Anatomy of an Itinerary

What is the genesis of your perfect travel itinerary? What concept kick-starts your plans, taking you to awe-inspiring destinations filled with rich, foreign cultures? Perhaps it’s venturing to the UNESCO sites. Or how about checking off countries and continents? Well, what gets me going is a far-flung hotel with an attractive award redemption rate—a new hotel in a new place means new things to do! That hotel becomes a home base from which a well-structured itinerary can frame an incredible travel experience.

This entry is all about how I have planned my future trip to southern Chile.

The Impetus

If a stay at a hotel prices out at $1,300, is it worth redeeming the 99,000 Club Carlson points alternatively required to book that same reservation? I figure about 1.3 cents per point here, and that’s thrice times what The Points Guy generally values them at. Lastly, this is for a total of 11 nights! I would say Yes, this is a great redemption opportunity!

This lengthy hotel reservation becomes a fixed-size element around which the rest of my travel itinerary is constructed. Flights are booked around the ends, days of sightseeing get scattered within, and even regional travel can reposition my eventual point of departure.

But first, how to actually get there?

I locate the nearest airport using Google Maps, Wikipedia, and WikiTravel. The Wikipedia article for the major international in Chile airport reveals which airlines fly the route from New York all the way down to the Los Lagos region, a further 550 miles south of Santiago.

By the way, here’s how I figure the cents per point metric (cpp) for an award redemption:

130000 (translate no. of dollars into no. of pennies for an end result in cents)
/ 99000 (number of points to evaluate)
= 1.31 cpp

Inbound – JFK to Santiago to Puerto Montt

routing: JFK-SCL-PMC

It turns out LATAM Airlines (LAN) offers a Boeing 787-900 Dreamliner out of JFK to Santiago (SCL) and back daily. Additionally there’s 1 or 2 other LAN flights that pause in Lima each way for an intermediate stop.

American Airlines (AA) also flies several routes down to Santiago, a few then piggyback on LA273 bound for Puerto Montt (PMC). Since there are only 2 flights to PMC daily, LA273 is one of the two legs that every route destined for Puerto Montt must use.

JFK-SCL-PMC – 5,666 total miles one way

I check award ticket availability for LAN using the British Airways (BA) website. searches LAN and other oneworld award availability. (Bold styling per the official logo.)

What is oneworld? BA, AA, LAN, and many other airlines hold membership in the oneworld alliance. (There are other competing alliances too.) An alliance is a group of airlines that agree to cooperate with one another to maximize operating efficiencies and increase their collective global footprint. Running an airline is a thin-margin business with loads of competition and so, as an airline, joining an alliance is a financially smart decision.

One neat feature an alliance offers to its constituent airlines is that an award booking can feature service with the host airline itself or on aircraft flown by a partner airline! Applicable to my itinerary, this means that my BA Avios miles can be used to book a flight on LAN if there’s award space available. Usually this availability is a minuscule subset of the total aircraft capacity and therefore unfortunately susceptible to shortages around the holidays, flux in point value relative to actual fare cost, unpredictable taxes, and other uncomfortable market dynamics.

Back to finding a LAN award flight. It is important to search for each segment individually. The whole JFK-PMC route (assuming the website will respect the stopover in Santiago) actually does return results, but there is a quirk. When award availability is found for the first JFK-SCL leg (and there’s usually quite a good lot open for booking) then it will automatically return an entire ‘valid’ JFK-PMC route. The route reports a price in miles (plus some taxes in revenue) and appears to even allow for booking it, but in reality the SCL-PMC end-portion is nonexistent ~95% of the time.

If you ignore seeking further confirmation and instead try to book the route then it will report the JFK-PMC route is not available. Yes, frustratingly, reality is not mirrored by the British Airways booking engine. But thankfully the workaround is simply to search the segments individually! Did you finally find a SCL-PMC segment? Great! Because unlike with SCL-PMC, the availability to Santiago from New York is usually wide open and there is likely a JFK-SCL flight arriving that very same day.

As an aside, if you clicked through the above Blue Marble graphic to access the route map, you might have noticed a time listed for each segment. It’s not entirely accurate because Great Circle Mapper (GCMap) only allows for a single total duration value to evaluate with the overall distance calculated. A better method of displaying time would be for GCMap to require a duration input for each individual segment.

