by Pete Barba

This is a continuation of a former post (click here) that talked more about the years of pre-planning for our “Trip Around the World”.  Now we will focus on the actual details of planning and how we approached our journey.  Many of these tips apply to “normal” vacations, so even if you don’t think you’ll do a long-term trip, read on!

What’s your timing?

How much time do you have to get away?  This matters for many aspects of the planning.  If you have less time (a few months), you will be able to go to fewer places but you’ll be able to maintain a faster pace for your travels.  On the opposite end of the spectrum, if you have a year or more, you can explore more places, but will need to go slower because traveling is exhausting (more on that in a later article).  For us, we planned for a full year, knowing that it would mirror the kids’ school calendar.  Knowing we had a year long marathon, we settled on about a week in each location to balance seeing as much as is reasonable while at the same time pacing ourselves and having time to homeschool the kids.  Of course, this actually varied from as little as two days to as much as three weeks!

Where to go?

It’s a big world and you can’t see it all.  We started with listing the big things we absolutely wanted to see.  For Drew, it was Iceland and the Ice Hotel; Kate wanted to visit New Zealand and Japan; Gwyn had her heart set on Paris and ALL the Disney parks; and I wanted to show the kids the animals in Africa and eat the food in Southeast Asia.  Then we discussed the concept of seeing a wide variety of cultures and locations.  Everything from the Arctic Circle to the Middle East; from Buddhist temples to grand mosques; from wealthy nations to countries with widespread poverty.  

We decided early on that some bigger countries/regions had to wait for other trips when we had more time, more money, or when the kids were older.  Australia and India will be month long trips in the future, the kids need to be a little older to appreciate the hiking in Patagonia and the Himalayas, China has too many political and COVID issues for us to visit there at this time, and an island resort in the South Pacific is too pricey for this trip.  Some of these we tried to include at first, but budget and logistics made for some hard decisions.  The kids are REALLY disappointed we won’t see the Disney parks in Hong Kong or Shanghai, but hopefully that will happen someday.

With all that in mind, we started planning our route.  In general, you should start in one place and keep moving east or west, but we decided that climate needed to be considered first.  We really wanted to see Africa in their winter for better wildlife viewing, so that is where we started.  After that the Middle East made sense, but that would have been summer, which is way too hot.  Instead we went further north to the Alps for late summer hiking followed by sailing in Greece while it was still warm.  At that point, the Middle East was cooled off enough for us to explore Egypt, Jordan and Turkey.  Then we knew we wanted to see Europe during the holiday season, which led to Portugal for (American) Thanksgiving with friends, through France for the Christmas Markets and an end in the Netherlands with other friends for Christmas.  The Ice Hotel is best in winter so that was squeezed in as well.  That was a lot of north-south bouncing!

Finally it was time to move westward to South America and New Zealand during their summer.  Then we keep going to many of the varied countries of Southeast Asia before enjoying springtime in Japan.  To complete the circle we fly back to Europe to meet another set of friends before finishing in Iceland during the summer of 2024.  When it’s all said and done, we will actually do 1 ½ times around the planet, but it made sense with what we wanted to see and when.

How to make the arrangements?

Flights

One option for a trip like this is to buy an “around the world ticket”.  It saves money and makes booking easier, but in general you have to keep going in one direction and you only get so many stops.  For us that wasn’t a great option.

For five years we have been saving up points on our Chase and Amex credit cards, and we started the trip with almost 800,000 miles saved up.  We’ve used these points to book our long haul flights, sometimes luxuriously in business class.  Before this trip we’ve never flown business class, and I would never pay cash for the upgrade, but by using points we saved huge amounts of money and got the opportunity to get these fancy flights for free.  

My method is to start with a search on Google Flights for when and where we want to go.  In general, we look for direct flights or fewer stops, balanced by a reasonable price.  One tip is to search for the dates before and after your planned days, as it can save tons of money.  In addition, it’s also worth checking out other airports nearby (for example Oakland, Sacramento and San Francisco). Finally bear in mind that some airlines charge for luggage, seat selection, meals and other costs, so lots of times the cheapest flight listed on google flights will not end up being cheapest in the end.  So I advise looking into the “extras” on the airline’s websites.   If Google Flights and I can’t figure out how to get from point A to B, for example Europe to South America, I also look at the website “flight connections”, which has a map of every flight leaving from each airport.   Once I’ve found my flights, it’s time to book.  

