I have planned every trip Greg and I have taken. The destination, the hotels, the flights, the experiences — the entire architecture of how a trip comes together has always been mine to design.

And I loved it. Planning was its own form of anticipation. The problem is that by the time you arrive somewhere you’ve spent months researching, you’ve already lived it — in your head, in reviews, in photos, in the mental model you’ve built of what each day will look like. The surprise is gone before you land. And then once you’re there, you’re managing it against the version you imagined.

Kenya changed that. 

We went in November 2018 for Greg’s 50th birthday — 18 days across four camps in some of the most remote conservancies in East Africa — planned entirely by an advisor who specialized in Kenya and knew it the way I know Italy. Every detail was handled before we landed. Every transition between camps, every bush flight, every activity. We just showed up.

I had no idea what to expect at each camp. I hadn’t researched them. I hadn’t read the reviews or built a mental model of what each place would look like. For someone who had spent decades doing exactly that, not knowing what was coming felt strange. By the end of the first day at Lewa, it felt like freedom.

Lewa Conservancy

Our guide at Lewa was Godfrey — a Maasai, second-generation safari guide, and someone who understood this landscape the way most people understand their own neighborhoods. 

Lewa is a complete ecosystem: marshland, savannah, forest, and hills, all within the same conservancy. Of the four places we visited, the natural diversity of Lewa was unlike anything I’d seen. We watched rhinos from close enough to reach out and touch them (we didn’t). We saw four of the Big Five in a single game drive.

One morning, Godfrey and John, the armed ranger, led us on a walking safari. We started from a high point and made our way down a steep embankment into a grassy clearing below. I spent most of the descent trying not to think about having to climb back up. At the bottom, the camp staff had set a beautiful breakfast table in the middle of the savannah — white tablecloth, china, comfortable chairs. I had no idea it was coming. While we ate, the guides drove the vehicles down to meet us. No hike back up.

I had never experienced a surprise on a trip like that and it really highlighted the value of not knowing everything beforehand.

Loisaba and the Maasai Mara

From Lewa we flew to Loisaba — a rockier, drier landscape that reminded me, unexpectedly, of Texas. The elephants there were plentiful but felt different: something about the prickly pear cactus and the terrain made them seem more agitated, less settled. What Loisaba gave us was the night sky. We slept on a star bed — a king-sized bed on a wheeled platform that rolls out of an open-sided shelter into the open air, covered only by mosquito netting. The Milky Way at that latitude, with no light pollution, is not a few scattered stars. It’s bands of light across the full width of the sky. Watching the sun rise from an open-air bed in the middle of Kenya the next morning is not something you forget.

Then the Maasai Mara, the northern extension of the Serengeti, where the camps operated by Great Plains Conservation sit on a private conservancy adjacent to the national park. This distinction matters more than most travelers realize. On the conservancy, we drove for hours and rarely saw another vehicle. The animals moved freely and close. One morning we drove into the national park before dawn for a hot air balloon safari over the Mara. On the drive out afterward, we counted 10 – 12 safari vehicles surrounding a single cheetah. The contrast with the conservancy, where we’d driven for hours without seeing another vehicle, was immediate and impossible to forget.

It was also in the Mara that we came upon Figlet. The guides knew her by name — a young leopard who had made her territory in the trees that lined the river near camp. We came upon her on an evening game drive, playing with a warthog she’d caught, or as we’d joked at the time, playing with her food. Tossing it the way a house cat plays with a toy. She looked up at us once, then went back to her business. We sat observing her for a long time.

ol Donyo Lodge

The final camp was ol Donyo Lodge in the Chyulu Hills — a Great Plains Conservation property and Relais & Châteaux member set on private Maasai-owned land between Tsavo and Amboseli, with views of Kilimanjaro on clear mornings. We celebrated Greg’s birthday at that camp, and the staff marked it with a private table and a rendition of happy birthday in their tribal tradition.

On an evening drive, our guide took us up a steep hillside to a place he knew a pride of lions frequented. Four females and ten or twelve juveniles. The females were preparing to hunt; the cubs were tumbling over each other and climbing on the adults. We were close enough to photograph them without zoom. I had my camera and just observed their ritual for a while.

The other experience I think about most from ol Donyo happened back at the camp. There is an elephant hide — a bunker set mostly below ground with an open viewing window at ground level, positioned beside a waterhole. One afternoon we skipped the game drive and went down there instead. The staff brought us glasses of white wine. We sat and watched elephants and various other animals come to the water, maybe twenty feet away, completely unaware of us. There is something about being invisible to wild animals that is very difficult to describe. I had a glass of wine in my hand and three elephants in front of me and I was absolutely, completely present.

That’s the thing I keep coming back to when I think about Kenya. Not any single moment, but the cumulative effect of not managing anything. I didn’t know what was coming next. I didn’t know what the next camp would look like. I just arrived and it was always more than I’d imagined. That’s not something you can create for yourself. It requires someone who knows the destination, knows what you’ll value, and has done the work of anticipating everything before you land.

It’s part of why I do this work now. I spent decades as the planner of my own trips. I know what it costs to carry that — the mental load of every detail, every contingency, every thing that could go wrong. Kenya was the first trip where someone else carried all of it, and I finally understood what travel could feel like when I wasn’t running it.