Where can one travel to in the Winter? (Euro-Africa-Middle East) (vacation, Rome)

[superseiyan]

Hello guys.

The deal is this, I'll be going to Africa and Italy over next Christmas, so ti'll be a december/january trip. I live on the east coast of the USA.

As it is winter, i'm assuming sunny sands on greek resorts or the french riveria is out due to weather.

I'd like to add a third (and possibly fourth) stop in addition to Italy and Africa--both of which I have to travel to for family reasons, rather than touristic reasons (though I will see what can be done in Italy).

My questions are as follows:
- In December/January, what places that fall within the connection routes can one visit?
- Is buying tickets 6 months out good enough to get a good deal?
- Should flights within Europe be booked as part of the overall package, or is getting around in europe better done impromptu?
- What is doable in Italy in winter?

Regards,

[slackjaw]

Africa is a big place, where are you going?

[superseiyan]

Kenya, but it's not for "vacation" even though I'll do stuff there. Same with Rome, Italy. Rome itself won't be for "vacation" and won't be my first time, but I wouldn't mind sneaking in something else within Italy.

So the three things I'd like to see if I can do (things that can be done relatively quickly) are:
- See something interesting in Italy outside of Rome
- Go somewhere in the Middle East or Europe as I connect back from Africa to DC.

I'm thinking of going USA to Africa (destination 1), then going somewhere else, then Rome, then returning to DC. This is a little challenging since I'm going in December. Is the middle east and southern europe too cold in winter?