For flights less than five hours, I then go directly to the airline’s website and book directly with them.  For flights more than five hours, I go to a website called point.me, which allows me to search for flights using points.  This is more complex, as point redemption tickets are a rare commodity and a lot of flexibility is needed.  For example, to get from Southeast Asia back to Europe later this summer, I couldn’t find four tickets available to be booked with points from Vietnam to Europe.  I had to search for flights from Vietnam, Singapore, Japan, or Thailand to Paris, Istanbul, Madrid, London or Amsterdam, on a wide range of days.  Eventually I settled on Bangkok to Paris on a date we hadn’t originally planned.  We then bought hopper flights from Vietnam to Bangkok, and then from Paris to Portugal to complete the trip from Vietnam to Portugal.  Even though I had to buy hopper flights and hotels for long layovers, we are using points to fly 19 hours from Asia to Europe in business class, for minimal out of pocket expense.  That’s a win.

Booking flights is probably the hardest thing I have to do (in our division of labor, this task is mine).  It requires hours of work for each flight, with lots of notes to figure out which flight is the best and cheapest.  At the same time, flights are one of the biggest expenses of this trip, and one of the most frustrating parts of travel, so it’s worth investing the time to do it right.  

Lodging

Where to stay probably has the biggest impact on your satisfaction with your trip.  You can suffer on a bad flight in an uncomfortable seat for eight hours, but seven nights in an unsafe bed is intolerable.  Lodging is also one of the biggest expenses of your trip, depending on your choices.  Therefore, we put a lot of time into our lodging.  Just like real estate, location is everything.  Because we love to walk, we want to be in a safe neighborhood that is walkable to the major sights.  In addition, our family of four needs space for privacy (if possible) and a place to homeschool the kids.

For stays of two nights or more, we typically stay at AirBnbs for a variety of reasons. The first reason is price.  Most hotel rooms outside the USA don’t accommodate four people, so we would have to book two hotel rooms.  This usually costs significantly more than a nice AirBnb.  That said, if you are traveling as a pair, a hotel may be a better deal.  A second reason is that most AirBnb’s have a kitchen, so we can eat healthier and cheaper by making a majority of our meals at the apartment or home.  Third, AirBnBs normally have a lot more space, so we can homeschool the kids at a dining room table and have our own space to spread out.  Finally, Airbnb’s feel more like home than a chain hotel, which is important when you are homesick.  We’ve even had some amazing hosts take care of us like family.  The downside to AirBnbs is you never know exactly what you are going to get.  Most of our AirBnbs have been stellar, but we’ve had a few misses that created some headaches. 

For shorter stays or long layovers, I book hotels.  Hotels make it easy- you check in, you go to your room and you’re done.  After a long flight, you want simplicity.  There’s something comforting about checking into a Hilton hotel when you’re exhausted.  You know what you’re getting, you know you’re safe, you know there’s a breakfast buffet, etc.  Tip #1: find what you like and stick with it.  We’re “Gold Members” of the Hilton chain so we preferentially stay with their brands, because we get free breakfast and room upgrades.  Through many credit cards you can get upgraded status with different hotel chains that come with perks.  If you are planning to stay in a lot of hotels, it may be worth looking into a hotel branded credit card or a premium credit card.  Tip #2: book directly with the hotel on their own website.  This usually saves money and improves service.  I search on Hotels.com for comparisons, but rarely book through them.

