Cadiz Pirates: How I Choose Where to Travel Next

“How do you choose where to travel next?”

It surprises me whenever I hear it, but this is one of the most popular questions I get. And as much as I think I just pick a destination and go, it’s actually a more complicated process. Why not write a whole post about it?

(And I’m not the only one! This week, the Traveling Canucks wrote a post on the very same topic. Do check their post out — it’s very different from mine and their blog is one of the best resources out there for traveling with young kids!)

Start With Your List of Travel Dreams

I have a long, long list of trips I’d like to take someday. (You can see my current top 10 travel dreams in the right margin if you’re browsing via desktop.) If you’re reading this blog, you probably have tons of travel dreams, too!

And truthfully? Those dreams fade in and out. Sometimes I’ll get hooked on a trip idea and research on my laptop until 3:00 AM, my heart thudding rapidly. And sometimes that dream will die. Most of the time they go temporarily dormant, only to resurface when I see a blog post or read a book or admire a certain good-looking Olympic team and get inspired.

Here are some of the biggest travel dreams I have right now:

I want to travel along northern Spain. I want to dive into the food scene in San Sebastian, explore the villages of Asturias, and photograph the dramatic Galicia coastline.

I want to go to the Galapagos Islands. I really got into wildlife photography in South Africa and I’m eager to shoot some giant tortoises and blue-footed boobies!

I want to spend a week exploring the Florida Keys in depth. The pretty Keys and the gritty Keys. The Netflix show Bloodline may have had something to do with that!

I want to explore Western Australia. These are the white sand beaches I dream about the most, from Esperance in the south to Broome in the north.

Those are just a few. If I have the opportunity to take any of these dream trips, I’ll probably jump on it quickly!

Tip: I keep a lot of travel ideas on Evernote, free organizational software. Hell, I keep everything on Evernote. If you don’t use it, you should!

Come Up with a Travel Window

I generally plan my trips one to six months in advance. I’ll look over my schedule and see that I have a block available, accounting for holidays, events, and habits. (For example, “I will be sick of the winter by March — I’ll be dying to go somewhere warm by then.”)

It might be two weeks in February. It might be two months in the summer. Spring and fall tend to be filled with conferences and industry events, so I’m more cautious about those time periods. As soon as I know how much time I have, I can figure out what kinds of trips would work best.

Tip: While there is no formula for figuring out the exact cheapest time to buy a flight every time (and anyone who tells you this is lying), the best fares tend to be available approximately six weeks to three months in advance.

Time the Weather Right

Weather is the most critical aspect of how I plan my trips. 90% of the time, I travel in either high season or shoulder season. (One recent exception was my trip to South Africa, which I took in July because my friend Beth is a teacher and needed to travel during the summer. It worked out well, but I haven’t always been that lucky.)

Some travelers are more flexible with the weather than others — you need to find your own comfort level. Britain and Ireland, along with much of Northern Europe, are prone to cloudy, rainy weather and have lots of things to do indoors. Tiny beach towns during monsoon season, not so much.

Personally, if I’m planning a beach escape or trip to an outdoor destination, I’ll never time it during the off-season because I don’t want to be stuck inside as it rains.

Example: Last year I traveled to Koh Lanta, Thailand, in November, the shoulder season. I love Koh Lanta in November because it’s cheaper, it’s less busy, it rains only about every 2-3 days, and the streaky clouds make for better sunsets.

Add On to Work Trips

Very often when I get a work trip somewhere, I extend it so I can explore further on my own. 99% of the time, the people flying me out won’t care if I want to fly back on a different date. (Just let them know before they actually book your flights!)

I know many business travelers who do the same thing. If you have a job where you travel, this is an easy way to add on a trip while saving on airfare.

Example: On my first trip to South Africa back in 2012, which was a press trip, I extended my trip an extra week so I could experience the country as a solo traveler. This way I got to experience bus travel, the Garden Route, and the hostel scene in Cape Town — all things I hadn’t experienced on the business part of the trip.

Factor In Spending Time With Friends

The best thing about travel blogging is that I’ve made so many friends around the world, many of them as itinerant as me. So visiting them is a major factor in my travels!

It can also be a cheap option. If you’re visiting a friend at their home, you can often stay with them for free and cook at home for some of your meals.

Example: When I planned an extra three weeks of hanging out in Europe, my friend Cailin invited me to join her at a villa in Mallorca (see her post here). Joining her — and our friends Candice and Vicky — made for a VERY fun week of tapas, cava, and listening to “Hotline Bling” over and over.

