We’re about halfway through our travel vaccinations for the trip. To figure out what we needed, we visited Passport Health, which gave us a loooong list of shots to get for the countries we’re visiting. We managed to get many of them filled at Walgreens, which saved us a TON of money.

Weā€™re nearly done booking all of our flights, accommodations, and toursā€¦and weā€™re still generally on track with our estimated budget! Not too shabby for estimating booking costs for a 100-day trip! šŸ™Œ

Exhausted with Trip Planning

One thing we’ve found about a 100-day trip is how daunting and exhausting it is planning and booking such a trip. When you plan for a 1-2 week trip, you might look up 1-2 countries for things like voltage; what type of plugs; what type of money; do they have Uber (or how to get around); what are the tipping policies for the country; what prescription meds can you bring into the country; do you need a visa, etc. It might be an hour or two of research on the internet. But when you are researching 21 different countries, well, it’s 22 times thatā€”a lot of work!

This is all on top of trying to figure out what an itinerary is for a 100-day trip. We have discovered that we do better when we have a plan in place of what we want to do, see, experience, etc. than if we just “wing it.” This doesn’t mean that we’re “locked in” to a plan, but instead that we have all the options and relevant information to choose from. That means we can just follow the plan if there’s no reason not to, but also allows us to remain very flexible (as you may know from our Portugal trip last December). But when we get up in the morning each day, we know what is generally on the agenda. That way we don’t waste an hour (or many) stressing out about figuring out what we want to do that day, etc. For this trip, especially, we decided we didn’t want to spend valuable time on our trip planning out the latter part of the trip (our original plan was to keep the last 20ish days unscheduled). We are planning on having “zero days” on our trip, but we went to spend those days on getting supplies, doing laundry, talking to friends/family (more on that later)…and not on trip planning. So, we knew that for a 100-day trip to 21 different countries, we need a general plan and have stuff pre-booked. (And we have travel insurance if we need it!)

With all this as a background, for the last 2 months, Jen has been busy researching what countries we’ll go to, what we want to do in the country, and what an itinerary might look like. Then, she’s been busy booking flights, hotels, and tours; and then starting to look up all the smaller details for each country. In the meantime, Scott has been researching what cameras we need for our trip, what prescriptions we can bring into the various countries, where we should campervan in Australia, and, most importantly, getting this website/blog up and running so we’ll be able to tell you all about all facets of our trip!

We’re both pretty tired already with the trip-planning. But we’ve done this enough to know that the time spent now planning and figuring out all these aspects of our trip leads to a much more fun, relaxed, and amazing trip later!

How we chose our itinerary

Once we decided that our primary goal with the trip was to see as much stuff as we could on the other side of the globe, we still had to narrow in where weā€™d target.

Our main considerations:

Nearly every place should be new to both of us. Again, the point is to see far-flung places that we couldnā€™t otherwise get to during our normal vacation time.

And our plan was to save most of the ā€œtop tierā€ destinations for later, as those worked well as standalone trips that we could pull off during ā€œnormalā€ 2-3 week vacations in subsequent years. So most of the places that ended up on our itinerary were places we wouldnā€™t book a specific trip to go see. Our strategy here might seem a bit surprising to many. But our eventual goal is to visit as many countries as we canā€”hopefully eventually all of them, so being strategic about what we do and what we save is important.

We knew we wanted to ā€œanchorā€ the trip around a long African tour and safariā€”which definitely is a top tier destination for us. Itā€™d be the easiest way to travel through, and between, a number of African countries. And, crucially, we wouldnā€™t have to book each dayā€™s transportation, lodging, and day tours separately, which took a lot of planning stress out of the mix immediately1.

We also wanted a diversity of experiences, and occasional ā€œWestern-ness.ā€ While this adds a lot of complexity in terms of packing (and forces us to check luggageā€”sigh), we figured that weā€™d really appreciate regular changes in vibe on such a long trip. And since we havenā€™t spent such a long period out of the country before, we tried to intersperse more familiar-feeling destinations in between those thatā€™d be more foreign to us.2

We added a ā€œzero dayā€ roughly every week, so we had built-in time to sleep in, do laundry, shop for supplies, and catch up with friends back home3.

We knew that this type of trip would entail a lot of flights. And, unfortunately, weā€™d need to check luggage for each of them. But we tried to keep the flights as reasonable as possible, limiting duration, layovers, and cost.

In addition, if we had to layover somewhere en route to the next destination, we should take a day or three to explore a bit before moving on.

We prioritized visiting Taiwan, Hong Kong, and Macao first, just in case future political trouble made them hard to visit later.

We originally decided to keep the last 20 days completely open. But after some reflection, we decided that itā€™d be better to plan something out; we didnā€™t want the added stress of trying to decide, research, and book things during the other sightseeing days of our trip. We also wanted to be sure to ā€œend on a high note,ā€ so we chose to finish in Australia and French Polynesia (read: Tahiti and Bora Bora). We wanted something near the end that weā€™d be looking forward to (Australia) and that would also be more relaxing and stress-free than other destinations, figuring that we could easily be getting tired of travel by this point. While Australia is the only exception to the ā€œonly new placesā€ rule (Jen visited previously), we could still ā€œleave it openā€ by renting a campervan, which would provide a lot of flexibility in how we traveled.

General thoughts

This will definitely be our most challenging trip ever.

Weā€™ll be stretching both of our comfort zones in a number of ways. There are a lot of logistics, and a lot can go wrong when youā€™re traveling for 100 daysā€”canceled flights, lost baggage, theft, illness, and countless other things. And weā€™ll likely have to pivot and skip something(s) on our itinerary to get back ā€œon track.ā€ Iā€™m sure weā€™ll make plenty of mistakes along the way.

