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 Kilimanjaro via Nairobi on Kenya Airways (9hr).
Day 6: If you arrive in the morning, take a helicopter flight to Mwiba Lodge in the Southern Serengeti. If later, you can overnight at Mwiba Lodge. Spend the next few days on safari.
Day 7: Safari
Day 8: Safari
Day 9: Safari
Day 10: Fly from Mwiba Airstrip to either Kilimanjaro or Seronera (1hr), and from there, catch a flight to Entebbe, Uganda (1hr). Overnight in Entebbe.
Day 11: Fly (1hr) to Bwindi Impenetrable Forest and your gorilla lodge – possibly Bwindi Lodge.
Day 12: Wake up early for a Gorilla Trek and spend a special hour with an acclimated gorilla family.
Day 13: Transfer back to Entebbe for your flight home.
Day 14: Fly back to New York via Addis Ababa or Europe.