In our family, Kate’s the details person so I leave the Airbnb choice to her, sometimes after narrowing it down for location.  She then sorts through the choices, reads reviews, checks the amenities and makes the best decision for our budget and needs in that area.  Besides cost, the factors that we consider include:

• Location – look for a location near downtown or the major sights.  Having to take a taxi or bus everywhere adds additional costs, headaches and time.  Being within ½ – 1 mile of key areas makes walking a better form of transport.
• Space – for long trips, space is key – no matter how much you love your family and spouse, you don’t want to be crammed in a small room with them all the time.  Living rooms, yard space, and balconies can add a lot to the quality of a home base.
• Bathrooms – ideally, for every two people you will want one bathroom.  Sure, you can get by with one bathroom for four people, but I can tell you from experience that teenagers take a long time in the bathroom for reasons I don’t want to know.  Plus two showers make mornings faster.
• Bedrooms – generally for every two people you need one bedroom.  Our teenagers will sleep on a couch rather than share a bed, and much prefer their own bedroom.  Since I am tall, Kate and I don’t fit well on a double so are always on the lookout for a Queen or King.  Sometimes these preferences are possible on our budget, sometimes not.  Airbnb, if you’re listening, please offer bed size as a sorting option!
• Wi-Fi – we live in a connected world and we are constantly planning our days and next steps, so for us Wi-Fi is key.  A warning, quality will vary and is hard to know ahead of time.
• Climate control – air conditioning and heating at certain times of the year and in certain places will absolutely make or break your stay.  Sleep is important and for us the temperature is key.  This one is also tricky to confirm quality, but you can filter for it, read reviews, and hope for the best.
• Laundry facilities – Unless you want to spend a fortune on laundry services or spend a day at the laundromat, having access to a washer is key.  Unlike a vacation, you’ll have to do laundry on an extended trip!  Note that in some places a dryer is common, in others it’s really rare.  You learn to make do.
• Kitchen – the ability to at least make breakfast and easy lunches is important.  Don’t underestimate the health benefits and cost savings of making eggs for breakfast, sandwiches or salads for lunch, and lentils for dinner.
• Free parking – if you are renting a car, you need somewhere to put it.   A city garage ruined our budget before we learned this lesson!
• Bonus points for outdoor space, views, extra cooking options like a grill, great beds/linens mentioned in reviews, and an especially attentive host.

Our final booking tip is to read the reviews – while a hotel may say it’s 4 star, the recent reviews may say that they are undergoing renovations.  Or the apartment’s “king sized bed” may now be a double bed.  A well-written description can fire the imagination, but a detailed review will give you the real story.  That said, learn to weed out the complainers.  Some people may not understand that an AirBnB isn’t a hotel, and as a result complain about the lack of room service or no cleaning service each day! 

Please note that expensive rooms with views or fancy hotels with spas don’t matter that much to us.  We use hotel rooms for sleeping, and typically don’t spend much waking time in the hotel room.  In addition, fancy hotels with expensive services add cost with little benefit.  On the other hand, if we’re going to spend a week at an AirBnB where the lodging is part of the experience, then it’s worth having a living room with a view.  (As I write this, I’m staring out open french doors at a beautiful lake with a volcano in the background, as the fresh breeze blows in my face.)

Ground Transportation

For short hops around town, we use Uber or the local equivalent.  Taxis are typically more expensive and unfortunately for the four of us, public transportation typically adds up to the same price with more headaches.  If it was just the two of us, public transport would be a better deal.  

For longer jaunts, we usually rent a car.  Once again, we’d love to take trains or buses more, but for a larger group they are typically more expensive than renting a car.  To rent a car, I prefer to search priceline.com and kayak.com first.  Then I typically book directly with the rental car company on their own website.  When renting a car I have two important tips.  1) Take pictures of the car before and after rental.  Three times on this trip rental car companies have tried to bill us for damage we didn’t inflict.  You need pictures of the car to prove it didn’t happen on your watch.  2) Do a quick search for “driving in ________”. While it may seem obvious, driving rules and styles change from country to country.  France is super strict about their speed limits.  In South Africa, if a truck puts their blinker on, they’re trying to tell you when it’s safe to pass.  Know before you go for more confident driving and fewer surprises.

Putting it all together

We try to plan far in advance.  Kate is a planner and doesn’t like surprises.  Also in today’s inflationary and post-covid market, booking earlier saves us a lot of money.  In general we book lodging and flights 6 months out.  Car rentals 3-6 months out.  Tours and experiences 1-3 months out, sooner if it is a popular place or activity that will sell out.

