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How far out to book for Namibia?

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Thinking of a 3-week self-drive tour of Namibia during the last 3 weeks of June. Namibia's been on my list, but I didn't seriously consider it until, on a whim, I called up UAL to check on award ticket availability, and discovered that there were indeed tickets available.

So, how far in advance does one need to book for Namibia? "As far out as possible," is usually the answer, but how likely are accommodations to be booked up 6 months out? I'm just starting to wrap my head around the idea of going vs. other options I had planned out.

Here's a prospective itinerary from my advanced planning spreadsheet:

SFO to JFK to IAD to JNB (Only routing for an award on this date)
Windhoek Heinitzburg Hotel
Sossusvlei Kulala Desert Lodge
Sossusvlei Kulala Desert Lodge
Namib-Nakluft Wolwedans Dunes Camp
Namib-Nakluft Wolwedans Dunes Camp
Swakopmund Hansa Hotel
Swakopmund Hansa Hotel
Damaraland Palmwag Lodge
Damaraland Palmwag Rhino Camp
Damaraland Palmwag Rhino Camp
Etosha Okaukuejo Camp
Etosha Okaukuejo Camp
Etosha Namutoni Camp
Etosha Namutoni Camp
Okonjima Okonjima Main Lodge
Okonjima Okonjima Main Lodge
Windhoek Heinitzburg Hotel

Estimated budget comes out to around $5500 including airfare (JNB/WDH), car rental, lodgings, and major activities. This is for one person traveling solo.

I'm not sure I'll pull the trigger on this one, as I have a friend that wants to go with me but can't this year. But, I'm very, very tempted.

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