I’m Spilling my Chile Travel Secrets

 In Travel


I realize there are some things I haven’t shared with you yet about our upcoming Adventure to Chile (March 8-13, 2020). I’ve given you many reasons WHY you should go on this trip: re-igniting your excitement for life, the Pacific Ocean, friendship, laughter, good food, good wine, connecting with a supportive community that is rooting for you and the adventure of a lifetime!

However, I haven’t really gotten into HOW to make it happen… so I’m going to share with you ALL my travel secrets plus a specific step by step plan to make it happen.

I am a firm believer that when there is a will there is a way. So if you’ve got the will… I’m here to show you a couple of different ways to get to Chile… because I want you by our side in Pichilemu, Chile!

First, I just want to give you a little background. In my early and mid-twenties I got the travel bug- and it bit hard… my heart and soul was calling me towards adventure but I was pretty broke since I was a part of the generation that graduated college in 2008 (remember the recession? that’s when I got my first job in the non-profit world… so I don’t remember the exact salary amount but ya’ll it was not good).

I tried the desk job thing but became somewhat obsessed with researching hacks and opportunities to travel the world. This is before digital nomads had become mainstream or that probably would have altered my life path. But I basically spent two years stalking travel blogs, deals, bought all the lonely planets as I daydreamed about my getaway.

In that time I learned about around-the-world tickets, hostels, the South American bus system, couch surfing, credit cards that give you the best travel points and more.  Armed with all this info I finally reached my lifetime quota of hours I could spend at a cubicle, quit my job, started babysitting non-stop and bought a $200 one-way-ticket to South America. I explored ALL the budget travel options mentioned above as well as hitch-hiking, sleeping in airports, camping out of a car, renting tiny rooms (closets?) to sleep in from locals and more misadventures I’m happy to share with you around a campfire.

Ok… I know what your thinking… “she’s going to tell me to hitchhike to Chile???”

No. I promise I have some much more practical suggestions for you. I just wanted to give you context and proof that there are tons of travel options available to us… some are better and more comfortable than others… so I’m going to stick to the more comfortable options for our purposes.  But I’m happy to tell you about the other ones if these options don’t work for you 😉 – although I think you’ll prefer the suggestions I’ve got below.

Before diving into the nitty-gritty… I’ll start off with some general travel best practices that will serve you for any travel occasion:

  • Best day to buy airline tickets: Tuesday (don’t ask me why but I’ve read this on multiple travel blogs and have found success in watching flight prices) – some places even venture to say 3:00 pm.
  • Cheapest days to travel: Tuesday and Wednesday tend to be the cheapest days to travel- so extending your flight by a couple of days could save you money on travel cost.  If you have a little extra time it is a great way to get some extra mileage out of your vacation & flight.
  • When to buy your ticket: Ok… this is where it gets to be a little tricky.  There is no clear answer. I’ve read everything from 6-3 months, 3 months- 30 days out and as little as 72 hours out (man that makes me nervous!!!).
    • So for a ballpark answer: I’d say between 6-2 months out because even I’m not gutsy enough to wait until the last 72 hours. CHILE NOTE: I am going to seriously start looking for my flight in October but I’m keeping an eye on prices now so I know what to expect.
    • Set an Alert:  Setting a fare alert is a great tool to start watching flight prices and get an idea of what a ‘good’ flight looks like so you know it when you see it. CHILE NOTE: my goal is to find a flight with only one stop for around $700 [then I’ll use points to cover most of that cost- keep reading for step by step recommendations]. Obviously, I can’t guarantee anything but I know it is helpful to have some ballpark numbers to go off of.  I’ve seen flights as low as $499 [which you could completely cover with travel points: read FREE TRIP] but you’d have to either be very flexible or very lucky to find a flight that price that matches up with your travel schedule- but it’s not impossible!
  • Pro Tip: The cheapest month to fly to Santiago is March (hey! That’s when the retreat is!!) or May.
  • Layovers: You’ll see that there is a tradeoff between flight cost and the number of layovers. If you have time on your side and want to save $$

Points Tips:

  • Use Your Skymiles or Credit Card points to pay for your trip- I’m not an expert on this but The Points Guy is a great resource for this and I’ve linked to his beginner’s guide in case you want to nerd out!
  • Phone A Friend option: Do you have a friend who travels all the time for work? Did you know that they can purchase your flight with their points and you can pay them back at a “friend rate” if they are open to it? Ex. I have a friend who puts all his business expenses on credit cards so he can get the points… so he has a ridiculous number of points to use for travel- because he has more than he’ll use he is down to take the extra cash.
  • Buddy Pass: Since many of you live in Atlanta, and there are a lot of people who work at Delta, there is always a chance someone might be able to hook you up with one of Delta’s magical buddy passes!! I once had a friend who got me and my fiancee a round trip buddy pass to Rio his wedding!  What’s a buddy pass… basically you get to fly standby at the cost of just the flight taxes and fees.
    • Reward: an extremely good deal
    • Risk: you are standby so you only get to fly if there is a seat available.  Since Delta has a daily flight from Atlanta to Santiago I’d recommend trying to get on Tuesday or Wednesday flight so if you miss the first day you can try again the next day and it shouldn’t rock your plans too much.  That said standby is never guaranteed but if you have some extra time it could be worth it!
    • Here is an article that gets into the Buddy Pass details
    • Tip: Don’t stress!! I mean isn’t this always key? It isn’t worth stressing out about- if you know it will negatively affect your experience having to fly standby don’t do it. I’m a weirdo who loves hanging out in airports (to an extent) so I don’t mind arriving early with a good book but if that isn’t you then there is another route for you.

