If I Could Travel Anywhere, Anytime: My Ideal Year of Living and Working Around the World
If I could travel anywhere, anytime, throughout the year, this is what my yearly itinerary would look like.
Not as a fantasy, but as a realistic, intentional way of living.
Travel has been part of my life for as long as I can remember. I started traveling for work in my early twenties, long before “remote work” or “digital nomad” became mainstream. Over the years, I’ve traveled extensively, from Hong Kong to Shanghai, London to Paris, across most major U.S. cities, through India, Europe, and beyond.
Each place shaped how I see the world: culture, health, creativity, food, rhythm, and perspective. Travel didn’t just broaden my horizons; it refined them.
Now, standing at the edge of full-time and location freedom, I often imagine what life could look like if I designed my year intentionally, not rushed, not excessive, but deeply lived.
I live in Canada, where winters are long and brutal, stretching from November through April. I don’t hate winter, especially during the holidays. December in Montreal is beautiful. There’s warmth in family gatherings, shared meals, and the collective pause the season brings.
But once the holidays pass, I crave light, warmth, and a different rhythm.
Here’s how I envision my year unfolding.
January–February: Winter Living in India
Right after the Christmas holidays, I would leave Canada and spend one to two months in India, at my parents’ winter home.
Their house is calm and sun-filled, with cool marble floors and fresh air. It’s about 20 minutes from the beach. Food is fresh, seasonal, and deeply nourishing: vegetables, lentils, fruit, and home-cooked meals that remind me how health and culture are inseparable.
This wouldn’t be a vacation. It would be slow living with structure.
I would set up a small office, my laptop, an ultra-wide screen (non-negotiable for my creative work), notebooks, and books. My digital publishing work allows me to plan content in advance, so my days can be spacious:
- Morning walks
- Focused writing sessions
- Long lunches
- Family time
- Quiet evenings
Winter doesn’t need to feel heavy when you follow the sun.
March–April: Back to Canada + Short City Escapes
By March or early April, I’d return to Canada. Spring here is transitional, not quite warm, but hopeful.
This is also when I’d take short trips tied to community, not sightseeing.
I’m part of a global stock market community built around daily learning, long-term thinking, and real connection. The group’s founder, Amit, hosts meetups in different cities throughout the year.
So during March and April, I’d plan long weekends around these meetups, wherever they happen:
- Toronto
- New York
- Miami
- Las Vegas
These trips would be intentional: one or two focused days of learning and connection, followed by a relaxed city stay. No rushing. No packed itineraries. Just presence.
May: Grounded Time at Home
May is for staying put.
This is when I like to reset, health routines, creative projects, and home life. Montreal finally begins to wake up. Windows open. Walks feel lighter. The city regains its charm.
This month grounds the year.
June–Early July: Europe, Slowly and Deeply
Summer belongs to Europe.
If I could choose freely, I’d spend two to three weeks traveling through Europe with my son, Krish. Travel with him at this stage of his life feels especially meaningful — he’s curious, independent, and deeply observant.
We’ve already done Italy together, and it was unforgettable. I’d happily go back — Italy rewards repetition.
An ideal European summer could include:
- Italy
- A few days in Amalfi
- A week in Tuscany – walking in vineyards
- Spain (again, he loved it)
- Greece
- Portugal
- Switzerland
- France beyond Paris
- London, of course (again and again)
Europe is about rhythm, walking cities, slow meals, conversations, museums, landscapes, beaches, and time that stretches.
Late July–August: Beach and Family Time
Summer wouldn’t be complete without the beach.
Every year, we do a family beach vacation, usually somewhere warm and uncomplicated:
- Jamaica
- Dominican Republic
- Mexico
These trips are restorative, not exploratory. Swimming, long meals, sun, rest.
The Bahamas are next on our list. And eventually, the Maldives, a destination my sister Rony has been dreaming about, and one I’d love to experience together as a family.
This period closes the summer gently, with salt in the air and no urgency.
September: Transition and Creation
September is a quiet power month.
Back home. Focused work. New ideas. Structure returns naturally because kids go back to school. This is when I build, write, and plan, without distraction.
October–November: London in the Fall
If I could slip away for a short trip in the fall, it would almost always be to London.
Fall fashion. Culture. Museums. Walking endlessly through neighborhoods I love. London inspires me creatively like few other cities.
This would be a 2–4 day trip: no pressure, no checklist. Just observation and inspiration. I would go with my sisters or Krish.
London fits beautifully into either fall or spring, but fall feels especially right.
December: Home, Family, and Stillness
December belongs at home.
We may not celebrate Christmas the traditional way, but the holidays are deeply meaningful to us. It’s when family gathers, time slows, and life feels shared.
I don’t mind winter in December. It feels intentional. Anchored.
Rotating the Years
Not every year would look exactly the same.
Some winters could be spent elsewhere:
- Bali
- Thailand
- Taiwan
One winter, I’d love to travel to China with my son — a place that shaped my early career and still holds deep significance for me.
The beauty of this lifestyle is flexibility:
- Winters rotate
- Summers evolve
- Europe repeats (because it deserves to)
The Quiet Truth About Freedom
This vision isn’t about escaping work.
It’s about designing life around meaning.
My digital publishing work allows me to schedule content in advance, work in focused blocks, and create without being tied to a desk or a city. That freedom didn’t come overnight — it was built intentionally.
This is how I imagine living:
- Rooted, but mobile
- Structured, but spacious
- Curious, but calm
Not everywhere, all at once, but the right places, at the right time, for the right reasons.
And that, to me, is the most elegant way to travel through life.
