Santiago
We take an annual birthday trip. If it’s March 28th or 29th, you probably won’t find us in the USA. This year (2025), I procrastinated a little too long. I had no real thoughts or ideas about where we wanted to go, and we were limited by both weather and time. With no firm requirements for a destination, we essentially spun a globe and went where our finger landed. Not literally of course, but there is absolutely no rhyme or reason why I bought plane tickets to Chile.
That’s the beauty of travel: there is something everywhere. You can pick almost any destination, and I guarantee an experience can be made.
The flight time was about 13 hours. Living in a Gen Z world, I naturally turned my Snapchat location on so friends could see where I was. My mind was blown when I realized how close we were to Antarctica. It’s also oddly hard to rewire your brain to understand the bottom of the world and its opposite climate. South equals cold. North equals warm. Also, fun fact: the moon is upside down.
We stayed in the north, because who wants to leave winter just to go to more winter? Santiago is a large city with a busy vibe. The roads are 4 lane highways, the tunnels have stoplights and multiple lanes, the traffic is on par with any American city. We rented a car and drove to our downtown hotel. For the first few days, we explored locally. It wasn’t much of a tourist area; our hotel was filled with work conferences and businessmen. At this point, I was slightly nervous I picked too much of a “non tourist” destination. The vibe was .. normal.
In a foreign destination where tourism isn’t the norm, there’s always a quiet, lingering question: Can I hold Jamie’s hand here? How is the LGBTQ+ community received? Since I am a traveler, not a tourist, I respect local customs completely. This is not my home and I am a guest in someone else’s culture and at times even their religion. We aren’t hiding who we are, but we were consciously aware of prejudice, as any minority group tends to be.
Our fears were alleviated early. Santiago is loud and expressive. One afternoon, while walking to lunch, we stumbled upon a restaurant that answered our question without us needing to ask. Thank you, Santiago.
That expressive energy only expanded from there. The town of Valparaíso was absolutely a joy to explore. They celebrate art… but not just any art: graffiti. This is hands down the best street art I’ve seen anywhere in the world (with Greece coming in a close second). Old brick roads and narrow corridors are filled with animals, abstract figures, vibrant colors, and scenes from Chilean life. The city breathes culture. The murals tell stories, reminding you that not all beauty is found in nature because some of it is created.
We can’t sit in a city too long. It only takes minutes to realize that downtowns are downtowns everywhere. Cabs, hotels, businesses, Asian-owned corner stores; same thing, different language. So we left. Apparently, there are wild penguins just a few hours from downtown Santiago. Say less.
We traveled to Zapallar and then to the Natural Isla Cachagua. This small coastal town smells like the ocean, dotted with fishing boats and natural beauty that rivals anywhere else. But warm weather (at least 65 degrees) and penguins? That’s not exactly intuitive.
The island where the penguins live is about a 20-minute boat ride from shore. Here is where mom should close her eyes: we absolutely should not have gone out that day. Weather warnings hinted at violent weather and waves and it escalated quickly. The wind and swells sent our small fishing boat airborne more than once. Full credit to our captain, who got us back safely just as the storm made landfall.
But we did see penguins. Sitting calmly on a rock. Would I do it again? Probably not.
Next stop: the Concón Dunes. This was an iconic experience unlike anything I’d done before. Rolling sand hills overlooking the Pacific Ocean. It was truly indescribable. A short snowboard with a waxed bottom turned into insane beach fun. Would I do it again? Absolutely.
I’d love to say Chile is known for its dunes, but let’s be real…. the title belongs to wine. Oh my God, the wine.
Chile’s climate is incredibly diverse. It’s the skinniest country in the world (only 100 ish miles wide) but stretches over 2,000 miles long. That range creates hot and cold climates, arid and humid regions which is basically a grape-growing paradise. The food complements it perfectly: meats, cheeses, and charcuterie that rivals anywhere. Every restaurant understands the assignment.
We picked Alyan on a whim and were welcomed like family; literally, the winery is their family home. Their grown children jogged through the vineyards, and the elderly couple greeted every guest personally. I touched a cork tree (it actually feels like cork!!), ate grapes, met strangers who became friends, and felt genuinely celebrated. I would highly recommend … and would absolutely return.
You can’t finish a South American trip without remote stargazing. A three-hour drive inland brought us to a mountainous region so remote there are no real roads so this is not something you do in a rental car. Sometimes, tour groups are necessary. I preach immersion through self-travel, but safety and local knowledge can outweigh independence.
Our guide was incredible. The truck handled the rugged, desolate terrain with ease. Halfway through, we stopped at a small local shack for refreshments. Eventually, we reached Colina Hot Springs.
The mud has healing qualities. The water flows naturally. The air is silent. No wildlife. No civilization. Just nature. It was deeply reflective. After soaking in nature’s juices, we were fed a barbecue and then stargazed. Feeling so small in such a massive, beautiful world… that’s the feeling that lingered.
We ended the trip at the world’s largest swimming pool, San Alfonso del Mar. It stretches farther than the eye can see. Was it impressive to look at? Yes. Would I ever go again? No.
The on-site restaurant (the only one we were allowed to eat at) had roaches and subpar food. You couldn’t freely swim in the pool; only certain sections were designated for swimming. Beach access was oddly limited, despite beaches supposedly being public. The Instagram photos are cool, but the experience itself was underwhelming.
I cannot say enough good things about Chile. Look what all we did in one week! With more time, we would have extended the trip to Patagonia, we could have wandered into Argentina, the possibilities of semi extended stay seem very reasonable. The long flight and our time constraints made that impossible this time…but it only gives us a reason to come back.
Thank you for your hospitality, Chile. You are a hidden gem.
Interesting Random Thoughts
- Skinniest and longest country in the world
- Closest to Antartica you will probably ever get!
- Walmart uses this as a test country. They have stores owned by Walmart that sell / test products to the population.
Gas Stations, Toilets, and Pigeons
The pigeons seemed happy. That’s enough for me. They had all their toes and looked well-fed. Plus, there are wild penguins. 5/5
Gas stations: Standard South American experience. Skinny nozzles, prices in liters that are too hard to mentally convert. Self-pump, self-pay.
Toilets:
- Tall, skinny kind.
- Nothing fancy, nothing offensive.
Food
Since wine is basically a food group, anything that pairs with wine thrives here. Excellent seafood, meats, and cheeses. It’s very easy to like Chilean food.
4/5
Be a Traveler Not a Tourist 
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