Help me to come up with a better strategy to choose where to go next

Question

I’m a digital nomad with a goal of visiting as many different cities as possible.
I travel each month to a different city (with good weather) in a different country and I never repeat the same country in the same year for diversity (except when visiting home).
I choose where to go next by pinpointing the top cities from the nomadlist.com (which is constantly updated according to the weather, if I’m not mistaken) in a personal Google Map, I then see what’s the nearest country according to my current location and I plan everything 1 or 2 months ahead.
In December I always go home (Portugal) to spend time with my family and then in January I start all again.
Sometimes in order to get to the “nearest” pinpointed country I have to take 2/3 flights which can be expensive and time consuming. This is when I think I might not be making the best move.
Do you guys have any advice that might improve my strategy?

lia9255 · Accepted Answer

I’m trying a new strategy that seems to work well.  I start from my home base in the US and fly to an inexpensive, central airport in Europe (wherever I get the best R/T fare), then travel via train or air within the continent before moving on to Asia and doing the same there, and then on to the next region (until I clear the Schengen visa limit of 90 days) or returning to Europe.
Using this method in 2017, I will be in Spain, France, Germany, Morocco, Singapore, Thailand, Malaysia, Hong Kong, Australia, Romania, Estonia and Finland.  I book the major legs (JFK > FRA > SIN > FRA > JFK) all at once and this time, all on Singapore Air and Lufthansa, then book cheap internal flights or train tickets as I go.
By only booking the long-haul legs in advance, I avoid change fees since I’m fairly committed to those travel dates anyway.  My annual air/train budget is USD $3600  or $300/mo and I just booked the long-haul route for under USD$2000 so that leaves me a couple hundred $$ to travel between each country within the region.  In future years, I can cash in frequent flyer miles to reduce the airfare.

wanderingdev · Answer

have you looked at flight special sites like secretflying.com to see if there are good deals you can take advantage of to reduce costs of flights?

kathrynoh · Answer

I often use Adioso, I think skyscanner does the same thing - you can put in a general region and get all flight details. If I want to go to Europe from Australia, often I don’t care that much what city I fly into.  If I have to have stopovers, I try to make them a longer visit rather than a few hours at an airport too.

lia9255 · Answer

$2k is economy class on Singapore Airlines from New York to Frankfurt to Singapore, then back to Frankfurt and finally to New York with several months stopovers in-between each leg so the price covers 4 flights.  The whole timeline is from August 2016 through June 2017.  A pretty good deal especially since SA economy is comparable to other airlines’ business class.  Includes priority boarding, 2 checked bags (I need 1 checked bag just for my chef’s knife kit and other supplies they won’t let me carry on the plane), preferred seat assignment, lounge access and other perks.  Plus I get over 20k KrisFlyer miles that I can put towards future travel.

nicknovitski · Answer

Wow, that’s cool.  How/where do you book a single “flight” with multiple-month stop-overs?

wanderingdev · Answer

wow…$2k for a flight?  business class?

nunoarruda · Answer

I know SecretFlying, it’s a nice resource, but it depends on me being lucky or not to find a deal from where I am or to where I wanna go.
I definitely need to pay more attention to SecretFlying though.

lia9255 · Answer

I booked it directly on Singapore Airlines website as a multi-city trip and just entered the dates I plan to travel from one city to the next.  You can choose to fly only that airline or open up the search to include their partners.  You should also be able to choose different booking classes (economy, premium economy, etc…).  Booking multiple flights all in advance is best if you know your travel plans, because you’ll need to pay a fee if you change dates later if you select the lowest possible airfare (higher airfares usually waive the change fees).  It also helps to know the airline’s major hubs.  For example, I know Singapore Airlines to Asia connects through Frankfurt (I’m actually not staying in Frankfurt, but I can take the train or get a cheap flight to where I need to go in Europe).  I’ll do the same when I arrive in Singapore - will stay there a week and then travel throughout Asia for a few months.

poppyjikko · Answer

I like to pick a distant place I would like to visit.
Then I check on Google Earth (or in my mind) what are other cities on the shortest route.
Then I check on skyscanner (and low cost carriers and sometime land transportations) the cheapest routes available.
For exemple to go from GVA to Ljubljana I took a plane to Venezia, then a car to roadtrip around Trentino and Veneto, then a bus from Trieste.

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