Chile
Pucón
Pucon is one of my favorite places in the world. Oddly enough, the vibe is pretty Southern Californian- even a bunch of people who work or live there are from Cali, but once you go you can totally see why. It’s a beautiful place with a ton of outdoorsy things to do: hiking, mountain biking, kayaking, volcano trekking, etc. but it also features the wonderfully relaxing network of hot springs.
Do
Volcan Villarica
This is the famous active volcano that a lot of people come here to hike. There are two ways to do the hike, the short way (easier) and the long way (harder). I did the trek through the company Aguaventura (which is located across the street from Hostel La Bicicleta) and they go the long way. The difficulty level varies depending on the season and amount of snow, so you can usually tell how hard it's going to be by seeing how far you could walk before having to put on your crampons. For my hike we were told to put on our crampons almost immediately, and about half our group had to turn back without reaching the top. In contrast, the friend who told me about the hike in the first place went in the middle of the season the year before said that the hike was hard but not too bad. Either way, the view both of inside the scay volcano and the world literally above the clouds makes it worth it. Plus, you get to sled on your ass down most of the volcano, which is super fun.
Another beautiful spot to visit, this is a collection of waterfalls that empty into sapphire pools. There's not much to do there except walk around and take pictures, but there are camping sites on the grounds where you can have an impromptu barbeque. You can get here by bike or car, but if you're going by bike be sure to take the trail going along the river and not along the highway (otherwise you're going to be biking on the side of the road with cars and trucks speeding by the whole time).
Watersports
There are a ton can do in Pucon: rafting, canyoning, kayaking, etc. I've rafted and kayaked with Aguaventura and I would totally recommend them. The rafting is intense (the guide at one point said, "do not be afraid of the carnival of rocks") but we're talking like a cat 4 or 5 so I wouldn't call it particularly life-threatening. I kayaked for the first time through the company on the local lake, and the experience was what got me into the sport.
Mountain Biking
This place is just teeming with beautiful spots to go biking, and if you stay at Hostal La Bicicleta you can just rent directly from them!
Eat
Alright, this place is run by Californians who've defected, but they seriously make some of the best food. Try the deer burger and the funnel cake. They could put carnival stands out of business with that awesome funnel cake.
Every time I go to Pucon I have to go to Trawen. The food is delicious, local, and high-quality. I don't really know what kind of cuisine category to place it in, but just go.
La Maga Parilla Uruguaya
I came here with a huge group of about 12 or so people, so we got a whole slew of meats. Solid, meat-filled BBQ deliciousness with a pitfire grill-vibe.
Stay
One of my favorite hostels (in the world, but definitely in this town) it's run by Jose and his wife, and you often see their two cute children running around after school hours. It's got a sun deck with places to hang your clothes to dry, a beautiful view of the volcano, and a bunch of tables and chairs to lounge on. If you grab one of the rooms facing the front of the hostel you'll get your own sun deck, which is super cute. The rooms themselves are dorm-style although you can book your own private room, and the interiors are made of this beautiful orange wood so it feels like you're in a cabin. Not to mention that there's a small bar with plenty of beer (bottle and tap) which is great after hikes and delicious breakfast you can order with a cappuccino. The living room is also spacious, has plenty of places to sit, and both there and the front cafe area have fireplaces.
Of course, they also rent bikes for you to take on the many beautiful trails in the surrounding area (the town is small enough that you can walk from end to end in less than an hour so you wouldn't need to rent for basic transportation). Jose knows tons of information about where to go and eat, and will help you book activities. He and his family are also easy-going and super friendly, and so this place is like another home for me.
A main thing that I should point out is that if you come in either the hot or cold seasons, the hostel is always a comfortable temperature. I've stayed at a bunch of other hostels before that aren't like this, and when you're talking about a place that turns into a ski resort town you'll appreciate not having to wear your snowboarding clothes to bed.
Get Around
The local buses are pretty infrequent especially in the off-season, so you'll need to make sure you know the time tables if you go off hiking. For the hot springs I recommend booking with one of the local agenices that take you on a mini bus and pick you up after a few hours (they leave around 7-8pm). For day trips, you can either rent a bike to go on local trails or take a bus to another small town to explore. If you can buddy up with people at the hostel, you could also rent a car to explore the area that way (day rentals as of April 2013 were around $50, but prices may vary).
Beware Get Around
Bus Jac is awful. Avoid them if you can- they stop frequently to pick up people on the side of the road and will overload the bus so that people are standing or sitting in the aisles the whole time.
Chiloé
This is a tiny but incredibly beautiful island you can reach by bus or car from Puerto Montt (you'll have to go on a ferry since there's no connecting road to the mainland, but the ride is nice). With a history of witch lore, an underwater forest you can kayak over (literally- an earthquake happened which caused parts of the island to be submerged), and the story of an unfortunate hiker who was lost for 31 days in an area he could've easily walked out of in less than an hour if he tried, this island is also one of my favorite places in the world.
Eat
This is one of my favorite restaurants in the world. It is run by a super sweet and friendly couple who have filled it with crafty (but not annoying) design-y items that give this place a sense of being in your cooler-than-you-but-doesn't-realize-it friend's home. Everything is local, and made from tweaked-out family recipes. There are very special clams that only exist on Chiloe and they bake them with Parmesan cheese- YOU MUST GET THIS! (I actually think about this dish pretty frequently, dammit).
