Four-Capital+ Latin Sampler Maximizing the New United Excursionist Perk

I have been thinking about exploring more of Latin America lately, and now that there are new opportunities for free one-ways on United bookings, I thought I'd work out an itinerary that incorporates both interests. In this post, I'll share how to see four countries, four capitals + one ancient mountain-top village using a very affordable number of United Miles. I'll also compare my "latin sampler" to the original "latin hopper" route that inspired it.

Itinerary Highlights

The itinerary I've constructed is based on having stopovers to visit cities I've never explored: Mexico City, Lima, Cusco (Machu Picchu), Panama City. In addition, I'd get to revisit one of my favorites, Bogota. Here's why I picked each place:

  • Mexico City - I'd never wanted to visit the capital of Mexico until I saw the opening scene of the most recent 007 movie, which put the city on display during Dia de los Muertos. Intrigued, I dug deeper to find that it was one of two Spanish colonial capitals in Latin America and also featured impressive indigenous ruins like the Aztec city of Teotihuacan. I am also blown away by the wealth of inexpensive hotel award stays available, like the Hampton Inn & Suites in the city-center for only 10k Hilton points per night.
  • Lima - Peru is known to have the best food culture in Latin America, they have a unique national drink (Pisco), and Lima is still a very inexpensive city.
  • Cusco - Machu Picchu is the big + in the title of this post. It's on just about every backpacker's list of places to see, and I feel the call, too!
  • Bogota - The capital of Colombia is coming into its own, in the wake of much progress with issues of violence related to the drug trade and rebel groups. Bogota is probably not for beginning travelers, but it's very energetic and, if you keep your wits about you, a lot of fun for a great price!
  • Panama City - The capital of Panama is an international hub, thanks to the Panama Canal and it's central location within the Americas. There is a big expat scene, an up-and-coming "old-town" (Casco Viejo), and numerous inexpensive hotel point redemption options (the hotels are cheap to book anyway though).
  • San Jose, Costa Rica (PTY Alternative) - While I do intend to visit Costa Rica in the near future, Panama is higher up on my list for this particular trip. However, if you've got the Southwest Companion Pass, San Jose makes an excellent alternative for reasons I'll explain later!

A New Latin Hopper with United: My Four-Capital+ Itinerary

MEX-CUZ: 20k United Miles in business class on an Avianca A319, with an overnight layover (read: one night to party in Lima!). This business product is not as good as the one on their A330's, but is at least as good as most US domestic first-class seats.

CUZ-LIM: I would use 4.5k British Airways Avios in economy class on a LAN flight of approximately 1.5hrs, but if lacking Avios, flights booked at least a few weeks ahead are usually in the range of $75-90 between these cities.

LIM-BOG: Free in business class using the new United one-way loophole. This flight is typically operated by Avianca in an Airbus A330, which is a very solid business-class product.

BOG-PTY: 10k United Miles in economy on a short COPA flight.

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I should mention that I left out flights to and from the US intentionally (fill in your own blanks!). For me, flying out of LAX to MEX for about $100 would be an obvious choice and then I'd probably redeem miles for the return from PTY. Redeeming Singapore Krisflyer Miles for the PTY-LAX flight would also set me up nicely for this award chart routing hack.

Comparing My New United Latin Sampler to the Old Latin Hopper from Drew at Travelisfree has lots of creative content in the same vein as what I have been exploring, and a few years back, Drew mapped out the original "latin hopper." His itinerary was from San Juan (Puerto Rico) to Quito to Lima to Cancun and it cost him only 20k United Miles in economy. Since both San Juan and Cancun are Southwest Airlines destinations, he used Rapid Rewards Miles and the Southwest Companion Pass to cut his positioning costs in half. If you'd like to know more about how that works and how you can get one, check out this post.

My new latin hopper can also be done for 20k United miles in economy (24.5k total miles to include the extra city, Cusco), but I chose to step it up another notch by adding 10 hours of business class flying for just 10k more miles. Considering that it would cost an extra 25k miles to get a similar amount of business class flight-time out of any domestic US travel with United, I find this to be a bargain.

