Your question intrigued me, and though I've never been to Somaliland, I did find some info which may be useful.
For transport, the following is an airfreight company which serves Somaliland, with connections to Europe.
"DAALLO AIRLINES serves mainly between the Gulf and almost every major city ( Djibouti, Asmara, Addis Ababa, Nairobi, Eldoret, Hargeisa, Burao, Mogadishu, Bossaso ) in the Horn of Africa region, its most important destination is Kalabaydh, a small town in Somaliland, close to the Ethiopian border.
Daallo Airline's interline agreement with Das Air and close association with the Chapman Freeborn group has ensured smooth, efficient and quality air transportation services between the US, Canada, Europe and Asia to the Horn of Africa at competitive prices.
As far as safety is concerned, I found the following news item, quite recent.
" Jan 18 2002 BBC Monitoring Service - The UN delegation which was in the country for a visit has today left for Mogadishu, Somalia. The delegation which visited Sahil and Hargeysa regions, was on a mission to assess the security situation in Somaliland and Somalia and report back to the UN Security Council.
During its stay in Somaliland, the delegation had met the president of Somaliland, Hon Muhammad Ibrahim Egal, and other officials, including Hargeiysa's mayor, the governor of Sahil Region and some members of the opposition parties who briefed the delegation on the real situation in Somaliland.
Members of the delegation were told they were free to visit any part of Somaliland without security escort - a fact that attests to the peace prevailing in the country. Source: Radio Hargeysa"
Accommodation might be fairly non-existent, the country doesn't sound like it has much infrastructure:
"The new USCR report, Welcome Home to Nothing: Refugees Repatriate to a Forgotten Somaliland, urges the U.S. government and other international donors to provide long-overdue humanitarian assistance to Somaliland’s 3.5 million people, particularly to former refugees struggling to reintegrate into the extremely impoverished, predominantly Muslim society.
Many inhabitants of Somaliland, including most repatriated refugees, live in makeshift camps and slums in an economic system devastated by war and neglect. Returnees to the semi-arid desert area must rely on decrepit water systems and inadequate health care and social services for their basic needs."
As for Entry Regulations, I found the following on what appears to be a Somaliland Government website:
" Hargeisa, 24/10/2001 - (Ministry Of Foreign Affairs, Somaliland)
ENTRY VISA - SOMALILAND
Entry Visa's to Somaliland will no longer be issued at port of entry. Visas must be obtained from Somaliland Missions aboard.
For further information on entry visa issues please contact the nearest Somaliland Mission."
Problem here might be finding a Somaliland Mission abroad, when so few countries actually recognize them as a country. There are contact details for them in USA, UK, Italy and Ethiopia on their website, which also has a lot of useful info under Country Profile. http://www.somalilandgov.com
Hope this helps. Please keep in touch with us as you plan your trip.
Good luck and safe travels!
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