Pre-planning while traveling – Our stop in Sydney and other cities

After almost 9 months of traveling, happy gal and I have gotten rid of the “fear” of the unknown of a new city. What I mean by this is not knowing the transportation system, the hotels, the currency, etc. of the city we’re visiting. It’s not because we don’t care about this new city, but more because we really care and want to learn from the locals. But also because we don’t want to spend the time reading about the future instead of enjoying the present and the current city we’re in. It’s a new strategy happy gal and I have decided to apply in the last few cities we’ve visited including Sydney, Bali, Gili Islands, Hong Kong, Sydney, and Cairns.

We put this strategy to the test most recently in Sydney, Australia. We only had 4 nights in Hong Kong before our 9 hour flight to Sydney and decided that planning our time in Australia was not a priority while in HK. We land in Sydney at 9 am after a comfortable and enjoyable flight (business class flights help– go get those miles) and start wondering around the airport. My mom graciously booked us a hotel in Sydney using her time share and our simple task of finding our transportation turned into a Sydney for Locals 101 course with Hugo from the concierge desk.

Not every airport has a Tourist Info booth but we were lucky that Hugo was present. We asked him straight out: “we’re on a long-term trip and we’ve heard Sydney is expensive, please share with us great stuff to do at student prices” He armed us with a list of must-dos for everyone visiting or living in Sydney including the best place to watch the sunset, a romantic walk in the botanical gardens, the free city shuttle 555, the ferry to Manly Beach, the free walking tour, plus some eateries recommendation including Kangaroo burgers and underground sushi experience.

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The walking tour was a 4 hour history lesson while roaming around the popular and not-so well known landmarks. We cannot wait to go back to SF and participate in one of the walking tours! Who wants to join us?!

Sydney has not been the only place we’ve gotten so lucky. When we arrived in Amman, Jordan, our original plan was to rent a car, drive to Petra, and head out. The only planning we had done was book a car and first night hotel. We ask our receptionist a similar question we asked Hugo and he sent us down a not-so typical road down to Petra enjoying a local beach at the Dead Sea and a visit to Madaba’s small town plus some inside info on Mount Nebo.

Actually, I thought we use this strategy of no-planning only recently, but now looking back at our previous city visits, it’s been mostly the same story. We arrive at a new city with maybe a lodging reservation and mostly zero knowledge of what to do there. Something that has helped happy gal and I consistently when we arrive at a new city (either by plane, train, car, bus, etc), is to sit down, look for options/locals/tourist booths and create a short plan during a 10-20 minute session. There is no need to rush to your hotel, or go look for a hotel. It gives you a chance to breath, rest a bit after your trajectory, and think clearly without being taken advantage of. I recently read a blog post by Wandering Earl where he talks about “the first 20 minutes in a new city”. It’s very similar to our strategy. It feels good to know other travelers feel the same way and we’re not crazy for not planning!

Not all the times it’s been a successful strategy, however. Most recently our visit to Cairns was a frustrated one.¬†Sometimes we realize if we would have planned ahead we would have enjoyed the city more. We arrive to Cairns with a hotel reservation for 6 days (something we advice against … but we booked it anyhow because it was a special on We had not read anything about Cairns except that it’s the closest point to the Great Barrier Reef. Our friends Vinay and Jodee had given us some recommendations but decided against them because we thought it was going to be out of our budget. Little did we know that Cairns is very similar to a suburban town in the USA with the added bonus of nice beaches and a huge reef nearby. To get from point A to point B you need a car or use their expensive public transportation. Just to get out of the airport it costs $20/person for a public bus. Thinking renting a car was out of our budget and having the lady at the bus counter rush us to take the bus (it was leaving in one minute) … we decided to take the public bus to our hotel.

We chose our hotel because it’s located on the best beach of Cairns area and it had 4 stars on … another thing we advice not to do… Our hotel is located on the best beach but it’s also located 20 km from the city center, away from scuba diving centers, budget eateries (they sell pad thai next door for $30!), and wifi. Even to get to the closest grocery store is 1km with suburban style houses in between. Would we have done a simple google search, we would have learned that 6 nights here is way too long and that a liveaboard scuba diving experience is $570 for 2 nights/3 days. Or, better yet, we should taken a 20 minute break after landing, look at our options, talk with locals or people on the flight and learned about the cool things about the reef and our surroundings … anyway … enough about Cairns.

Even with the Cairns story, the point here is that regardless of where your next adventure takes you, I want to convince you that there is no need to plan everything. Actually, the less you plan the better. Make sure to take advantage of locals’ advice and take those 20 minutes after arriving at a city to make a simple plan. I am also writing this for myself, hopefully in 10 years from now when I re-read this, I remember that planning takes the fun out of traveling.

What’s your take on pre-planning? Let us know in the comments!

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