The time data below I have recorded into my FlightMemory profile, which in turn is sourced from the officially listed flight duration on the airline website. FlightMemory is a website that allows for logging the flights you’ve taken. Then, based on the flight data entered, statistics and metrics are generated. This provides an insightful look back into personal flying history.

To make things a little more interesting the flight duration information along with the distance computed by GCMap is all that’s needed to start figuring out average flight speeds. These are the equations for calculating miles per hour:

JFK-SCL 10:40 h = 640 m
SCL-PMC 01:44 h = 104 m

JFK-SCL 5,097 mi
SCL-PMC 569 mi

Individually computed MPH values:
(5097 / 640) * 60 = 477.844 MPH

(569 / 104) * 60 = 328.269 MPH

Combined MPH value for input to GCMap:
((5097 + 569) / (640 + 104)) * 60 = 456.935 MPH

(Ever wondered the difference between speed and velocity? I have. It turns out velocity is speed with direction. Interesting!)

A Stop for Essentials

Because the entire route is on LAN, note that there’s a 4 or 5 hour layover in-between flights. I guess this is to make up for possible inbound delays. But it also captures a greater number of passengers going to Puerto Montt by pooling them first in Santiago, which is a major LAN hub. For me this affords an opportunity to run a couple of errands.

Getting Connected

If the prices aren’t set to extortion level at the Claro, Entel, WOM, or Movistar cell phone shops in the Santiago airport I may acquire a $3 USD prepaid SIM card with a data package. When driving around Italy two years ago it turned out to be incredibly helpful to have Google Maps accessible at the touch of a finger.

I have an iPhone 5s that is currently carried by T-Mobile, hence with AWS (1700/2100 MHz) it supports WOM at their 4G LTE level. The wireless coverage, however, is frighteningly thin in some key areas and even patchy on highways.

Per the frequency list for Movistar, my phone should be supported for 3G. The provider, however, opted to deploy their 4G implementation on the 2600 MHz band (similar to how Italy has configured their own 4G infrastructure) and therefore my device will not operate at LTE speeds. The final nail is a disappointing coverage map.

Entel offers the best coverage for some of the more far-flung areas that I will be staying and driving in. Santiago, of course, is well covered. A fourth carrier, Claro, looks promising on the price front. Wireless coverage is also consistent across the region I am staying in. My choice is between either Entel or Claro and so will look for their shops first.

Other carriers competing in Chile operate as MVNOs. They either piggyback on Movistar, are difficult to acquire in an airport, or run a regionally sparse network.

Getting Cash

Getting Chilean pesos will also be a priority and unless I wait to purchase a SIM in Puerto Montt I may start needing them as soon as right there in the Santiago airport. Then there’s the $1.25 USD Andrés Tour bus to Puerto Montt after landing at the airport and the $3.75 USD micro bus to Puerto Varas, and I will definitely need to have pesos at that point. For this tricky financial maneuver it could either be more cost effective in terms of minimizing exchange rates and fees to use an ATM at the Santiago airport or wait ’til the final destination to get cash and make the SIM purchase.

From using it in Italy (and Canada) I know that my Capital One 360 card is internationally fee-free. This means that Capital One won’t hit my account with fees from their side when I use it in another country. Conversely the foreign ATM bank (and perhaps also the business that provides space for the ATM) is totally free to charge fees, but from what I read it sounds like Banco del Estado and Scotiabank abstain from the levy.

To delve a little deeper into currency sourcing, I now understand that the exchange rate is highest at the airport exchange kiosk and lowest at the downtown exchange house. Reportedly these exchange house establishments are usually clearly marked as such, but then downtown is also 15 km (10 miles) from the airport and getting there and back in 5 hours might be tight. The sweet spot considering cost and convenience is certainly the ATM.

Finding the Flight

Starting with the hotel arrival and departure dates, I search oneworld inventory and double check with around 40 points worth of help from AwardNexus. A little about this fantastic tool. Unlike the booking portal, the AwardNexus search engine runs queries based on a given date range to eliminate tedious date-by-date hunting. Additionally, if your travel plans aren’t too specific or restricted by regionally dominating alliances then AwardNexus can easily be toggled to check for award availability on all three major alliances.

