Here’s a rough trip outline based on our conversation:
Day 1: Depart Newark for Cape Town in the evening.
Day 2: Arrive in Cape Town around 5 pm. Transfer to your hotel and have dinner.
Day 3: Take a day to relax and explore the city. You could take a food tour or explore on your own.
Day 4: Catch a car down the coast to a shark dive outfitter in the morning. Dive in the afternoon.
Day 5: Take a morning hike or walk to the beach. Transfer to the airport for an overnight flight to Nairobi (5.5hr).
Day 6: Arrive in the morning. Your driver will take you on a private David Sheldrick Wildlife Trust tour. Giraffe Center visits are also available. En route to your hotel, the Emakoko, take a short safari. (This day could also be dropped if you want to fly direct to Tanzania to save time/money.)
Day 7: This morning, transfer back to the Nairobi airport and fly to Kilimanjaro Airport in Tanzania (1hr). If you can get on an early flight, you might be able to catch a flight to your safari lodge today, but I need to confirm the flight times in January. You may have to overnight at Legendary Lodge, a great little hotel in Arusha.
Day 8: Take a one-hour bush flight to Mwiba Lodge in the Southern Serengeti. Spend the next few days on safari.
Day 9: Safari
Day 10: Safari
Day 11: Safari (Optional helicopter flight over the Serengeti)
Day 12: Fly from Mwiba Airstrip to either Kilimanjaro or Seronera (1hr), and from there, catch a flight to Entebbe, Uganda (1hr). Overnight in Entebbe.
Day 13: Fly (1hr) to Bwindi Impenetrable Forest and your gorilla lodge – possibly Bwindi Lodge.
Day 14: Wake up early for a Gorilla Trek
Day 15: Transfer back to Entebbe for your flight home.
Day 16: Fly back to New York via Addis Ababa or Europe.