Compare Bargain Destinations vs. Spendy Destinations

Cost is one of the most important factors in planning a trip. And it’s not just about how much the flights cost! If you’re based in North America, a two-month trip to Southeast Asia or India could be cheaper than a two-week trip to Europe because the ground costs are so much lower.

I figure out whether I want it to be a cheaper trip or if I can handle a pricier jaunt. Keep in mind that cheaper destinations tend to mean dealing with less development and poorer infrastructure.

Pre-trip costs can be a factor as well. You might spend more on gear for a trek or camping trip, or lens rentals for a photography trip.

And don’t underestimate the joy of finding an error fare or crazy flight deal, or using your points or miles for something awesome!

Example: I was so set on visiting the Caucasus in August, but once I tallied up the cost, I realized it would be more expensive and complicated than I was comfortable with, particularly when it came to flights and the Azerbaijan visa. I decided to cancel it in favor of going somewhere closer and cheaper and settled on Colombia, which was cheaper to get to, cheaper on the ground, and had no visa costs for Americans.

Other Factors

Some of the other factors that can affect trips include:

Ease of travel. Some destinations are easier than others, and more challenging destinations can take a lot out of you. A significant language barrier or lack of travel infrastructure can end up affecting how your trip goes. After South Africa and Colombia back to back, which are both a bit mentally taxing, I’m eager for easy European travel this fall!

Distance. Further trips tend to be more expensive and often result in greater jet lag. For this reason, I don’t think it’s worth it to go to the other side of the world for less than ten days. I would be a zombie for most of the trip.

Variety. If you’ve been spending a lot of time in Latin America, you might start to crave Asian food. If you’ve been stuck in cities, you might be up for a trip somewhere rural. And we all know that a few months of a frigid winter makes you want to head for tropical beaches! Before I traveled full-time, I would escape Boston for somewhere warm every winter.

Personal goals. Everyone has goals, whether it’s to hold a koala in Australia or take crazy perspective photos at the Salar de Uyuni. My goals include visiting every country in Europe (so close!), visiting 100 countries before I turn 40, and visiting tons of UNESCO World Heritage Sites whenever I can.

Travel Blogger-Specific Factors

Travel bloggers have additional factors in choosing where to visit, including but not limited to:

Branding. We round out our brands by becoming experienced in different parts of travel. Sometimes that means becoming an expert in a region, as The Blonde Gypsy is in the Balkans. Sometimes that means planning offbeat or extreme adventures, as Expert Vagabond does. Alex in Wanderland is always covering interesting dive sites around the world.

We plan our trips based on what will play well for our readership and our business. For me, I try to cover solo female travel in popular regions, like Southeast Asia and Central America, in lesser-known places, like Albania and Macedonia, and in countries where women tend to be more concerned about traveling solo, like Colombia.

Photography. If you’re an Instagram star or photography professional, you know what kinds of photos your audience loves. Palm trees. Sunsets. Tropical beaches. Iconic sites like Machu Picchu. Cities people dream of like Paris. Ridiculously photogenic countries like Iceland. And you’ve also got your own personal photography goals.

Conferences and trade shows. Conferences and trade shows take place around the globe, and while we attend them primarily for business reasons, they’re also a chance to hang out with our blogger friends!

Gigs, partnerships, and press trips. Much of the work we do requires us to fly out to certain destinations and experience them first-hand. Some bloggers live off constant press trips; some never take any sponsored travel. Most pros are somewhere in the middle.

Standing invitations. Travel bloggers receive invitations from small businesses on a regular basis — mostly along the lines of, “If you’re ever in _____, I’d love to have you come on my food tour/stay at my guesthouse/take you out to my favorite bar!” And while this will never be the primary reason why I go anywhere, if it’s a cool thing to do, sometimes it influences my decision a little bit.

Putting It All Together

And then it all falls into place. “Hmmm, I’m doing nothing in the fall so far. Well — maybe I should finally plan my dream trip to New Zealand. That’s when the lupins are in bloom, which will be great for photography. It will be spring but it won’t be too busy. I’d miss all the pre-Christmas craziness at home but return in time to spend the holidays with my family. I can visit Liz and Edna and Bethaney. Let’s look up some fares out of curiosity…OH MY GOD I CAN FLY TO NEW ZEALAND FOR $780 ROUND TRIP FROM SAN FRANCISCO. I’m doing that!”

That trip came together beautifully, but sometimes my decisions can be more random. I have an impulsive side that revels in buying a last-minute ticket to a destination I wasn’t even considering. I think you’ll be seeing more of that next year when I plan fewer trips and have more chances for surprise getaways!

However you choose your destination, you can turn it into a memorable trip. Now, I want to hear from you! Do you think I’m too crazy? Did I miss something major? I’d love to hear it.