My itinerary can also be positioned on the front-end with Southwest flights, and could be adjusted to return via San Jose (Costa Rica) instead of Panama City to return in the same fashion. In doing so, the Southwest Companion Pass could be put into play the same way Drew did on his hopper positioning flights.

While Drew's itinerary began and ended with beach destinations, my route takes in more large cities, but overall, the results are very similar. We each hit Lima, Peru and another Northern South America capital, and have stopovers for as long as we want in at least four Latin American cities (although I add a 5th with Cusco using Avios, hence the "Four Capital+" designation). In all, I'd call it a draw, which is good for miles and points travelers in these changing times.

The Bottom Line

Despite several United Airlines MileagePlus Program devaluations in the two years since the first latin hopper route was widely published, it's still possible to do basically the same thing today. Using my route, you can see some of the coolest places in Latin America and travel in style and comfort without using up too many precious miles or breaking the bank. The miles and points game is alive and well!

If you'd like to create your own route using the United excursionist perk as a "free one-way," check out: A Helpful Resource for Free One-Ways with the New United Award System

A Helpful Resource for Free One-Ways with the New United Award System

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I need to start off this massive post by saying that none of this would have been on my radar had I not been a long-time follower of Drew Macomber over at His content is unique, creative, and refreshingly short on sale tactics. My goal for this post is to explore and expound upon his recent discovery that, when United recently devalued its awards through changes to its booking system, it simultaneously opened up new opportunities for savvy miles and points enthusiasts in 2016 and beyond.

Use these links to jump to the section you want to explore:

Section 1: The basics of the new free one-ways loophole with United Miles

Section 2: Guidelines to increase redemption values

Section 3: Nesting multiple itineraries to create savings in economy and business

Section 4: The longest flight segments for free one-ways sorted by region

Section 5: Known limitations of the new United free one-ways loophole

Section 1

The basics of the new free one-ways loophole with United miles

Basics of the New United Free One-Way Opportunity

When United changed its booking rules on October 6th (2016), it closed several loopholes in the system, including one that allowed for adding "free one-ways" to the beginning or end of flights. This loophole was reliant upon United allowing a free stopover on any international award flight. While this is no longer possible, the new rules stipulate allow for an excursionist segment. It turns out that this segment can be anywhere in the world besides the ticket origin and it must remain within one region, as designated here.

To simplify as much as possible, what Drew discovered is that you can essentially book any two one-way tickets that begin and end in the same region (even two domestic flights), and then stick any one-region segment you like in the middle at no extra cost. Even better, booking a premium seat on the first leg of the ticket will make that excursionist leg premium also, and at no additional cost.

Minimal Point Outlay for Maximum Free Flight Hours

One way to maximize the benefits of this loophole is to book the cheapest first and final segments, so that the relative value of the free one-way stuck in the middle is higher. For example, one of Drew's readers from Hawaii commented that he could book an inter-island flight for 6,000 MileagePlus Miles.

If you happen to live in Hawaii or need some inter-island flights as part of a vacation there, that means you can spend as little as 12,000 miles to earn a free segment in another region that might normally cost as much as 20,000 miles. You can do even better by booking a business or first class inter-island segment (8.5/10k each way), which should make the free one-way a free premium class flight!

Assuming most people won't be able to take advantage of the inter-island flights, the next cheapest are domestic US flights on United metal that are less than 700 miles between city-pairs. These flights cost just 10,000 miles each. Doing this, you'd pay 20,000 miles for a pair of shorter domestic one-ways and receive a free one-region segment in economy that could be more than twice as long as the two domestic flights combined.

Section 2

Guidelines to increase redemption values

Booking an all-economy award with a free one-way

When booking an all-economy class United award, the best way to maximize the value of the free segment (based on percentage of miles saved) would follow these rules:

  1. Make the first and last legs (the segments you'll pay for with award miles) as cheap as possible. For example, inter-island flights in Hawaii are 6,000 miles each, flights within Japan are 5,000-8,000 miles each, and US domestic flights less than 700 miles in distance are 10,000 miles each. In these scenarios, you will pay between 10,000-20,000 miles for two one-way tickets and receive a third one-way in any other region in the world for free.
  2. While your "paid" award segments might ideally be short, you'll get maximum free flight-time by making your free segment in the middle as long as possible. Try for flights that cross the entirety of a region, such as Los Angeles to New York or Reykjavik to Istanbul. You can reference my resource post to learn about some of the longer one-region free one-ways.
  3. In a similar fashion to rule #2, if you want to maximize value, you would also want your free segment to be in a region that typically charges more for flights within that region, such as the Middle East (20k within the region). The Africa regions, South Asia, and Australia/New Zealand are also high-value options (17.5k within the region).

