As a family, we’ve traveled extensively within India, some parts of Sri Lanka, and Thailand, but our trips never exceeded two weeks. A month-long trip felt like an ambitious dream—managing work, school, and budget seemed almost impossible.
That changed in mid-2024 when I unexpectedly lost my job. The four months that followed were challenging—I was out of work and grappling with uncertainty. But this period also gave me time to reflect deeply on my 14-year career and what I truly wanted moving forward.
When it came time to choose between a stable hybrid managerial role in a corporate or a remote individual contributor role at a startup, I faced a tough decision. Having just been let go from a startup, the uncertainty was daunting. But considering my goals and desire for flexibility, I chose the remote role.
The first thing I planned after that decision? Our long-awaited, month-long family trip!
Choosing the month and place to travel
I joined my new role in June, and the first challenge was finding a month that worked for both my job and my son’s school schedule. October turned out to be perfect—it had the most holidays, my son’s school vacation, and a few work holidays for me, making it an ideal time for our plan.
We started researching destinations, considering countries like Vietnam, Bali, Georgia, and even parts of India. After weighing factors like budget, experiences, work-life balance, and what we wanted to explore, we chose Georgia.
Georgia promised a completely new experience compared to our previous trips. The eastern European region felt raw and unspoiled, with less touristy and more remote places to discover. Our plan focused on exploring remote areas during non-working weeks and staying in locations with reliable internet during work weeks.
We also prefer traveling in the off-season to avoid crowds and stay within budget. October was perfect for Georgia since the peak season typically ends in September, giving us a quieter, more budget-friendly experience.
Planning the Trip: A Thoughtful Beginning
We decided the duration and destination after careful consideration and lessons from past trips. Traveling with a child isn’t always easy—we had to create an itinerary that worked for him while ensuring we didn’t fully compromise on what we wanted to experience. Over time, we’ve found that kids adapt well to travel routines, and ours has embraced the way we explore.
To plan our Georgia trip, I relied heavily on travel blogs, which were far more useful than social media videos. We prioritized nature, hikes, local experiences like food and transport, and staying in homestays to make the journey authentic and enriching.
We drafted two plans for the trip. Plan A involved a long remote hike through villages, slightly challenging but manageable. Plan B included shorter day hikes for a more relaxed pace. The reason for two plans was the unpredictable weather in Georgia during the off-season and the onset of winter. This flexibility ensured we were prepared, no matter what conditions we faced.
After finalizing a rough plan, we didn’t overthink before booking the flights. That became our first major step toward the month-long adventure! As always, taking that first big step sets everything else in motion.
Next came the visa process. Georgia offers an e-visa for Indians, which is straightforward and usually takes just five days. However, our initial application was rejected because we didn’t show sufficient bank balance to cover a month-long stay for three people. We reapplied with stronger documentation, and it was approved without further issues.
Since this was a month-long trip, we created a high-level plan for four weeks but had a detailed plan only for the first week, as it was a work week for me. We booked an Airbnb that supported my work needs, including reliable internet, a functional kitchen for daily cooking, nearby grocery shops, good transport connectivity, walkable roads, and parks to keep my son engaged.
Beyond the first week, we kept the rest of the itinerary flexible, planning our days spontaneously as we explored Georgia.