Straighten Up and Fly Right: Planning RTW Flights

A former coworker and good friend recently landed a stellar internship for this summer working with victims of human trafficking in Greece. It will be her second time out of the country, so I probably shouldn’t have been too surprised to get a flurry of Facebook messages from her over the holidays that ultimately boiled down to “When should I buy my plane ticket?”

I threw out a rough estimate of three months in advance, but I think my follow up to that question — detailing alternative flight search engines and which airlines have the lowest fares — was way more helpful and important. Plus, it got me thinking about how I’m going to book airfare on my RTW trip.

I’ve known for quite some time now that a RTW ticket, even a more flexible multi-stop ticket from Indie, is not for me. I am but one more tick mark in the column of DIY flyers who want the total freedom of booking one-way flights as needed.

Rome Spanish Steps

Table of Contents

My RTW Flights

Flight 1: BWI to KEF (early July)

If you live anywhere near Washington D.C. or Boston, and you have Europe on your bucket list, you damn well better know about Wow Air. This Icelandic budget airline started servicing BWI and BOS within the last year or two, with round trip flights to Reykjavik falling as low as $300, and one-way tickets even cheaper. In fact, even though I’ll be starting my trip during peak season for Europe (July), I should be able to make my initial long-haul flight come under $250. I’ll plan to book this ticket directly on Wow Air’s website in early April.

Flight 2: KEF to BCN (early July)

While I probably will spend a few days in Reykjavik, my true first destination is Spain. Why am I not flying directly to Barcelona? If you can find me another flight from the U.S. to Europe at the height of summer for less than $300, point me to it. Wow Air can get you from KEF to many more European destinations, and actually even after I’ve accrued frequent flier miles to more expensive flights, I’ll still have enough to make this jaunt from Iceland to Spain free. I’ll book this flight with my AAdvantage miles at the same time as my flight to Reykjavik.

Flight 3: BCN to NAP (early-mid August)

Much as I would like to trace the Mediterranean coast completely overland, the prevalence of budget airlines in Europe makes flying straight from Barcelona to Naples much cheaper than taking buses or trains. I’ve already traveled a lot in the south of France and other parts of Italy, so I feel comfortable skipping over this section of the continent this time. I’ll check fares for this flight in early May, but I may wait until I’m on the ground in Spain to book it.

Flight 4: ATH to IST (early October)

Because the Balkans are a big part of my itinerary, I can quite comfortably travel overland for the rest of my time in Europe. Fortunately, Athens and Istanbul are close enough that I can still land a flight between the two for under $100. I’ll check rates for this when I land in Barcelona, but may wait to book it until I’m actually in Athens.

Flight 5: IST to DEL (early November)

This may be my fifth plane overall, but it’s only my second major flight. Getting from Istanbul to Delhi overland would necessitate crossing the Caucausus, Iran, and the ‘Stans. While tracing this legendary Silk Road path is something I think would be incredible to do at some point, it’s not the focus of my current trip, and I would definitely feel more comfortable doing that with an organized group. Because we’re switching continents, though, this is the first flight on my itinerary that will be more than a couple hundred dollars. Thank goodness for frequent flyer miles.

Just as it’s important to check multiple search engines for the best airfare cost, it’s important to shop around with award flights and make sure you’re getting the biggest bang for your miles’ buck. Much as I love the Barclaycard Arrival MasterCard for its flexibility and super-fast accrual rate, I would probably need over 40,000 Barclay miles to reimburse myself for a flight like this. United Airlines’ interactive reward map says a flight from Europe to Central Asia could cost as little as 25,000 miles. A sample search on American Airlines though, confirmed I could fly from Istanbul to Delhi on 20,000 miles.

I’ll book this award flight with AAdvantage miles while I’m in Athens, and save my Barclay miles for routes that American Airlines won’t accept rewards on.

Flight 6: DEL to KTM (mid-November)

A bus through the Himalayas would keep me cooped up for almost two full days. No thanks. Meanwhile a direct flight from Delhi to Kathmandu can easily come under $100. As far as price-to-agony ratios go, flying is much more attractive than going overland here. I’ll book this flight at the same time as my flight to Delhi.

