Colombia
I love Colombia. Since I was in High School, it had been my dream to travel there. Part of it stemmed from my favorite book, Love in the time of Cholera by the inimitable Gabriel Garcia Marquez. I ended up going, by myself, for three weeks when I was 21 and travelling all over the country. I fell in love with the different cities and the incredible people. Since then, I have produced shoes and artisan goods there for Teysha, and been back many times both for fun and work.
Cartagena - nothing is more romantic to me than wandering the streets of Cartagena. Both the walled-city and Getsamani are so unique and incredibly inspiring.
Santa Marta - wonderful, beach side community to visit
Parque Tayrona -- shhh... my top favorite destination in South America (?!). Get lost here for days, with nothing to do but read, swim, hike, and relax in the emerald ocean and jungle.
Bogota - absolutely love Bogota. So many incredible museums including the Gold museum, Botero museum, and tons more art museums. To me, it offers the same quality of restaurants and experiences as NYC but at a fraction of the price. I love staying in La Candelaria. If you go, I recommend starting your trip with Bogota Bike Tours - an amazing way to get a feel for the city's landscape and fascinating history.
Medellin - the Paisa people of Medellin are one-of-a-kind. I don't think i've been anywhere with such boisterous, hardworking, friendly and amazing folks. Medellin itself is gorgeous, full of parks and places to visit. I highly recommend spending time crusing on the Gondolas. Don't forget to make it up to Parque Arvi.
I also recommend visiting Cali, Popayan, and Villa de Leyva