It ‘costs’ 1 point to run every date and alliance search, even if no availability is returned. So, as shown below, an eight day search for JFK-SCL-PMC on both Star Alliance and oneworld requires 16 points. At this rate you can see how quickly the points deplete and how important it is not to squander them by searching airlines and alliances that do not fly the desired route. 100 points are freely available every 90 days (which is how I access the tool) and when those run out additional points can be purchased.

JFK-SCL-PMC search in AwardNexus

JFK-SCL-PMC search in AwardNexus

My search returns an economy flight that will get me to Puerto Montt from Santiago. I must, however, move the hotel check-in up a few days to meet that flight as the SCL-PMC leg proves quite elusive to find and unfortunately rather rare. Not a problem! The initial JFK-SCL portion is, as previously discovered, wide open with award availability. With both segments available I book them as a complete itinerary and just like that I now have a date, my anchor at one end of the foundation.

Had I not found availability for the SCL-PMC portion, that same segment on LAN would cost around $485 USD—which is a bit exorbitant for a 569 mile flight and therefore why it was so important to have it covered under the award booking! Also, I checked, a regional Sky Airlines flight leaves Santiago at 10:00 am. This permits me a little over 2 hours to land in Santiago and find the Sky Airlines flight to Puerto Montt. That connection might happen, but then again it might not …

If not, bad news. I’d be stuck in Santiago without a quick way to get down to Puerto Varas and check in at the hotel. The slow way would be to take one of many buses, though I certainly do not want to pay ~$20 USD for that 10-14 hour time commitment. Finding the bus that even gets me to the final destination by the next day … just think of the hassle. It all sounds like a horrible connection nightmare that I do not want to deal with.

So, by flying instead, the BA Avios cost breakdown is 25,000 award miles for the JFK-SCL leg (5,097 actual air miles) and 4,500 miles for the SCL-PMC leg (569 miles). This is a total of 29,500 Avios miles and 5,666 air miles. Very reasonable! Now, because my BA Avios balance is currently only around 15,500 miles, I have to top it up with an additional 14,000. How to do this?

Conveniently enough British Airways is a transfer partner of Chase Ultimate Rewards (UR) and the 14k points transfer over quite easily. So for 29,500 Avios plus $16.57 in taxes I can get myself over to the other side of the world. Not bad! Incredibly the actual revenue cost for the LAN ticket is over four thousand! (This brings the redemption close to a 14 cpp Avios valuation, pretty fantastic!)

Outbound – Puerto Montt to Santiago, Santiago to JFK

routing: PMC-SCL & SCL-JFK

Next, because, I am able to forego using AAdvantage miles by instead spending Avios I decide to splurge and check for both economy and business on the PMC-SCL-JFK return trip. Unlike with the British Airways zone-based award chart, American Airlines determines an award ticket price by the beginning and ending regions. Not surprisingly there isn’t any award availability out of Puerto Montt; I resolve to take a revenue regional airline flight to Santiago for around $74 USD. But then …

Then something occurs to me:  Because this regional airline ticket obviously doesn’t continue on to the US I’m now in control of when I actually leave Santiago. This means I can afford to wait for my SCL-JFK flight. The added flexibility will allow for possibly finding award availability for that segment. Hmm, I might be able to work with this …

The holiday season routing to get me home isn’t producing much availability. However just at the last minute I check for seat space two days after my regional flight lands in Santiago and there it is:  Premium Business class on a nonstop return Santiago to JFK flight. Nice! Now I have to spend a couple days in a big city just waiting around and finding things to do and food to eat—what a difficult life!

This is what I think the LATAM Biz class looks like on a Boeing 787 – source

A final note on actually securing the flight. Because LAN award availability doesn’t show up on (which is why I searched BA and AwardNexus), AAdvantage reservations on LAN must be made on the phone with a booking agent. Sure it’s tedious and very last-century, but it gets the job done. I try to remind myself to be grateful that it’s at least still possible to find award availability on a website that, however buggy, blissfully avoids asking a phone rep twenty thousand questions to figure out all of the route combinations.

