Recently, I posted about how we can get amazing value from the fact that the Singapore Airlines KrisFlyer program considers Hawaii to be part of the same region as Central America. We can also use this sweet spot for great value on travel to South America too!

On the Singapore Airline's award chart, it costs fewer miles to fly between Hawaii and South America, routing through the continental United States, than it does to fly directly between the continental United States and South America.

Adding Honolulu to Houston lowers the price of Houston to Buenos Aires

The biggest mistake in the miles game is collecting the wrong miles for the job.

That's why I always advocate that people start at their end goal and work backwards. Figure out your dream trip and then figure out the best miles and points to collect for that trip.

I've collected and redeemed millions of frequent flyer miles over the last three years. By the end of 2014, I will have visited over 50 countries, often flying in First Class.

Singapore Airlines' award chart has an amazing sweet spot: Hawaii and Central America are in the same region!

Flights "within" the Hawaii/Central America region are only 35,000 Singapore miles roundtrip in economy and 60,000 miles roundtrip in business class.

That 35,000-Singapore-miles award would cost 80,000 United miles.

You can see three "destination" cities on one United award, but you need to book a separate ticket with Avios or cash to tie the trip together.

Why is three the limit?
Why does seeing even three cities require a second award?
How can you see four or more cities with United miles?

You get one stopover and two open jaws on a roundtrip United award in addition to your destination and origin cities.

When you look at what possibilities that opens, you see that you can have three "destinations" on your award, kind of.

For instance, you can fly

Delta allows one open jaw per roundtrip award that you can use to see more cities on a single award and to unlock free one ways.

A simple, valid open jaw routing on Delta. The open jaw is between Amsterdam and Paris.

Delta allows an open jaw to straddle two regions, so that your outbound can go to Bangkok in Southeast Asia and your return can start from Sydney, Australia.

I looked at the upcoming reservations in my United account. There are three trips:

Honolulu to Sao Paulo
Frankfurt to Los Angeles
Honolulu to Chicago

One trip was booked with United miles, one with US Airways miles (before US Airways lost United as a partner), and one with Lufthansa miles.

The award booked with United miles flies Asiana, Lufthansa, and Air Canada. The awards booked with the other types of miles both fly United planes.

These three awards illustrate two simple and counter-intuitive truths about frequent flyer miles that I want everyone to understand.

1.

Tuesday news broke that US Airways is not collecting fuel surcharges on British Airways flights on award tickets, which is surprising since American Airlines and British Airways have long collected fuel surcharges on British Airways flights.

US Airways miles are the most valuable miles around because of:

US Airways' very cheap award chart
US Airways' impressive roster of partners including surcharge-free British Airways
US Airways' lax routing rules on award tickets

Combining those three elements, I just put on hold a US Airways award from New York to Sydney with a stopover in Hong Kong one direction for 140k US

Update: Super reader Dave made a map of the locations of the Category 9 and 10 properties for visual learners.

Super reader Jeremy has created the most valuable spreadsheet imaginable for the Hilton HHonors program that you can download for free here.

The spreadsheet lists:

all 34 Category 1 hotels
all 131 Category 2 hotels
all 46 Category 9 hotels
all 10 Category 10 hotels

For each hotel, the name, location, and a link to its Trip Advisor reviews are listed.

Jeremy took the information from Hilton's PDF of all its hotels' categories and made it much more useful and

My friend has big trip aspirations for this summer, but nothing booked.

Approx July 12: Boston to France, Italy, or Spain
July 13/14 to 24/25: work on a vineyard in France, Italy, or Spain
July 25: vineyard location to Croatia
July 26 to August 2: Yacht Week
August 2: Croatia to Greece
August 10/11: Greece to Boston
August 22: Boston to Colombia
August 31: Colombia to Costa Rica
Sept ~7/8: Costa Rica to San Francisco

She emailed me for my suggestions.