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5 Steps for Planning the Unplanned Trip

“It is good to have an end to journey toward; but it is the journey that matters, in the end.” ―Ernest Hemingway

We’ve all heard it, the famous quote splattered across the internet on travel blogs and inspirational imagery. It instills a sense of freedom, exploration, and bliss; of losing oneself in the moment. I heard it, I felt it, and five months ago, with these words ringing in my head, I stepped out into the world without a plan, ready for adventure.

Sure, I had an end to journey toward, but it was the journey I was seeking—and I decided that no plan was the best plan. My dad was a pilot and agenda is his middle name. Growing up, my family trips were a blur of checking things off “the list” and the frantic flurry of jolted experiences left me exhausted and depleted by travel. A 5-month unplanned trip seemed to be the perfect anecdote to an over-planned past. My first step was a one-way ticket to Bangkok. Five months ago, that ticket was all I had. Now, after journeying throughout Thailand, The Philippines, Bali, California, and Mexico, I know that the unplanned definitely needs to be planned.

What I experienced along the way were golden moments paired with missed opportunities. I had taken Hemingway’s words to heart but overshot the meaning. While I wasn’t bogged down by a stressful itinerary, trying to fit it all in, I hadn’t done my homework and wasn’t aware of the unique and diverse offerings the regions I passed through had to offer. I didn’t know about local traditions or festivities, the accessibility of neighboring countries, or the main attractions and dishes that I should seek out—I was missing the things that made these places destinations in the first place.

planning the unplanned tripSo, how do you do it? How do you take a trip (of any length) without tying yourself to an itinerary so thick that you lose sight of where you are? The truth is, an unplanned trip—a trip that is flexible and fluid, leaving space for spontaneity and genuine interaction—takes some planning.

1. Do Your Research

Where are you going? Read about it. Wikitravel is a great place to start and will help you build a foundational knowledge of the most basic and important travel information. Continue your research with area-specific travel guides and blogs that provide a local’s insight. The tips and tricks you learn before you go may very well be game changers on the ground.

planning the unplanned trip

2. Pack Light

Don’t lose out because of “stuff.” The best decision I made for my trip was to leave home with a single backpack, half full. Sounds crazy and intimidating doesn’t it? But the simplicity and light weight allowed for ultimate travel ease. Planes, trains, buses, bed to bed—I was quick to my feet and not weighed down by excess material. How often do you go on a trip and arrive home with clean clothes still folded in the corners of your suitcase? A half-full backpack also allows room for must-haves along the way—those things that go beyond your standard souvenir, that will be adorning your walls and floors as you grow old.

3. Don’t Book Accommodations for Your Whole Stay

Staying in one place can prove to be rather limiting. Choose a destination for arrival and book for only a night or two, then use that time to get a feel for where you are. If you like it, stay. Or if you find there is a different part of town you prefer, find a place there for a night or two. And then the next, and the next. When you find a place worth staying longer, you’ll know.

4. Make Friends with Locals

Baristas, bartenders, waitstaff, store owners, cab drivers—engage! The more open you are to the people and experience, the more open they are likely to be with you. When you start with a smile and a question, you will find that conversation easily follows.

5. Ask a Lot of Questions

Don’t be shy. As a traveler in a new destination, there is no limit to the amount of questions you can ask in one day. Where am I? Where is this? Who are you? Where are you? Ask locals what they prefer. What do you think? Where do you hang out? Where would you stay? Where do you eat? What do you eat? The answers you receive will be better than any guide book could possibly curate.

Nicole Lindstrom, along with Sasha Juliard, are the modern globetrotters behind GLDMNE. Follow AFAR Media on Instagram for a GLDMNE takeover April 29–30.