“How do you plan extended trips through multiple countries?” is a question we get often.

Sometimes people even ask us to plan their trip for them… which I’m happy to do for a nominal 200% commission.

For those who are less brazen or aren’t into paying triple, I can do the next best thing… here are the process and the tools that we use to plan and organize our extensive travel.

Trip Planning

Prior to becoming parents we wandered the globe via the time tested method commonly known as “winging it.” We would just show up somewhere and try to find a place to sleep. Next destination: TBD.

Nowadays we do a little more advanced planning via this process:

  • Consider destination options – beach, skiing, family, new to us countries?
  • Frame the trip with (free) flights
  • Determine intermediate travel options – bus, train, plane
  • Find a place to sleep – Airbnb, hotel, friend’s place
  • Plan activities – museums, theater, must-see architecture/places/events
  • Purchase travel insurance if going to a country with expensive medical care


Over the past few years we’ve settled into a pattern of summer in Europe, early fall in the US, and winter in Asia.

But seldom are we committed to a single destination up front. Instead, we might have a vague notion such as “summer in Europe” or “relax on a beach” or “visit family in the US.”

Beach wise, if a flight to Koh Samui requires 2 connections and costs $675 whereas I can fly direct to Cebu for $175, I would probably be more inclined to skip Thailand in favor of the Philippines. So first order of business is booking flights.


Flights can be the least flexible and most expensive part of a trip. Ideally we will be able to arrange free tickets using airline miles or credit card rewards points. For any flights over 6 hours duration, If that can be business class, even better.

My initial goal is to frame or bookend the trip. For example, 2 years ago we spent 4 months in Europe. At the time of departure we had booked our flights into Portugal and onwards from Iceland to the US, but the middle was still open. All we knew was that we had a few days in an Airbnb in Lisbon and a departure flight from Reykjavik 4 months later.

My main tool for flight planning is Google Flights. It graphically shows airfare to multiple destinations from our target airport (in this case Taipei.) Within minutes I can see that it is cheapest for us to fly into London or Athens, which often (but not always) means award availability should be high. Or if the flights are cheap enough, just pay cash.

1-way economy fare prices on random June 2018 day from TPE to Europe

I can explore deeper, looking at prices on multiple days into one airport or region, e.g. London. Changing our departure date from a Saturday to a Tuesday could save $83 per ticket. Nice!

This initial review only takes a few minutes. Now I can look into award ticket availability on the various airlines. A good example is how I recently booked ~$7k worth of round-the-world tickets for ~$200.

Intermediate Travel

This year we have flights into London and a couple months later out of Oslo. Somewhere in between those dates we will be Poland, with plans to visit the Baltic countries of Lithuania, Latvia, and Estonia. Pray tell, what is the best way to get between Warsaw and Vilnius? Answering this kind of question is where Rome2Rio really shines.

Rome2Rio will enumerate (nearly) all possible ways to get from A to B, with time estimates and cost. Sure, the flight is only 1 hour but you also need to get from city center to the airport and vice versa. Rome2Rio factors that in, even providing details on public transit.

I first assumed train travel would be best for this leg, and for detailed train travel guidance throughout the world The Main in Seat 61 can’t be beat. I’ve used this site extensively for planning train travel across Europe and Asia, and the schedules, ticket purchasing guidance, and photos of trains and stations are incredibly helpful.

In this case, one train route involved going through Belarus with potential visa issues. The other train option was faster and avoided Belarus, but involved 2 transfers. Ultimately based on time and relative costs, we decided to fly.

A Place to Sleep

At the end of a busy day exploring it is nice to have a comfortable place to rest your head. It is even nicer if it comes with a big discount.

How long we stay in a given place depends in part on how we plan to pay for it. Starwood hotels give the 5th night free when booked with points. IHG hotels offer the 4th night free when booked with points, if you have the companion credit card. There are cards that will reimburse the cost of a 4th night when using their credit card and travel portal. Airbnb often has discounts when booking a full week, and you can earn Delta points in the process. Hotels.com has a Pay 10 Get 1 Free program, which is even better when combined with the Capital One Venture Rewards’ 10 Points/$ on hotels.com.

Have a trip coming up and interested in some free hotel nights? See the various hotel credit cards here.

When the daily rate favors Airbnb, that is now our preferred option. Having a separate bedroom, a living room, and a small kitchen make a stay more enjoyable. (Get $40 off your 1st stay here.)

Hotels are sometimes more convenient however, especially if we have a late arrival or a short stay. I love that we can stack multiple discounts for great savings of 20%+.

In both cases, I’ll use Google Maps to evaluate public transit and park access before booking. It is nice to be able to step outside and hop on a bus or the subway, and we make daily trips to the park so Jr can enjoy the slide and swings. It’s also nice to have a grocery store nearby. For example, a couple years ago we spent a few weeks in Paris. Our Airbnb had easy access to 3 different subway stops (2 different lines), was a 5 minute walk to a big playground in the Jardin du Luxembourg, and 10 steps to a small grocery.


To get a general feel for a new place I’ll often check out the travel wiki. These will usually cover getting to/from the airport, a summary of the various neighborhoods, a list of popular hotels and restaurants at different price ranges, and maybe a bit of history or a cultural introduction. I figure this covers 80% of what I would have wanted to read in a Lonely Planet, but for free.

On our recent trip to Vietnam I read through Wikitravel for Ho Chi Minh, and used it to plan our arrival transportation, to learn some of the common phrases (e.g. hello, thank you), and to understand the main historical sites in the city.

Next I’ll search for travel blogs to see what is popular with other travelers. Blogs written by expats who live there are ideal, but it is also interesting to see what long term nomads think of a place. For example, I knew James Clark of Nomadic Notes was a big fan of Ho Chi Minh, so I read through a bunch of his site. Winnie also looks through Chinese blogs, and these seem to have completely different “favorites” to the English language blogs, so we get a few different perspectives.

If I don’t know a particular travel blogger with great content for our destination, I’ll just Google “travel blog <destination>” and assume those with good SEO know what they are talking about.

We try to target at most 1 big activity per day, which allows adventures to unfold organically. It’s a vacation not research for a thesis.

Flexibility is key, and we are happy to throw our list out the window if we meet some locals or enthusiastic travelers. For example, while in Mui Ne, Vietnam, we met a family who lives in HCM. They commandeered our schedule for our last few days in the country, taking us to the White Sand Dunes and showing us their favorite spots in Ho Chi Minh. Hard to beat that!

[instagram url=https://www.instagram.com/p/BfUrWIrD3vT/  width=480]


For a trip of any duration we need to pack life’s necessities and some money to purchase all the stuff we forgot. We work off a packing list to minimize forgetfulness, and we find that packing for a year isn’t much more involved than packing for a week.


We follow a simple process to plan our nomadic lifestyle and use some popular tools to make it smooth and easy. Above all, being flexible on where, when, and for how long means we can enjoy some quality travel without breaking the bank.

How long we stay in a given place is often based on how we plan to pay for it, to get maximum advantage out of the various hotel rewards programs. Why only stay 3 nights if the 4th one is free?

We do the same with flights. Why fly on Sunday when flights are 25% less on Tuesday? Or why pay at all, when award tickets are available on Wednesday?

Our process and tools:

How do you plan your travels? Any tools or apps you love?