“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
Destinations
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
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.
Activities
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]
Packing
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.
Summary
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:
- Consider destination options – beach, skiing, family, new to us countries?
- Frame the trip with (free) flights – Google Flights
- Determine intermediate travel options – Rome2Rio (also has a great app)
- for train travel, The Man in Seat 61
- Find a place to sleep – Airbnb & hotels.com (affiliate links) and Google Maps
- Plan activities – Wikitravel and blogs (various)
- Purchase travel insurance if going to a country with expensive medical care – World Nomads (affiliate link)
I love seeing how you do it, as we do much of the same. Good to see we’re not completely doing it wrong :)
We bookend the trip with flights into and out of somewhere. Then figure out easy/convenient/cheap travel links in between those 2 places, aiming for 1+ week in most places. Then drill down to the details of airbnb or hotel.
For lodging, we look at mostly the same factors – convenient access to a grocery store is probably equal to access to transit (and those two go hand in hand usually). Access to parks is a strong secondary factor.
I’ll be excited to see any travel updates out of Latvia, Lithuania and Estonia since I’d like to visit those three one year (maybe 2019!) plus Poland and possibly some other countries around there.
Another tip in case you weren’t aware .- GoEuro.com is a good resource for travel within Europe (maybe elsewhere, dunno). Very similar to Rome2Rio but I actually like it better. Seemed to give better and more accurate results for train vs plane vs bus and especially with the kids (I think their algorithm adjusts better for discounted or free kid tickets on trains/buses for example). I used GoEuro more than Rome2Rio when doing our planning for Europe last year (hat tip to Kristy since I think she was the one that mentioned GoEuro to me).
Nice, now I know who to ask to plan our next big trip! ;)
Will check out GoEuro, thanks!
Sure, I’ll be glad to do it for the standard going commission rate. Still 200%, right?
So if one were into hiking and out of the way places within a country, is renting a car the only way to go? Since I’m from the U.S. I only have experience of hopping into my car and going to a national park or the beach which is a few hrs by car but would turn into a nightmare if i tried to take a bus.
We will travel in Norway mostly be car for this reason. Sometimes a car is the only way.
I’m sure you’ve heard of it already, and the name does sound pretty cheesy, but “Norway in a Nutshell” tour between Oslo and Bergen (with coordinated travel by trains, buses, ferries, etc.) ended up being really quite wonderful.
We saw some reviews of this and it looks nice. I think we are basically doing a version of that but by car (Winnie planned it.)
Sometimes it is possible to use transit to go hiking or visit remote places. Switzerland is probably the best case situation for that in Europe. I got to a bunch of hikes and climbs using transit. Even then, a couple of destinations require a car, but many don’t. In other parts of Europe, scooters may be an option, especially if you have a motorcycle license. And in, say the Balkans, getting someone to drive you isn’t that expensive and probably better than a rental car.
Thanks for these tip, from someone who travels as much as you this is great stuff! I traveled probably more than you back in my 30’s, half for work an half for play. But that was before AirBnB, Google Flights, and mostly even before smartphones. The tools are different now and it’s great to see how you optimize tools for planning.
And I used to follow the “wing it” system as well. So many great things would happen when I’d show up in a new country with no plan. Ah… the good ole days…
To be young and free again :)
I like the combination of being organized enough to minimize the big expenses (flying) while maintaining enough flexibility to really meander wherever you want while traveling. Good stuff, GCC!
P.S. I used to live in Riga, Latvia. Let me know if you need any insider guidance on the Balts.
Anything that you would say is an absolute must do or eat?
Seeing the method and tools of your process is very helpful. Great post. As a relative newbie to snowbird travel these last 3 years I planned lodging for longer durations during my first 2 years using VRBO https://www.vrbo.com/ 6 months the first year and 4 months the second year both the same destination. All flights to and from were with points. This past winter I changed it up a bit and started using TrustedHouseSitters https://www.trustedhousesitters.com/ in locations I’d always wished to visit like Costa Rica. This of course was a game changer with regards to budget as accommodation was free. With 5 different winter locations i used a combination of flight points and if the flight was a cheap one via Google Flights I’d pay cash. Thanks again for a nice Monday morning read on a topic of interest.
House sitting is something we haven’t done. We should definitely look into it, thanks!
