Traveling Without An Itinerary: 20 Tips to Maximize Your Trip For The Adventure of a Lifetime

It was the beginning of June 2011. Me and my good friend, Danny, were about to embark on an adventure.

About a month and half before, we sat across each other on our cheap comforters we had probably kept since Freshman year of college in our L-shaped room discussing travel plans for a trip we had both been bugging each other about for quite some time. See, both of us had caught the travel bug early on in our adult lives. We both had been lucky enough to have been gifted the opportunity to live and study abroad among numerous other trips we were able to take with family and friends across the globe when we were younger.

We had travelled together before and what made it easy was the fact that we were easy. Simple as that. We didn’t get lost on schedules or plans. We didn’t bicker about going to one museum over another. Or attending one event over another. We were flexible. If we missed our train, we’ll just catch the next one. No sweat off our back. I’m pretty sure it helped that we subtly had a ‘pay it forward’ system working in the shadows to our favor where we trusted each other enough to make a good choice about what to do next and knew the next time around we’d concede to the other person’s interest.

Ultimately it was a given we were going to decide on a place neither of us had been to. We toyed with the idea of traveling to South America, South East Asia, Africa and Eastern Europe till one day it clicked and we made a choice: Australia and New Zealand. Bingo.

As we started diving into the planning we realized that neither of us wanted to go on a rigid trip filled with itineraries and pre-booked excursion, hotels and pub crawls. We wanted an immersion trip. A total adventure.

So we decided to only purchase a plane ticket to Auckland, New Zealand and a plane ticket back from Sydney, Australia.

How we got between the two during that 3-week gap was up to the travel gods. As time got closer we started realizing in order to maximize our trip, we were going to have to make some plans.

We put together a loose, and I mean loose schedule, of where we knew we needed to be by what date. We both looked at a couple of other things we knew we wanted to do and tried to plan ahead for these as well. For instance – neither of us had ever scuba dived and what better place than to pop that cherry at the Great Barrier Reef. Check that off on the bucket list. We also knew that in order to do that, we’d have to start our Australian adventure way up on the Northeast coast in Cairns. How do we make it down to the Southeast where Sydney is? Planes are cool but we weren’t having it. Road trip with a rented camper van it is.

Flying out of SFO, I think both of us were strangely comfortable with the predicament we had just put ourselves in. We knew when we landed we did not have a place to go or stay. WE also had no clue how we would fill that first week in New Zealand.

We arrived at 5:00am in Auckland, gathered our bags at the claim and started our anxious walk out the airport. We hadn’t a clue where to go or what we wanted to do. Next to a small coffee and pastry kiosk was a tourist stand filled with loads of eye popping, generic flyers for every excursion, hostel, hotel and restaurant Aukland had to offer. We pulled off the rack the biggest magazine and started flipping through the pages.

Eventually we found a hostel that seemed rather central and decided to make moves and try our luck there. When we arrived we were greeted by a man in his mid 50’s who hadn’t opened up the hostel to new folks yet as they opened shop at 8:00am. We explained our predicament as being tourists with no plan, farts in the wind, trying to gather our bearings in this new city. He was kind enough to let us use their small Internet cafe with 90’s Gateway computers sitting side by side while we tried to come up with a formidable plan.

We both started cruising the web looking for other exciting things to see, do and stay. We had a week to fill and a 100% open schedule. During our research we stumbled upon a backpacker excursion called the Kiwi Express that shuttled other ruffians like us through the countryside to see the lot of New Zealand. You could hop on and hop off if you wanted. You could sign up and tackle the North Island or the South Island or do both. This was right in our wheel house since we still hadn’t a clue what we wanted to really see and do so we politely thanked the man for letting us borrow free internet for an hour and left to the Kiwi Express office to see if we could commandeer a ride on their coach.

For a week, we travelled around the North Island with other backpackers from across the globe. It could not have worked out better for us. We bungee jumped, rafted during a storm through a underground river in a cave filled with glow worms, attended traditional Maori exhibitions, hung out with a lot of locals (who are delightful by the way – New Zealanders are great people), played a lot of pool, explored the country side, forged some close friendships and drank enough Snake Bites to put an alcoholic to shame.

New Zealand was absolutely beautiful. The universe gifted us that excursion because without it, there is no way we would’ve done half of what we did during our time on the North Island.