Booking an award to receive maximum free business/first class air-time

Selecting a business class flight as your first segment will allow you to book your free one-way as business at no additional cost. In this case, you'll benefit from a different set of rules than with all-economy awards:

  1. Make the first leg as long as you want, since there are no short-distance discounts for business-class award options.
  2. Try to fly the first leg in a relatively cheap United business class region and then fly the free one-way segment in a relatively expensive region for business class.
  3. Try to make the first leg a transcontinental or other longer flight within one region to get a better business class product.

Section 3

Nesting multiple itineraries to create savings in economy and business

Nesting Two New United Free One-Way Bookings in Economy Class

First, you'll need to do some date-selection, because once you know your flights, they will be intermingled between two separate bookings that will have date overlaps. In the example below, Booking #1 has the first leg of what will be a free roundtrip between Bogota, Colombia and Lima, Peru, but Booking #2 has the first flight you will actually take.

  • Booking #1: LAX-PTY (17.5k), BOG-LIM (free), SFO-EWR (12.5k)
  • Booking #2: Any domestic economy flight (12.5k), LIM-BOG (free), EWR-SFO (12.5k)

Combining these two bookings in the order they would be flown results in a one-way from San Francisco to Panama City (with an optional stopover in Los Angeles), a round-trip between Bogota and Lima, and a roundtrip between San Francisco and Newark.

  • Combined: SFO-LAX (10k), LAX-PTY (17.5k), BOG-LIM (free), LIM-BOG (free), SFO-EWR (12.5k), EWR-SFO (12.5k) = 52.5k United miles
  • Booked Separately: SFO-PTY (17.5k), BOG-LIM-BOG (20k), SFO-EWR-SFO (25k) = 62.5k United miles

The result of nesting two United bookings such as these allows the traveler to utilize the new United free one-way loophole to save 7.5k miles + add a free flight anywhere in the US. You can see this as an approximately 12% savings + a free flight or a 30% savings if you convert that flight to miles, but it is contingent upon several things:

  1. A nesting strategy like this is complicated enough that some people could get tripped up...focus will be required to make sure all the dates are correct and that it all prices out right.
  2. There must be a desire to book these routes anyway (i.e. saving 10k doesn't help if you didn't want to go to all of these places anyway).
  3. There are still open legs in these routes, such as the return to San Francisco from Panama City if you want to create three distinct trips, or the flights between PTY-BOG and BOG SFO if you want to make two trips (long multi-stopover trip to Latin America + transcontinental flight between San Francisco and New York City)

Nesting Two New United Free One-Ways in Business Class

Achieving greater savings on free one-ways through business class is one of the tricks I pointed out in Section 1. Since there is no additional benefit to booking business class on the final leg of either booking, I will show examples with two legs in business and the third in economy class, which maximizes the best discount by percentage of total cost.

  • Booking #1: SFO-PTY (30k), BOG-LIM (free), EWR-SFO (12.5k)
  • Booking #2:  EWR-SFO or any domestic biz flight (25k), LIM-BOG (free), SFO-EWR (12.5k)
Booking #1

Booking #1

Booking #2

Booking #2

Combining these two award bookings in order of date flown results in a one-way biz class flight from any two cities in the US, a one-way flight biz class from San Francisco to Panama City, a roundtrip biz class between Bogota and Lima, and an economy roundtrip between San Francisco and Newark.