Flight 7: KTM to BKK (early December)

Overland travel through Bhutan, Bangladesh, and Myanmar isn’t the easiest recipe for getting from Kathmandu to Bangkok. The cheapest direct flight I can currently find is about $300, and that is in fact less expensive than making my flight from Delhi to Kathmandu round-trip and then flying to Bangkok from India. I’ll book this flight after I land in Delhi.

Flight 8: LPQ to HAN (early January)

Laos is another country that is undeveloped to the point that overland travel is a long and arduous task. So, while I’ll be bussing it around most of Southeast Asia, I will be working in a quick regional flight to get from Luang Prabang to Vietnam. This should easily come in under $150. I’ll book this flight while I’m in Thailand.

Flight 9: BKK to DPS (early February)

Bali is on my list of places to slow down in, and flying is pretty much unavoidable when island nations are involved. Fortunately, Asia is full of budget airlines, so this quick hop from Thailand to Indonesia will probably fall under $100. I’ll book this flight at the same time as my other Southeast Asian flight.

Flight 10: DPS to TYO (early March)

There are a few experiences in Japan near the top of my bucket list, so I definitely have the motivation to squeeze a flight to Tokyo into my itinerary. Asia’s budget airlines also serve this capital, so getting to Japan falls in the $150-200 range. Once I land in Bali, I’ll feel comfortable securing this next regional flight.

(Upon researching visa requirements, I’ve found that to enter Brazil I need to apply from my home country no more than 90 days before my arrival. That puts too much pressure on my schedule and budget, so I’ve updated this post to reflect an edited itinerary that does not include Brazil as originally planned.)

Flight 11: TYO to BUE (mid-to-late March)

This flight from Japan to Argentina will be my longest and my most expensive, which is why you haven’t seen more mention of frequent flier miles yet. I’ll plan to cash in 55,000 miles on United Airlines. To ensure award seats aren’t all taken, I’ll actually book this flight sooner than some of my smaller regional flights in Asia, and make the reservation when I’m in Thailand. That will give me some flexibility on the ground in Southeast Asia, but a deadline for the end of that overall leg of the trip.

Flight 13: MDZ to LIM (mid-May)

Visiting Machu Picchu is perhaps the biggest pillar of my trip, but airfare in Peru is exorbitantly priced and little mountain roads make overland travel far from schedule-friendly, which means I’ll have even more of a high wire act to perform in getting from Argentina to Peru without blowing my budget. In many search engine experiments, I think I’ve cracked the code. Arrive in Lima on your international flight, paid for with frequent flier miles. That ticket still isn’t cheap and using 45,000 miles from my Barclaycard may not be the world’s best value, but it’ll pay off. I’ll book this flight about a month in advance, while I’m in Buenos Aires.

Flight 14: LIM to CUZ (mid-May)

A flight from Argentina to Cusco, Peru, the starting point of most expeditions to Machu Picchu, is easily $700. But by flying to Lima, the country’s capital, first, the sum airfare for those two flights is closer to $500, before using any frequent flier miles. And most flights to Cusco layover in Lima anyway. So by doing a tiny bit of extra work myself, and booking those legs separately with frequent flier miles, I save about $600. I’ll book this flight at the same time as my flight to Lima.

Flight 15: CUZ to LIM (early June)

The same rule applies to outgoing flights. For whatever reason, a direct flight between Cusco and Lima is staggeringly less expensive than the same flight incorporated into a larger flight itinerary. Both this and my flight to Cusco come well under $100 each. I’ll book all Peru flights at the same time, in early-mid April.

Flight 16: LIM to SJO (early June)

Getting from South to Central America is notoriously expensive, but with some flexibility in dates and 33,000 frequent flier miles – this time from my Bank of America Travel Rewards card – I’ll get from Peru to Costa Rica for free. I’ll book this flight along with all my Peru flights. Because Machu Picchu requires visitors to be part of an organized, pre-booked tour, this will be one of the most rigidly structured parts of my trip, and I can afford booking lots of flights at once.

