I’m based out of Brooklyn, New York—but I’m rarely there for more than a few months at a time. My life as a remote worker has taken me from the highlands of Peru to the cobblestone streets of Lisbon, and just about everywhere in between. While it might seem like I just throw a dart at a map and book a flight, the truth is that my year as a digital nomad takes a surprising amount of planning.
Balancing work deadlines, visa restrictions, personal goals, and, of course, a healthy dose of adventure, isn’t something that just happens. It’s a mix of intention and flexibility. I sit down every year and loosely map out where I want to be, what I want to accomplish, and how I can structure my travel around my remote work life. It’s not rigid, but it gives me direction—and it makes sure I don’t wake up in a hostel bunk one morning realizing I forgot an important client meeting.
Starting With the Anchors
The first thing I do is identify the non-negotiables—mostly work-related. I look at major deadlines, big projects, and anything that requires me to be particularly available or connected. I build around these anchor points, making sure I’m in reliable, well-connected cities when I need to be. For example, if I know a client campaign is launching in April, I won’t plan to be off-grid in Patagonia that month.
Because I’m based in Brooklyn, I usually try to return home at least once or twice a year. These trips home give me a chance to reset, reconnect with friends and family, and handle any stateside logistics. I might also use that time to do deep work on a project in a familiar space. Brooklyn is where I started my remote work journey, and having that home base gives structure to a life that could otherwise feel a bit floaty.
Timing Travel Around the Seasons
Weather plays a big role in how I plan. I love warmer climates, so I’ll often spend the winter months somewhere tropical—Thailand, Costa Rica, or southern Spain have all made the cut. Conversely, I avoid monsoon seasons or stretches of extreme heat unless I have a really good reason to be there.
Another part of seasonal planning is keeping an eye on local holidays or events. If I’m heading to Japan during cherry blossom season, I know I need to book way in advance and prepare for higher prices. If I’m aiming to be in Colombia during Carnival, I block out time to enjoy the festivities without worrying about work.
Navigating Visas and Travel Logistics
Visa rules are the invisible calendar every digital nomad needs to consider. Some countries offer 90-day tourist stays, others only 30, and a few generous places will give you six months without blinking. Before I book flights, I make sure I understand the visa situation and whether I’ll need to apply in advance.
Some of my travel decisions are completely shaped by these visa windows. I might spend three months in the Schengen Area in Europe, then hop over to Croatia or Georgia to reset the clock. I’ve learned the hard way that overstaying—even accidentally—can lead to hefty fines or trouble re-entering later.
I also give myself buffer time between destinations. Jet lag, travel delays, and simply adjusting to a new place can throw off your rhythm. I never schedule client calls on the day I land, and I always assume it’ll take a day or two to find my work groove in a new environment.
Making Space for Dreams
As much as I plan around work and logistics, I also try to honor the dream that got me into this lifestyle in the first place. This isn’t just about ticking off countries from a checklist. I think about the places I’ve always wanted to visit—not just because they’re beautiful, but because they call to something in me.
A few years back, I made it a priority to hike the Dolomites in Italy. I knew it would take time away from work, so I built my schedule around that experience. I worked longer days leading up to the trip, cleared my calendar, and made sure I had offline systems in place. That week in the mountains is still one of the most memorable experiences of my life.
Each year, I try to include one or two “bucket list” experiences. Maybe it’s scuba diving in Indonesia or attending a music festival in Berlin. Whatever it is, I don’t see it as an interruption to my work—I see it as part of the lifestyle I’ve chosen. Work is important, but these adventures are the fuel that keep me inspired.
Leaving Room to Be Spontaneous
Even with all the planning, I always leave space for spontaneity. Some of my favorite destinations weren’t even on the original itinerary. I once met a group of travelers in Morocco who convinced me to join them in Slovenia—and two days later, I was on a flight to Ljubljana. That kind of freedom is what makes this lifestyle magical.
When I plan my year, I make sure not to pack it too tight. I’ll have open months where I know I want to be “somewhere in Southeast Asia” but won’t book anything until closer to the date. This keeps things fresh and allows me to follow opportunities, both personal and professional, as they come up.
Wrapping It Up
Planning a year as a digital nomad means balancing structure with freedom. From my home base in Brooklyn to the far corners of the world, I’ve learned that remote work isn’t just about logging in from cool places—it’s about building a life that works for you. My calendar isn’t just filled with deadlines; it’s filled with memories in the making. And every new year, I get to ask myself the same beautiful question: Where do I want to live, work, and grow next?