  • Combined: EWR-SFO (25k), SFO-PTY (30k), BOG-LIM (free), LIM-BOG (free), SFO-EWR (12.5k), EWR-SFO (12.5k) = 80k United Miles
  • Booked Separately: EWR-SFO (25k), SFO-PTY (30k), BOG-LIM-BOG (40k), SFO-EWR-SFO (25k) = 120k United Miles
  • Booked only in economy: EWR-SFO (12.5k), SFO-PTY (17.5k), BOG-LIM-BOG (20k), SFO-EWR-SFO (25k) = 70k United Miles

In this example, we get the six-hour roundtrip between Colombia and Peru for free in business class on a nicely outfitted Avianca A330! This amounts to a savings of 40k miles or a 33% savings versus booking the same flights without the new free one-way loophole. Another way of looking at it would be to compare with an all-economy booking. For just 10,000 more points, you get up to 19 hours of business class air-time and it's sometimes easier to find business class space on busier flight dates, so this helps with booking availability, too!

Section 4

The longest flight segments for free one-ways sorted by region

Mainland US, Alaska & Canada

The best plays for this region include the longest flight Anchorage-NYC at about 7hrs in the air (though most flights between the city-pair involve a connection through Denver) and the big transcontinental routes. Pairing Newark and LAX or SFO will likely produce the best results if you're looking for a premium product on transcon flights with United (if you want to know what that looks like, check out this review).

  • Los Angeles-New York City: 2,451 miles on United
  • Los Angeles-Boston: 2,608 miles on United
  • Los Angeles-Washington DC: 2,286 on United
  • Los Angeles-Montreal: 2,471 miles on Air Canada
  • San Francisco-New York City: 2,561 on United
  • San Francisco-Boston: 2,700 miles on United
  • San Francisco-Washington DC: 2,439 miles on United
  • San Francisco-Montreal: 2,535 miles on Air Canada
  • Seattle-New York City: 2,398 miles on United
  • Seattle-Washington DC: 2,303 miles on United
  • Seattle-Toronto: 2,057 miles on United
  • Anchorage-New York City: 3,364 miles on United
  • Anchorage-Chicago: 2,841 miles on United
  • Anchorage-Denver: 2,403 miles on United
  • Anchorage-San Francisco: 2,017 miles on United


The longest non-stop flight of significance that I could find was between Moscow and Lisbon coming in at round-about 5hrs of flight time. Another interesting play for Europe would be using Lufthansa hubs in Germany or Scandinavian's hub in Copenhagen to connect Reykjavik, Iceland to a number of Mediterranean destinations. Check out the sample below:

Reykjavik to Istanbul via Copenhagen is be 7:20 of flight-time. Using two flights in the US to bookend this award ticket makes the Europe part show up for free, creating a free one-way! Even after recognizing that no miles were charged for the intra-European flights, you might be wondering why this award shows up as 22,500 miles instead of the 25,000 two one-way US flights usually costs. Since Newark to Baltimore is a short flight, United offers it for 10,000 instead of the usual 12,500 each way.

Perhaps the best part about this award came when I switched the LAX-EWR leg to BusinessFirst for 25,000 miles. When I did that, I was able to book the 7+hr European portion in business as well, without incurring additional miles or tax charges. That means that I can fly nearly all of this route in business class for just 35,000 United miles.

Here are some of the city-pairs for Europe I found interesting:

  • Lisbon-Copenhagen: 1,537 miles on TAP
  • Moscow-Lisbon: 2,433 miles on TAP
  • Moscow-Geneva: 1,503 miles on SWISS
  • London-Istanbul: 1,546 miles on Turkish
  • London-Athens: 1,509 miles on Aegean
  • Reykjavik-Munich: 1,674 miles on Lufthansa
  • Munich-Rhodes: 1,169 miles on Aegean
  • Reykjavik-Frankfurt: 1,493 miles on Lufthansa
  • Frankfurt-Istanbul: 1,159 miles on Lufthansa

Northern South America

Last I was aware, Avianca flies mostly their A330 aircraft from Peru to Colombia, which is a solid offering for these 3.5hr flights. If one were combining travels through Central America and/or the Caribbean with Northern South America, one of these free segments could be tacked on to two flights in those regions for a total cost of 20,000 United miles in economy, or 30,000 miles if you want to fly the front end + the free one-way in business.

