I’ve put together an outline for your trip below, based on three safari stops on the dates you suggested. Unless otherwise noted, most of these hotels are in the $1-1.5k per person per night range. Availability is still ok but starting to fill up.
Overnight via New York or Europe. Flights usually arrive in Nairobi around 11 p.m. the next day, so I suggest staying the first night at the Radisson Blu by the airport. Depart for a safari at Wilson Airport or stay a day at Giraffe Manor.
Optional Day in Nairobi at Giraffe Manor
This is the best place to stay when visiting the Giraffe Center and David Sheldrick Wildlife Trust. It’s also a super unique hotel. However, it does limit your lodge choices and adds to the cost. If you are still on the fence, I’ve included other ways to see giraffes and elephants below.
Lewa House
I think it’s a great idea to start by revisiting old memories. I’d stick with Lewa House if possible. However, Lewa Wilderness and Borana Lodge are also great backup options.
Optional Activities
I love the wide range of activities you can do at Lewa Conservancy, so it would be fun to do a non-traditional safari here. It’s an excellent place for horseback riding, mountain biking, hiking, or a scenic flight to the top of Mt. Kenya. You could also do an extra day to revisit Rutundu or try an overnight walking safari.
Fly north to the Samburu National Reserve. It’s an arid landscape with a great culture – the Samburu isn’t as touristy as the Maasai Mara. If you didn’t do the Sheldrick Wildlife Trust in Nairobi, I would stay at Sarara Camp.
Sarara Camp or Sasaab
Sarara Camp has fantastic mountain views in a remote part of the Samburu reserve. It is the best place to stay to visit the Reteti Elephant Sanctuary, which is less well known than the Sheldrick Trust, so it should be easier to secure a private visit.
If you stay at Giraffe Manor, I would pair that with Sasaab, a stylish lodge in the south. It’s more luxurious, with private plunge pools in the tents and a spa, but more expensive.
You have a couple of ways to spin the trip’s last stop. The Maasai Mara is the traditional last stop in Kenya, but since you have seen the migration in the Serengeti, you could end at an incredible lodge in Chyulu Hills instead.
Maasai Mara: Multiple Camps
Cottar’s 1920s Camp is done in a classic safari style and has a fantastic record of conservation and community. It is in the best location in the far eastern Mara, which is best positioned to see a late-season migration. Their honeymoon suites have outdoor baths.
Sala’s Camp, owned by the Giraffe Manor and Sasaab team, is also in a good position near Tanzania. It’s more luxurious, with private plunge pools, but it also costs more.
I also like House in the Wild in the Mara. It probably won’t be close to the migration in October, but the game viewing is still good year-round, and it is in a large private reserve. Finally, you could also stay at the stylish Angama Mara. It’s in a busier area, but it has one of the best views in Africa.
Chyulu Hills: Ol Donyo Lodge
Chyulu Hills is a large community conservancy in southern Kenya with views of Mt. Kilimanjaro. It is between the massive Amboseli and Tsavo East National Parks, which have the largest population of elephants in Kenya. Ol Donyo is one of the nicest lodges in Kenya and has an underground hide next to a waterhole visited by supertuskers. Prices are a little higher, around $2k per person per night, but it would be an amazing way to end your trip if you want to splurge a little.
Most flights into Nairobi are in the morning, and international flights depart around midnight, so it’s good to book a day room for your last day. The Retreat at Giraffe Manor is one of the best. The driver will take you to the airport after a relaxing day by the pool.
If you stay four nights at a Safari Collection Camp (Sasaab, Sala’s Camp, Giraffe Manor), you get 25% off your booking. This makes the camps more affordable ($1.5-1.75k) but still more than Lewa, Sarara, or Cottars.