This is super helpful; we just booked travel to Berlin in August, and are about to pull the trigger on an AirBNB. It’ll be the first time we’ve visited Europe staying in one place for nearly two weeks, rather than bouncing around a few days here and there. Our Barclaycard Arrival Plus is getting kinda rusty, so it’s also nice to see what cards and rewards programs everyone’s using these days.
We cycle through them fast enough that they don’t get rusty :)
Berlin in summer is wonderful, with so many parks and outdoor activities.
Thanks for sharing your process. We’ll need to plan a lot more when we travel longer. For now, we take short trips and it doesn’t need a huge amount of planning. Rome2Rio sounds like a nice tool. I’ll check it out.
Sounds all too familiar! We plan our trips the same way.
Have you tried http://www.kiwi.com? It’s the only site I’ve found with a “radius search”, so you can choose departure airports within your desired radius (you customize the distance) and arrival airports within your desired radius. So if you know you want to leave from somewhere in Northern Italy/Southern France/Switzerland and arrive in NY/Philly/DC, it will find the best combos. Combined with flexible dates, it’s pretty fun to play with.
I came down here to the comments to recommend kiwi.com, too! After using Google Flights for years, I seem to be slowly transitioning to kiwi.com due to it’s options for flexible travelers like us. You can, for example, say that you want to go to the Caribbean or to Western Europe (or some other vicinity or list of airports), sometime between October 15th and November 15th (or some other date range) for a 4-6 day trip (or some other duration), and it’ll give you a list of dates and options very quickly! It’ll also create cheaper connecting flights out of two one-way flights on different airlines for you to consider.
Wow, google flights was incredibly helpful! Never even knew about it! Though if possible we plan to mainly go by ships and trains. Your schedule sounds a lot like our planned schedule for the future! (Europe in summer, US in the fall and Winter in Asia) Maybe we’ll bump into you one of these days after we become location independent. :)
Well this is timely! My wife and I just happen to be planning our first 6 mth mini-retirement with our 2 boys, and we also decided to try out eastern/central Europe (besides stuffing ourselves silly with the awesome food in Spain). :D We’re flying into London too as we’ve family and friends in UK (free stay…ahem) and London is a good base to get budget flights out to the rest of Europe.
For accommodation, is it still possible to get discounted AirBnB gift cards? I’ve been monitoring but good discounts seem pretty hard to come by these days. Would love to hear any pointers you may have.
Sign up for Raise.com if you haven’t already. About once every month or two they’ll email you about a sale where they tend to give an extra 5% off their gift cards. Yes, Airbnb gift cards tend to run only 3-4% off, so with the bonus, it’s a more significant 8-9% off. And as GCC wrote, look for Airbnb properties that have discounts if you rent for a week. Finally, some folks have had success asking hosts if they can give the weekly discount (e.g. 15%) even if staying for less than 7 days – Google it, it might be worth trying.
I haven’t seen real Airbnb GC discounts for a year or more. When the GCs are available for just 3-4% off, I will just book directly since I’m getting 3 pts/$ on travel with the Sapphire Reserve, so at least 4.5% back. If I could get 10%+ discount on GCs that would be nice though.
Thanks Mike and GCC. We’re definitely planning to make use of the long stay discounts…and maybe try our bargaining skills too. :) Pity that the generous discounts aren’t around anymore. They must have realised it was very popular.
I use a process identical to yours! One tidbit I can add is to use Inspirock.com for the local planning. You can set it to a variety of interests: family, cultural, sporting, arts, etc. I first tried it out in our home town, and was impressed with the options it came up with. And once you’ve selected the things you want to do, it provides a daily itinerary, optimizing travel time, to see the site you chose. And then you can rearrange things on the calendar and get a new map for each day. Very cool tool. https://www.inspirock.com
Barely 1 minute on the website and it has totally blown me away, thank you for sharing! We’re planning a massive (by our standards) 6 months trip and it seems like a mammoth task, this is so very useful!
Thanks for the resources. They are very helpful. We are especially interested in making great use of Google Flights and Rome2Rio.
I’m curious about major differences between what the Chinese blogs recommended vs. English-language ones. For instance, is there any consistency to what kinds of “favorites” different cultures seemed to have?
Thanks!
