Getting off the plane in Santiago, Chile, we congratulate each other on breaking our personal record for longest flight. Fourteen hours! Kristin and I make our way to the customs line and wait with passports in hand. I am running very low on available passport pages, so the new phrase I learn when I get to a country is, “Can you stamp this page please?”

Passport Essentials

There are a few passport tidbits I pick up on our trip and want to share. First, US passport holders used to be able to add more pages to a passport if they were running low and the passport wasn’t expired. Unfortunately, the State Department stopped offering this option in 2016. Now, when you run out of pages, you are required to get a whole new passport. The standard passport is 28 pages, but you can request a 52-page passport for no extra cost.

You should also know that the last few pages aren’t intended to be “Visa” pages. This means they don’t officially count as a recognized blank page. I don’t know how strict countries are about this because in my travels I have multiple stamps on these pages. If you find yourself low on pages and are travelling abroad indefinitely, visit the closest US Embassy. At the US Embassy in Santiago they said it would take a couple weeks for me to get a new passport expedited.

My last word of advice is to have a picture of your passport information on your phone. After about country number eight I memorize all my info, but it’s handy when booking travel.

San Jose de Maipo

After driving every day in New Zealand, I catch a break, and my lovely wife takes the wheel of our Hyundai Creta rental. We have an Airbnb in an apartment building on the outskirts of Santiago for the night. Walking into the building’s front desk, we immediately struggle with the language barrier, but eventually figure out where we can park our car.

The next morning, we pack up and drive to our next Airbnb in a small town 2 hours from Santiago, called El Ingenio. This is in the San Jose de Maipo region. El Ingenio is a very rural town with dirt and gravel roads. Lucky for us we have a SUV because the Airbnb driveway is an off-road adventure (The only time I got behind the wheel). I should mention that on the way to El Ingenio we are supposed to stop and pick up my cousin Adam and his wife, Megan, from the airport.

For months we have been communicating back and forth, discussing where we all could meet for a week in March. We finally end up picking Chile. Now, through a series of unfortunate events, they are stuck in Dallas because of a delay and lose a full travel day. Thanks American Airlines…

We do end up stopping at the Chilean equivalent of a Super Walmart to stock up on groceries. I decide to make breakfast burritos, so we can quickly head out the door in the mornings. An essential ingredient I need is salsa. I laugh to myself when I go down the “salsa” aisle only to then remember that “salsa” is Spanish for “sauce.” Word to the wise, there is no Mexican salsa in the “salsa” aisle. Definitely on that struggle bus.

The next day we pick up Megan and Adam and the adventures begin.

Embalse El Yeso

Our digs in El Ingenio are nicknamed the Cabaña Mirador. If you are looking for a place with central heat, air-conditioning, Wifi, TV, a washer, a dryer, or towels, this is not it. But, if you are looking for a place with a gorgeous view, then click here.

As you can see, we do not book this place for amenities, we book it for the mountains. I looked at the posting recently, and the house now has a hot tub outside, so that’s a plus.

After dropping off luggage, we hop in the car and head towards Embalse El Yeso, which is a reservoir in the Andes. Our plan is to drive until we can find a place to hike. On our way, the road goes from pavement to gravel, and then gravel to dirt. Also along the reservoir, the road has a 30-meter drop, with no guard rails, and at times only room for one car. Rock slides are common place around the area, and sadly, a few months after our visit, two Brazilians perished in a rock slide. If you are in this area, be aware and be careful.

It’s possible to get through the area in a regular sedan, but I highly recommend an SUV. The road along the reservoir also has a daily closure time, so make sure you check the hours. We have to park near the entrance and we walk the road along the reservoir and campground areas. There are some hot springs (Termas Del Polmo) in the region, but because of the road closure, we don’t make it all the way down there.

Pulperia Del Arriero

Driving back from Embalse El Yeso, we see a weathered wooden building off the road and decide to take a chance. Jumping out of the car, there is a group of people sitting outside and they assume we are lost, or just want to use their toilets. Nope, these gringos are looking for a beer. As we sip on some big beers and talk about our upcoming adventures, a random chicken strolls through the doorway to greet us. Uninterested she does a couple of laps and then heads back outside. This is why we travel. The bar doesn’t have a website, but it’s on google maps.

Colchagua Valley – Wine Country

Honestly, our self-guided bike wine tour does not go exactly as planned. Renting bikes is easy. It’s a beautiful sunny day in South America. We are surrounded by wineries. What could go wrong? Well, Chile doesn’t make it easy. We make an incorrect assumption that all of the wineries sprinkled around Santa Cruz in the Colchagua Valley have tasting rooms… not the case.

This is a far cry from the Marlborough region of New Zealand where everything is set up for travelers and tourists wanting some vino. I think our first mistake is embarking on a Monday, because a couple of the wineries are not open. The majority of wineries that are open don’t really have options to taste their different types of wine. You either have to make an appointment or buy a bottle or two. Keep in mind we are still on our daily struggle of the language barrier. I should have paid more attention in high school Spanish.

There is some success at Viña Montes and Viu Manent. We have a delicious outdoor lunch on the patio at Viña Montes accompanied by a crisp white wine. After striking out at the next few wineries we start calling around and end up heading to Viu Manent for a tasting of 7 or 8 different types of wine. We follow the tasting with a few more glasses of wine (and this is why we are on bikes).

Getting Lost

During our tastings at Viu Manent, our sommelier recounts the history of Carménère, AKA the lost grape. Considered to be one of the original six red grapes of Bordeaux, this little guy basically became extinct in the late 1800s thanks to a phylloxera plague. I think that means some bugs came over from North America and wreaked havoc on all types of vineyards. Anyways, when the vineyards were replanted, growers could not replant Carménère as it was extremely hard to find and more difficult to grow than other common grape varieties.

