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If you are amidst planning or trying to decide on a trip, I think you’ll find these questions helpful. The process of planning requires a bit of digging to ensure it’s the right fit. There is so much to consider and vet out before hitting “confirm” on your plane tickets.

When it comes to planning our trips, I do a lot of research. My background is in travel planning, so I spent a good chunk of time hedging for risk for my clients. Today for our family, I am considering even more elements before we book. Details I’d never even thought of before, it has required me to be even more thoughtful than ever.

And with all of those nitty gritty details in mind, I think there is an even more important question to ask oneself. I’ll talk more about that below — an element often overlooked and not even considered. Something that I think will likely help you to plan and choose where to go.

While you may not be able to find the right destination or trip for all of these questions and there are some sacrifices to be had, it’s worth considering them in advance. These are the questions I like to ask myself before deciding on a trip.

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Questions to Ask Yourself Before Deciding On a Trip


1. Deciding where to go — “what do I need in my life right now?”

This is the number one question that I get asked — how do you decide where to go? Yes with endless options one could spend months never coming to a decision. So I want to start with what I think is the most important question to ask yourself BEFORE even planning or researching. I think this question will save you in the long haul from misplaced expectations and get you on the right trip.

The question I ask always is: “what do I need in my life right now?” I’ll give a real-world example: right now we are in a burnout phase, living very functionally in a city. My mind feels busy, constantly. I can tell you I need time in nature, I need rest, I need to quiet my soul. The operative words are nature, rest, and soul. These are my parameters for what kind of destination I will be looking into for our trip.

I will not be booking us on a two-week, city-hopping trip through Europe. I think that would actually feel quite stressful right now. At other points in my life where I needed inspiration, design, and culture, that may be more fitting. I’m looking into places where we can be connected with nature, low stimulation, and so on.

The other elements will naturally shape the final decision, like budget, timing, length of time, and so on. But I think narrowing down what you need right now is so helpful in clarifying and imagining where it is you want to be on your trip.


2. Getting there — can I fly there?

I know this may be such a simple and obvious question, but I surprise myself from time to time! I recently looked into a trip to a remote destination in Mexico. Spent hours looking at vacation rentals, guides, and tips. All to come to the flights and realize, well this is not going to happen because the flight journey is too much! Somewhere in my mind I thought we could get there easily only to turn out it was a 20-hour travel day with 2 plane changes — a big nope for us right now.

So my suggestion is once you get to the point of picking a few destinations and planning, spend a quick 5 minutes on this. Look to see what average prices are on Google Flights (my guide on how to find cheap flights on Google Flights) and see what the routes are before getting too invested. Maybe you’re looking for somewhere you can fly direct, so if the itinerary involves 2+ stops, it won’t be a good fit right now.

My favorite tool right now to use to search for flight routes is called FlightConnections. Simply put in the destination you’re headed to and you can see which airlines fly direct and their routes, and the times of the week they fly. So helpful!


3. Ocean-based trips — is it warm enough to swim in the water there?

This can make or break a trip. Have you ever booked a trip to a coastal destination, only to arrive and the ocean is too cold to swim in? No fun at all. I know the cheaper airfare is enticing, but it’s well worth considering what the ocean temperature will be IF this is a big part of your trip. Some destinations are almost always in the clear but others need more careful planning.

One area that gets this “it was too cold to swim” is Portugal’s coast and a few Mediterranean destinations. May is arguably the cheapest time to fly but for a reason. So I’d consider this before deciding on the cheap flights if you had it in your plans to have beach days and swim. I like to use this website to find out the average temperatures globally. The best part is it breaks down what it will feel like.


4. Timing and weather — what seasonal weather issues should I be aware of?

Destinations that need extra care in planning are places like the Caribbean, Mexico’s Pacific coastline, Thailand, Vietnam, and other Indian/Pacific Ocean destinations. You have to consider natural disasters like hurricanes and typhoons BEFORE booking that trip. Again, the off-season pricing can be really enticing, but it comes at a major risk of weather cancellations or on-ground emergencies.

It’s good to do a quick search of what average weather is like year-round in a place. If you’re going to risk it, I would definitely purchase trip insurance for your trip.  My preference for travel insurance is with World Nomads. Let’s just say we risked it for a Tulum trip in the mid-fall months (amidst technically the hurricane season) and well, we survived but spent a lot of time worrying and on hurricane watch.


5. Amount of days — should I travel abroad or stay local?

The decision to embark on a long-haul trip or do a more local trip lends itself to how much time you have. I’ve always had a general rule on the number of days in the country: at least 1 day for every hour on the plane.

An 11-hour flight to France I feel is best for a trip that has at least 10 days on-ground. For a 5-hour flight to Hawaii, I feel that 5+ days on-ground is appropriate. That gives you an idea of how to decide where you go and if you there’s the right amount of time to be there.

Could you fly abroad for less time on the ground? Sure, you can and I have as well on the rare occasion. I just don’t recommend it. Or rather, take those more limited vacation blocks to visit something nearby. The world is grand and there is always something to experience everywhere. I’d rather travel closer and have it be a more relaxing experience with fewer hours to get there if I’m limited on days.