We are still winging it much more than I expected we would after having a kid. But we are mainly doing road trips in North America so it’s a bit different. We just got back from a fun road trip out west to the Rockies. We didn’t even plan where we were going to stop and stay along the way at night and I was wondering how that was going to work out for us. Lol. Luckily it all worked out well overall. It’s definitely more work and more tiring traveling with a two year old but I also completely love it :-)
Were you camping or staying at road side hotels?
We had planned to camp in our van but changed our plans last minute. There was a freak heat wave and that doesn’t work so well with our toddler. We stayed in hotels on the road but once we got to the mountains we stayed in a cabin for a few days – that was the best part :-)
How do you typically document all of your plans, reservations, and activities for future reference? Google Trips has been helpful for me and allows easy access to confirmation numbers, times/dates, and important addresses. But while it’s great at importing from my emails, it’s not as flexible as I’d like with allowing me to create unique entries or collect related information that I may want to access once I arrive.
Right now I just supplement Google Trips with a word doc that I manually type up and fill with all of the miscellaneous stuff that I find when I’m doing my research and want to save.
What approach do you (or any of the commentors) use?
I use Tripit. I’m not sure how different it is from Google trips though.
I use Tripit as well, it is easy and has some flexibility. It also keeps track of your past trips, so you can quickly pull up the name of that great hotel, or outfitter you worked with.
I recall trying to use both google trip and tripit last year for our trip to Europe. My memory is a bit fuzzy on it, but…
They seem to be great tools for normal vacations.
When I sent them 20 different 1-way flights and 25 airbnbs and a couple buses and a few hotels…. they both got confused. For example they said we had a trip to Amsterdam, but that was really just a few days in between Spain and Greece. An airbnb got lumped into a different “trip” and it took me awhile to figure out why the info was in the wrong place. Long story short, I just stopped using the apps and managed things mentally in my inbox.
Yeah, TripIt requires curation (which is possible but annoying). Not sure the inbox is a better way to go. I also often use spreadsheets, which may be better in some ways but have a worse interface.
We booked our last 48 flights through Kiwi.com using our Chase Sapphire card and liked the price to anywhere else feature and price by day of the month feature. They have ticket combinations that no one else does. I don’t know if you’ve ever filed a claim with World Nomads, but they use Trip Mates as their claims processor and they are absolute crap. It took nearly 3 months and dozens of hours of my time to receive simple claim payment, or is that the idea? Make it so hard YOU GIVE UP. I will never use them again….
have you filed a claim with any other travel insurance company for comparison? Who would you use instead? I don’t know of any insurance company that makes fast easy payments
World Nomads is mostly “secondary” coverage so you can expect longer delays and more hassle. Yes, I have filed with other companies: Chase card benefits reimbursed my trip delay 7 days after submission. Travel Guard reimbursed a trip cancellation during the arab spring but they didn’t cover violent uprising as a reason not to go so I had to wait until there was a “terrorist” incident in the destination city. Unfortunately someone had to die for me to get a refund which was paid promptly. Trip Mate has a one star rating for customer satisfaction. Just saying….
Yeah, that is why I was asking. There is nothing like a miserable customer experience as motivation to shop around. :)
I’m just did a price check on 2 months in Europe since we leave tomorrow. Travel Guard was $528 and World Nomads was $222.50.
Medical coverage is my main reason for having insurance at all. Trip delays and that kind of thing we can just roll with it. Travel Guard covers up to $25k and World Nomads $5 million. That is a bit of a ridiculous marketing number, but I’m really only worried about the “hit by a bus” scenario.
World Nomads did finally pay, just be prepared for a ride. I’m going to try Allianz Global Assistance next time.
I use Tripit.com to forward all reservations so I have everything handy when I travel. You can edit anything into the Tripit itinerary, so maybe try it out and see if it works for you.
I tried tripit for a time, but ended up just using gmail as it was easy enough. All of the emails are there and a quick search brings up all of our reservation info.
I switched to Wikivoyage for my travel facts a while ago. Wikitravel got bought by a company which tries to extract money, while Wikivoyage is run by the non profit Wikimedia Foundation and doesn’t have ads. But sometimes the paper guidebook from the library really does have more info. (Not always, though.)
oh, good to know. Thanks!
