Yasaka Pagoda at Hōkan-ji Temple Yasaka no Tou in Kyoto Japan Photographed by Annie Fairfax

Q&A Vol. 4 – How I Plan My Travels & Craft Itineraries

It seems that two of the hardest things to do when it comes to planning a vacation are picking a travel destination and then figuring out what to do once you’re there. In this 2 part Q&A series, I’ll answer a reader-submitted question and share my tips and tricks for picking the perfect location for my travels. Then, in part 2, I’ll share how I decide what to do, how to schedule out my days, and how I make sure that my travels don’t end with me getting lost, schlepping back and forth across town, or with too much or too little leftover time.

Q: How do you select the places you’ll visit next when the world is so huge, and there’s so much to see and do? I have a really hard time narrowing it down, and my anxiety makes it really difficult for me to commit to a place, so for the past three years, my indecision and inability to decide have kept me home. I want to travel again, but I just don’t know how to pick the perfect spot for my next vacation. Can you share how you decide where to go and what your process of picking a travel destination looks like?

A: Here’s my decision-making process when I’m picking a travel destination. It makes trip planning much easier and more enjoyable for me, so I hope it helps you get out there and travel again!

Mealt Falls on the Isle of Skye Scotland's Scottish Highlands Photographed by Annie Fairfax

How to Select a Destination

Sometimes I know exactly where I want to go, particularly if it’s somewhere I’ve dreamt of visiting forever. Sometimes, particularly if I don’t have much more than a weekend to travel somewhere, it’s a bit harder to prioritize the places I might like to visit. Over the years, I’ve developed an easy way to figure out exactly where I want to travel now while simultaneously beginning the process of planning future adventures.

1. To select a destination, I always begin by compiling a list of all of the places I might like to go in the notes on my phone or my computer so I can easily rearrange, organize, and prioritize. I set a timer for a few moments and just brainstorm locations no matter how far away, expensive, or difficult to reach they may be (example: Charleston, Seoul, Yellowstone National Park, Luxor, Palm Springs, Kyoto, Phnom Penh, Bali, Seville, Okinawa, Santa Fe, Santorini, Kauai, Banff, Vienna, Tuscany, Cairo,  etc.).

I also recommend using Pinterest to seek out “travel destinations” you might not have heard of or places you may not have considered. If you’re interested in backpacking, search for something like “best backpacking trails,” or if you’re more of a luxury traveler, seek out “luxurious travel destinations” and see what comes up. Add anything that inspires you to your list.

2. After a few minutes of writing out my dream travel locations, I look back and consider which destinations are actually feasible for my budget, the duration of my trip, the season I’ll be traveling, and what I’m interested in doing. If I really want to swim and hang out on a beach, then Northern Canada won’t be a good fit in the middle of winter. Cross off the destinations that aren’t feasible at the moment, or add them to a separate list of your dream travel destinations to plan a visit further in advance.

3. I narrow the list down until there are only 3-5 locations. I begin researching flights, hotel availability, festivals, and events happening when I’m considering visiting. I also check the seasonal hours of restaurants, museums, attractions, and other activities I may be interested in checking out to ensure that if I did visit one of those places, I’d have plenty to do during my stay.

4. Usually, step 3 narrows it down to 2 or 3 destinations that really pique my interest, which is when I write a pro and cons list for each of the remaining places. I research what the weather will be like, what the crowds are like. I look into the safety of each destination and begin compiling more specific lists of things I’d like to do in each place. I then compare these lists to see which destination really suits me the best. At this point, I can usually shave off another destination leaving me with one or two that are both feasible and exciting.

5. Occasionally, I know exactly which place I want to visit next after doing the above steps, and I make my decision and begin planning my travels, and sometimes it’s a bit trickier than that. If I’m really torn between two exceptional destinations, I sleep on it or ask my friends and family if they have some insight on either destination I’m trying to decide between.

6. Once I’ve decided which location to visit next, I book my next adventure and begin planning!

Zamna Tulum Eco-Chic Glamping Overwater Jungle Bungalows Concert Venue Cenote Hotel Luxury Hotels of the World

In the next part, I’ll answer questions about how we design our own itineraries to maximize our sightseeing time without overexerting ourselves, wasting time, or missing out on iconic landmarks and experiences at our destination. If you have a question for me, comment below, or email me at anniewearsit@gmail.com.

Check out more of my travels on my Instagram, @AnnieFairfax.

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