Planning A Trip: Deciding Where To Travel To?

I realize it might strike some as ironic that I’m giving tips on planning a trip. Obviously being full time travelers we get around, but you might also know that I often book tickets to a place and don’t book the hotels until I land. Or in the case of my last Italy trip, I asked a lady at a ticket sales counter where I should go within Italy. Based on her suggestion we were arriving via train to Verona (which was a good suggestion).

But sometimes I actually do plan ahead and so I thought I would share some of the techniques I use when choosing where to go. For example, we’re [likely] going to Bulgaria later and I didn’t know much about it and so I’ll share some very simple tricks on how I decided where to go.

In general I believe in the follow planning order:

1. Pick the country
2. Find the super cool places to visit
3. Look for points hotels and flights using miles

Of course, I also like that not planning option, but I just want to mention that “free” or using points isn’t the top priority. If you can’t afford to go one place, then might as well go a place you can afford or use points on. After all, there are tens of thousands of points hotels out there. Getting a free night and free flights is not hard at all.

That being said, we travel enough that we often have to forgoe the points hotel option, but most of the time my plan aligns with the points hotels. Either way, my first priority is following dreams, and miles/points should be a tool to aid that. Most trips can be free, but if they can’t… you should still go if you can afford it/the price difference is worth it.

 

Picking A Country (or two)?

My assumption is that you know what part of the world you want to go to.

Although people often ask my opinion on which place they should go, and then they give two options.

Who cares what I think? And that’s not to belittle myself (although I’m fine with that), but it’s just the simple fact that different people like different things. For example I had two friends who recently went to Prague at the same time, and one hated it and one loved it. Both were well traveled, but they are super different people. Prague is great for cheap beer, which just isn’t a draw for me. Having been there, I see both sides. It’s super beautiful and super touristy.

Really, I don’t know what you’re interested in. Personally, my bias is for anything in Asia because the culture has remained more un-westernized than anywhere else… as a whole. Although I haven’t been to a ton of Africa yet.

But you? Are you going for farflung? Culture? Mountains? Beaches? History? Architecture?

Follow your interests. For example if you like snorkeling, go to East Indonesia, Yap, much of Polynesia, etc… People really into snorkeling just know all the hotspots.

If you want my recommendations, my favorite countries are:

• Indonesia
• Italy
• India and Sri Lanka
• Austria
• Peru
• Kenya

These aren’t in order, but Indonesia is probably my favorite. Beaches, mountains, wildlife, and an amazing culture.

Oh also, we have two videos up on how unique Bali is:

• A video of a super weird ceremony in Bali.
• A video of the unique food in Bali.

 

Picking Places Within A Country?

Google Images

This may sound too simple, but I actually love it… mostly. And while sometimes touristy destinations show up, it’s usually because they are pretty. It’s a good mix usually.

Unfortunately not all pictures that rank in the top actually have the town name when you click, but you’ll likely see a ton.

In general, I love this method. If you just google image search “Bulgaria” you’ll get some of the most scenic images of all Bulgaria. But it’s not just scenic nature, but cities, and even culture. You’ll see people in weird outfits. In a sense, you can get the best of nature and culture in the pictures and hopefully it will map out some places to go.

Sometimes you’ll get the name of a specific church of fortress and you can just use google map to figure out where that place is exactly.

Using this method with “Bulgaria”, here are some of the cool places I noted:

• Plovdiv (super old town)
• Belogradchik (fortress in weird rocky area)
• Rila Monastery
• Veliko Tarnovo
• Lots of black sea pics
• Lots of mountain pics

 

Two warnings:

• Make sure it’s the actual place
• Make sure it’s not skin deep

For example, if you Google “Bali” you get pictures of Bora Bora and random places. Know it’s not a full proof thing. And make sure places are interesting beyond that one photo. For example, two temples show up a lot, Ulun Danu and Tanah Lot (both I’ve recommended), but I wouldn’t plan a trip nor fly around the world to see either of these places.

And on the other hand Amed probably won’t show up at all. Unfortuantely it tends to show popular places, because that’s how google works. However, it won’t just show the most popular destinations. For example, Kuta and Denpasar are by far where all the hotels are, and they don’t show up at all. Likely because it photographs like total crap (because it is), but whatever, at least it didn’t show up.

Also it’s worth mentioning that I use Google Image for narrowing down bigger places, not figuring out what to do in a city, or even Bali. When you search “Indonesia” you get Bali, Raja Ampat, Mount Bromo, Yogyakarta, and some farflung pics of Sumatra and Borneo. Try it. That is an awesome and inspiring mix of pictures.

 

Wikipedia

Keeping it simple, this should be obvious, but just reading about that place is important. Knowing the history can not only tell you what the interesting places are, but make the experience itself actually more interesting.

Not much of a trick, but… I just like Wikipedia. But also, I’d be lying if I said I didn’t also use wiki pages for the pictures as well. :-p Hey, they are always properly labeled.

 

Tours

My tip here is to look for small to medium size folks, that don’t have a super commercial feel but offer tours. Then just check out the “itinerary” they list to give you an idea of what your own itinerary could be.

It helps if you know of some weird blogger that offers tours or something. The more mass appeal and commercial, the less I’m interested. So I avoid places that are like “Bulgaria Tours” or [name-of-country]tours.com. But the problem is that these jokers show up in google searches. So you just have to weed em out. Instead try to pick a blog that monetizes with tours. Or try to pick someone with a personal or funky name… or both, like Yomadic.

You may be familiar with the blog, but perhaps you’ve never noticed Yomadic’s Tours. Unfortunately there are only two different tour itineraries up right now. So that’s not too helpful for 99% of the trips you’ll plan, but it’s a great example of what I look for. Someone who is passionate about the area and is confident, researched, and organized enough to tour, or in this case, lead “untours”. So if you’re interested in Albania and Macedonia tours, check out Yomadic’s route… or copy it.

