The Freedom of Winging a Trip

What should we do next?

What should we do next?

In this post, I’ll take a detour from the travelogue to talk about the benefits of winging it.

After the wedding, people began to go their separate ways. The people with jobs prepared for their flights back to their homes where they would return to being productive members of society. Given my current status as a man of leisure, such responsibilities and obligations don’t apply to me, so I headed off to Pokhara, a lakeside town seven hours north of Kathmandu, with Ellie and Adea, two of the bride’s friends that we’d been hanging out with. In true flashpacker status, we rented a car and driver to take us to the city. I personally wanted to fly, but was soundly overruled when Ellie discovered that Yeti Airlines is ranked one of the least safe airlines in the world. So we set off for Pokhara.

Just before we left, I needed to find a place to stash my wedding clothes. My plan was to take an eight-hour bus ride from Pokhara to Varanasi, the holy Hindu city on the banks of the Ganges River, and I didn’t want to lug around dress shoes and a kurta for 20 days around Nepal and India. My friends couldn’t fit it in their luggage back to the US, and I didn’t know when I was coming back, so I got the hotel to agree to hold onto it until I got back, knowing that there was a small chance I would need to buy a new pair of shoes when I got back to the States.

This isn’t an important detail, except to illustrate one of the key themes of this trip for me: the tradeoffs for planning vs. just winging it. When I first started traveling seriously in 2009, I was much more of a planner than I am today. I would loosely plan a trip, booking a bungalow or hostel days in advance to make sure that I had a place to stay. On trips with friends, we’d have an itinerary, with a few days in each place before taking a bus or a flight to the next place. As I traveled more, my philosophy changed, along with my priorities. Increasingly, keeping my options open became more important, and freedom trumped certainty. Cutting my teeth in Southeast Asia helped – you can show up in Bangkok with your passport, wallet, and a toothbrush, and make your way around the region without ever picking up a phone or turning on a computer. But it is also something that is personality-driven, with Type A people putting more emphasis on the plan, and others preferring to go with the flow.

In the past, I’d winged a few trips, but had organized them around activities or events, which made jettisoning the original plan easier to do on the fly. In the Philippines, I spent a month island-hopping to hit the best dive spots. After spending four days in Coron, a major naval battleground of the Pacific Ocean Theater during WWII, I flew to Luzon and thought I would head north to a beach known for being one of the only places in the Philippines with good surfing. When I arrived at the Manila airport, I looked out at the nighttime city skyline, and remembered how much I didn’t like Manila. So I turned around, walked up to the Cebu Pacific counter and bought a ticket for Cebu that left an hour later.

Regions like Southeast Asia, with well-trafficked destinations, multiple low-cost airlines, and accommodation to fit every budget, enable this kind of travel. You may end up spending more money than you’d like or sleeping in a barely-passable hotel, but, as long as it is not peak season, you’re almost certain to find a bed in the place you want to be. It is a bit more difficult in Africa, but even there you can roll up to a place that attracts tourists – like Cape Coast in Ghana, Diani Beach in Kenya, or Zanzibar – and figure it out.

The downside of this approach is that you are more likely to experience some discomfort and added stress from not knowing what you are doing. Also, when you only have a limited amount of time and want to see a lot, plans are necessary. But the benefit of winging it is that you are completely free to do whatever you want, unconstrained by flight itineraries, hotel deposits, and, most importantly, plans. And that freedom, which it may cost you a little more in dollars and peace of mind, is invaluable in other ways.

In the next post, I’ll relay my adventures trekking in the Himalayas.


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"Josh Weinstein is a visionary. I read his blog every day." - Bono
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One Response to The Freedom of Winging a Trip

  1. john galt says:

    What happened to the shoes and suit? were they still in the hotel?

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