I like skyscanner for flights – has map, multiairport and good multi city options for open jaw round trips. Just tested them against kiwi and much faster/cheaper options on skyscanner (Australia to Europe). Google maps for hotels but also for plotting possible sightseeing and activities – helps decide area to stay, then I look for good transport, groceries etc. Trailwallet app not only for recording costs, but also record what’s been booked (flights, accommodation, transfers etc) and planned/booked activities so we can adjust, swap out etc as the mood or weather dictates. Thetrainline.com has been good for booking, and alerts on cheap tickets.Generally use rome2rio but like the look of goeuro so will check that out too. About to go into planning mode for Europe Dec/Jan so good timing 👊🏼
Some of these sights I’d never heard of before! Thanks for the tips!
This really is great information. My wife and I are set to become parents later in life, but we don’t want that to stop us from traveling and having our child see the world. Your blog really does give me some inspiration.
Thanks Jason. I’m always happy to be a bad influence :)
As always you have many good suggestions for saving money on travel. I have been traveling to Europe for 2-3 months per year since I took early retirement 4 years ago and have a few suggestions that you helped save me money.
I have found Hotels.com usually works best in larger cities especially if you stay over a weekend. They also have some special deals for members with some hotels that aren’t found on other sites.
Booking.com has worked well for me in smaller cities that don’t have many large hotels, there are many apartments and small family run hotels that only list on this site. Additionally they had some great promotions last year such as $40 off an $80 booking.
Airbnb is the site that I use most often and is very good if you book well in advance in the more popular tourist areas since the best places with the most positive reviews can be difficult to book if you wait to the last minute. One thing that changed with Airbnb recently is that you now have the ability to pay in the local currency of the place that you are booking, therefore avoiding the 3% currency conversion fee that Airbnb had charged in the past. Obviously you only want to do this if you have a credit card that doesn’t charge a foreign transaction fee.
https://www.airbnb.com/help/article/95/can-i-pay-with-any-currency
I also use hotels.com preferentially to booking.com but resort to booking.com when I have to. I find that booking.com tries too hard to be manipulative and I really don’t like that.
It’s interesting that no one mentioned tripadvisor.com (TR). TR is usually my 1st stop when I look for “things to do” as well as hotel options. Although I often book hotels from hotels.com eventually, many options are simply not available on hotels.com, such as my top choices in London – the chain of “hub by Premier Inn London”. Also, rarely are there any points of interest that are not mentioned on TR, except for hiking trails. I won’t blindly trust the scores people give on TR, but it definitely tells me the options out there, and gives me the confidence that I’m not missing major sites.
By experience, I noticed that Google Flights does not cover as many airline companies as kaya.com does. So I usually combine both when checking flights. Of course if people manage to use points for their air tickets, probably those minor airlines not covered by Google Flights won’t matter much.
Recently I’m using safaribookings.com and tourradar.com to look for organized safaris and trekking trips in Africa, Nepal and India where I’m not confident enough to go by myself. If anyone knows other good search websites for organized tours, that will be greatly appreciated.
I have never tried GoEuro.com and rome2rio. Something new to learn everyday!
TR does have most of the attractions, although an activity that is almost always available and doesn’t require TR is just to walk down the street. More viable in some places than others. I kind of find the forums to be not as high quality as I’d hope.
The City Mapper app came in really handy for navigating public transport in Paris. We liked it better than Google Maps. It covers many big cities in Europe, Asia and NA.
https://play.google.com/store/apps/details?id=com.citymapper.app.release&hl=en
This is a great guide! Thanks for sharing. You guys will enjoy the baltics – we did a road trip from Lithuania to Estonia and then continued to Finland via ferry. It was a wonderful time. The car rental to drop off and pick up in different locations was quite expensive, but worth it for us.
I’m interested to see how people are getting to Greece. I haven’t found a flight there from the US for under $1K even with stops. $1K is $1K even if it’s spent in parts.
Using the GCC trip planning method, we would avoid committing to Greece. When you absolutely must go to a specific location on specific dates, the price is what it is.
Hi there! I’ve noticed you come back to Poland this year, excellent! If you decide to visit Kraków once more – ping me via email, me and my wife would love to host you for some dinner :)
Thank you Karol. This time around we will be in Warsaw only, sorry
Awesome that you are going to visit the Baltic Countries – I am from Estonia, if you want some tips where to go etc :) It’s awesome during the summer!
We are in Tallinn now, leaving tomorrow. We really like it here, and would love to hear any recommendations.