Filling in the Time Segments

At this point in the planning stage there’s a timeline with Puerto Varas sitting on a large first portion followed closely by a couple days worth of Santiago on the end. This provides two trips of varying lengths across two different locales, each with their own offerings for distinct experiences.

The shorter time in Santiago relative to the longer time spent in Puerto Varas, for example, will affect a much more local but abbreviated cultural experience. Explorations will occur closer to where I stay, though the time spent won’t be for as long. (I don’t think this rationale is applicable for transient backpackers.)

Puerto Varas

Within the Puerto Varas portion I think it will be a neat adventure to have a few days on my feet followed by a few days of access to a rental car. Walking a town is, I’ve found, a really great way to get to know my way around! The view from the street taken in at a walking pace is very valuable to me. And by not requiring a vehicle for the first few days I can save a bit of money.

Going back to Puerto Montt a few days into the stay I will retrieve the rental car to be returned back to the airport the morning of my Sky Airlines flight up to Santiago. By dropping the car at the airport, the connection should be simple and uneventful. By having the mobility of a vehicle I’ll be able to access the surrounding towns, some of them reached by the Pan-American Highway! Driving the circumference of Lake Llanquihue and heading down to the Grand Island of Chiloe will, I think, be a fun change of pace and an interesting look at the countryside of the Americas on the other side of the equator.


This one is easy, and I’m so excited to have a couple days to hang out here before heading back! There are hundreds of places to stay for a night or two in downtown Santiago. For $3 USD ($1,500 CLP) a bus from the airport will get me as far as Los Héroes metro station. From there the subway zips directly downtown where I have booked a room near the Plaza Baquedano square. Over the next couple of days I’ll trek about downtown snapping a lot of photos and discovering delicious foods from corner cafes and tasty taquerias. Sounds idyllic.

Distance analysis between airports with a fictional variable

Maximizing Cash Back

It’s important not to lose sight of the value of actual USD. For example, my two night stay in Santiago costs $178.27 after taxes. I booked it using Ultimate Rewards points which are normally valued at 1 cent apiece. However because I opt to navigate through my Chase Sapphire Reserve (CSR) card to book via their travel portal the points redeem at 1.5× their usual value. They’re effectively being supercharged by 150%! This is the equation to figure out how many points must be spent:

.015 × X = 178.27

What is X? Well, 178.27/0.15=11,884:  That’s how many UR points are needed to book the hotel.

Unfortunately, too, with this Santiago hotel I am obviously only getting 1.5 cents per UR point. Now I’m not sure it really qualifies for the ‘supercharged’ label! At that kind of redemption it might worry you since the valuation is much lower than the 14 cpp I am getting with the JFK-SCL-PMC LAN airfare. Yes, 1.5 cpp is rather abysmal, but in reality the points do not cost very much upfront to acquire, probably on average 5% of their basic value of 1 cent. (Any original costs of the UR points would include annual fees (AF) or when manufacturing spend.)

At a basic 1 cpp valuation that’s a reduced rate of only $118.84, or $59.42 per night all in, which just occurred to me is a really fantastic deal given that most hotels tack on 15% or so in various taxes.

Travel Credit

The Chase Sapphire Reserve has this cool prize of awarding 100,000 Ultimate Rewards points after spending $4,500, but then charges an immense $450 annual fee (AF) right after signing up! While this 100k bonus is certainly the main draw, the big fee is a real downer. $450 is a lot of money!

Wonderfully enough Chase offers a $300 travel perk that provides reimbursement when spending on travel-related purchases (airfare, taxis, hotels). Those expenses are immediately reimbursed to you as a credit on your card account. The $300 limit resets every calendar year.*

Since you were going to spend money on travel anyway, having it reimbursed negatively impacts the AF (yay!) bringing the effective fee down to $150.** $150 is a fine price to pay for 100,000 Ultimate Rewards points, especially since each is worth the basic 1 cent value. As a lot you could redeem them for $1,000! Whether you choose to keep the card account open after using the points and travel credit is up to you.

