How I Choose Where To Travel Next & How Often I Travel

Where I travel to next depends mostly on cost and sometimes proximity. If I’m planning a trip that is more of a vacation, cost is a major factor. Although I do work remotely, I don’t make a lot so I have to travel on a budget. Plane tickets can be very expensive, depending on the destination.

If I’m planning future house sits then proximity becomes a factor. Because I drive to each house sit, I have to make sure that I can drive to my next house sit within a day or two or else I’d have to worry about paying for hotels in between house sits. So if I’d like to travel up the east coast of the US for a few months and I was starting in Florida, I’d look for a house sit in Georgia. I’d then look for a house sit in South or North Carolina. That’s how I’d slowly make my way up the coast.

As a digital nomad, I am constantly traveling from one place to another. Because I do have to work though and because I do need to have somewhat of a routine, when I look for house sits I try to find ones that are at least 3 weeks long. That gives me plenty of time to work and to also explore my new temporary home. The longest I’ve stayed in a new destination was two months.

My Scariest Travel Moment

I’d have to say my scariest travel moment was when I rappelled off the side of Table Mountain in Cape Town, South Africa. It’s one of those experiences where, I’m glad I did it but I would never do it again. It was definitely a rush! But it taught me to always be willing to try something at least once.

Some Of My Travel Challenges

The biggest thing to prevent me from traveling more is money. Even when you travel on a budget, things like food and gas add up. One of the biggest challenges of working and traveling is balancing your time. It is possible, though, so it just takes practice. For example, my remote work usually keeps me busiest the first two weeks of the month, so I know to plan less travel days or sightseeing during those weeks and plan more for the end of the month.

My Advice For New Adventurers Who Want To Work And Travel

Advice that I would give to new solo travelers who want to work and travel: Don’t overthink it. Yes, you have to research and have a plan, but if you overthink and are constantly waiting for that “perfect” time, you’ll never go. There is never a perfect time. Things will always come up. But if you really want to travel, you’ll figure out ways to adjust to things as they come up. Travel now so you have no regrets later now.