, stay closer to home.

Who Will I Be Going With?

When planning elements of your trip, like how exotic you want to go and where you want to go, consider who you’ll be traveling alongside. If you’re traveling as a family, you probably want to skip more strenuous locations. Otherwise, kids can become overwhelmed and derail the itinerary. 


If you don’t have children, you have more options. If you’re going on a trip with friends, you might prefer a party location like a big city. Are you headed on a couples’ holiday? You might select a romantic place, like an exotic beach locale.

How Much Can I Afford to Pay?

Determining your travel budget in advance will help you save money and make it easier to plan your trip. When tallying up your travel costs, consider basics like food, accommodation, and transportation. There are also extras to consider, like funds for activities.


Of course, there are ways to cut corners wherever you go. For example, if you’ve always dreamed of a trip to Paris, you can save money on the flight ticket by booking non-direct or opting for flexible dates, i.e., flying mid-week instead of a weekend.

What’s My Schedule Like?

You don’t just need money to travel. You also need time. Take a look at your schedule and determine how much time you have available. If you only have one week, taking a long overseas flight may not be ideal.


When considering your schedule, you should also contextualize it within broader travel trends. For example, if you can only travel during the summer months, you’ll be competing with the rush of American summer holiday tourists. If you can go away in winter, prices may be lower.

How am I Willing to Travel?

Last but not least, consider what modes of transportation you’re open to. Do you prefer going by bus, train, car, or plane? If you absolutely can’t stand air travel—those with plane anxiety, for example—your options will be more limited.


The question of how you’re willing to travel gains significance in light of the COVID-19 pandemic. Some people still prefer to avoid air travel because it exposes them to many people in a recycled-air environment. If you fall into this camp, a road trip may be your best bet.

The Final Word on Vacation Planning

Planning the perfect trip takes some careful consideration. However, the effort will be well worth it once you’ve got your ideal trip details laid out. Asking yourself the right questions will streamline the process, making your holiday organizing more effortless than ever.


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Andi Perullo de Ledesma

I am Andi Perullo de Ledesma, a Chinese Medicine Doctor and Travel Photojournalist in Charlotte, NC. I am also wife to Lucas and mother to Joaquín. Follow us as we explore life and the world one beautiful adventure at a time.

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