Recently, Jamie Ridler expressed a desire to become a more confident traveler. And my little brain went “Bing! Now THERE’S some advice I can offer!”

I’ve been on an average of 6 business trips per year for the last dozen years – some short and some long. On business, I’ve been all over Canada, into the US a few times, to Kenya, Tanzania, Ethiopia, India, Bangladesh, and Rome. Plus I’ve backpacked around Europe, traveled to Mexico, and did lots of road trips with the family all over North America. I’ve taken planes, trains, automobiles, boats, rickshaws, bicycles – you name it – all over the world. When I traveled to Ethiopia, India, and Bangladesh, I was responsible for all of the (complicated) logistics and management of a film crew. So I guess you could say I’ve learned a thing or two about travel.

  1. To increase your confidence, before you leave, prepare a little travel notebook (or file folder) where you keep all of the phone numbers, addresses, back-up phone numbers, etc. of all of the people you need to meet, all of the places you’ll be staying, the airlines, etc. You never know when you’ll need to reach someone in a panic and you’ll be glad you have it all in one place. Plus if you have it in a notebook, you can add any new information you need as you travel, like – for example – the phone number of the nice cab driver who delivered you to your hotel.
  2. Do the research you need ahead of time to increase your confidence. Now that the internet makes it so easy, I’ve become fairly masterful at taking public transit in strange cities. Print out transit maps, find out where the nearest subway stop is to where you’re staying, find phone numbers for taxis, etc. Some airports and/or transit systems even tell you how to get from your gate to where you need to be to get transportation to your hotel. Remember: information is power – the more you know ahead of time, the less you’ll have to worry when you get there. (It’s also good to find out ahead of time what you can take onboard the plane. Your airline will have that information on its website. With security changing so often these days, you have to stay on top of the new rules.)
  3. Speaking of transportation, I highly recommend learning how to use public transit in the place where you’re going. It’s cheaper, often more efficient, more interesting, and you get a much better flavour for the city you’re staying in. When I was in Dallas, I found out there was a vintage trolley car that would take me to the conference centre every day for free (or next to it). It was so much fun and I met the most fascinating trolley car enthusiasts who were volunteer drivers and conductors.
  4. When it comes to things you feel uncomfortable with, though, take baby steps. Like public transit, for example. For the first trip, take a taxi almost everywhere, but make up your mind to take at least one subway ride. You don’t have to figure it all out at once and nobody will fault you for taking the easiest way.
  5. One of my favourite pieces of advice – skip the ‘big box hotels’! You know what I’m talking about – the ones lined up in a strip by the airport with about as much character as a MacDonald’s Happy Meal. Check out I have stayed in some of the most amazing apartments, old inns, character homes, etc. through If you’re not thrilled about sharing a bathroom (and truthfully, it’s really not a big deal – people who tend to stay in B&B’s are usually pretty respectful, polite & clean), a lot of them have private washrooms, so don’t let that stop you. Be sure to check the comments and ratings because I’ve found them to be very accurate. The only time I was disappointed with my stay was the one time I ignored the negative comments and took a chance.
  6. Find people who genuinely know their city/neighbourhood and ask their advice about great restaurants, where it’s safe to walk, how to catch public transit in the area, etc. One of the best things about booking through is that most of these places are owned by people who truly care about their homes and about hosting people.  Over breakfast, ask them about their favourite local haunts – the hole-in-the-wall restaurant no tourist would set foot in – and you will find the BEST local culture. (Twitter has also become a good resource for this – when I was headed to Chicago, I asked people about what things I shouldn’t miss in the city.)
  7. Bring a little comfort with you. I always travel with a portable candle (in a tin cup with a lid) and lighter in my toiletries bag. Sometimes it’s the best way to relax in the evening after a harried trip. Plus I usually travel with a light weight silk shawl that’s wonderful to wrap around my shoulders when I get a little cool and/or sleepy on the plane. And when you’re dealing with jet lag, one of your best friends may be your mp3 player – at least if you’re lying in a bed in Bangladesh in the middle of the night trying to sleep while geckos are having a conversation on your wall.
  8. Pack light. I made a few mistakes early on and packed way more than I needed, but now I just bring the bare essentials. You never know when your flight might be delayed and you have to run from one gate to the next. When you’ve got nothing more than a small roller bag and a backpack, you’ll be thanking me for the advice. Plus it’s a lot easier to take public transit when you’re not overloaded. I spent three weeks in Africa with a suitcase that was small enough to be a carry-on bag and I didn’t miss anything – trust me, it can be done.
  9. Trust people. This is a biggy. I’m not saying you should be naive and let some strange man take you home in his car (you still have to use your discretion about who’s trustworthy and who’s not), but almost every single time I decided to trust the person who was willing to take me under his/her wing and help me navigate their city turned out to be a good thing. I have only once gotten scammed by a person (and really, it was pretty harmless – he just got a little more money out of me than I should have parted with for helping me get to the market in Addis Ababa, but I was never in any danger), and on the flip side, have had some truly exceptional experiences when I’ve chosen to trust. One of my favourite travel moments was when a family in Ethiopia felt sorry for me dining alone and invited me to eat at their table. They ended up taking me out on the town to see some great Ethiopian performers.
  10. But even when you don’t find friendly local families, you can still have a great time alone. When I first started solo business travel, I’d order room service instead of eating alone in a restaurant. That got old pretty quickly, and I really wanted to experience more interesting food and surroundings. The first few times felt a little awkward, but now I take great pleasure in savouring a good meal alone in an interesting restaurant. If you’re uncomfortable at first, bring along a magazine, a book, or your journal to fill the time while you wait for your food, but don’t miss the opportunity to people watch and listen in on a few conversations.
  11. No matter how well you plan, now and then, things will fall apart. The best you can do is learn to roll with it. Sometimes the best surprises come when your plans fall apart. I flew to the other side of the world with a film crew minus a videographer (he’d jammed out at the last minute), and without a film permit or visas for India. I had to hire local videographers in both India and Bangladesh AND hope that the Indian consulate in Bangladesh would treat me better than the one in Canada had. In the end, I hired the most amazing videographers (who are both now my Facebook friends) with all kinds of local knowledge I wouldn’t have had otherwise, and my hosts helped us navigate the consulate and everything fell into place beautifully.
  12. To make your travel more interesting, be open to new experiences and new people. Chat with cab drivers – I’ve heard some of the most fascinating stories from them. Go for walks around the neighbourhood you’re staying in. Be an explorer! Some of the best treasures I have found have just been discovered by wandering aimlessly through a city.

Is there anything I missed that you’re dying to know? Or other tips you’d like to share?

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