150 years later, in Chile, everyone thinks they make a mean Merlot, but guess what? Yup, there is some Carménère sprinkled in that deep red Merlot. It is discovered that Merlot from Chile was up to 50% Carménère. The grape somehow made it’s way over and was misidentified as Merlot. Nowadays, Chile is known for their Carménère wine and it is amazing.

And, just like that crazy red grape, we too find ourselves lost in the vineyards of Chile, except we are on bikes. Word to the wise, Google Maps isn’t always right. We know we are cycling in the right direction, but the road ends. We sneak through multiple gates and may be trespassing at this point. Pedaling towards our destination we finally reach an iron gate, a locked iron gate. Luckily, we are able to squeeze through and continue on our way.

Santa Cruz, Chile

We clean ourselves up after our bike ride and explore the quaint little town of Santa Cruz. Adam leads us to Plaza de Armas where we walk around a few shops and then stumble across a restaurant called Envero. After an exhausting day our minds are not necessarily firing on all cylinders and the menu is a struggle.

A nice gentlemen sees our confused looks and comes over to the table to help us out. We think he is an employee at the restaurant. He helps us order some drinks and recommends some food, then vanishes, without a trace. With the advice of mystery man and a little broken Spanish, we order one of the top 10 meals of our whole adventure.

We start off with an appetizer that fell from heaven. Kilometers of biking helps boost the ranking of the Chorrillana. The Chilean dish consists of a plate of french fries topped with different types of sliced meat, sausages, cheese, and other ingredients. Reminds me a bit of poutine. This is followed by an amazing cut of meat. Food coma takes over and I think I black out after this. Have you ever blacked out after eating too much delicious food?

Valparaiso, Chile

From Santa Cruz, we make the 3-hour drive to Valparaiso, our home for the next few days. In an attempt to show Adam and Megan the true backpacker style, we book the Planeta Lindo Hostel. We have 4 of the beds in an 8-bed room. This hostel has an amazing rooftop patio, which is also where the kitchen is at. When we check-in we get the rundown of what dangerous neighborhoods to avoid. More on that later.

First order of business is one of the free walking tours in Valparaiso. Not sure if I have clarified this, but the free walking tours run on tips. They normally last about 2 hours and you should always tip your gracious and informative guide. The Valpo tour takes us through the whole city (even the neighborhoods they tell you to avoid at night). We jump on a public bus that winds through the steep streets and drops us off high above the city. We get a breathtaking view of the colorful seaside city that inspired the likes of Pablo Neruda.

50% Chance of Getting Stabbed

Valparaiso has a bit of a reputation for being a rough city in Chile. According to our hostel and other locals, there are certain pockets and neighborhoods that are not safe (mainly at night). There are also a few places you don’t want to be during the day. At dinner one evening, we are trying to figure where the night will take us. Kristin brings up the idea of karaoke and we ask our server if there are any good karaoke bars in the area. He mentions a bar, but tells us it is in a dangerous part of the city… two blocks away. Kristin, unrelenting asks how dangerous it can really be.

Our server says his friend got mugged outside the bar last week and goes on to say that if we go down to that neighborhood, there is a 50% chance we will be stabbed. No thanks.

You may think that would deter Kristin, but these odds don’t phase her. It takes a couple more locals to finally convince my karaoke queen that it’s a no go.

Kristin gets in on a Drug Deal

Traveling in a foreign country tourists are targets for people selling everything under the sun. That includes drugs. I couldn’t even count how many times I’ve been offered weed, coke, and ecstasy. It normally happens when I am by myself. Through all of our countries, Kristin has yet to be approached… until now.

Taking the local advice and avoiding karaoke, we eventually stumble across El Viaje Bar. When we walk in, everyone is dancing in a circle with their partner and swinging around bandannas. We sit down, grab a drink, and Kristin befriends a magician who is in the bar. She’s a sucker for stupid human tricks, including magic. After a few card tricks and some back and forth conversation via Google Translate, he types in “Do you want to buy some coke?”

She politely declines explaining how she just likes magic. I love my wife.

Santiago, Chile

Our time with friends is coming to an end. We hop in the rental and wind through the steep streets of Valparaiso. The incline is so crazy on these roads that it feels like the car is going to start skidding backward. An hour and a half later we find ourselves back in sunny Santiago.

With some time to kill before dropping Adam and Megan off at the airport, we head to San Cristóbal Hill. Our brains are a little fried from the late nights in Valpo and when we get to the entrance, we inquire where we should park the car. The language barrier strikes again, and we literally have a 20 minute back and forth before someone points to a parking lot 100 feet away.

Chilean Spanish is different than what I remember learning in high school and college. Most notably, whenever there is a double “l” sound, it is more like a hard “j.” It made me feel better when I heard that even native Spanish speakers have trouble understanding Chileans.

The summit of the hill boasts a sanctuary dedicated to the Immaculate Conception, with a 22-meter statue of the Blessed Virgin Mary, an amphitheater, and a chapel. There are a few ways to get to the summit, depending on where you are coming from. If you are in the Bellavista neighborhood, you can hop on the funicular. If you find yourself on the opposite side of the hill, take the cable car. For those of you who are looking for a little exercise, you can walk, or jog, up that big hill.

Goodbye

We get close and personal with the Virgin Mary and take the funicular down to grab a bite to eat in the Bellavista district before heading back to the car. We all pile back in the car and head to the airport to drop off our dear friends. Kristin and I return the car and hop in an Uber to our next destination… a nap.