Chiloé's culture is best observed in February and March, when many towns and villages celebrate their annual fiestas. Visitors can enjoy traditional foods like curanto (an ingenious feast prepared in the ground, with a mixture of meat, vegetables and seafood all thrown onto glowing coals and left to steam under nalca leaves), theatre, exhibitions and other events. Castro hosts the Festival Costumbrista Chilote, which lasts for a week, in February.
Summertime (December-March) is also when the flowers bloom, presenting a riot of colour along the roadside. Chiloé is renowned for its inclement weather. The western coast tends to be cold and wet and windy, even in summer; however, the eastern coast and islands are more sheltered. Summers in Chiloé are similar to those in England: a blazing sunny day can be followed by 2 days of rain, and sometimes summer just doesn’t happen!
Note: flight, boat, train and bus timetables change constantly, and airlines come and go, so please do not rely solely on this information for your travel planning. Check with relevant companies, or a flight search engine like Skyscanner, first.
Chiloé is easily accessible. Ferries run frequently from Pargua, 59km southwest of Puerto Montt, to Chacao on the northern shore of the Isla Grande (look out for dolphins) and take about 30 minutes. There are loads of buses operating between Puerto Montt and Castro, Ancud and Quellón on Chiloé. The bus goes on the ferry and the cost of the crossing is included in the bus ticket. To get to Puerto Montt from Santiago either fly direct (there are several flights a day with LAN) or take a sleeper bus (a journey of about 14 hours) with Turbus. There are also direct buses from Santiago to Chiloé with Cruz del Sur which take 17 hours. If you're staying at Puerto Nativo, the owners can arrange for you to be picked up in Puerto Montt or Castro.
If coming from Patagonia, Navimag operates ferries from Chaitén to Quellón on the south eastern coast of Chiloé. Ferries also operate further south from Puerto Chacabuco (near Puerto Aisen) to Quellón, useful if you're coming from Coihaique.