Is unplanned travel more fun?


If you listened to the most recent Podcast episode, you already know that we had a sort of exciting week, albeit a bit chaotic. You should listen to the episode to get the full story of an amazing opportunity that came our way for all 5 of us to fly ANA First Class in “The Suites”, but I’ll summarize a bit here as well.

Like probably many of you, the Frequent Miler team uses the messaging tool “Slack” to collaborate together, and yes, sometimes just to shoot the breeze. So when I was working on other projects this past Wednesday and heard my little Slack notifications clicking away in my ear buds, I didn’t think too much about it. At a quick glance, it just looked like Greg and Nick were sharing excitement about some new discovery related to Seat Spy.

…but then I noticed this message:

Greg's slack message

This was my first indication that we weren’t just bantering about Greg’s cat Stripey this time and that I should do some catching up lest I miss out on something exciting. Again, you should go listen to the most recent Podcast episode to catch the rest of that (ongoing) story, but the whole stir got me thinking about the ways in which points and miles seem to favor this kind of “book first, plan later” attitude…(and how that’s kind of a feature, not a bug…)

Cheap, on target, or timely: Pick 2

We freelancers often have to tell our clients that we can deliver projects “on budget, on time, or of high quality…but you’ll have to pick 2.” Similarly, miles and points can help you achieve just about anything, but getting a really good deal often means allowing a little flexibility with your destination, schedule, or both. You often have to compromise something.

“Mistake fares” for example typically are so random and restrictive that they not only dictate a trip’s destination and schedule, but they require you to book immediately, before there’s time to do much planning or research. Or as was the case for our team this week, surprise award availability can work this same way. None of us had a specific plan which included Tokyo or San Francisco.

I think these constraints are a feature…not a bug

One of the reasons I actually like the “book first, plan later” ecosystem is because I’m just “that kind of person” – I like to maintain a (likely delusional) view of the world as some exciting place where there could be an adventure waiting around any corner. I realize it’s a luxury that comes with working remote and having no kids – we’ve jumped on more than a few spontaneous ideas that we’d never have been able to do if we were responsible for children or even animals. I get it.

But I think the constraints that come from jumping on a deal can be a huge benefit for even people who don’t (or can’t) favor spontaneity.

(As usual, I’ll demonstrate with a completely irrelevant analogy.) When I was an art student I could sit all day in front of a sketchbook not knowing what to draw until my art professor provided some sort of constraint for our assignment, and then I’d start to have ideas. To take the analogy a step further, before I had any constraints to inspire me, I would often just draw whatever was on the cover of my National Geographic magazines.

I think trip-planning can be the same way. I didn’t know anything about Oman before we booked a mistake-fare there (and it probably wouldn’t have occurred to me to go there without the impetus). And the detour Drew and I made to Fiji for our first anniversary was entirely inspired by the InterContinental Fiji’s appearance on the IHG “Points Breaks” list. (“Points Breaks” was a list of hotels IHG would feature for 5,000 points a night.) Points Breaks inspired quite a few trips for us, in fact.

Of course, this has backfired a few times too. We booked a mistake-fare once for an obscure hotel in some industrial park outside of Hamburg. That hotel was a total dud, but even in that case our dud-booking inspired us to ditch the whole thing and spontaneously hitch-hike to the incredible (and now rebranded) InterContinental Berchtesgaden instead. At ~$7 a night, I can hardly regret that booking, especially since ditching it turned into an adventure of its own. (That hotel is now the Kempinski Berchtesgaden Hotel.)

Getting past the bucket list

While we all have bucket lists of places we KNOW we want to see (and miles and points are an excellent way to get to those places), there are so many hidden gems out there which maybe wouldn’t get our attention without a little curve ball deal to get us there. When I first started traveling, Ireland was at the absolute top of my bucket list for instance. Don’t get me wrong – Ireland was just as magical as I hoped it would be and is still a place I adore, (and hope to get back to again). But I now also have lists of places which never would have occurred to me to visit if it weren’t for miles and points – places which I’ve loved. I’m willing to bet many of you have a few serendipitous spots which you’ve visited primarily because of a good deal, and which have made it to your favorites list.

