Port-au-Prince is the capital and largest city of Haiti.
The city’s recent history has been dominated by the aftermath of a devastating earthquake in 2010, which leveled many buildings and left hundred of thousands dead. Reconstruction effects are ongoing but many historic sights have been lost.
Port-au-Prince Airport (PAP IATA) is served by several major airlines, primarily Air Canada, JetBlue Airways, American Airlines and United Airlines and smaller flights from the Dominican Republic, Cuba, and other spots in the Caribbean. The Haitian airline Sunrise Airways, in operation since 2010, offers regular scheduled flights to Orlando (2017), Cuba (2016) and Chile (2017) among other locations. Taxis from the airport to your destination in Port-au-Prince will be about US$20 for standard fare. Tap Taps going to all places past the airport will cost about G15-25 (gourdes) (US$0.25-0.50) and a community-created route map can be found here.
From Santo Domingo: Caribe Tours, Capitol Coach Line and Terra Bus each run very modern buses daily to Port-au-Prince, each of the 3 companies departing from their own station along Av. 27 de Febrero. Caribe runs to Pétionville (in the hills above Port-au-Prince) that leaves at 11:00. Most all tickets currently cost US$40 one-way, plus serious tax/border fees of about US$26 and RD$100 (Dominican pesos), depending on the direction. Unfortunately, Caribe Tours’ bus drops you off in Pétionville after dark so make prior arrangements with a trustworthy person to meet you and transport you to your lodging.
Another, less expensive option, is to take a guagua (Dominican minibus) from Santo Domingo departing 4 blocks NW of Parque Enriquillo, just West of Av Duarte, from a small parking lot within the elevated expressways of Espresso 27 de Febrero). suggests guava buses leave every 45min, but this is not always the case. Price is RD$400 (about US$10), allow about 5h for the journey including a quick rest/meal sto) and arrive in the border town of Jimani. From there it is a 4km walk or a RD$50+ ride by motoconcho to the border post. The border is apparently open 08:00-18:00 (if it respects its times).
In the past it was very easy to cross the border without submitting to any immigration procedures on either side, and although probably illegal, saved a few dozen dollars in bribes and was much faster too. Things are changing: passport control is now generally required leaving the Dominican Republic, not just entering the DR. Entering Haiti legally is quick: fill out the green form and pay whatever amount the official asks (around RD$100). There are no ATMs at the border. Moneychangers give gourdes for Dominican and US currency. Rates are fair. Protect Haiti’s small green card in your passport, allowing you to leave Haiti without risking a penalty.
There’s usually plenty of local transportation from the border to Port-au-Prince. Crowded tap-taps and buses can take you to Croix-des-Bouquets for about G75 (1-2h), from where it is another hour to Port-au-Prince (bus, G5+ per route, summary network map. Road ranges from very bad to good, and is prone to flooding. Peruvian UN soldiers at the border have confirmed that the road to Port-au-Prince is safe to travel with no incidents of robbery or kidnappings, but definitely try to arrive in Port-au-Prince before dark.