Being Rudderless with Christopher Rudder

by Jul 9, 2018Travel Resources2 comments

I was sitting in the awesome Porter Lounge at Billy Bishop, Toronto Island Airport waiting for my flight to New York. As I spoke with my brother over the phone regarding video work for his company The Cap Guys, I noticed a lovely young lady periodically staring at me.

Just as my ego started to get the better of me, I suddenly remembered the pretty lady who was smiling at me in a Paris subway train while her cohorts pickpocketed my iPhone.

I stopped making eye contact immediately and clenched my iPhone tightly.


Porter Airlines | Billy Bishop, Toronto Island Airport

When I ended my conversation with my brother our eyes accidentally locked again. She smiled and said.
“Excuse me, sorry to bother you but your voice sounds familiar, I’ve heard it before. Are you on the radio?”
Making sure my voice was as deep as it can go I cleared my throat and replied.
“No, but I have travel videos on YouTube and a travel blog called Rudderless TRVL – I’m a travel blogger”

She snapped her fingers

“That’s it, yes I saw your videos on YouTube”
After a brief explanation of my travel blog and brand which went like this…

In roughly 48 hours I take a city; see the sites, taste the food, sniff out the hidden gems, hear the stories and feel the energy.

She was intrigued, and started asking me questions about my travels which went a little something like this:

Be Rudderless

Gordana Grubor & Christopher Rudder

Name: Christopher Rudder with Gordana Grubor
Travel Blog:
Rudderless Travel |
City & Country of Birth:
Toronto, Canada.
Gospic, Croatia (Gordana)

be Rudderless

It’s all I know how to be

Blog Content:

Rudderless specializes in Short Trips & Mini-Breaks; Weekend Getaways, Business Travel & Stopovers & Layover Itineraries – as well as travel app & travel gear reviews.

Short Weeks & Long Weekends have always been my thang!

And as if this blog wasn’t already consuming enough of my time, I went ahead and added a few other travel sections that interest me: travel blogger interviews and tourism and hospitality reviews. I am also the admin of this amazing Toronto Based Facebook Group called Toronto Bloggers Collective and the host of its upcoming podcast. I’m also the host of my own podcast called Travel Horror Stories.

As a professional videographer and photographer, all short trip posts come embedded with a creative travel video, gorgeous photography and a custom map (This map includes all places mentioned in the post and the videos and at times includes the accommodations).

What’s in a name?

For those who wonder about my coincidental last name…yes, my last name is actually Rudder.

For those who don’t know what a rudder is – a rudder is a primary control surface used to steer a ship, boat, submarine, hovercraft, aircraft, or other conveyance that moves through a fluid medium (generally air or water)Wikipedia.

Hence the name rudderless as in; no fixed direction, it’s all about the journey, not all those who wander are lost *sigh* (you can insert your favourite travel quote here:_______)

All I know is, Rudderless is my life and my life is rudderless.

I was quite literally born to travel and I didn’t even get into the whole St. Christopher who is the saint of safe travel stuff.

What Rudderless isn’t.

  • You will not find pictures of myself chilling on a beach with a laptop bragging about my wonderful nomadic life in an attempt to convince you that you can be like me if you buy my ebook. I love my career and at this point, I don’t feel the need to choose between it and a nomadic lifestyle. Oh and for the record I’ve travelled to more that than most people who claim they travel full-time.
  • Slow travel. Although slow travel is ideal when trying to learn about a city, I simply don’t have the time.
  • I refuse to promote products and services that I don’t use myself or wouldn’t use myself

Make sure to subscribe to my YouTube channel to see all my latest videos!

  • How do you incorporate Short Trip and Travel Apps into your travels? How do you prepare? Do you have any tips?

There are a couple of ways to approach this but for me, it starts with research. Lots of research. But first, you have to understand and accept the fact that you will not be able to experience everything a city has to offer in 48-72 hours. I’ve lived in Toronto my whole life and there are things I still need to see, try and do. And that’s just my city. It doesn’t include all the things I still need to see, try and do in my country (Canada).

That being said and coming from a travel vlogging mindset with regards to capturing the footage that make great and interesting videos; Using my Notes app, I start by making a list which includes:

Points of Interest – things to see, Cultural foods, (dishes, and drinks), popular restaurants, bars, and clubs. Festival dates. Things to do. Museums to visit etc.. I then cross-reference this list with posts and articles written by fellow travel bloggers, the Google Trips app and the Sygic Travel app with Fodor’s articles and various travel guides.

