I’m planning a trip to Europe for late September / early October. When I plan trips, I usually just try to book flights and lodging ahead of time, and plan daily activities much closer to the actual trip. Most of the time, I have a loose idea of what I want to do (and that usually takes up less than a day), and then just walk around and let serendipity take care of the rest.
However, earlier trips I’ve planned have been easier than planning this Europe trip. With other trips, I usually only have 7 – 10 days to travel because of how much PTO I can take. In that amount of time, I usually stick to 1 city, with some day or overnight trips, or 2 locations that are close by. Anything more feels more rushed.
I don’t have that same constraint with this trip, since I’m not working and thus don’t need to be back on a particular day. It’s also easier to do multiple cities on trips to Europe. You can generally hit a new city every 3 – 5 days since they’re so close together.
Besides London, there’s no other place that’s “on my bucket list” so to speak, so I can’t use that to narrow down my options. With the relative lack of constraints, there are hundreds of different itineraries that I could build.
I’ve researched travel destinations and recommendations for where to go, but I haven’t seen many people sit down and write out their thought process for how they arrived at a particular travel arrangement. I thought it would be fun to do so, and I’m hoping that other people can benefit from seeing my decision process explicitly laid out.
Decision Making Process Goal
The goal of this decision making process is that I need information to book round trip or multi city flights. Specifically, I need to know:
- outbound flight information (date, US departure city, European departure city)
- inbound flight information (date, European departure city, US arrival city)
I don’t need to decide on this right now, but it will help in booking flights
- cities I want to visit
- how long I want to spend in each city
Here are some guiding questions that might help me:
- What is the purpose of my trip?
- I want to see London, have some adventures, meet people, and practice the languages I speak (Spanish, French)
- I also won’t have housing in a big city (New York) from mid-September onward, so this is also a way for me to entertain myself in the meantime
Constraints / Considerations
Here are some things that constrain my decision making:
- I want to keep the budget for this trip under $3,000. Flights will be between $500 – $700 to Europe. Assuming $70/day for daily expenses, I can travel for ~28 days.
- I need to be back in the US no later than October 20th, but probably earlier
- I can’t leave until after September 15th
- I have tickets for a concert that I want to see in New York City on October 14th. I could sell them and skip it, but would like to try to make it.
- There’s a reunion event for Venture for America, the fellowship I did after college on 9/24 in Pittsburgh (“OktoBURGHfest”). I could skip it, but have enjoyed previous fellowship events that I have gone to and would like to attend if I can.
Available Options
When making decisions like this, it’s helpful to outline what the options are. Based on my constraints and considerations, here are some of the options I’m thinking through for the outbound and inbound flight information:
- Outbound
- Date
- 9/27
- 9/22
- Considerations: If I left on 9/22, I wouldn’t be able to attend OktoBURGHfest. I would be able to attend it if I left on 9/27
- US departure city
- Pittsburgh
New York- Considerations: I would probably leave from Pittsburgh, because I think I would be there either way (since I won’t have housing in New York at that time)
- European arrival city
- London
- Paris
- Considerations: I have a friend who’s going to be in London on 9/28. If I don’t want to do Paris, I would just arrive in London on 9/27. If I wanted to re-visit Paris, and leave early, then I would fly into Paris on or around 9/22 and then head to London on 9/27
- Date
- Inbound
- Date
- 10/13
- Returning on this day would allow me to make the concert. I also have travel planned to the west coast on the following weekend, so I don’t want to return any later. I also have to factor jet lag into this, since I’ll be going from Europe to Seattle over the span of ~a week
- European departure city
- London
- Paris
- Madrid
- Considerations: I think I would want to do more than one city on this trip, especially since I’ll be there for 15 days and that’s enough time to squeeze in another place. In that case, it makes sense to book the return flight from a different city instead of flying out of London
- If I wanted to do Sevilla after London, then I would fly out of Madrid. If I wanted to stay in Northern Europe (France or Amsterdam), I would do Paris. If I ended up just wanting to explore the UK for 15 days (unlikely), then I would do London
- US arrival city
- New York
- Unless I don’t go to the concert and opt to go straight home, I would probably fly into New York. Even if I fly into New York, I can still go home since one-way tickets from New York to Buffalo or Pittsburgh are pretty cheap
- Date
Option Set
This list of options can be reduced to an option set. The inbound options are much simpler than the outbound options.
