The question I get the most is how do you get to travel so much? Well like a fine art, I have crafted the art of my own experiences and making available to me the things I really want to do in life. Life is to short to do the things you don't want to do for very long. Most peoples resistances stop right there, they just can't get more time off of work. But do you want to live to work, or work to live, or just live? But what happens when you tell work "I'm going". I've only had one job tell me that means I won't have a job when I came back, and really it was a blessing to be released from that job though it was one of my hardest decisions of my life it also made me who I am today and opened me to a whole other world of opportunity and experiences.. and 4 AMAZING months in South America.
So work.. in Canada we are restricted to two weeks a year which means you basically get to do an exhausting trip somewhere far, or some short local trips. To me that isn't even worth it if you can't get a month in a place. I recommend when taking a new job to negotiate your holiday time to include more. Everyone in Europe gets at least four weeks and what is it in our culture that says we don't deserve the same? If you are a hard worker, and you are worth it they will give it to you. If they don't give it to you I would think you may need to find a better fit, and believe me the better fit is out there. What Canadian companies have not caught on to is that you actually being happy means you will work harder and actually deliver more on your projects. Of course this doesn't apply to all work, especially if you are just starting out in your career, or working in bureaucratic positions with no grey areas.
The best work is the flexible, contract work where you often work for short periods and often can take space between these contracts. The reality of many jobs now don't need you to even be in an office anymore and by slowly introducing a work from home option to your employer it will often lead to extended holidays where you can work from the beach rather than home. That means taking your computer with you on holiday but it means enjoying your stay in a different culture a bit longer, it's worth it in my eyes. Flexibility is key. Knowing when it's a good time to take a holiday for yourself and your company/organization is also a way of showing the people around you that you care enough to not take off during the busy time.
Timing is everything. I tend not to travel in high season in order to save on high season accommodation, though some of the best times to have extended holidays are over Christmas and New Years as a lot of peoples work slow down so just go when you can go.
Money. If you have never learned how to save or pay off your debts, I would probably start there. Don't take a holiday until you have learned that skill. That being said sometimes opportunities are dropped in your lap at the last moment and saying No isn't just isn't an option. The one article I read about what you think about on your death bed isn't about the money, but the amazing time you had on a holiday. Look at the big picture always. If you need 5 star accommodations, then lucky you or unlucky you has you are at risk of having little exposure to the cultures outside your compound. Sometimes that is what people need and I respect that. If you can afford it or have awesome friends who hook you with friends discounts do that because what goes around comes around. Share the wealth if you got it, what's the point of having a benefit if you can't share it? Often one night in a 5 star can pay for a whole week in Thailand, Ecuador, Spain or Turkey. Thanks to the internet there are so many options available now. My favourites are often guest houses, casa's, or any place where you can interact with the locals or meet other people from around the world. Find a place maybe that has free bike tours, group dinners, or great reviews. The choice is yours where you want to stay and spend your money. But don't go into debt to go on a holiday, but I am ok with going into debt to extend a holiday. Last minute decisions to stay in a place are often some of the best decisions I have ever had to make because who knows if you will ever get to that place on the earth again. Getting to a place sometimes takes work, and money and backtracking or going another time will cost you more in the long run. More debt isn't what you need to relax, and to me that just creates more stress. It is not something that is taught in school and it is one of the biggest issues I see in friends who want to travel but can't. Living cheaply doesn't mean you are cheap, it just means you may so no to some stuff that isn't logical. One of the biggest expenses in a city like Vancouver is rent, and a vehicle. If you can get rid of your car you can save an upwards of $7000/ year (yes do the math because it's true).
I have always rented out my home when I went away travelling, even before the days of Airbnb. Craigslist has allowed me to not increase my expenses while away and allowed someone else the comfort of my home. My home is simple, comfortable, and is in Vancouver so there is always a demand. I don't charge people more than it's worth as I want to attract the right person that is worthy of staying in my place. I have been fortunate to have dozens of different people stay in my home and have never had any issues. Airbnb makes this easier as well now with insurance and checking of people's IDs. I have always taken copies of peoples IDs just so I know exactly who is in my space. I have always trust my intuition when it comes to someone staying in my home. If something doesn't feel right just say No. And that goes with all of lifes situations really.
I don't have a big income but I am very happy with life and lifestyle, but I am able to save even with a vehicle. If you have attachments over having a stranger have sex in your bed, you aren't going to want to share your home. But imagine how many people have had sex in the bed you are sleeping in on holiday. If you want to travel you have to let go of some things. It is all possible if you want it to be possible. It sounds like a lot of work but it work and for me it isn't that much of hassle when I am saving a couple thousand dollars on holiday expenses. I've been to Prince George, Montreal x2, Boston, NYC, Seattle, Cuba, Ottawa, London, Paris, Turkey, and Desolation Sound this year and am heading to Bali next week for a month. Get a travel credit card and charge everything to it (if you pay off your debt immediately!). I travel somewhere once a year on points. Life is what you make it, you create your own obstacles, and set your own goals. Sometimes things don't happen but that doesn't mean it won't happen. If you really want to get out and see the world you can do it. I'll even help you.