The 10 Questions to Ask Yourself Before Deciding On a Trip

6. On-ground — what will be open at the destination?

Another great thing to consider for any part of a trip or the trip itself is what will be open at the destination. Some areas are closed seasonally, European city museums close down a few days a week, and so on. It’s good to double-check before you book, what will actually be open when you’re there. If you have a list of must-see things in a city or place, cross-check holidays and schedules AHEAD of booking.

A few examples of where we learned this (the hard way):
The Dolomites — a lot of businesses close for a break between summer and winter.
Greek Islands — a lot of hotels and restaurants close for the season.
France cities — a lot of attractions are closed Mondays and Tuesdays.


The 10 Questions to Ask Yourself Before Deciding On a Trip

7. On-ground — how will I get around?

You’ve planned an entire trip with flights and hotels sorted, but never cross-checked transportation. You quickly realize that you’re going to need to rent a car and that rental car is $1000 for the week. An expense you didn’t expect or budget for. My recommendation is to have a quick look at how you plan to get around a destination, especially if it involves a rental car.

With historically high rental car prices, it could make or break a trip for you. I’ve seen rates in places like Hawaii for nearly $180 a day. So as you start to plan your trip and look at a location, ask how you plan to get around. One quick search will give you an idea of whether the rental car or other modes of transport will work within your budget and expectation.


8. For family travelers — are the accommodations here the right fit?

One of the hardest parts of traveling with a young child or infant is the accommodations. I like to make sure there is an appropriate solution for where we are going to stay in a location. It’s almost always a yes that there is (granted pending budget) but worth considering.

There are so many elements to consider when it comes to safety, practicality, and location. I have my checklist here that I like to consider when I book a place to stay:

  • Location: is this close enough to visit things we want considering naps/schedule
  • Safety: any open terraces, open doors to pools, and other design features that could be an issue
  • Functionality: do I have what I need for my family? Maybe it’s a kitchen, washer, portable crib, and so on.
  • Air Conditioning: I cannot tell you how much I regretted booking an Airbnb with no AC with our infant during the summer months in Mallorca. I’d highly consider this when traveling in the heat of the summer.

READ: The Best International Places To Travel With Toddlers (As Recommended By Frequent Travelers)


9. Budget — does this make sense financially right now?

A topic I like to avoid is money and especially when it pertains to travel because everyone travels differently. Different needs, wants, and desires for experiences. However, I think it’s good to set parameters around a trip for what the budget is. I tend to have a quick process for vetting whether or not a location will fit in the budget.

I’ll do a quick look at three factors:

  • average flight cost
  • average Airbnb cost per night (they share on their site when you search for a destination)
  • transport (what is it going to cost to get around)

Generally speaking, these are the BULK of the costs of a trip (unless staying at a resort that is far from food, so you’re at the whim of their restaurant pricing for example). It gives me a good idea if this trip will fit within reason of the budget I’ve set out for.


The 10 Questions to Ask Yourself Before Deciding On a Trip

10. Inspiration – were the social media photos accurate?

In a world of highly edited and curated social feeds, it can be quite misleading from reality. Were the turquoise waters not so blue on arrival? The disappointment is real at times. A few hacks to seeing what a destination actually looks like:

  • Look at location-tagged photos. I’ll search on IG for a location, and scroll through recent posts. You can get a quick sense if that one edited photo is accurate of reality.
  • Follow people you trust. Some accounts highly edit, and that’s okay, it may be their art form. But maybe not the most accurate for depicting what’s on the ground. Find a few accounts or maybe magazines that you trust, and follow those for your inspiration.

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The 10 Questions to Ask Yourself Before Deciding On a Trip

PS — Are You Booking a Trip Soon? Use My Booking Checklist!

These are the sites I use most to book my own trips. Using the links below is a great way to support Bon Traveler’s travel journalism at no extra cost to you. If you need help organizing your itinerary, get my free travel itinerary template here.

1. Book Your Flights

Use Skyscanner to find the best flights. It searches 100s of airlines and websites across the globe to ensure you’re not missing out on any route options or deals.

2. Book Your Accommodations

Use Booking.com for hotels and guest houses. They have the biggest inventory and consistently offer the best rates.

3. Book Your Tours & Experiences

Use Viator or Get Your Guide to find the best tours and experiences. They are my favorite tour search engines. I always check both as their inventory varies depending on the destination.

4. Book Your Car

Use Discover Cars or Rentalcars.com to find the best car rental deals. I recommend comparing rental agency reviews on Google to ensure you are booking with the best company in that destination, as the reviews are often more accurate than the car rental search engines.

5. Don’t Forget Airport Lounge Access

Get a Priority Pass membership to gain access to 1,400+ VIP lounges and airport experiences worldwide. The Priority Pass app is the first thing I check when I have a layover. I’ve been a member for over a decade, and having a comfortable place to relax before and between flights makes air travel so much more enjoyable.

6. Don’t Forget Travel Insurance

I never leave the country without travel insurance. It provides comprehensive protection in case anything goes wrong (ie. illness, injury, theft, and cancelations, etc.). I use it frequently for my travels to stay protected.

My favorite companies that offer the best coverage and rates are:


Xx,
Jessica

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