You'd still have some connecting flights to book, but this works out to potentially 10+ flight hours in business and an additional domestic flight in economy for for a very low rate. Most normally-booked business class flights of 10+ hours (think US-Europe or US-Southern SA) cost at least 55,000 miles each way, instead of only 30,000 here for the same amount of air-time.

  • Lima-Bogota: 1,175 miles on Avianca (see my "latin sampler" post for an example using this segment)
  • Lima-Medellin: 1,267 miles on Avianca
  • Cusco-Bogota: 1,270 miles on Avianca
Avianca A330 Business Class Seats

Avianca A330 Business Class Seats

 Southern South America

While Southern South America doesn't offer many long flights, the routes I did find happen to be "5th Freedom" flights. This means that for your 1.5-2hr flights, you'll be flying an aircraft that's meant to go long-distance, so the quality of the seats and service is likely to be higher.

  • Santiago-Buenos Aires: 709 miles on Air Canada
  • Santiago-Sao Paolo: 1,071 miles on Turkish Airlines

Central America

  • Panama City-Belize City: 838 miles on COPA
  • Panama City-Guatemala City: 845 miles on COPA
  • Panama City-San Salvador: 722 miles on Avianca

South Asia

The longest practical free one-way I have found in the South Asia region would involve flying on United partner Singapore Airlines between Hong Kong and Bali via Singapore. This combo would be over 2,600 miles of flying and would result in a savings of 20,000 United miles in a high-end economy seat or 40,000 miles in a very solid business class product for a medium-haul flight.

  • Hong Kong-Singapore: 1,595 miles on United or Singapore Airlines
  • Hong Kong-Phuket: 1,429 miles on Thai Airways
  • Hong Kong-Bangkok: 1,051 miles on Thai Airways
  • Bali-Bangkok: 1,840 miles on Thai Airways
  • Bali-Singapore: 1,040 miles on Singapore Airlines

Australia/New Zealand/Tasmania

While United flies from the US to Australia and New Zealand, flights within this region will be on Air New Zealand. Air NZ opens a decent amount of economy award space, but very little in business class, so although you can get some decent-length free one-ways, the larger benefit of business class award bookings is unlikely. 

Auckland and Perth stand out as a city-pair with serious potential, but the 7+ hour flight is 17.5k United miles normally and, unless you were planning to go to Perth anyway, doesn't offer much utility.

  • Auckland-Perth: 3,320 miles on Air New Zealand
  • Auckland-Sydney: 1,343 miles on Air New Zealand
  • Auckland-Melbourne: 1,641 miles on Air New Zealand
  • Auckland-Brisbane: 1,428 miles on Air New Zealand
  • Christchurch-Brisbane: 1,553 miles on Air New Zealand
  • Christchurch-Sydney: 1,323 miles on Air New Zealand
  • Christchurch-Melbourne: 1,501 miles on Air New Zealand
  • Queenstown-Sydney: 1,206 miles on Air New Zealand
  • Queenstown-Melbourne: 1,335 miles on Air New Zealand

Section 5

Known limitations of the new United free one-ways loophole

Limitations of the New United Free One-Ways

  1. The region of origin must be visited twice for the itinerary to be eligible for the excursionist perk.
  2. The free one-way must be within a single region and that region cannot be the region of origin.
  3. Intra-region flights tend to be shorter and therefore, usually less valuable in terms of premium class product quality.
  4. Utilizing the new United free one-way loophole to maximum benefit requires planning multiple trips in advance.

The Best Award Mile Redemptions for Traveling to New Zealand

As part of my research into a forthcoming expedition to New Zealand, I have been scouring the internet to learn everything I can about how to get there and making the most of my time. As is always the case, I have a particular interest in how I can do this on a budget, or maybe even for free. This post is the first in a series about NZ and will detail my findings on the best award redemptions from the United States to New Zealand and back again.

UPDATE, 1/11/2016: I found a goldmine of economy award space today for United redemptions by searching from SFO. Remember to search from multiple west coast hubs as it might be worth repositioning to find availability!