I found on Google Bulgaria Tours with Rick Steves (yes, commercial, but it follows my personal name rule). Here are some things he emphasizes:

• Sofia
• Rila Monastery
• Plovdiv
• Veliko Tarnovo

He also spends a lot of time on the Black Sea, which I’m not interested in. Partly because I read on Wiki that Varna was a very commercial port, and the pictures don’t sell me either. At all. But wiki did sell me on Veliko Tarnovo, which this tour reinforces.

In general, I take these recommendations and look them up on google image search and/or wiki.

 

As you can see, you start to get some ideas of what “the” places are to see. I see this working for everyone. You can pick out the most beautiufl and most interesting places. And if you’re trying to avoid tourists and see unique culture, you can also get that impression from these methods. Like if it shows up on google/wiki but tours and blogs aren’t talking about it, maybe that’s a good sign to you. To each his own.

 

Following Interests

I mentioned this in the beginning, but it’s probably a great thing depending on your hobbies and interests. Without being judgmental, it seems to me that interests can help you dive into or avoid culture. If your “interests” involve not leaving your hotel… then that interest doesn’t help your travels, and travel probably doesn’t help your interest.

But I have friends who are super into rockclimbing and spend time in mildly obscure places but beautiful places because of it.

History: Back to the Bulgaria theme… 

Recently I looked at the wikipedia page, List of Oldest Cities. Wikipedia does rule. This list was perfect because I love being in really old cities. But also I ran a search in the browser for “Bulgaria” and came across Plovdiv, nearly 6,000 years old. This makes it one of the oldest continually habited cities on earth, similar timeframe as Luxor. I’m not too sure why that didn’t make the “Bulgaria” wiki page.

I’m not too sure what interests I have… guess I need more hobbies.

 

Asking the locals is still my favorite

I admit this doesn’t work if you’re trying to book hotels ahead of time, but without a doubt the best way to find unique places to go is ask a local who has traveled their own country.

Of course, sometimes people are biased, but that isn’t always a bad thing. In our carpooling time across northern Italy, our new friend, the driver, was selling us on how Southern Italy is better, and he totally sold me. But that was the first time I heard of Matera, which is now on my list.

 

Don’t listen to everyone: Don’t ask the concierge

Actually, I took an Uber the other day from the bus station into Central Tallinn and on the ride I asked the taxi driver what I should see. He was super friendly and energetic about telling me places to see. But when I asked him where to eat, he told me that my hotel would better know.

Huh? You don’t know what food you like? Like the case is that he doesn’t know what food I’d like, and the hotel would. But 1,000 times out of 1,000 the hotel sends me to a place that is filled with tourists. I see at least 4 problems with that.

1) Tourist places are more expensive.

2) You didn’t fly all the way around the world to eat the food you like back home.

3) The restaurants leave out the spaces that make the local food unique… because you’re not used to it.

You may have seen that Buzzfeedy type article with travel complaints. Loved one of em which was:

“On my holiday to Goa in India, I was disgusted to find that almost every restaurant served curry. I don’t like spicy food at all.”

4) The food doesn’t have to be good for the business to survive. Tourists aren’t daily customers, instead, most often they are once in a lifetime customers. Think about it, why aren’t the locals eating in the same restaurant as you? (Answer: it’s expensive, lacks local flavors and the food isn’t even good compared to other restaurants).

For this reason I have completely stopped asking concierge for any advice. I might ask about public transit, but even then I have to clarify “how do you take the bus to the airport” and certainly not ask “how do you get to the airport”.

Case in point, I recently listened to a radio/podcast interview with Anthony Bourdain, and his biggest travel tip was to not ask the concierge for a restaurant. His explanation was that their mental process will be, “last time I sent someone to my actual favorite restaurant they didn’t like it, but when I suggested the touristy version they did like it”.

Again, we live in a world packed with stupid people who have bad taste. There are people out there who complain that all Indian restaurants serve curry (which is just any Indian styled dish with sauce), and complain it’s spicy. Sad fact, most Americans don’t want to eat at legit Indian restaurants.

In the same way, people actually choose to go to Milan, Italy. Out of all the incredible places in Italy, somehow Milan is a destination people want to go to.

If there’s anything I learned from TripAdvisor, it’s that “popular” and “best” are often not related.

 

Conclusion

I’m not anti-tourists. I just hate killing culture.

I don’t want to give the impression that I avoid touristy places, and I’m fully aware that I am a tourist. I love Krakow, Budapest, Vienna, Edinburgh, and many other popular travel destinations in Europe. It’s not about that. But I will say that in Riga and Tallinn, a number of the restaurants downtown had waiters with medieval costumes… and one was a pirate costume. For this reason I like Lithuania best of the Baltics. It might have more tourists, I don’t really know or care… it just didn’t have pirates.

Or you might have seen what Carrie wrote about the great wall. The exit portion of the Badaling part had circus-like bears, camel rides, and a roller-coaster. I went to the great wall to experience a peaceful part of antiquity and instead got loud speakers, roller coasters and a circus. Insane.

Sometimes the most popular is not the best. But sometimes it is.

Getting the best

Hopefully some of the techniques above will help you choose some places within a country that are up your alley.

But also, you can do these things to decide on a country. Let’s say you’re trying to decide where to go between Germany, Czech Republic, and Poland… or whatever region you want. You could easily google image search, look up some tours and google those places as well.

These tips may be stupid easy, but it’s nothing complicated. Again, my other option is not knowing where I’m going. This is just to see what compels you to get on a plane. For me it’s often as simple as a picture. Remember I booked a trip to Zakynthos, Greece right after seeing a picture of it for the first time. That’s all it took for me.