Thanks for the tips! I saw a couple of organized walking tours on guruwalk.com too and I'm planning to join some of them. I also probably won't stay for a month but I'm considering extending it to 2 weeks to make the flight expense worth it. Alternatively, would you also suggest that I stay for 1 week in Medellin (I will have time to do Guatape and lots of the walking tours) and 1 week in Cartagena? Source: over 1 year ago

Check out visitacity.com to help you arrange an itinerary. Used it for a number of trips including Paris. Stayed at an Airbnb close to the downtown but should have picked a nicer place further out if I had taken time to understand their public transit system before hand. Source: 6 months ago

I use Visit a City for my vacation planning. Based on the city you're visiting and types of attractions you're interested in, an itinerary is built for you that includes travel time between points of interest. You can also add/remove attractions based on your own interests. Source: about 1 year ago