We keep track of everything on both a google doc as well as a budgetary spreadsheet.  The google doc contains dates, locations, reservation numbers, travel companies and agents, how much we paid, how much we owe, baggage policies, cancellation policies, etc.  It is our go to document for everything on this trip.  Trust me, you’re going to forget the details in 24 hours, so put it all in one place.  For the same reason we also keep track of paid and outstanding expenses on a spreadsheet to make sure we are living within our budget.  We reconcile the budget at the end of each country so that we can learn and also change future budgets if needed.

So here is an example of what it all looks like:

• We want to go to (awesome country)!
  • When is the best time to go?
  • What do you want to see and where do you want to stay?
  • We like Lonely Planet and Intrepid itineraries to get us started.  Videos, friends, and family have also influenced our plans!
• Check for flight availability and cost on google flights and/or point.me
  • Verify cost of “extras” – seat selection, baggage, meals
  • Book flight as soon as possible, directly with airline
  • Document in travel document
• Check for AirBnB/hotel availability, amenities, and cost (airBnB.com; hotels.com; booking.com)
  • Verify essentials – Wi-Fi? Climate control? Number of beds? Number of bathrooms? Parking?
  • Read recent reviews carefully
  • Book lodging as soon as possible, directly with hotel if using
  • Document in travel document
• Search for car rental if needed, checking availability and cost on priceline.com and kayak.com
  • Book directly with car company (but double check the price compared to Priceline)
  • Document in travel document
• Rest and congratulate yourself on a job well done.
• Use the next few months to plan activities, restaurants, etc.
  • Pay special attention to the “must do” activities and book as soon as possible to avoid disappointments.
  • Document reservations in the travel document.  
  • Document options in the travel document, or consider a second “ideas” document for longer trips like ours.  

Other random thoughts:

• Before you book non-refundable things, confirm the passport and visa requirements for each country.  We are privileged to have a passport welcome in most places, but immigration control is not a joke.  Do the research and fill out the forms ahead of time.
• Check the State Department’s recommendations for safety concerns.  They tend to be conservative, but you should know and make the choice with open eyes.
• When reading reviews, check recent reviews first.  In this post-covid world, a lot of establishments have gone out of business, changed offerings or had decreased staffing.  Newer reviews reflect the current state of a business.  
• Trip insurance probably isn’t worth it for a year long trip.  Trip insurance adds 10-20% to the cost of a trip and provided you are in good health, you probably won’t need to cancel 10-20% of your bookings.  Yes, there will be days and maybe weeks where you may have to change your plans, but absorbing those lost reservations is probably going to be cheaper than insurance.  After all, that’s how insurance works; they charge more than they know they will pay out for a certain percentage of bookings.
• Have someone double check your work before hitting “book now”.  Kate and I work as partners, I’ll find 3-5 AirBnBs, and then she’ll dive into the details.  Once she has selected her top choice, one of us will double check it and book it.  I find the flights, but she double checks the dates and times when my brain is spinning from all the options. (Yes, I have booked a flight for the wrong month!)
• Whenever possible, choose the option “pay later” and/or “free cancellation”.  If you aren’t getting travel insurance, it’s best to pay later in case something happens.  However, if it costs more to pay later, it’s probably best to pay now.
• We don’t limit our flights to any one airline or airline partnership.  It’s not financially worth sticking with one brand or alliance, there’s just too much variability in pricing between airlines. 
• The whole airline points thing – I could say so much on this topic, but that would bore you.  Let’s just say, it’s worth getting a credit card that gives you airline points, provided you pay your balance on time every month.  The points that we have accumulated have probably saved us $25,000 in flights had we booked economy.  They have also allowed us to upgrade to business class, so the actual “value” is closer to $75,000.  To find rewards flights, use a dedicated points search engine like point.me.

Thanks for reading to the end.  Next up: Chile!  Don’t forget to check out our past stories and subscribe for future articles as well.  Find us on Facebook and Instagram for bonus content!  Please note that any links or business names provided are for information only, we did not receive any compensation for our opinions or recommendations. As always, if you are planning a trip to any location we visit we are happy to provide more details and opinions, so feel free to contact us.