Our trip was coming to a close in New Zealand and it was time to catch the next flight out to Australia for part II of the trip. For the next two weeks we dived the Great Barrier Reef, visited the white sands of the Whitsundays and Airlie Beach, drove on the left side of the road, almost hit a kangaroo in the process, camped in the camper van, spent a day exploring a hippie commune that has been around since the 60’s, hiked the coast, surfed the beach breaks in Byron Bay, visited the Sydney Opera House, went to the zoo, realized we could probably dominate a lawn bowling league, played even more pool, hung out with even more locals, and broke bread with some old friends who were making a new life in Australia. There are some stories we will probably keep between us for reminiscent times over a cigar and whiskey when we finally don 50 years of age. Until then, I will keep these memories happily with me till the day I die.

There are two types of travelers in this world

Those that Plan
Those that Don’t

Every good adventure has a slight combination of both. Even though each night we had no idea where we would be staying and the next day what we would be doing, we still needed structure in the trip to make sure we got the most out of it.

Here are 20 tips I would recommend to get this most out of traveling without a real plan:

  1. Go it alone or find someone who shares the same passion as you do – Memories are better made when you share life with others so choose the latter whenever possible.
  2. Choose up to 3 things you MUST do or places you MUST see when you are there – No one goes to Rome without at least trying to see the Sistine Chapel. No one travels to New York without trying to fit in seeing the Statue of Liberty. No one goes to Sydney without making time to visit the Opera House. Don’t be stupid. Make time in your trip to see the things you have to see and keep the rest of the days free to see the things you normally wouldn’t.
  3. Give yourself a loose timeline to get from Point A to Point B – We had five days to travel between Cairns and Airlie beach given the amount of time we rented our camper van for the roadtrip. We had so much fun in Cairns, we stayed for 3 additional nights and on the fourth night had to roadtrip our way down the coast against the instructions of our camper van company for fear we’d total the car hitting a Kangaroo or not really get the whole driving on the left side of the road thing.
  4. Break bread with locals once a day – Whether over a beer at a bar or at a coffee shop in the morning. You’ll meet some of the most fascinating people if you open yourself up to approaching locals and making yourself approachable. They are also the best source to recommend what the best things to do, places to see and eat are
  5. Respect the culture, customs and traditions – You are a guest in their country – It’ll keep you from squaring up after a long night at the bar and from the back of a foreign police car.
  6. Say yes to things you normally wouldn’t – like bungee jumping over a river or suiting up on an overhead day to surf Byron Bay
  7. Pack light
  8. Bring a world phone – In case of emergency and to keep your loved ones informed where you are
  9. Take the boat
  10. Ride the train
  11. Rent the Moped
  12. Walk whenever possible
  13. Take lots of pictures
  14. Bring a journal and write in it daily – Since you don’t know where you might be headed, it’ll help jog the memory when you go home want to share where you went and what you experienced with others
  15. Trust your instincts – You are a traveler not a tourist. Do traveler things and don’t put yourself in a bad situation as an oblivious tourist. Practice situational awareness everywhere you go
  16. Be flexible to changing schedules, weather, and different styles of accommodation.
  17. Keep an emergency stash of cash, your passport and an extra copy of it on you at all times – Some Hostels and Hotels have better security than others. Still better to be safe than sorry.
  18. Memories > material possessions – Buy some souvenirs for friends and family and none for yourself. Spend your money on activities, excursions, cultural sites and local cuisine. You’re traveling here while others aren’t. Maximize the memories.
  19. Send a postcard home – Even if it is to your own apartment if you live alone. You’ll hold on to that for a long time as a reminder of where you have been
  20. Smile – You are doing something most people in the world can only dream of doing. Acknowledge that reality and humble yourself for it. It’ll make you appreciate everything so much more while on the trip of a lifetime.

Now go book your round trip ticket and have an adventure of your own.


One thought on “Traveling Without An Itinerary: 20 Tips to Maximize Your Trip For The Adventure of a Lifetime

  1. Awesome write up, brother man – bingo, bango, bongo. He shoots, he scores.

    That black water rafting excursion is still one of the coolest things I’ve stumbled across. Weekend warrior road trip soon.

    ” ‘You miss 100% of the shots you don’t take.’ – Wayne Gretzky” – Michael Scott


    And for those wondering, this is Danny – the guy who got to share this great trip with good old Nicky boy.


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