Inbound (to US)
| Option No. | Date | EU departure | US arrival |
| IB1 | 10/13 | Madrid | NYC |
| IB2 | 10/13 | Paris | NYC |
| IB3 | 10/13 | London | NYC |
Outbound (to Europe)
| Option | Date | US depart | EU arrive |
| OB1 | 9/27 | Pittsburgh | Paris |
| OB2 | 9/27 | Pittsburgh | London |
| OB3 | 9/22 | Pittsburgh | Paris |
| OB4 | 9/22 | Pittsburgh | London |
First pass
The easiest thing to do with decisions like this is to figure out what options you can eliminate. On my inbound (back to the US) flight, I probably don’t want to stay in the UK for 15 days, and thus can eliminate London (Option IB3).
So it’s between Paris and Madrid. Flying back from Madrid drops down my price by $135, and I want some sun. So Option IB1 it is for inbound.
For the outbound flight, I can eliminate Option OB4. I don’t want to spend that long in the UK. In theory, I could use this option and then just go to Paris immediately when I arrive in the UK. However, this is less cost effective than just flying directly to Paris and then going to the UK on 9/28. It’s around $200 extra to fly to Paris and take the Eurostar ($60), whereas the roundtrip Eurostar from London to Paris is ~$260.
So that leaves OB1, OB2, and OB3. Honestly, I can probably skip Paris on this trip. I studied abroad in Paris and lived there for six weeks, so I don’t feel as much FOMO if I don’t do it. I did want to practice French, but I can use iTalki for that or plan a separate trip to Québec. Thus, I can eliminate OB3 and OB1, which only make sense if I wanted to go to Paris. By process of elimination, I’m left with OB2.
My tentative plan is now:
Outbound: Pittsburgh to London on 9/27 (or 9/26)
Inbound: Madrid to NYC on 10/13
Second pass
I could stick with this and be done. But let’s think through this a little bit more. What are some tradeoffs I can make to get a better outcome?
If I follow this plan, I’ll be in Europe for 16 days (not including travel days). I’ll make it back in time for my concert, and will leave after the Pittsburgh event.
With ~16 days, I could do 10 days in London and 6 days in Spain. Or, I could do 7 days in London, and 9 days in Spain. Specifically, I could do 7 days in London, 5 days in San Sebastian / Bilbao, and 3 days in Sevilla before heading back to Madrid.
But I could also make some tradeoffs and extend my time in Europe. I could skip the Pittsburgh event, depart on 9/22, and spend three weeks (21 days) in Europe. In that case, I could do 10 days in London/UK (and maybe even a trip to France), do 5 days in the Basque Country, 4 days in Sevilla, and then 2 days in Madrid.
Or I could skip the concert, and then fly out on 10/17, which would give me 5 extra days (21 days total). I would overlap with my friends in London for the entire time they’re there, and still have an extra 11 days in Spain. I would also be able to spend a weekend in Madrid.
I could totally turn this entire process on its head by flying to Madrid on September 15th, spending 14 days in Spain, and then 10 days in London before flying out on 10/8. That would probably bump the ticket price up to $800 or $1000 though (I probably won’t do this). I would also have to find housing in New York, or find transportation from home back to New York for the concert. That extra cost might not be worth it, in which case I would skip the concert and just be better off doing one of the earlier plans.
Tentative Options
So here are my tentative options:
- Option A (tentative plan)
- 16 days, plus 2 travel days
- Estimated total cost: $1900 (Flights: ~$600, $1120 total daily costs at $70/day, $180 contingency)
- London and one of Sevilla or San Sebastian
- Outbound: Pittsburgh to London, 9/26
- Inbound: Madrid to New York, 10/13
- Option B (longer trip)
- 25 days, +/- 2 travel days
- Estimated total cost: $2450 (Flights: ~$700, $2450 total daily costs at $70/day)
- London, potentially Paris or day trips within the UK, San Sebastian, and Sevilla
- Outbound: NYC to Madrid, 9/16
- Inbound: London to New York, 10/13
The second trip would be an inversion of the first trip – I would start in Spain and work my way up to London. I would be able to do two Spanish regions comfortably and do more trips in the UK.
I might be able to squeeze in the Basque Country and Seville into Option A, but if I could only choose one I would probably go with Seville. I think the big determining factor between the two trips is if I want to do both regions and try to spend 10 days in London – I don’t think I would be able to do them all with the first option.
This post ended up being way longer than expected, so I’ll end it here and aim to book these flights by tomorrow.