Crossing the Pacific Ocean to Oceania and Australia/New Zealand has typically been a very tough redemption space, but with renewed interest from US airlines, there's hope for some positive change in availability. Meanwhile, if you've got the desire to visit New Zealand on miles, there are already some valid options if you have United, American, or Alaska miles in your account!

Using United Airlines Miles for New Zealand

This is the partner that unlocks Air New Zealand flights, so if you've got United miles you've got a good shot. While Air New Zealand doesn't open up much availability on its own flights, when it code-shares with UA there are often 4 economy seats bookable with miles if you plan way ahead (like 11 months ahead, the first few days they become available). A roundtrip to Auckland or Queenstown from LAX will cost you 80,000 miles and typically will route through Australia (Sydney or Melbourne).

To make the most of your points, you could organize a "stopover" in Queenstown for a few days on a roundtrip flight from LAX-AKL, giving you both New Zealand cities for no additional miles. Alternatively, you could also use an "open-jaw" award to fly Los Angeles to Queenstown and back from Auckland to Los Angeles. You'd need to find your way between the two New Zealand cities (typically $100-200 for a one-way), but this would save your stopover for Melbourne or Sydney if you want to see a bit of Australia, too.

Using American Airlines Miles for New Zealand

Continuing to look at our late-November window, there is lots of economy seat availability on partner airline Quantas to Queenstown, via Sydney. I also found space for the same route on Wednesdays booking directly through American Airlines. Flying back from Auckland to LAX, via Sydney should be easier, so just a one-way flight from Queenstown to Auckland would be needed to complete the loop. 

A third option, and perhaps the best, is partner Fiji Airways. There is ample availability (if booked 11 months out) for both economy and business class routing from LAX to Auckland, via Nadi Airport (Fiji). A roundtrip flight to and from Queenstown would still need to be booked to complete the loop. 

All of these awards would price out at 37.5k each way in economy and 62.5k in business (although soon American is raising business award redemption rates).

Using Alaska Airlines Miles for New Zealand

There's one obviously good play with Alaska miles that needs to be added to the award options. Alaska, like American, is partnered with Fiji Airways. The difference between the two programs is that Alaska allows a free stopover, so you can actually spend some time enjoying Fiji on your way to New Zealand. Alaska allows you to do this for 40k miles each way in economy or only 55k in business and I have seen availability for both options.

The Hybrid Miles Option for Getting to New Zealand

Johanna and I have a rather substantial supply of American Airlines miles and a growing supply of Alaska miles as well, so we will probably do a hybrid redemption. Both airlines offer one-way awards, so we'll be looking to book with American miles on the way and Alaska miles in order to relax in Fiji on our way home.

Since Alaska miles are harder to come by and include things like free stopovers (which American no longer allows), I value them more highly. Using the AA miles on the outbound (when we wouldn't use a stopover anyway) preserves more of our higher-valued miles. We may even decide to use our additional Alaska miles to make the long return trip in business class, which would be a first for us in seven years of traveling together.

Note: Don't get me wrong, American miles are valuable! However, there are lots of AA credit card sign-up bonuses in the 50-60k range to pad your accounts and they have announced a devaluation of their award chart for March of 2016.

Other Options for Award Travel to New Zealand

It's also possible to get from the US to New Zealand using Hawaiian (via Honolulu) or KLM (via Tahiti) and I did do a fair bit of research before concluding these options to be less desirable. The exception would be if you wanted to visit those places anyway, in which case the issues in award availability and routing might be worth fighting through.

Using Miles within New Zealand for Domestic Flights

Once in New Zealand, you may find yourself wanting to hop between the two islands by plane, in which case, you should be looking for cheap flights or an alternative mode of travel. United is partnered with the domestic monopoly that is Air New Zealand, but its a rip-off. It costs 17,500 United miles for a domestic one-way, making those points worth a cent or less each, whereas you'd be redeeming United miles for at least 1.5 cents-per-mile when flying from the US to New Zealand.

The Bottom Line for Award Travel to Kiwi Country from the US?

As American and United announce new routes from the US to New Zealand and Australia, we should see more space come available as well as a decrease in the cost of a paid ticket. If, however, you're like me and just can't wait to get to New Zealand, there are still plenty of options if you plan far enough in advance and know how to find the award space.

