Philip Weston – Around-the-World Traveler

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Philip Weston is a 38-year-old managing director from Petit Valley, Trinidad and Tobago, who took a round-the-world trip in 1998.

The Snapshot

  • Departure: 1998
  • Age at departure: 38
  • Nationality: Trinidad and Tobago
  • Location: Petit Valley, Trinidad and Tobago
  • Duration: About 4 months (August - November 1998)
  • Occupation: Managing director
  • Regions: North America, Europe, Asia, South Asia, Southeast Asia

The Route

New York, London, Delhi, Agra, Bombay, the Maldives, Malaysia, Thailand, Indonesia, Bali, Hong Kong, China, and Japan.

In Their Words

Here's what Philip Weston shared about their RTW journey:

How did your travels affect your career when you got back?

Lost a ton of money. You know what they say, “when the boss is away”.

Why did you decide to take this trip? What got you into this type of travel, and/or influenced you to go?

I love to travel, and I have always traveled extensively. I would do it more but children and business are preventing any exotic opportunities.

What was the best moment of your trip?

So many of them…

What was the worst moment?

Beggars in India.

What was your biggest hurdle, obstacle, or difficulty?

Trying to travel light.

What was your biggest surprise?

Didn’t get Delhi Belly.

Who is the most memorable person you met on your trip and why?

Lots of people. The most friendly people were in Bali.

How much planning and preparing did you do?

Just enough.

What was your favorite piece of gear? What did you bring, that in hindsight you could’ve left at home?

Camera was the most important item.

How did your round-the-world trip change your life? How did it affect and change you as a person?

It makes you appreciative of what you have and how very lucky we are.

If you had to sum up your round-the-world trip in one sentence, what would it be?

I still think about it most days with very fond memories.

Are you planning more trips and travels for the future? Are you planning another round-the-world trip?

Yes most definitely. When my youngest baby is five, in two years.

2026 Context

  • Budget inflation: This traveler did not report a trip budget, but late-1990s round-the-world costs are substantially higher in 2026, reflecting roughly 90% cumulative inflation over the intervening years.