Another destination advice post. My situation is a bit different than most here, mostly about age and budget - don’t kill me.

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35M, Canadian, have been semi full-time nomading for a couple years with a lot of pre COVID backpacking before then. Lucky to have a quite high paying job (high six figures USD) that is semi flexible in terms of work. Recently purchased a small place in Canada that will be my “home base”, but my plan is to spend about half the year abroad, mostly during our winter months (December - April-ish).

Recent longer term stays have been Medellin, Buenos Aires, Bali. Although I’ve loved these trips, I find I am often meeting/hanging out with a very different demographic of nomad - early/mid 20s, still building their careers, much smaller budget. While this is still fun, it’s starting to become monotonous as our life and career stages are just so different. Especially when in developing regions my budget means most doors are pretty open in terms of accommodations, last minute flights, activities, etc. and it can be hard to find people to do these things with.

Eastern hemisphere is better for me as the time zones work, so South America is mostly out. I’ve considered a second base in Europe (Berlin, Amsterdam), but the weather would also be bad during the same months I am trying to seek the sun. Australia is an obvious option, but a little too similar to my home town and want to avoid living in two of the most expensive cities in the world rather than having my $ go further while away. Similar thoughts for the ultra bougie options like Dubai. Have considered elite Thai visa, Bali second home visa, etc.

Some other things I’d like:

• good nightlife, but not a solely party town
• near a travel hub
• good networking opportunities with similar lifestyle people - business opportunities, creative excursions, etc.
• developed infrastructure
• options for longer term stay/buying property if I fall in love with a place

Again, I realize this is a very privileged position to be in. I have very much enjoyed the last decade+ of hostels and budget friendly travel, but I’m looking for the next step.

Thanks!

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