Flight 17: SJO to MEX (mid-June)

I would love to see more of Central America by traveling overland from Costa Rica through Nicaragua, Guatemala, and Belize before reaching Mexico, but my budget may or may not ultimately allow for extending my trip like that. So for the time being, I’ll plan to fly directly from San Jose to Mexico City. At this point in my trip, I’ll have more frequent flier miles saved up than I have time, so I can use them on less expensive flights. I’ll only need 10,000 miles on my Bank of America card to get to Mexico for free. I’ll book this flight after I arrive in Costa Rica, so if I do have the money and time to continue through Central America overland, that’s an option.

Flight 18: MEX to IAD (late June, early July)

My final flight will of course get me home. A flight from Mexico City to Washington D.C. only takes 17,500 miles on American Airlines. I’ll book this after I arrive in Mexico, so a longer route through Central America doesn’t throw me off.

Estimated Total: $1,450

Broken down this much, it seems like a lot of flying. But at least half of these flights are quick regional hops that largely fall under $100 a pop. By pricing out all my flights first and getting estimates from multiple frequent flier programs on the most expensive flights, I also make sure I get the most out of my miles. Of the half of my flights that aren’t on budget airlines, seven of those I’ll get for free with frequent flier miles. Only three of my flights will cost more than $200, and only one is over $300.

Twelve months, three continents, and no 30-hour bus rides for under $1,500 (less than 10% of my overall budget) total? That’s actually a pretty good deal.

Pope's Revenge

The secrets to finding cheap airfare:

  1. Be flexible
    Airfare costs can fluctuate wildly from city to city and day to day. Skyscanner in particular has great tools for nailing down low prices by allowing you to search multiple ports of entry or an entire month at once. Arriving a day later than you originally planned, or flying into a different city and taking a train the rest of the way can save tons of money.
  2. Put in the extra time and effort to do your own research
    The number one reason most Americans think travel is too expensive is because we are so accustomed to taking the path of least resistance. You decide where you want to go, plug it into Expedia or Kayak and book the first result you get because it’s easy. But if you truly care about traveling and you’re on a tight budget, you simply have to do that work yourself. It 100% pays off. If I trusted the first quote I got, I’d be spending over $4,000 on flights. By taking the time to learn how to use frequent flier credit cards and spending lots of time testing out itineraries on different search engines, I’ll be spending closer to $1,500 on airfare. A little elbow grease goes a long way.
  3. Never trust a single resource
    As amazing as Skyscanner is, it’s not the only source I consult. In fact, no single resource should be taken as the be-all end-all of travel research. Over the past year, I have priced sample itineraries out on airline alliances like oneworld (American Airlines) and Star Alliance (United Airlines), multi-stop booking engines like Indie, and aggregate search engines like Kayak, Skyscanner, Hipmunk, and Skiplagged. Even when I know I can get a flight for free, I always check both American and United to see where I’m getting the best value for my miles. I also always double check to ensure that overland travel isn’t the better option before deciding to fly. When I’m actually booking flights, I’ll always check at least three resources to get the best estimate possible.
  4. Don’t be afraid to get creative
    I thought I was doomed when it came to getting to Machu Picchu. But by staying the course and testing out every variation of my itinerary I could think of, I found a great solution that allows me to spend less than $200 getting in and out of Peru, one of the most expensive countries to fly in. It may seem less direct to fly first to Lima and then take a separate flight to Cusco, but it saves hundreds of dollars.

This may seem like a lot of flights to take on a RTW trip, but they’re spaced out over the course of a year. See what overland travel I have planned.

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  1. What an amazing itinerary! I’m totally sure that you’ll have a more than just amazing time! 🙂

    For now, I got flights to India (Bengaluru, Mumbai, Jaipur, Delhi, Mussoorie), Brazil (Sao Paulo, Iguazu, Rio and Florianopolis), the US (Dallas), Japan (Tokyo) and a few shorter trips to European destinations planned. It’s definitely gonna be an amazing year 🙂

  2. Great destinations for people to work in creative professions. I found this post because I had heard that there is a new Blogger house in Vilnius, Lithuania that supports creative free lancers for a week while showcasing the capitol city! Love that so many places cater to those of us who are laptop freelancers!

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