Questions to Ask When Choosing Your Next Destination
People are always asking me “Where are you traveling to next?” Sometimes it’s a destination they’re familiar with, sometimes it’s a far-flung locale they’ve never heard of and there’s a blank stare after my response. More often than not, I am flying into a large city, using the international airport, and then getting the heck out of dodge and into the more authentic countryside. So how do I choose our next destination? Whether on the traditional tourist route or into the depths of a culture, here are the questions and considerations I ask when narrowing down the choices to see if a place is a good fit.
Who will be on this trip? (I am going alone. I am going with friends or my husband. I am taking the twins. What is our total party size?) I think this is the most important questions to ask. A trip can be perfectly planned and executed, but if you’re with the wrong crowd it won’t matter. Some things just don’t mix- like spicy ethnic cuisine and toddlers. Or my husband and an art-centric funky city trip. Or my pregnant sister and a fly fishing trip in the sweltering jungle. It’s not the other person’s fault, it’s just not their cup of tea. Make sure you align the travelers and the destinations from the get go.
What is the purpose of this trip? (I’m ready for adventure. I’m ready to recharge my batteries. I want to feel inspired. I want to learn __. I want to eat/ drink myself silly. I want to connect with husband/ friend/ family member. I want to give myself time to reflect or grow.) Some destinations automatically lend themselves to create these environments and jump to the top of the list. Rocky Mountains or New Zealand for adventure. The beach or wide open spaces to recharge. Italy, France, or Portugal to feast. Lock in to what some of these destinations are “popular and known for.”
How do I want to feel at the end of this trip? (I want to feel energized. I want to feel happily exhausted. I want to feel relaxed. I want to feel like I did and saw it all. I want to feel grounded. I want __ question answered.) Some destinations are more intense than others. India for overstimulation. New York for happily exhausted after walking. London to see and do it all. Africa for feeling grounded and amazed. This question will help refine your itinerary and daily sites. It may also affect the length of your trip.
What travel radius am I looking at? How many hours am I willing to travel?(This will be a weekend trip and driving distance is preferred, or I have 3 weeks and I’m ready to fly to Asia.) You don’t want to spend all your time getting there so try to keep the travel days proportionate to how many days you’ll get to spend sight-seeing. I once had a couple that honeymooned in the Maldives and they had 1 week. Their departing flight was delayed 24 hours, and in addition to how long it actually takes to get there from the States anyway = they arrived on day 3. Their luggage was lost and arrived on day 5. On day 6 they started their journey home so that they could arrive home on day 7 and return to work on day 8. All said and done they spent 2 full days in the Maldives and 5 days in airports. If you love airport lounge culture, go for it…
Are there any seasons or holidays that affect this destination? This can be something that you’d like to join or you’d like to avoid. St. Patrick’s Day in Dublin for example, or fire season in Thailand. Hurricane season in the Gulf, or Carnivale in Rio. Whether you’re trying to join into events or avoid them, you’re going to see the change in your budget. Rates will increase or decrease depending on the season so factor this in (flights, accommodations, restaurants and businesses closed for seasons, shoulder/ peak/ low season, etc), as well as the amount of people there the same time as you.
Keep a short list. I always keep a list of places that sound cool or interesting to me. (“That sounds like a great family trip. That sounds like the ultimate 40th birthday with the girls. That sounds like where I need to go recharge for a weekend.”) Once you have a short list of 5-10 places then…
Watch airfare and deals related to your short list. Google flights is my best friend. I set notifications for flexible travel dates and let it alert me with price drops. I can’t tell you how many times I’ve woken David up in the middle of the night and said “Flights just dropped. I’m buying them now fyi.” He rolls over, goes back to sleep, and I save us $500 on airfare. If you’re eyeing a resort, cruise, or property get on their mailing list! Viking does a huge sale every year and boutique properties are always looking to sell rooms last minute. If you have a specific company or brand you love get on the info list to save money.
Once in a lifetime or easy to accomplish? (Is this a once in a lifetime African safari and I want the best of the best, or is this an easy trip to the coast and we can decide later if we want to make this a yearly tradition?) Some trips have higher expectations to be amazing or wow-factor producing because they feel like they will never happen again. While I do have trip ideas like that, I’m also very careful to set realistic expectations.
What are your Non-negotiables? Along with keeping it real… be honest with yourself. If you hate hiking, you’re going to hate a 4 day hiking trip to Machu Picchu. If you enjoy air-conditioning and a luxurious bathroom, you’re going to hate the off-the-grid eco lodge. I think travel should be transformative and create growth in a person, but let’s baby step this. I have always been a pretty low-maintenance “roughing it” kind of traveler, but now with young kids there is absolutely no reason to throw our family into misery when it can be avoided.
Our non-negotiables-
Air-conditioning. The twins need a place to cool down and sleep comfortably at night. If they are restless and sweaty they don’t sleep = I don’t sleep = next day ruined = complaining and we are in a negative cycle. I have spent many months in Southeast Asia without air-con but let me tell you, always pay the extra money for it and give your family a place to cool off. (We have done stays without air-con for short periods, or tent camping, but I always mentally prepare myself if the nights are going to be full of tossing and turning.)
Outdoor patio/ garden/ green space area at accommodation. Kids have a lot of energy, and holing them up in a hotel room is asking for a family fight. We always book an Airbnb or guesthouse that highlights a patio space so we have a chance to get some fresh air and spread out.
Living and kitchen area separate from sleeping area. We keep the twins on a regular bedtime routine when we travel (again, if they get good sleep everyone in the family is happier). But sometimes David and I don’t want to go to bed at 8pm, the same time as lights out for the kids. We always make sure the “hangout area” has a divider or door to close it off from the sleeping area so that we don’t disrupt each other staying up late or getting up early to start the coffee and check emails.
Down-time built into schedule. I was ambitious with newborn twins. Overscheduled, can’t tell me attitude, I’ll make this work mentality… I now enjoy afternoon siestas and days when nothing is planned. And down-time on the trip itinerary is a must. Now I plan something for us to do in the morning and leave the afternoons open for whatever the family needs (a nap, a walk, an ice cream break, an early dinner, a dip in the pool, solo time for mommy). If we accomplish one sight seeing thing per day, we’re on track. If we accomplish two sight seeing things (and no one has a melt down), I feel like a super star.
Resources for checking a location’s additional compatibility. After you have considered the above questions and made your short list of destinations, use the following resources for additional research.
Rough Guides favorite for off-the-beaten-path info and destination. Also show 1 or 2 week itineraries with maps. (They have a newer planner service but I haven’t tried it.)
Rick Steves still my favorite for European ideas
Google Flights I NEVER purchase a flight without consulting their date calendar. Amazing if you have flexible travel dates or time to watch the trends.
Pomelo sign up to receive amazing flight deals (I have done their paid tier for years and have saved thousands of dollars because of it).
