Ask These Questions When Creating Your Travel Itinerary

Booking a Successful Long-Distance Vacation Requires More Than Savvy Scheduling

Creating a multi-layered itinerary that includes airplane tickets, hotel stays, restaurant visits, and various types of ground and regional transportation can get quite complicated, especially when you’re traveling for a week or more.

However, it’s not just the scheduling that you need to think about when putting all the pieces of the puzzle together. Sure, getting to your activities on time and finding the most advantageous way of traveling throughout the country is important, but so are the finer details you’ll encounter within each of those reservations.

There are some great questions you should ask for every booking, whether you’re selecting a hotel, looking for a rental car, or considering different places to eat in your destination country. Getting these questions answered is key to creating a complex itinerary without any hiccups.

Not only can these questions help your scheduling fall into place, but they can make your vacation a little easier. You might end up getting to enjoy more time for fun or relaxation on your vacation, or you might save enough money to add a day to your itinerary.

Let’s discuss some of the important questions to ask when booking a vacation itinerary.

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Important Questions to Ask When Booking a Flight

The first concern you might have when booking a flight is the cost, and the second is usually the schedule. If you find a particularly cheap fare, you might have the opportunity to upgrade your fare class. Or, you might focus on the schedule, paying a little more so you can arrive at your preferred time in your destination city or country.

Consider asking yourself this question before finalizing your schedule or flights:

Are luggage and seats included with the fare?

One of the sneaky things that airlines do after showing you an amazing fare for a ticket is charge you extra for baggage, seat selection, and other niceties.

That $190 flight from Los Angeles to Boston might look great, but is it so affordable when you realize you have to pay extra fees to bring a carry-on, check your luggage, and choose your seat?

At the end of all those charges, the fare might be almost the same as a better class of seat that includes all those services for free. You’ll sometimes see this discrepancy on domestic flights in the United States, where the basic fare for ultra-basic economy looks great, but all the added fees make the fare the same as regular economy anyway.

In some cases, you may even encounter these devious charges on international flights. That $700 round-trip basic economy ticket during high season from New York City to Paris looks like an affordable option.

However, when you add the baggage fee and the fee to choose your seat, you’re paying close to $900, which is the price of the second level of economy anyway.

Will your baggage fit the airline’s size requirements?

Every airline has a size and weight requirement when it comes to luggage, whether it’s a carry-on or a checked bag, and those size requirements definitely differ between airlines.

Furthermore, some airlines are quite stringent with those rules, while others will let a few centimeters slide when your bag is just a smidge too big. Some airline workers will even give you some advice on avoiding extra fees when you fly.

I know Spirit Airlines has a terrible reputation for added fees, but when I was flying on Spirit to New Orleans, and I had a small purse along with a backpack, the gate agent told me to stuff my purse into the backpack, so I wouldn’t get charged for an extra carry-on.

Understanding the absolutes of the airline you’re flying with can help you avoid serious headaches, particularly in the case of budget airlines that want to charge you for everything.

Also note that the size requirements for carry-ons (not the under-the-seat ones, but the over the head) have a size limitation that matches the size of the bin. If your wheels don’t fit in the size checker box, they won’t fit in the overhead bin.

Vital Questions to Ask When Booking a Hotel

The hotel, bed & breakfast, motel, or other establishment you choose to stay in during your travels may offer much more than a simple place to lay your head between your adventures.

In addition to giving you a comfortable bed and some basic facilities, a great hotel may also offer some other services that will make your travels a little easier.

Asking these questions may help you save money and time, which may mean a few extra dollars in your pocket for souvenirs, or the opportunity to add some extra fun to your itinerary.

Does the hotel offer free shuttles or taxis from the airport or train station?

One of the best ways to get taken for a ride (in the negative sense) when you’re traveling is to take a taxi in an area where the drivers are notorious for taking you on a longer route than is necessary, so they can artificially increase the rate you’re paying.

You can bypass this possibility by seeing if your hotel offers a taxi or shuttle from the airport or wherever it is you’re arriving. Even if you have to pay for the service, getting it directly from the hotel almost always means you’ll know the exact price ahead of time and won’t have to guess at the final cost.

Don’t worry if your arrival time in town doesn’t exactly coincide with the check-in time at your hotel. Most hotels will still send a driver (when they offer the service, that is) even if the time is before you can check into your room.

Where is the room located inside the hotel?

One aspect of a happy stay is getting a room that offers you the best chance of getting a good night’s sleep. Maybe you’re one of those people who can fall asleep anywhere, and it takes a huge amount of noise and disturbance to wake you once you’ve knocked out.

If you’re lucky enough to sleep deeply all the time, don’t assume that any old hotel room will do just fine. One thing to remember about traveling is that the hotel or motel room will feel and sound different than what you’re used to when you’re at home.

Even if you’re used to traffic outside your window at home, the traffic in another country will often sound quite different and might make it difficult to all asleep. For example, if you’re on a busy road in the old quarter of Hanoi on a trip to Vietnam, you’ll hear lots of (LOTS) of honking.

This doesn’t mean all the drivers are mad at one another. It’s simply the way drivers communicate with one another while driving. If you’re used to traffic but not constant honking, you might want to request a room that’s as far away from the street as possible.

What Pieces of Identification Do You Need to Travel?

If you’re traveling internationally, you probably assume you need a passport, but you might be surprised to learn that the passport isn’t a universal travel document, and you may need other items or additional pieces of identification alongside your passport.

Sometimes, you might even need specific documents or identification numbers to book activities or flights or make other arrangements. For example, when I booked a flight on Air Arabia, I needed to include my passport number on the booking form.

Do you need a visa to travel to your destination country?

The visa process can differ in various countries, so if you’re visiting more than one country, you may need to secure visas for each of those places.

For example, when I traveled to Vietnam, I needed a visa that took some time to procure. I also needed a visa for Cambodia (I visited Vietnam and Cambodia on the same trip), but I was able to get the visa in about a day by applying online.

If you’re traveling from the United States, all it takes is a visit to the official State Department website, which lists all the requirements for Americans when they travel internationally.

If you’re outside the United States, your government likely has a similar website that offers details on travel requirements to countries around the world. If you’re not quite sure, a visit to the official government pages of the country you’re visiting is another option.

If your travel plans will require a visa, I recommend securing it as soon as you make your international flight arrangements. The visa process often requires that you enter specifics about your flights, where you’re staying, and the reason for your visit.

Do you need a passport on you at all times when traveling inside a foreign country?

In many countries, you can leave your passport in the room wherever you’re staying, which means you can avoid carrying it and losing it while on a tour or activity.

However, you’ll want to conduct a little research on your destination country to see if they require that you show your passport at odd times.

For example, I’ve heard that as an American, you might need to show a passport upon boarding a train in China. A paper copy might work, but it’s always best to know when you need to have a passport on you at all times. I’ve heard that Russia is another country where it’s a good idea to keep a passport on you.

For several of the activities I booked in Vietnam and Colombia, I needed to send the tour operator pictures of my passport and the passport of my traveling partner, so you may find it helpful to have a picture on your phone of your passport so you can send the picture along when requested.

Just an FYI: you’ll often communicate via WhatsApp when traveling internationally and when texting with tour operators and hotel proprietors).

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