Next up in this series, I will tackle all the ways to visit both Auckland and Queenstown (on opposite ends of the country) in one trip. Stay tuned!

Do you have an interest in New Zealand and lots of miles to cash in? I can help you find those flights and get you headed out on your next adventure. Contact Thorpe Travel for more information.

Getting Creative to Book Award Flights to Hawaii During Spring Break

Dilemma: The airlines know when most families have a week-long chance to get away for some tropical fun. Accordingly, there is almost ZERO award space on American, United, Alaska, and Delta at the saver level for a convenient trip to Hawaii, even from a West Coast hub. Paid tickets are super-pricey, as are hotel accommodations. In short, this is a terrible time to be hunting for bargain travel, but my miles/points game is irrepressible!

Getting to Hawaii on Alaska Air Flights

After searching availability to all Hawaii airports from every Alaska Air option on the West Coast (and all the other airlines, too), I learned that Seattle gave me the best shot at a flight out during the early part of spring break week. Like the other airlines, Alaska basically only had flights in and out of Hawaii mid-week, which meant too little time on the islands to make it worthwhile.

I found two exceptions, the best of which was a Monday morning flight going directly from SEA-TAC to LIH airport on Kauai. Score! I was then able to find a flight from Santa Barbara to Seattle the previous day that I could tack onto the award booking at no extra charge. We get to fly out of our home airport early Sunday morning, hang out in Seattle for about 24 hours with family, and then continue to Hawaii Monday morning, all for a saver-level award redemption!

Miles/Points Used: 40,000 Alaska Air miles total for our two tickets.

Getting Back Home

This one turned out to be an even greater challenge than going to Hawaii. I thought I'd found two tickets available on an American flight from LIH to PHX (Phoenix). Then, we'd use our Southwest Companion Pass and miles to get back to California. I called to book the AA flight to PHX with Avios (British Airways) because they offer the cheapest redemption to and from Hawaii, but they didn't see two seats available. Sometimes airlines won't release the same award space to partners, so we were stuck without a way home.

Then, I remembered that Alaska is also a partner of British Airways and I quickly found a Thursday afternoon flight to Portland (PDX). We'll fly there on Thursday, use a few hotel points for a free hotel stay, and take a morning flight back to California on Southwest. While not the simplest route, the savings are worthwhile it.

Miles/Points Used: 25,000 BA Avios + 6,000 SW Miles

Why I Went to All This Trouble

Award space on the major US carriers to Hawaii is basically non-existent at the saver level for our dates. Even if it was available, it would cost us more in miles that have better redemption value when applied to international routes.

Of course, we could always pay for our tickets to Kauai. American is currently the best-priced major US carrier, offering our dates at just under $700 per person.

We're applying 71,000 miles to get to Hawaii and back during a very busy time of the year, instead of spending about $1400, which means our redemption value is 2cpm. For a "domestic" flight, that's very good, and all three airline currencies we are using are relatively easy to come by. There is the 10,000 points we'll use for a hotel in Portland to consider, but that is nicely counterbalanced by the opportunity to see family in Seattle at the front end of our trip.

Bottom Line

This trip was brought about by our desire to use Wyndham points for a very specific award use (the beautiful Koloa Landing Resort). Check! We wanted to use miles to significantly reduce our biggest travel expense: transportation. Check!

Koloa Landing Resort goes for about $500 per night and they have now sold all of the cheaper rooms for our travel dates, so we saved $1500 minimum on accommodations. Add that to the airfare and we've saved nearly $3000 that many would spend for just three days in paradise. We don't have that kind of money to toss around, but if we did, we'd probably still use miles and points.

Think about the adventures a couple or family could have in Hawaii with $3000 if they didn't have to spend it on flights and hotels (maybe take a helicopter tour with Blue Hawaiian?). We'll use a fraction of that savings and live it up! This is why we play the miles and points game.

Want to learn more about the miles and points game? Check out The Miles and Points Primer: How to Start Living Your Wildest Travel Dreams. Right now you can download your e-copy for free!!!