You cannot always ask permission, of course. If you are shooting a street scene or a wide shot of a market, you can't run up to everyone and ask if it's OK. In general, people do not mind this sort of photography—it's only when they're singled out that they get uncomfortable. But not always. Be sensitive to the scene in your viewfinder. If people are getting nervous, ask permission or move on.
You cannot always ask permission, of course. If you are shooting a street scene or a wide shot of a market, you can't run up to everyone and ask if it's OK. In general, people do not mind this sort of photography—it's only when they're singled out that they get uncomfortable. But not always. Be sensitive to the scene in your viewfinder. If people are getting nervous, ask permission or move on.
If you are a top notch, worldwide known photographer, it is very likely that customers from all over the world will want to use your services (for fashion, events, sports, architecture, products etc.). But as we are focusing on travel photography, commercial organizations that deal with traveling and tourism are more likely to hire you. Notable examples are hotels, tour companies, airlines and so on.
Whether you're licensing photos through an agency or you're working with local businesses, destination photos sell. If you're just starting out, consider uploading your best work to sites like 500px, where you can offer your images for license quite easily. If you already have a strong portfolio of work, consider applying to Stocksy, the most reputable agency in the stock photo business. Interested in reportage? You can sign up for a Demotix account to get started in travel photojournalism.
I left home in 2009 with $500 to my name, a point and shoot camera, and a desire to spend the rest of my life exploring the planet. Looking back, I was beyond naïve. However, without that naivety, I would have never made the first step towards chasing my dreams. Today, I struggle to get by. In a heart beat, my income streams could all dry up. But I don’t worry anymore, I just take pictures and love every minute of it.
The third image is of Jinru Lee; a student and part-time model in Georgetown (Penang Island, Malaysia). It was made in late August 2018 under the sweltering sun of Penang, and inside the Cheah Kongsi Clan House Temple on Lebuh Armenian. I was in Penang to photograph the various Hokkien operas during the Hungry Ghost festival, and took the opportunity to set a photo shoot in its streets for a forthcoming audio slideshow (aka photo film) titled "The Phantom of the Opera". 
For example, a product review I did in December of 2014 led people to the product on Amazon via an affiliate link. That product sold extremely well, and people also bought other things well they were shopping. That affiliate link earned me a pretty penny. Of course, that’s not always sustainable. In January and February I earned $300 and $400 respectively from affiliate sales. In March, I only earned $50.

Whatever kind of landscape you are shooting, think about what the essential qualities are—and not just the visual ones; think about how the place makes you feel, what kind of emotions it stirs in you. Then look for ways to get those qualities and feelings onto film. Is it a rocky, violently wave-washed coast or a bright and sandy one? If it's the former, you want to show waves crashing against the shore, probably in stormy weather. Blue sky and sunlight are more appropriate for the latter unless you want to show the desolation of a resort beach in winter.
As an approved photographer on stock libraries, you can possibly get access to client briefs where you can submit your work direct to the client, meaning they’ll consider you for the project and see your profile. Otherwise there’s usually a marketplace type system for you to upload your images and have them added to collections based on themes, destinations and seasons.
My still-embryonic idea is to enlist the help of a local acquaintance who would wear a cheongsam (aka qi pao), and take the role of a sing-song girl. The photo shoot would take place in the streets of Yau Ma Tei, and in the parlor itself. Whether the parlor would allow it or not is an open question that will be answered when I'm there. The owners and clients seemed very laid back when I made these photographs.
Get lost. Wander down alleys. Sit in cafés and watch life pass by. Don't eat where the tourists do, but where you see locals. Just set off down a street and see where it leads. Look around the bends, over the rises. Get away from the crowd. I find that if I meander away from the tourists and tourist sites, away from what is too familiar and comfortable, it's much easier to adapt to the rhythm of a place, and to be more observant.
Another place to capture expressions are the subways; either on the platforms or in the cars themselves. My favorite images are the one of a young woman avidly watching a movie on her smartphone, while wearing a single hair roller to tame her fringe....and of the young girl who appears to be viewing a smart phone screen on an ad on a subway platform while her mother is busy texting on her real phone.

Hi Claire, thanks for your message. That’s correct, it’s not possible to upload photos from your computer to Instagram however it’s quite popular to get around this by emailing the photos to yourself, then opening the email on your phone and storing the attached image in your phone’s library. This then allows you to post to Instagram. Alternatively there are a number of apps or plugins that allow you to upload to Instagram, most however will require payment. This is one I suggest looking at ‘LR/Instagram‘ but I can’t promise anything as I don’t personally use this method.
You can offer photography services to any business in the travel/tourism industry at your destination of choice. Opportunities are plentiful, whether you're selling your services or offering a trade. Going skiing in Colorado? Get in touch with local lodges about trading photography for a free stay. Vacationing in Vienna? Talk to the local tourism board about shooting a few photos for a fee. I recently made a deal like this in Cape Town shooting a month-long campaign with their tourism board, which resulted in a promotional blog post and lead to even more work. Remember that a strong portfolio goes a long way, and as it grows, so will your opportunities.
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