But itā€™ll be an adventure, thatā€™s for sure!


  1. It’d also give us a taste of what to expect on a safari, as we plan on returning for more focused safari tours in the future. ↩︎

  2. This might be most important when it comes to food. Scott is very much not an adventurous eater, and that may be the toughest part of the trip for him. ↩︎

  3. Weā€™re planning on having an open Zoom room available for anyone who wants to pop in and catch up. ↩︎

An unexpected concern: make sure any cash you’re bringing to Africa was printed after 2013, as bills printed before then were subject to widespread counterfeiting and often aren’t accepted as payment.

Choosing where to go when you can go anywhere

When we first started embarking on a plan for taking a mini-retirement, we naturally started considering where we might go.

The first plan that emerged was a tour around South America. Itā€™s a continent Iā€™ve never been to, contained a number of ā€œtop tierā€ destinations we want to visit, and would pair well with a Dec-Feb trip timeframeā€”which is one we often struggle to fill. Thatā€™d also allow us to divide vacation time into two calendar years, making things much easier. We could also do it rather cheaply.

A little while later, Jen put together another option of bouncing around the Balkans instead. Itā€™d be more expensive, but would be better timed for the late spring. It also seemed a bit more strategic because itā€™s easier to travel from Arizona to South America than across many timezones to Europe. So perhaps we should save various South America destinations for ā€œnormalā€ trips instead.

Of course, this was all just theoretical conversation; several factors would have to align to make a trip possible. We wouldnā€™t be able to entertain any substantial time away until my dad passed away. And then Jen would still need to convince her bosses to let her take an extended leave of absence, a very rare event. To our surprise, both of those factors recently aligned. So the destination discussions got real, quite quickly.

Where do you go if you can go anywhere in the world? Itā€™s not a common question to think about. Dream about? Sure. Seriously consider? Not really.

But suddenly, it was a question weā€™d have to actually answer. (And believe me, I am NOT complaining!)

When we calculated out the specific days and discovered that the time off would be exactly 100 days, the answer seemed obvious. Wouldnā€™t it be epic to visit all seven continents in 100 days? Wow! 7 in 100. That would be a story Iā€™d never get tired of telling. So we put together a trip that would do that. Jen has already visited each continent, but I have only been to Europe and North America. Itā€™d be quite a bit more expensive than the other two options we had plotted out, but itā€™d be worth it. 7 Continents in 100 Days! How cool is that? We nearly pulled the trigger.

But we decided it was smart to chew on it for another night first before booking. We went to happy hour at a local brewery the next day and stepped back a bit to ask a bigger question: ā€œwhat did we really want from this trip?ā€

Jenā€™s answers were different than mine. Sheā€™s more than half way through her career, with a dozen years remaining before retirement. Sheā€™s incredibly burned out and needs a big break from work. And sheā€™s excited to see as many new things as possible. She wants to make a lot of progress on her quest to see all the countries of the world. She wants lots of new experiences. Thatā€™s what would really re-energize her.

And it was suddenly immediately clear. We needed to ditch the seven continents plan and focus primarily on the countries it would be logistically difficult to visit during our usual 2-ish week vacation window, given their distance from home. We should shoot for the antipodeā€”the places on the far side of the globe.

We might not hit as many of those top ā€œbucket listā€ destinations, but weā€™d set ourselves up for easier international trips in the coming years.

Weā€™ll have an amazing time no matter where we end up. I mean, we once let the internet choose our road trip destination and we still managed to have a fun time at the winning entry, the (not so illustrious) International Banana Museum. So it doesnā€™t really matter where we go.

Turks and Caicos (Nov 2021)

In November 2021, Scott and I headed to the Caribbean island of Turks and Caicos to join friends for one of our wedding celebrations. Turks and Caicos was a location my Umbrella Drunk girlfriends and I have been wanting to visit for awhile but haven't made it to yet. A wedding celebration seemed like the perfect opportunity for us to go with our significant others.

NOTE: Unfortunately, none of the photos made it over in the import. Weā€™ll fix this after our big trip.

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Guam, Saipan, Tinian (Nov 2017)

To help anyone traveling to Guam, Saipan and Tinian (both in the Northern Mariana Islands), here is an outline for our trip there in November 2017.Ā  We traveled to Guam from the U.S. mainland via Honolulu, Hawaii.Ā  We arrived late in the evening, picked up our Thrifty rental car and drove to our hotel - the Days Inn Guam, where we crashed for the night.Ā Ā 

NOTE: Unfortunately, not all of the photos made it over in the import. We’ll fix this after our big trip.

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Estonia, Latvia, Lithuania (Oct 2018)

(Jen took this part of her trip solo in October 2018).

Recently, a friend of mine, who I met in Antarctica and who has traveled all over the world, asked for recommendations for a tour guide company for his trip to the Baltics (Estonia, Latvia, Lithuania). I was a bit surprised because I never considered those countries to be so difficult to travel to that a tour company was needed, but maybe I was wrong. So I figured I would write a trip report to help anyone else traveling there.

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Alaska (Jul/Aug 2018 and Jun/Jul 2019)

Alaska is a beautiful state, full of mountains, glaciers, and wildlife. In the summer of 2018 and again in 2019, we spent two-weeks exploring the National Park units there. Alaska is an expensive place to visit and finding information on how exactly to visit these park units can be difficult. As such, I have put together this resource guide not only documenting our trips, but providing the information and links I gathered in hopes of helping future Alaskan adventurers. Due to the parameters of posting Articles in this Questing Community, this resource guide is broken up into a four-part series.Ā  I hope you enjoy and benefit from the information and the stories I have outlined. Keep in mind, there may be many other ways to visit some of these places. This guide only outlines the adventures we had and the outfitters we used or gathered research on.

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