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I used to do more unplanned trips while I was an airline employee. The whole concept of employee travel was very last minute. Now married to a person who has to have everything set up and laid out for them, there is no spontaneity. The whole idea of just going, gives them a panic attack.


Unplanned is great but so is planning, saving, and looking forward to a trip. We have another month until we fly but we’ve had the past 8 months to scheme and plan and dream about visiting expat family in Saudi Arabia and side-tripping with them to Jordan and Egypt. That’s what we as a couple are excited for and I, Mr av geek, am probably equally excited about flying qsuites there and back. Last minute is fun but huge trips are better when oh so anticipated

Dave Hanson

That’s a fair point, Robert. I’d just add that the two types of trips aren’t mutually exclusive.

Take their Japan example. The trip won’t occur for months, and my understanding is that they have yet to build a departing flight and itinerary while there. Now they’ll enjoy engineering a really memorable rest of trip–and even after that, have months to anticipate it.

My family is currently planning a trip to Chat next December that has a similar combination of an unplanned origin and lots of planning and anticipation built in.


Great take on things. I’ve discovered places I never would have consciously considered, like Merida, Zagreb and Cambodia due to sudden bargains. There’s a certain sense of freedom in not knowing where your next adventure lies. At least it’s nice to mix in with the heavily planned trips.


depends on the purpose of travel. Just wandering from place to place may be fun for awhile, eventually I suspect for most, that will get old. Maybe more expensive?

If you seek understanding, one needs to plan where to go. Religious sites, industrial sites (Peeking behind the consumer facade – factory tours, mines), cultural, or history.

This year I want to visit the NNSS – Nevada National Security Site – where lots of atomic bombs have been tested/exploded. Need to secure tour tickets for that well in advance. March 2023 is the next window to get a ticket — for visits in July+.

Now, contrast that with a ~3 week road trip nearly 20 years ago when at a hotel I looked in one of those racks of places to visit – and I saw a pamphlet for the TITAN MISSILE MUSEUM, just south of Tucson, AZ. Had never heard or read of it.

I went to that on a whim and it was one of the most profound places I ever went. 100 foot 9 Megaton Nuclear Missile Still in the silo! …sans nuclear material (and fuel presumably) of course. But a pre-planned place was the (US MILITARY) AIRCRAFT GRAVEYARD – out of the Pima Air & Space museum in Tucson, AZ. I saw that on the doc- Baraka. was a mix. Spontaneity and planned.

[As an aside…learning more about nuclear weapons might be a good idea now…]

atomictraveler is a good place to start.

This year I’ll be camping a lot and visiting Australian beaches. You know how many beaches are in Australia? Finding the best swimming beaches takes a little planning…unless you don’t swim and just want scenery. I’ve been more like that too…in the past. Then there’s seasonal issues/needing to pre-reserve camp spots in certain places. So a mix…is what I am doing. Some campsites/occassional hotel pre-reserved, others will just find/go to as I drive on that very day. [But I’ll have some idea on the area though] Yeah…I hate setting up camp at night…but I’ve done that.

My first two multi-month one-direction RTW trips (of 3 now) were a sharp contrast.

#1 – business class OneWorld award ticket, with the stops pre-planned – but moveable dates – which I did a little. I bought separate air tickets in various places, but the general structure of the trip was planned over a full year…but ended up skipping Europe..7 months of near constant moving in the end – except for a 2 week? vacation/scuba in Palau. I didn’t book hotels/hostels until a week or two out usually from recollection. Or in West Australia for example – took a backpacker bus for a week or something – so did not book a stay until arriving at a stop.

