New communication technologies are changing the way travellers gossip and trade advice while on the road. This paper presents initial results from our studies of backpacker culture and identifies gaps where future technologies could assist backpackers in existing situations. Our research included contextual interviews with backpackers, tours of hostel accommodation, and reviews of online discussion and blogging sites. Results so far indicate the need for mobile devices which can help a social, distributed community to connect and coordinate. To address this, we have developed methods of depicting community interaction and context of use, and prototype mobile travel assistants.