Then using Google Trips with Google Maps and the Sygic Travel app, I plot out where everything is including airports and train stations. Once I get an idea of where everything is visually then I start looking for Airbnb or Hotel accommodations.


Getting the most out of short trips is all about logistics – knowing what time a place opens and closes, where your accommodations are, where the places are on your list and/or what subway or bus stop is close by ahead of time…will save you time when you reach your destination.

Also, for those on a budget; 48 & 72-hour fire sales for both flights and accommodations are always popular so if you have a flexible work schedule then take advantage. Skyscanner is a great app for the weekend traveller that will allow you to check out cheap last-minute flights to many random destinations. The Airwander site will show you ways to turn layovers into stopovers and save money.

  • Share one of your favourite travel stories…How do these type of experiences change you as a person?

So many stories…wow. I do have a funny, yet digesting story which is from my blog podcast called Travel Horror Stories. I wrote a series of posts called Tales From The Throne and as you can guess by the title it’s a collection of my infamous washroom stories. The condensed version of those posts goes like this…


Cappadocia, Turkey


During our time in Cappadocia, Turkey we explored many cave type houses and churches, spent two nights in a cave hotel, got a Turkish bath and ate delicious lamb cooked in a pot. The highlight though, was the magical Balloon ride over the moon like terrain.

It was late in the evening and I decided to get something to eat. Nothing fancy, just something quick and cheap. I found a Kebab stand which barely had any meat on it and some left overs at the bottom. For some reason (against my better judgment) I ordered one.

I woke up in the morning with serious diarrhea and to make matters worse, not only was I was flying out to Athens that morning it’s a 45 minute drive to the airport. From Cappadocia airport, it’s a flight to Istanbul and a transfer flight to Athens.

During the ride from the hotel to the airport I fell asleep, which probably saved me. When I arrived in Istanbul we saw a pharmacist in the airport and I remember thinking that was odd but I had no time to ponder or be embarrassed. I told the pharmacist I had diarrhea. Now, my man did try to keep a straight face…but it did not last. He started laughing so hard that he must of pee’d himself. Meanwhile, I was trying so hard not to sh*t myself…

Just give me the damn pills. PLEASE.


Athens, Greece

I made it to Athens. Scared to leave the airport, we pile into a cab and make it to the accommodations. Normally, I wouldn’t care if the Airbnb host is a few minutes late but in this case, every minute felt like an hour.

The capper isn’t that I made it to Athens but if you’ve been to Athens then you know that the cities washrooms have small pipes and the toilet bowl will clog real easy if you flush toilet paper down the toilet. So every washroom in Athens has a garbage bin with a lid for you to dispose of the toilet paper. Yeah gross, I know…

So you can imagine after making it all the way to Athens in my condition, my desire to burst out laughing when Tatiana explained the rules for the washroom. (Toilet paper cannot be flushed down the toilet) Bless her heart. She’s one of the sweetest Airbnb hosts with one of the most beautiful apartments in Athens. But I’m gonna be honest and tell you that I did not always follow the washroom rules.

  • What are your top 5 travel rules that you follow every time you travel and why?

    I will not compromise my safety. If the shortcut I took earlier during the day looks sketchy at night. I will take a long well-lit way or take a cab. It’s not a female or male thing, it’s a safety thing.


Marrakesh, Morocco

2. I will not compromise my health. (With the exception of the previous question). If it’s not clean, I don’t eat there. I always get travel insurance for both myself and my stuff. Health includes drinking water or wearing sunscreen when hot, dressing warmly when cold etc…

3. I try not to compare the way of life in my city/country with the way of life in another city/country. What’s the point of travelling if you’re going to compare everything to where you’re from?

4. I always try to respect the people, places, religions, and customs of the country hosting my visit. No matter whether I disagree or no matter how strange it may seem.

5. I always make sure I learn, love and laugh. I take time to eat, drink and explore. I love hearing stories, I love sharing stories and Iove trying something new. I take thousands of pictures and video clips but I always take time to absorb with all my senses that moment in time.

  • What are your top 5 travel hacking tips and tricks?

