How to Plan Crazy, Cheap Trips

2 Trips. 6+ Bookings. 11+ Countries. 16+ Flights. Only $1,040.93.

And Points.

And I’ll be earning over 23,000 points across 3 programs.

Trip 1. 8,941 miles.

Trip 1. 8,941 miles.

Trip 2a. 3,335 miles.

Trip 2a. 3,335 miles.

Trip 2b. 24,662 miles.

Trip 2b. 24,662 miles.

I have some pretty crazy travel coming up, mainly in December… but it all started because of a great deal that I booked for November. The Flight Deal is always publishing great deals, and a while back they posted a fare that was good for travel from New York – Europe – Asia, one-way. It worked to and from various cities in Europe, and to various cities in Asia. Once you were in Asia, you would have to find either another paid ticket home, or book a ticket with miles.

So, I don’t live in New York, but when we’re talking $150 ish to get from the US to Europe and on to Asia, it’s a no brainer for me to get myself to New York. Initially, I didn’t even care about the Asia part. $150 from the US to Europe, one-way, is a bargain in and of itself. The friend I was booking these flights with had to be in Asia in December anyway, so he asked if I minded if we flew from New York – Europe in November and then had the Europe – Asia segment be in December. I told him I didn’t really think I’d use the segment to Asia anyway, so he could do whatever he wanted.

Well, fast forward a few days, and I had a ticket from JFK to Milan, Italy (MXP) in November and from PRG – Tokyo, Japan (NRT) in December. I decided that I really didn’t want to let that ticket go to waste… So I started planning how I could make it all work out… and it got CRAZY (!!!!!!), especially since I already had a ticket booked to St. Maarten in mid-December, also note that by far, this is the most expensive part of the trip.

I was able to get everything to line up by booking another cheap ticket from Europe to the US and back in December. As it turns out, I have to throw away a segment from the first trip I booked, because I didn’t have enough time to make it all the way back to Michigan and still catch an early enough flight out to Europe. So, I’m just extending my layover in Miami in order to fly to Europe instead.

I didn’t have to be back to Michigan until mid-January, so that gave me some time to play around with in Asia. I’ve never been to Japan, so I wanted to stay there for a few days and I wanted to go back to Cambodia, the rest was up in the air. After doing some research I decided that the best way to fly from NRT to Phnom Penh (PNH) was through Hong Kong (HKG) booking with British Airways Avios. Since British Airways’ award chart is distance based and paid by the segment, I decided that if I had to fly though Hong Kong, I should definitely stop there for a few days.

The Singapore DO is usually planned for January, so I checked the dates of that, and realized that it lined up pretty well, so I started checking for availability home from Singapore to the US, and found some that worked out pretty well, though not perfectly, I wanted to be home 2 days earlier. I ended up booking the flight anyway, and can always change it for $50 if something opens up.

I still have a few things I have to book for my trip, however.

  • Washington DC to New York City by Amtrak or Megabus (leaning toward Megabus)
  • Dusseldorf to Prague by plane or rental car (driving in Germany could be fun?)
  • Phnom Penh to somewhere in Malaysia by plane? (would love recommendations here too!)

If you want to plan some awesome trips that are really cheap (considering how much you are doing/seeing anyway), here’s what you need to do.

  1. Always be on the lookout for a great deal.
  2. BOOK IT. Seriously. BOOK IT NOW. Especially for the great deals, they will not be there tomorrow. You always have 24 hours to cancel for a full refund.
  3. Every once in a while book something that isn’t ideal, and turn it into something that is awesome enough to make up for it.
  4. Be flexible. So you have to get from DUS to PRG? No problem. It’s a cheap flight ($50-70), or rent a car and enjoy the scenery. No problem. Travel is an adventure anyway 🙂

Below is the CRAZY infographic I made of how all of these bookings, flights, and trips fit together. I have to say, I’m pretty impressed that I was able to make it all work. Also, note that flights here are not actually direct, in many cases. The bookings are listed in the order they were made.

crazy trip

13 Comments

      1. very impressive. i though i did well by sticking in short revenue tix to fill the gaps in a united usa-asia via euro with 2 stopovers & 2 open jaws.. but i still cant quite figure yours out.
        did cambodia in May

        1. Yeah it was a bit complicated. I had to update how I was keeping track of my flights to make sure I wasn’t missing anything on this one. I was in Cambodia earlier this summer as well, I really liked it there!

          1. i bet! i appreciate your lil chart lol.
            i remember the JFK-MXP, PRG-NRT deal.. on travelocity, was it? but where did you find BA CPH-JFK, MIA-DUS for $371?!?!

          2. I had some fun making that chart 🙂 The JFK-MXP, PRG-NRT deal was booked through Priceline (maybe it was bookable elsewhere too… I don’t remember). I booked CPH-JFK, MIA-DUS straight through BA if I’m not mistaking! There are a lot of good Europe-US RTs on BA if you’re willing to double openjaw. I don’t think they’re intentional though.

          3. I don’t think TFD publishes much that’s ex-Europe (it didn’t work in reverse). I was playing around after seeing something similar, that didn’t work for me, on FT and was able to find flights that worked out for me!

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