A variety of other minor card benefits exist, one of which is a $100 balance credit when signing up for Global Entry (GE) or TSA PreCheck. With the United States border re-entry process becoming ever more arduous, GE allows you to expedite or skip portions of immigration after returning from international travel. At $85, yes, PreCheck costs less but it only gives you access to the domestic TSA PreCheck lines at the airports. Global Entry also includes the benefits of PreCheck and since you’re covered up to $100 it makes sense to apply for GE, that is unless you absolutely have no desire to travel outside of the US.

* To receive the $300 reimbursement twice (and subsequently come out +$150 ahead instead of -$150), charge another $300 in travel-related purchases and then close the card account right after the limit resets in January 2018 but before the new AF hits in, say, March. Don’t miss it though! This feature will be going away in 2018.

** $150 with the implication that each year $300 in travel related purchases are made. Buy Southwest or American Airlines gift cards or something!

Preferring Cash Back

Because I have recently earned over 200,000 Ultimate Rewards points, I am considering cashing some of them out at 1 cent apiece (1 cpp). This would be their most basic value (to me) and I would be getting money directly deposited into my bank account. (That money would even be tax free—wow!) Though 1 cpp is less than the 1.5 cpp hotel redemption in Santiago and even further behind the 14 cpp JFK-SCL-PMC airfare redemption, I am very tempted to just take the cash.

Something to keep in mind is that it may be worth keeping 35 to 45 thousand Ultimate Rewards points around for last-minute award booking flexibility. The ability to immediately top up a Southwest Rapid Rewards or World of Hyatt balance in order to snag that future lucrative award always seems to come in handy, especially when compared with spending money by having to book a revenue fare or hotel stay. It is for this reason why I have a few Air Canada Aeroplan, United MileagePlus, and British Airways Avios miles sitting in reserve.

The decision of going with a lowly 1 cpp redemption rate or waiting until the moment award travel is needed oscillates closely between a mathematical and personal choice. There are many ways forward to evaluate:  Upcoming personal travel plans, booking flights and hotels for others, risky initiatives to privately resell points, the tempting need or want of hundreds of dollars of immediate financial benefit. All these and their possible combinations must be carefully weighed before making a decision.

Of course, taking no action is indeed another option. But like cash deflation, and perhaps even more so, points and miles sitting unused eventually decay in their spending ability. Airline programs periodically shift the number of points required to book tickets, and it’s usually toward an increased amount. This is why it is important not to hold on to points for too long lest they degrade in worth. Furthermore, acquiring points only when award travel is actually being planned and booked can help avoid idle miles from sitting lazily around, scattered and jailed within their disparate frequent flyer accounts.

Structure and Schedule

I have noticed that an itinerary can be thought of like number line in-nested with segments of varying lengths. These segments touch one another at their endpoints and so the visual ends up looking like multiple short hotel bookings in a row, each with their old check-out and new check-in dates overlapping. By visualizing an itinerary in the way, it’s possible to even nest events like the car rental or hotel stay within a period of several days. One day outings and sightseeing adventures are easily represented by just plopping them onto the line on a scheduled day.

Google Calendar is amazing at organizing and visualizing this kind of data. Additionally, because Gmail automatically inspects and interprets e-mail, any booking confirmations with date, time, and location are automatically added to my Calendar. It’s a great system!

Example of a Google Calendar with event overlap

Example of a Google Calendar with event overlap – source


On the 22nd of September the daylight will last for a little over 12 hours in both NYC and Puerto Montt. Then, from that point on, the days will begin to contract over here while in Chile just the opposite will occur. All this probably has a lot to do with opposite latitudinal values. The longitude, being on the same side of the number line, is actually only off by 2 degrees. It becomes clearer once envisioned on a map.

Going to a location that is right about mirrored directly across the equator from where I presently live means the climate should be somewhat similar. Right? Well, from the measurements taken over the years, it appears that the average high and low temperatures for the latter months of the year are a lot more like how San Francisco weather is supposed to feel.

This itinerary is most certainly a work in progress and there are some blank spots, both inadvertent and not. Those that are not are my built-in pockets of downtime, a rather crucial element to my style of traveling. Then there is the continual act of refining this itinerary and every time I do that I’ll feel I’m stashing little nuggets of opportunity for me to find once I’m over there.

Map of the World – source

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