At the risk of sounding boastful my passion is doing road trips everywhere in Colombia and even down into Ecuador, always starting/ending my road trips at my home in Medellin.
I do 3 or 4 of these long road trips every year and am gone from a few weeks to a couple of months, sometimes my best Colombian buddy is with me and many times it is just me solo.
In 5 years I turned 100,000 km on my once new KIA.
Been driving all over Colombia in this fashion for 8 years and before this had a motorcycle for a few years which is a whole other conversation.
Now 10 years ago I jumped at the opportunity when my Colombian friend in Medellin offered that I ride shot gun in his tractor trailer so spent a week delivering cargo from Medellin down to Cali then over at the port into Buenaventura then north to Manizales and a few other load drop-off's and pick-up's along the way back to Medellin..................what an eye opener and invaluable experience this was.
Here is a sampling of cities, pueblos, seaside villages, attractions and regions/departments where I have driven:
Santa Cruz de Mompox, Aracataca-Magdalena (home of Gabriel Garcia Marquez), Gral. Farfán/San Miguel-Putumayo, Cali, Yarumo, Mocoa, Ipiales (including nearby Santuario de Nuestra Señora del Rosario de Las Lajas), Pasto, Silvia, Popayan, Villavicencio-Meta, Puerto López & Puerto Gaitán-Meta/Los Lanuras, La Plata, El Florián-Santander and the nearby Las Ventanas de Tisquizoque, Jamundi, San José del Guaviare-Guaviare, Vereda Cerro Azul-Guaviare, Tierradentro, Parque Arqueologico San Agustin-Huila, Salento, Palmira, Buga, Cartago, Armenia, Santa Rosa de Cabal (including nearby Termales), Filandia, Manizales, Pereira, La Chamba-Tolima, Ibaque, Anapoima, Girardot, Quibdo, Moñitos, Jerico, Jardin, Salgar, Ciudad Bolivar, Santa Fe de Antioquia, Tarso, La Pintada, Neiva, Villavieja, Tatacoa Desert, Guamo, Paracuachon @ Col/Venz border, Honda, Villeta, Facatativa, Fusagasuga, Soacha, Bogota 40+ visits over 34 years, Chia, Zipaquira, Villa de Leyva, Puente Boyaca, Puerto Berrio, San Basillo de Palenque, San Gil, Barichara, Guane, Villanueva, Chicamocha-Santander, Bucaramanga, Barrancabermeja, Cucuta, Buenaventura, Nuqui-Choco via flight from Medellin, Nueva Venecia via boat ride from Cienaga, Barranquilla, Tamalameque, Valledupar, Maicao, Riohacha, La Guajira, Uribia-La Guajira, Cabo de La Vela-La Guajira, Cartagena, Bocagrande, Getsemani, Rosario islands, Archipelago de San Bernardo including Mucura/Tintipan/Santa Cruz de Islote, Palomino, Buritaca, Los Naranjos, Tayrona, Minca, Taganga, Santa Marta, Rodadero, Cicada Perdida/Lost City (4 day hike), Tolu, Turbo, Covenas, Maicao, Rincon del Mar, Mendihuaca, Baru, Monteria, Caucasia, Yarumal, Segovia/Remedios Antioquia, Necocli, boat to Isla Fuerte, Capurgana via boat from Necoli, Apartado, Guatavita-Cundinamarca, Tunja-Boyaca, Sogamoso-Boyaca, Mongi-Boyaca and of course Medellin and dozens of pueblos. in the outlying areas within 50km where I live and call home.
And as I mentioned in the above I also drove from Medellin into Ecuador a few times and returned. Here is a sampling - Drove the complete 800 km coastline from top to bottom on the E15 La VÃa del PacÃfico o Troncal del PacÃfico, from San Lorenzo, Esmeraldes, Atacames Canton, Mompiche, Pedernales, Canoa, San Vicente, San Jacinto, Manta, Portoviejo, Montecristi, San Lorenzo, Puerto Cayo, Machalilla, Puerto Lopez, Salango, Olon, Montanita, Ayangue, Monteverde, San Pablo, Salinas,La Chocolatera, Quito, Ibarra, Guayaquil, Cuenca, Banos, Ambato, Nueva Loja.
So in summary how, when and where should you/could you and more importantly areas that you should not drive in Colombia just depends on so many factors, too many to list here. If anyone has a particular route they have in mind just ask.
In the meantime when I am not on my road trips you can find me driving the roads of Medellin from one end of the Aburra valley to the other.
And mind you I first visited Colombia in November of 1990 on a months long extended visit so in addition to driving these roads I have used buses, hired private cars, rentals and have been a passenger in my friends car/truck/van.
Godspeed to all!