#2 Just bought air tickets as I went. 3-4 months. No pre-determined path.[Pre travel hacking, 2010]

And experienced with #2…I had to spend more time planning on the road. So — either way — you have to “Pay the piper” of travel planning.

oh…and trip #2…I DID NOT have a camera. That’s right…I took ZERO photos on a multi-month trip.

..more spontaneous might be…”we have a eurail / JR rail pass” — let’s just get on a train to ____. we’ll just be “happy go lucky.” Or with a car — let’s just go for a drive toward _____. So I guess that’s akin to buying a mistake unplanned fare to ____. It’s just the vehicle / range has changed…from a train/car to a plane.

more travel info/internet definitely enables over-planning. but sometimes — the devil is in the details. And to catch the devil, u need to really plan!


I agree take a Peek at Port Douglas (Barrier Reef 5*) booked on the Fly unspoiled..ALOHA


I’m still very much a planner but totally agree that our “hobby” can take us to places that would have never gone on the bucket list. Before I became Globalist, I was looking for places to use my club access awards–and found out there are Hyatts with clubs on both Guam and Saipan. Incredible trip that would have never, ever showed up on the radar screen. A few years ago, when I was looking around for fancy Ritz Carltons (I am Lifetime Titanium), I noticed one in the Canary Islands. I filed that away, having no idea where in the world were the Canary Islands. Then United announced a nonstop this past summer from Newark to the Canary Islands. Figured that was fate. We were treated like royalty since there were so very, very few tourists there from the United States. It’s a great hobby!

Bobo Bolinsky

About your photo: Standing on a coral reef kills it. Just touching coral with your finger may kill it. Coral is not dead rocks, they are live animals, very fragile, and disappearing across the world, in many places because clueless tourists are killing them by walking on them. Please stay off the damn reefs and stop encouraging other tourists to be idiots by standing on them, as you are doing in that photo. Incredibly irresponsible.


I don’t see the photo, but yeah that’s a great point. More info from NOAA about that here:,damage%20or%20even%20kill%20them.

Bobo Bolinsky

Here’s a link to the photo (a larger version displays on the blog feed but I can’t link to it directly because WordPress):

comment image

Here’s what that NOAA “Coral Etiquitte 101” web page (linked above by Aloha808) says about touching or standing on reefs:

Observe corals from a safe distanceDon’t touch! Corals are fragile animals. Be careful not to touch, kick or stand on the corals you see in the water because this may damage or even kill them.

I’m sorry if it inconveniences you or makes you feel uncomfortable when someone tells you that when clueless tourists stand on a coral reef, it kills them. It’s still true even if you don’t want to hear it, and that’s exactly what the author is doing in that picture. It’s incredibly irresponsible to defend or justify, encourage, even proudly brag about this kind of behavior. Shame on you.

Get educated. Here’s more on the subject:
What risks do tourists pose to coral reefs? Are we loving reefs to death?
(Short answer: Yes)


If she’s jumping off a section of live reef then you’re the King Of Spain. Look before judging.

Tim Steinke

What makes you think that’s a live reef? It looks like seaweed and barnacle covered rocks to me (and I’ve spent a lot of time around actual live reefs over the years). Pretty strong words given there’s nary a question about what you’re seeing.

Last edited 1 year ago by Tim Steinke
Dave Hanson

Great piece Caroline! You’re channeling Nick’s interesting think-piece style–but with more brevity. 😉

FWIW I very much agree with your take. As someone working in finance, I’m always asking “what assets are Mr. Market currently inviting us to buy (because they’re atypically cheap) or sell (because they’re expensive or even bubblicious, as many assets have been in recent years).

Travel hacking is very much like that. Just before your piece dropped, my fiancée tasked me with, “see what Mr. Market says about where we should go for weekend trips during the next few months!” There’s an excitement that comes with optimizing the unexpected opportunities that head your way. This is what your team managed to do with this Japan return trip. It was fun hearing Greg and Nick’s palpable excitement at the prospects. I’m guessing (and certainly hoping!) you’ll all have a fabulous time.