If you and your SO are a developers, then I would highly recommend a work-cation in Prague. I spent a few weeks at a really cool co-working space, PaperHub, which was part of the Institute of Cryptanarchy (lol). They take BTC for everything, the transit system is a dream, and there are tiny little specialist grocery stores everywhere. If I was ever going to return to the same place twice, it would be Prague.
Beware of burnout, though - there is no rest in this lifestyle. The home office wants me online during their business day, and constantly learning new cultures is a huge cognitive load. After two years of this, I needed to settle down for a while; right now I am resting between jobs, thanks to a very supportive mother. Oh, make sure to take good care of your parents, they may end up being the only solid, reliable people in your life.
I honestly don’t get the attraction of co-working spaces for most digital nomads. The costs often outweigh simply working from a cafe or the balcony of your AirBnB – 3G internet is cheap in most of the world now. In my hometown, co-working spaces attract locals who set up small teams with other local freelancers and could benefit from in-person collaboration. But for a solitary digital nomad all of whose contacts are remote, what's the point?
There are some extra perks to a good co-working space, though. It is library-quiet, and you are surrounded by people who are living and working a similar plan. I was actually able to informally recruit a guy who often worked near me, when we needed to bang out a bunch of UI components and their services, for a design that the client and I had already detailed fairly well.
Because there are two of us, we're being conscious of not spending every waking moment together. A coworking space helps with that.
We're planning on staying places for 3 months at a time. Here in CDMX, that's let us get a coworking space, gym membership, and a semblance of a routine.
We're planning on spending extended time in our hometowns, too (though maybe not 3 months).
When we shut down [1] my last company, my girlfriend said "it's now or never." I had realized that I dreaded going to an office every day, so I'm working on making my new company 100% remote.
[1] https://blog.staffjoy.com/staffjoy-is-shutting-down-39f7b5d6...
It is different for Americans, though, they are on the hook for income tax regardless of where in the world they reside.
We're using Earthclass Mail for a mailing address. Works super well. They even cash checks for us.
It works because I am flexible about renting studio apartments or rooms in Airbnb-dorm-like houses, and I don't have other responsibilities or attachments. Compared to the up-front costs, commitments, and assorted bills connected with an annual lease, I prefer it.
We're planning on staying in places for 3 months at a time. It gives us the flexibility to join a gym, take time to relax, and get a routine.
I spent ~2 years as a completely untethered nomad, and love having my feet planted somewhere I love while I still travel+work 3+ weeks at a time regularly so so so much more.
Besides the means (financial) and freedom (remote-friendly employment/relationships) to do this, there are a lot of cultural/social aspects that influence the viability of the long-term nomadism.
1) White privilege: Are you white? Being a nomad is WAY nicer! People are nice and welcoming to you almost everywhere, and go out of their way to involve you in their local stuff, making life more interesting and fun. Also, everyone wants to bang you, if you're into that. Otherwise, get ready to lead a lonely life, struggling to build deeper connections, and having a hard time experiencing the "serendipity of traveling".
2) Your support network's relationship with this lifestyle: This is a romanticized lifestyle for the western world, whereas it's treated as a vagabond-like, evasion of responsibility in Asian culture. This can be draining if your family is mostly disparaging of your lifestyle choice (or others are of your parents for bringing you up wrong etc).
3) You always have a home when you want it: There is a place where you feel safe, you belong, you love and can easily go back to and stay whenever you want for however long you want to recharge in between. If you end up nomading to someplace that doesn't work for you, you can bail on short notice and re-plan. If something happens or if you need to just take a break from the nomadism, you know where to go. If you don't have this (you don't care for your hometown, or was in my case, you have/had legal visa complications preventing you from "calling where you wanted to stay home"), being a nomad can be stressful and uncertain.
As a brown entrepreneur raised in Asia who wanted to settle in the Bay, and chose the nomad life while waiting for my visa to come through, I learned the above the hard way.
It is very enjoyable, but at the end of each stretch I was ready to go home and reconnect with my family and friends.
Personally I found it difficult to feel connected in a place when I don't speak the language, and move every month or so.
Your personal needs may vary. Either way it should be a great time, at least for a while.
I don't know how long we will continue this lifestyle, but AirBNB makes it easy. For multi-month rentals, payments go through monthly.
After dealing with so many headaches in personal and commercial rentals in SF, I'm welcoming this lifestyle. I'm tired of setting up internet, enrolling in utility payments, disputing issues with landlords, and moving crap between apartments. The last year has been a nightmare for this stuff, and having to deal with long leases has been a root problem preventing me from walking out of bad personal and business rentals. (Fun fact - even canceling a month-to-month Comcast business internet account requires 2 months notice.)