Step by Step Recommendation to Maximize your Travel Savings to Chile:

This is what I would do if 33 year old me wanted to go on this adventure to Chile. Disclaimer: these methods are recommended for people who comfortable with using credit cards. If that’s not you, skip this section and head to the Make yo

  1. Sign up for one of these two cards from CapitolOne- I like CapitolOne because you can use your points on ANY airline of your choice and their miles convert at $1 for 100 points (so 30,000 points = $300).
    1. Venture Miles Rewards Card (50,000 bonus miles = $500 for travel) If you don’t carry a balance and plan to pay your full amount every month this is the card for you because you get the most points toward your trip.
    2. VentureOne -0% apr for the first year and 20,000 bonus miles (which is the equivalent of $200 in travel)
    3. Chase Saphire – offers up to $750 in travel rewards when you spend $4000 in the next three months (read christmas shopping, chile trip, and groceries)
    4. NOTE: be sure to read the fine print- both cards have a minimum you have to reach in your first three months in order to get your travel points (but I have a tips for that as well) and I would also recommend going ahead and signing up for autopay so you don’t miss any payment deadlines.
  2. Once you’ve got your points card, place your deposit for the Chile trip $500 -or- go ahead and put the full retreat payment on your card so that you can get all of the points now [note: you’ll save an additional $200 if you place your deposit for Chile by Sept. 2nd]
  3. Look at your savings:
    1. With Venture Miles you’ll have a savings of $500 for travel points =$500 (this could almost cover over half of your travel cost)
    2. With VentureOne you’ll have a savings of $200 for travel points = $200 savings still a pretty good deal!
    3. With Chase Saphire  you’ll have a savings of $750 for travel= $750 (this is the best deal out there I’ve found unless you already have points saved up from business or frequent travel)
  4. Set a Fare Alert: Wait for prices to hit your target range – this could happen anywhere from 6 months- 3 months before the trip- but now you have extra savings to make even a little more pricy flight in your range!
    1. Note: I’m aiming for a flight in the $700-$800 range because my travel dates are a little flexible.
  5. Disclaimer: so I’m not an expert and am not trying to give financial advice. These are just strategies I’ve personally used to travel the world even when I had little cash on hand. Be sure to read the fine print, make your credit card minimum payments on time, and choose the card the makes the most sense for you depending on if you plan to carry a balance or not.

These are not the only two points cards out there by the way- they are just the cards that I have experience with. I’ve heard really great things about Chase Sapphire and Credit Karma has some great resources that will assess which cards are best for you. Here is another article from the Points Guide on other strategies to get to Chile on Points and Miles… there are so many possibilities!

Make your own flight route:

These are the best deals I’ve found by combining 2 individual round trip flights.

If you are able to leave on Thursday, March 5th and return on Tuesday, March 17th these are the dates that I’ve found the best deals.

Make Your Own Route #1:

  • Buy one round trip flight from Atlanta -> Lima (around $500) March 5th- March 17th
  • Buy a second round trip flight from Lima -> Santiago (around $150-$200) March 6th- March 16th
  • The great thing is both of these flights are direct so you can spend an extra day in Lima (Miraflores is a GREAT little neighborhood to explore and have some of the BEST culinary cuisines in South America)

Make Your Own Route #2:

  • Buy one round trip flight from Atlanta -> New York (around $100 or less) March 5th-17th
  • Buy a second round trip flight from New York -> Santiago either March 5th-17th -or- March 6th-17th (around $650)
  • New York is awesome of course- you could extend your stay overnight -or- book your flights close enough together that you just catch the next flight without having to leave the airport)

Both of these flights options will generally bring your flight total between $700-$800 which will save a little $$ – but if you combine that with your points discounts then you could bring the cost down to $300-$500 potentially!


Please feel free to shoot me an email at jessica@dirtysouthyogafest.com if you are considering joining us and want some advice on your specific travel dates and budget.


Finally, if you want to get SUPER Advanced with your travel hacking here are some other strategies:

  • Instead of buying a plane flight with a layover, fly directly in to Lima (or another South American city you’d like to visit) then buy a connecting flight from Lima to Santiago- sometimes flights within South America are less expensive than when you are coming from the States.
  • I’ve heard of people who get lucky by purchasing a series of one way tickets instead of round trip again this could be another opportunity to visit another cool South American city (like Buenos Aires) for an extra day.

Ok! I hope you find this helpful. There are lots of options but I don’t want to overwhelm you.  If you want to come to Chile with us please feel free to reach out to me as a resource.

I want you by our side when we put our feet in the Pacific ocean.

If you are ready to join us go ahead and reserve your room here!

We are rooting for you!

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