A look into my planning process for Iceland

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Travel

I recently went through the process of planning an upcoming trip to Iceland. I am sharing that process with you all below. Please don’t hesitate to reach out with questions.

I break my process into 4 buckets:

Pre-trip logistics — flights, local laws, regulations, and health or visa requirements (Note: this does not include accommodations, that comes later).

Information collection — This piece is the majority of the work. It includes sifting through recommendations from friends, reading travel blogs, perusing Reddit, and watching YouTube videos.

Mapping — I then take everything I have found and map it. Mapping helps me get a feel for where I will want to concentrate my time, which will influence my accommodation choice(s).

Final Bookings — Finalize reservations for big-ticket items.

The first thing I do is secure flights. Sometimes that’s not the case but most of the time it is. Flight prices will fluctuate more than anything else, and it helps to set my dates first so I know what I’m working with.

Then I’ll do a quick scan to see if I’ll need a travel visa, or any other important items to kick off early like an international driver’s license or health requirements.

Fortunately, for this trip, there are no significant things to note in this department (although starting in 2025, Americans will need ETIAS authorization).

Now the fun stuff! The depth of my information collection process will differ from trip to trip. I usually skew toward underplanning — it enables spontaneity and keeps expectations neutral.

For example, if traveling solo to a new city, I will briefly research where to stay and what to do. I’ll then rely on on-the-ground recommendations and exploration for the rest.

In this case, I’m going to Iceland with my fiancée and her dad where we’ll spend most of our time driving through the country. I felt a little more planning was necessary to decide roughly where and how we’ll spend our time with only 6 days.

Now that my collection process is done, I have this lovely map. The map gives me an idea of where I’ll book accommodations.

Based on the map, we plan to focus on the western fjords, the highlands, and the southern coast.

With that information decided, we’ll book accommodations.

I first pull up a map of Iceland on Airbnb and zero in on our focus areas. From there, I save everything that jumps out as a unique stay in my eyes. Then, I’ll filter through what I’ve saved to see if there are any dealbreakers regarding amenities.

I’ve narrowed down my options. Now, I can focus on logistics.

We arrive in the morning. We would rather do Reykjavík on the back end versus the front end. We decided to start with the Western fjords before driving south where most of our remaining exploration will occur.

We booked two nights near the Western Fjords, which gives us time to explore that area. We then booked two nights in Selfoss, which will be a good spot for access to both the Golden Circle and the Icelandic Highlands, and one night further east, which allows us to cover a bit more ground before turning around and heading back to Reykjavík for our final night before returning home.

We opted for Airbnbs for most of our stays because the platform offers more unique stays and better options for accommodations outside of Reykjavík. For our last night in Reykjavík, we opted for a cheap hotel with free parking since we’ll just be sleeping there.

With accommodations booked, that mostly completes my final bookings bucket.

Usually, the only thing I want to be locked into is lodging, and even there I try to pick places with flexible cancellations. Flexibility is always my friend. I like to get on the ground before committing too much.

I hope this was either interesting or helpful. If you’d like to learn more about my approach to trip planning, you can check out this free email course I’ve put together here.

Weekly Write-up

In the course of our discussion this week, my therapist stopped me and said, “I notice you tend to take on a lot of responsibility in relationships.”

In a sense, I’ve always known that.

My protective and controlling instincts kick into overdrive in my relationships with others, especially those in my core circle. I want to do everything in my power to ensure my loved ones are taken care of and I generally don’t rest until I know that is the case.

Those feelings lead to frustration when a situation turns sour and I cannot help.

Even though it isn’t mine to take on and doesn’t help the situation, I have a habit of taking on that burden with others.

In the last year, I’ve noticed the emotional toll that takes on me and I’ve been working to change my approach.

I’m reading a book called The Courage to be Disliked. In it, the philosopher and his student discuss the principles of Adlerian philosophy. One of the core principles is that all problems are interpersonal relationship problems.

To solve those problems, the philosopher poses the idea of separating tasks.

The separation of tasks works like this, “Calmly delineate up to what point one’s own tasks go, and from what point they become another person’s tasks. And do not intervene in other people’s tasks, or allow even a single person to intervene in one’s own tasks.”

Now you may think this translates to something like, “mind your damn business,” but that’s not necessarily the case.

The philosopher provides the example of parents struggling to get their son to study. How can his parents help?

The parents cannot intervene in the son’s task, or the son will not learn to study. Instead, the parents should tell the boy that studying is his task and they are there to assist him when he is ready. Then it is on the parents to build the trust required for the son to feel comfortable asking for help.

“When no requests are being made, it does not do to meddle in things.”

As one who likes to meddle, this was a unique perspective.

People only change when they want to change. You may influence at times, but those times are few and far between. This concept is something I’m beginning to understand.

Of course, philosophy often paints situations as cut and dry.

In practice, there is more nuance.

But I found this to be a useful perspective at a time when I needed to hear it. Sometimes timing is everything.

Content Recommendation

My Reading List

I’ve put together a list of all my favorite books at the link above. I’ve been reading more recently and plan to add to this over time. You will always be able to find it in the “Travel Guides & More” section at the bottom of each email. Let me know what you think and feel free to reach out with any questions or suggestions on anything I’ve included!

AI Travel Art Piece of the Week

Cheers ‘til next week,

T.O.