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ITA Matrix can help with this (note that it is strictly a flight search tool and not a booking engine; it cannot book any flights). Choose "advanced controls" and add the MINMILES code to the "extension code" field. For example "MINMILES 5000" will filter the results to only show routings of 5000+ miles. (The number of miles may not match the frequent flyer ...


Computing this is for freaks ;) Already flight searches are a very expensive problem computation wise and if you want to make a trip as long as possible I am afraid you will need to rely on your creativity because the search space becomes too big. For example, I tried to put SIN as a layover between EWR and LHR in ITA Matrix and it let me do so and ...


Take a national bus to Penas blancas, walk over the border and the take a national bus to your final destination, on the way back you can take a boat and cross over to Los Chiles (Costa Rica). I did it when I was visiting Nicaragua after arriving by plane to Costa Rica


In Belgium you can expect to eat quite cheap. I never pay over 20 EUR for a 3-course lunch or a decent dinner. Just walk the extra 250m from the city center, and be assured to pay less and get less touristy options. I can give you lots of good ideas if you have further questions, for I am a 54 year old "Brugger".

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