  1. When booking flights, I use the Hopper App and the  Skyscanner App to monitor flights in order to get the best deal. Typically, flights out of season for a particular country are usually cheaper. For example, the peak season for Europe in July & August so heading to Europe in September tends to be cheaper. Plus I always get insurance for my flight.
  2. When booking accommodations, I tend to use the Airbnb App and the Trivago app. Flights, accommodations booked out of season for a particular city/country are usually cheaper.
  3. I tend to use OffMaps2 for navigation. As I mentioned earlier, after I download a map for a city and pin all my points of interest so when I arrive in the city I can use that map with GPS and without the need for data or wifi. I use Sygic Travel as my guide and itinerary.
  4. Try to choose Airbnb accommodations or accommodations in general that give you access to a kitchen or at least a fridge and if possible access to a washer and dryer. Being able to prepare your own meals saves you tons of money. Naturally, you must go out and eat breakfast, lunch or dinner at a local restaurant to try local dishes but when you not eating out…eat in.
  5. Open a high-interest savings account that will be your travel account in a different bank other than the one you use for your regular everyday banking. Set up an automatic saving plan that funnels money from your regular account to your travel account bi-weekly (when you get paid is best) then forget about it. (Outta sight, outta mind). When it is time to travel, purchase your plane ticket using a credit card that offers travel points than pay the credit card off right away using the money you saved. I personally use Tangerine and put away $200,00 biweekly. Oh, and if live in Canada, open a Tangerine account with my Orange Key 14589030S1, deposit $100.00 and both you and I will get a $50 bonus! It’s a Win, win 🙂 Truthfully, I am terrible with money…

Venice, Italy

  • Besides your passport, what are your top 5 travel things you must bring in your carry on, backpack, purse or satchel?

  1. My iPhone, headphones and charging cable (My iPhone is my music, movies, internet, and apps. Guides, accommodations, notes, and maps…)
  2. My Mophie Powerstation Mini (gets my iPhone charged when the battery is low and not a power source in sight.
  3. My medication (High blood pressure, unfortunately, is genetic in my family)
  4. Napkins, wipes, hand sanitizer & hand cream.
  5. Cigarettes (I quit), My Vapour (E-Cigarette) but I actually hardly use it…I may need a new item for #5.
  • What is the most prized souvenir you brought back from abroad and what’s its story?

My prized souvenir is my satchel. I was in the market for a good satchel and visited a few stores in Toronto, Canada and some in Niagara Falls, United States.

When I visited the Grand Bazaar in Istanbul, I immediately felt the long history of buying and selling along the Silk Road. Amongst the colours and smells, I was sure to find a satchel here in a place known for the best in rugs, carpets, leather, and silk.

As I visit several stores, I started seeing the same things and repeating the same haggling techniques. Final I stopped at this one store which had different products all made with the finest quality of leather. I immediately spotted my satchel.



I believe it spoke to me.

Now I must prepare to haggle but the owner told me straight up, “I am not going lower than $150.00 euros as I know I can sell it for that much. Feel free to shop around in other stalls for something cheaper as there are plenty of options.
I respected that. Especially after spending the morning haggling with various store owners. I bought it on the spot. He did give me a traditional “first sale of the day” discount.

I’ve had my satchel now for 3 years and I take it everywhere with me, both at home and abroad. Plus, it feels good to say “Oh, this…I bought it in the Grand Bazaar in Istanbul, Turkey…” when people say they like it…


Where are you off to next and what are you hoping to experience, eat, see and/or learn?

Now I’m off to New York City. Also this year I’m heading to St. John’s and Fogo Island in Newfoundland Canada. I wanna start exploring my own beautiful country. Later this year I’m heading back to Italy and back to Rome but adding Naples for pizza and limoncello, Pompeii for some history and Syracuse and Catania on the Island of Sicily in search of the Godfather. I’ll be adding a new Country to my list – Valletta in Malta for some Game of Thrones location scouting!

With that, they started calling my flight number to the gate. I thanked the girl for her interest in my travel blog, said bye and left her with the links to my social media accounts. I also shared the Facebook Group for content creators that myself 3 other admins run called Toronto Bloggers Collective and the Facebook Group for my podcast Travel Horror Stories.

As I boarded the plane I checked my pockets to make sure my iPhone was still with me.

Rudderless TRVL’s Social Media Network:


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