I had a similar idea sometime ago. I think you can try a ton of things before deciding that it's failing. Let users create their own guides, which they can sha

I had a similar idea sometime ago. I think you can try a ton of things before deciding that it's failing. Let users create their own guides, which they can share with others for free. User generated content can be a huge driver of traffic. Then your business model becomes freemium. Normal users' guides are free, but you pay a little for "expert" guides. Get professional tour guides on board. For example, in the UK we have blue badge guides who are certified. Getting them on your site will add some credibility. Make some deals with existing tour companies, either to offer discounts through your site or just a cut of ticket sales. Have you considered selling your existing guides as ebooks on Amazon or other platforms? Even if you have some awesome guides, I don't know about them because I've never heard of your site. I do go to Amazon to buy travel guides when I'm travelling. If I see your guides show up in the search, I will at least look at a sample on my Kindle. You could do both - have some free guides for promotion and have some cheap ones to make some revenue. Have you considered selling hard copies of your guides? Most people don't have a way to read a PDF when they are travelling. Use the Foursquare API to show a "hot destinations" chart on the homepage. Show where people are checking in and link to your guides for those places. Use buysellads or call businesses directly to place very targeted ads on the site. Affiliate links for tickets and hotel bookings may also work. AirBNB has an affiliate program - ride their success wave. There are lots more things you could try. The important things I feel are generating lots more content and being creative about distribution channels.