Often FF Award tickets have really lousy routing, as you appear to be indicating above. Also, and others who might know... seems if not flying with the OAT flights, your transfers from/to airports will not be included. That said, seems the planes arrive at the same time and even if those flying on FF tickets or own flights do manage to hop the ride with the group... but there's no guarantee.

To me, peace of mind is better. Let's hear other comments.

I use miles/ points etc only for premium cabin travel where the value of the miles is way higher on a per mile basis. For example a 120k to 180k business ticket to Africa compared to an 8k paid ticket is 4 to 6 cents per mile vs say 80k points for a 2k coach ticket which is 2.5 cents per mile.

Have you checked what kind of routing you can get through OAT vs on miles? I've used miles for every trip to Africa and have often found good routing.

For the situation you describe, I would go with OAT. Then you won't have to worry about transfers or delays.

I'm with AKR1. I try to only use my miles for Africa for Business Class travel. That said, I'm surprised that OAT's difference between their "land only" price and the tour with air is that much. It used to be a smaller variance because they got good deals on airfares. You don't have much choice when flying in to Kilimanjaro Airport (JRO.) KLM is the main carrier (Delta partner). Ethiopian Airlines goes in there via Addis Ababa and I think Sandi mentioned Turkish Airlines is planning to start flying there. If you have United miles, you could use the latter two airlines. Another option would be to fly in to Nairobi (NBO) using miles (more choices there) and buy a flight on Precision Air into JRO.

Unless it's a situation of free flight or busted travel budget OR unless it's a situation of use it or lose it miles, THEN I'd do the OAT flights.

good routing is provided by miles

Well the way you've framed it it's a no-brainer. But I wonder a couple of things..

First, is the $2500 for one person or two, and second, what FF program do you use and how many miles do you have? Are you talking about economy/coach travel, premium economy or business class?

Second, many air packages sold by tour companies use very highly restricted tickets, where any changes, delays, etc. are just not allowed (upon pain of forfeiture) and where you're completely locked into the arrangements they make. These tickets, typically sold through consolidators, are sometimes not even recoverable through trip insurance. Read the fine print.

When is your trip? And where are you flying from/to? One thing to note is that frequent flyer seats are not all released at one time, and with many airlines it's very hard or impossible to see availability on partner flights online; you need to phone your airline's FF desk and ask for them to see about availability using partners. There are some ways around this problem, but it depends on what airline's miles you'd be using. For example, if you'd be using United or US Airways miles, you could fly using several European or African airlines that are UA/US partners. You won't see open seats for these on UA's or US's websites; who knows, there might be much more convenient flights using that approach. More information is needed.

Whenever we used ff miles for flights to join a tour we arranged to go a day(s) early to be sure to have no problems meeting the tour and to get over jet lag before the tour began. Always worked for us.

I'm with those who use their FF miles only for updated seats ( business or first) to Africa.

Here's why:

Depending on the routing (which airport you fly thru) the cost of economy, even WITH FF miles, might not be worth using so many FF miles
For example, the airport fees/taxes/fuel surcharge for routing through LHR are now so high that it would hardly be worth saving $ if you were booking a FF coach/economy class ticket.

I hope the way i said that makes sense. I'd rather save FF miles. Maybe net time you can fly in First!!! (-;