Stay
This is probably one of the cutest hostels I've ever stayed in, the staff is incredibly nice and helpful, and you get to stay in a Mondrian/Lego-esque house on stilts right on the lake. Plus, when the tide is up you can rent a kayak and paddle away straight from the hostel's own dock.
Beware Do
Okay, so I went with my friend at sorta a bad time- Easter, when a lot of stuff either shuts down completely or is in the process of shutting down so you've got to plan your kayaking trips early. Also, understand that the island itself is rather long, so "a quick day trip" to a nature park could mean a 4 hour drive.
Puerto Natales and Torres del Paine
Puerto Natales
Puerto Natales is where you take the ship up to Puerto Montt or stay to gear up and rent things before going to Torres del Paine. The multiple day backpacking hike at Torres del Paine is probably one of the best things I’ve ever done.
Do
I didn't end up booking a kayak place there or anything, but I think you can kayak around the glacier waters there if you're good with that.
Stay
This was the hostel I stayed at, it was very quiet (I came at the end of the season) and felt like you were in someone's house. They'll keep your luggage for you while you're in the park, have a laundry service, and will cook you a hearty meal if you want. To be honest I was recommended this place because a special guide who worked in the park was working at the hostel for that season, and was told that his advice was invaluable (it was).
This is another hostel that comes highly recommended, which is where I rented my equipment for the park although I've never stayed there myself.
Beware: Buy
If you do want to do the Torres del Paine hike be warned: Chile has the same hiking/camping equipment brands as the U.S. but they’re about 3x the price. Come prepared.
Torres del Paine
Torres Del Paine is about 2 hours away from Puerto Natales by bus and the bus leaves pretty early in the morning, like 5am or 6am.
Bring
Before you leave you'll need to choose if you're gonna stay in refugios the whole time or camp. I don't remember the cost and prices went up in Chile since the last time I went anyway but you should look that up before you go so you'll know how much money to bring. I knew someone who stayed only in refugios and she traveled with practically just a normal school backpack with her clothes. You can even drink the water from the streams in the park, so you really won't need a water bottle, the main thing is to bring a headlamp with extra batteries, waterproof clothes- a jacket and pants- and a big plastic bag to keep your clothes dry while you're walking, as this time of year (April) it's probably started storming.
If you camp, a tent, good sleeping bag (April: this time of year it'll be getting cold so a 5 degree bag would keep you nice and warm), a sleeping pad, a stove and kettle, a bowl and spoon, and even a large camping backpack to put it all in can be rented. You'll need some pretty good hiking boots (waterproof preferably) since the terrain is crazy at parts. Also, remember to bring enough food, and a lighter or pack of matches.
Weather
You have to know that the park has completely different weather from the area surrounding it and within each valley so you can't look up the weather in Natales and assume it's the same. On my hike which was towards the end of the season (the back of the park was already closed due to snow), the valley I was walking through had nothing but wind, but the next valley I traveled to (3 hours of hiking) there was a blizzard at the north end of the trail. If you can, find someone in Puerto Natales who just came back from the hike and ask them how the weather was.
Do
Within the park people do the main W, and usually tie their giant backpacks to a tree or set up their tents at the bottom and hike up one of the prongs and just return to their bag or tent at night. Be sure to hang your food up in a tree as there are small animals like mice around and they'll eat a hole through your tent to get to the food. Also be sure to keep your boots in your tent at night, as there are foxes that will steal your stuff if it's not inside. Aside from that, there really aren't any animals to worry about there.
If you're starting from the main side (the first stop on the bus) you would hike to the end and take the boat back to the beginning or do another day of hiking to get to a lodge and wait for the bus (I'd say go on the boat, I did the extra part and it wasn't as impressive as the rest of the park). Otherwise, if you're doing the hike from the other side (2nd stop on the bus) then you'll be doing that extra part and hiking to the end where the bus picks everyone up from the main refugio.
Just enjoy the view, be careful, and try to follow the neon orange spray painted signs as much as you can.
Getting to Puerto Montt
Leaving Puerto Natales you can go on the Navimag boat to Puerto Montt, it takes like 3-4 days and cost around $300 the last time I was there. DON'T DO IT. It's just a container ship with sleeping quarters and the whole ride is insanely boring.
Santiago
Honestly, I was there for only a few days and it was pretty boring (even Lonely Planet says so, which is a bad sign). To me the place didn’t really have defining features, although there is a lot of business and money in the city (they have malls there that are like our malls in the U.S., and some of our chain restaurants), which means that there might be more opportunities to teach and more people who want to learn English for business.
Do
I went to the fish market for fun, if that gives you an idea. I also got my first palm reading at an artisan fair there, and the "psychic" basically just gave me random unsolicited dating advice and told me to cut down on eating meat.
Get Around
The buses there use this scan card system that I didn’t understand at the time so my friend and I just flubbed our way around the city.
Valparaiso
This place is a Seattle-like seaport town (weather-wise) with people who are pretty subdued and wear a lot of black. But aside from that, there are cool art murals on the walls around the streets if you’re in the hills, and a lot of cute cafes and coffee shops in those areas. Beware of where you wander though, since the place is small and the bad part of town looks very similar to the regular part.
Do
The Pablo Neruda house is pretty cool to visit, and supposedly he kept cocaine in a large sugar bowl in his living room. In another part of town, there are also "elevators" that take you down the hillside to the beach (I didn't go on them, though).