My strategy in planning a 38-days Eurotrip

I am currently in ice-cold Vienna, Austria, one week into my 38-days Eurotrip and have just completed the final puzzle piece of my itinerary! Yes, I am a travel nerd and I create my own little puzzles so that I can have the thrill of solving it all by myself for some personal fun.

Step 1: Decide departing and arriving dates

These dates were influenced by my wedding photography assignments. I had a shoot on 11 January and the next one is on 29 February. I planned to depart Singapore on 19-21 January so that I would have time to complete my editing work before the trip. I wanted to fly home by 27 February at the very latest so that I would be well rested by the next shoot date.

Step 2: Decide on which flights to book

As this decision for a trip was made around 10 December 2019, I decided to wait and hope for a Spontaneous Escapes deal to Istanbul on Premium Economy or Business Class (which is on my SQ sweet spots list) around 15-16 December. At the same time, I was looking at Qatar Airways Business Class (QSuite) availability from a European city to Singapore for my return flights via Doha.

On the 16th of December, Spontaneous Escapes deals for January 2020 were announced. There were deals on Premium Economy to Istanbul but sadly, no Business Class. But hey, 25,900 miles for an 11 hours flight is a pretty good deal. That’s until I saw this month’s crazy deal!

I saw plenty of availability for Qatar’s Business Class from a number of European cities to Singapore. I planned to initiate a points transfer from DBS to Cathay Pacific’s Asia Miles on 29 December so that the miles would be in my Asia Miles account after 1 January, when Asia Miles expiry changed to activity-based.

Little did I know that on 1 January, Cathay Pacific would announce that credit card points transfers from 1-31 January would receive an additional 10%. Now that’s unfair! The transferred miles eventually appeared in my account on 3 January. I’m not sure if it qualifies for the 10% bonus. I’ll have to wait till 31 May to find out.

As soon as the miles were in, I went ahead and booked Amsterdam-Doha-Singapore on Qatar’s Business Class for 70,000 Asia Miles and HKD 2,196 ($383) in taxes and fees (YQ). I chose to depart from Amsterdam because of the following reasons:

1. Flights departing AMS have slightly lower YQ compared to other European cities.

2. Features the latest Business Class seats (QSuites).

3. A little bit further from Doha when compared to other cities, giving me over 6 hours of flying time instead of just 5 hours from Budapest, for example.

4. Nice departure time of 3 in the afternoon instead of a morning flight from a lot of other cities.

Yes, when you are not a rich man flying Business, you want the flight to be as long as possible!

Like a true-blue kiasu Singaporean, I have also chosen an 8-hours layover in Doha to enjoy the massive Al-Mourjan Lounge instead of a 2-hours one like a normal person would.

Barring any last minute airplane swaps, this will be my first experience on Qatar’s QSuite. Fingers crossed!

Step 3: Let the flight prices decide which cities I visit

I knew that I want to spend a few days in Istanbul as I have made a redemption for St. Regis Istanbul. I also knew that I have to end my trip in Amsterdam to catch the Qatar Airways flight to Singapore. Those cities are fixed but I left everything in between open.

The bias was towards countries and cities that I have not visited. Using Google Flights’ map view, I could see how cheap I can fly into Europe for (from Istanbul). With the calendar view, I could also somehow guess when the prices will be at their lowest.

The plan was to also spend about 4-5 nights in each city as I wanted to fully utilize the 4th-night-free benefit with my Citibank Prestige Mastercard. After setting price alerts for all possible flights, I ended up with the following:

Istanbul – Vienna: $65
Bratislava – Malta: $20
Malta – Luxembourg: $20
Luxembourg – Porto: $16
Porto – Eindhoven: $40

Add $35 to each of the prices above to include checked-baggage. My partner and I shared one large suitcase for better mobility. We considered going hand-carry only but…it’s winter!

From Eindhoven, I will be travelling to The Hague by train, spend 4 nights there and then catch another train to Amsterdam.

Step 4: Set price alerts for target hotels

Similar to tracking flight prices, hotel prices can be predicted with a fair level of accuracy. I use Skyscanner to track hotel prices on pre-selected dates. Even as an Elite member with Marriott and Hilton (M&H), my rules are pretty straight forward:

1. I will not pay more than 20% higher than the cheapest night of any particular hotel.

2. I will not pay more than $130 (incl taxes) a night for any hotel.

3. I will not stay in an M&H hotel if breakfast is not complimentary.

4. I will not stay in an M&H hotel if it costs more than twice the price of a decent Airbnb or independent hotel.

As my trips are usually fairly long, these rules cover me for most scenarios and keep my travel expenditure reasonable. The M&H hotels that I ended up booking are:

1. Sheraton Istanbul City Center

2. St. Regis Istanbul

3. Hilton Istanbul Kozyatagi

4. DoubleTree by Hilton Bratislava

5. Hilton Malta

6. Marriott The Hague

7. DoubleTree by Hilton Amsterdam NDSM

Other nights will be spent in AirBnbs or independent hotels.

Conclusion

If all goes well, I would have visited 6 new countries and flown on a dream Business Class seat by the end of this trip. I enjoyed the surprises of letting an external factor decide where I travel to. Would you do the same? Cast your vote in our telegram group.

Share some of your most nerdy travel strategies with me via the comment section below or contact page.