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Taking that first solo trip overseas can be a daunting endeavor. What if I get lost? Are these countries safe? Will I get bored or lonely traveling by myself? Those are the questions I think anyone would have asked themselves making that first step.

After taking two lengthy road trips in the USA, I figured I was ready to try it out. I had airline miles to spend, and a new thirst for traveling adventure. Spain & Portugal were chosen because they seemed like a good starting point: I figured an English-speaking country like England or Ireland would be cheating, and I figured my rudimentary knowledge of Spanish would get me through any language difficulties I came across. Yes, I knew that they spoke Portuguese in Portugal, but I thought they'd be close enough (I was wrong. More on that here). Spain and Portugal are also the closest European destinations to my home on the east coast. 

Even so, I was hesitant. My first version of this trip was massive, involving train and bus rides all the way down the Mediterranean coast, and visits to Gibraltar and even Tangier, Morocco were penciled in. Then came the cold feet. I canceled the whole damn thing.

A couple months later, I reconsidered, this time deciding it would be OK to scale it down to just the cities. Both Madrid and Lisbon have decent public transportation, and since they both have major airports, the horrifying prospect of getting stranded in the middle of nowhere in a foreign country would disappear.

Looking back, I'm glad I did it this way. The laid-back cultures of the Spanish and Portuguese were perfect introductions to solo travel, as I found navigation fairly easy and friendly locals to help out when I did get turned around. Madrid and Lisbon are both great cities with decent weather and plenty to do, even in the middle of February. I never felt unsafe, even at night, and the best-dressed drug dealer I've ever seen even tried to sell me hash (I politely declined). I ate tapas, sampled the wares in a street market, explored the castles of Sintra and took in a couple of Portuguese fado performances. I enjoyed Madrid, but completely fell in love with Lisbon and Portugal.

It was the perfect, 'toe-in-the-water' introduction to solo foreign travel, and it helped me gain the confidence to continue 'leveling up' into more complicated transportation connections in countries with more difficult language barriers. Spain and Portugal will always be the places I learned to love solo travel.


Walkabout III: Iberian Capitals

My Spain & Portugal Itinerary

Spain & Portugal Tips &Tricks



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