A 75% transfer bonus from Chase made the math even better. We took advantage of Marriott’s “Book 4 Nights, Get the 5th Free” benefit, and our total came to 900,000 points for five nights — an extraordinary redemption for a property of this caliber.

For flights, there’s only one nonstop from the U.S. to Nairobi, operated by Kenya Airways out of JFK. We used Flying Blue miles at 115,000 points each for business class.

Then, 48 hours before departure, a snowstorm out of JFK canceled our flight. The airline offered to rebook us two days later, which would have conflicted with our resort reservation, so we opted for a full refund of our points instead. With no business class availability remaining to Nairobi on such short notice, we made the call to fly economy rather than cancel the trip altogether. We rerouted through Paris on what turned out to be a very long journey, but we made it.

My sister and brother-in-law met us at Nairobi’s airport, where we spent our first night at the Four Points by Sheraton Nairobi Airport. I’d strongly recommend it: it’s just minutes from the terminal, comfortable, and has a solid restaurant.

One small moment worth noting: I’m used to being the one who receives upgrades as a Hyatt Globalist. But here, it was my brother-in-law’s turn. His Marriott Ambassador Elite status earned him a welcome fruit and cheese plate and a very nice room upgrade — and he enjoyed every second of it.

Getting There

We booked all of our round trip airport transportation through Viator, a popular online travel experience platform, taking advantage of a Rakuten 22% cash back promotion over Black Friday. For those unfamiliar, Rakuten is a cash back portal that rewards you for shopping through their links, and stacking it with a Viator booking was a nice way to save on logistics.

The next morning, a driver took us to Wilson Airport for a short hop to Keekorok Airstrip — about 45 minutes by small bush plane.

I’ll be honest: it was bumpy enough that I was very ready to land. On the return flight, I took Dramamine, which made a world of difference. If you’re at all sensitive to motion, don’t skip it.

At the airstrip, we were met by our guide, Lorna, who would be with us for the entire five days. Spending that much time with a single guide can go either way — and we were extremely grateful we got the one we did. Lorna was warm, funny, and endlessly knowledgeable. Her go-to phrase was “Hakuna Matata,” and she meant it. Whatever we wanted, she made it happen.

I had read that the JW Marriott Masai Mara was a “luxury tented camp.” What we found felt more like luxury cabanas — spacious, beautifully designed, and far more substantial than the word “tent” implies. There’s no air conditioning, and yes, the afternoons got warm. But the fans kept things manageable, and the nights were perfectly comfortable.

The staff instructed us that once the sun goes down, we should request a golf cart to escort us back to our rooms each night. I thought this was a bit of theater and not necessary. Sure enough, on our ride back one night, a hyena was waiting in the path to our room. I didn’t second-guess the policy after that.

We were particularly taken with the outdoor showers and hot tubs. Small touches like these added to the feeling that this place had been designed with real care.

One of my favorite perks was the daily camera rental and free use of binoculars — something that wasn’t offered at another safari property we had considered. The difference between a high-resolution safari camera and a smartphone is stark, especially when you’re 10 feet from a lion. To top it off, the in-house photography staff reviewed our shots each evening and offered personalized tips, which our entire group found incredibly valuable.

The resort offers several additional activities: archery, spear throwing, beadmaking, and a visit to a local Masai village. The village visit costs $40 per person; everything else is complimentary.

We did all of them over the course of our stay. I wouldn’t call them exceptional, but they were genuinely informative and a nice way to fill the time between drives.

While the resort rate covers meals, drinks, and game drives, there are a few additional expenses worth budgeting for before you go.

The Masai Mara National Reserve charges a $100 per person, per day entrance fee, which added up to $1,000 for my wife and me over five days.

The camera rental is $25 per camera for the entire stay; we shared one between the two of us, and it worked perfectly.

The Masai village cultural visit is $40 per person.

The resort also provides recommended tipping guidelines, and you can settle tips either in cash or on your hotel folio. We tipped our guide, Lorna, directly in cash and put the remaining tips on the bill.

I was struck by how many guests were returning visitors — annual regulars who had built real relationships with their guides over years and even decades. One couple on our bush plane had been coming back every year for 14 years, and their guide was practically family. I usually prefer to explore new places each trip, but after this one, I completely understood the appeal.

It was also surprisingly easy to connect with other guests. Since everyone is essentially experiencing the same activity each day, conversation flows naturally. Comparing notes over dinner about which animals you spotted or where your guide took you makes for an instant icebreaker with total strangers.

This was one of the rare trips where we traveled with another couple beyond immediate family, and it made a real difference. Good travel companions elevate the whole experience, and this trip was proof of that.

Getting to Kenya from the United States isn’t easy, and it isn’t cheap — even with points.

We traveled in January 2026, which turned out to be a wonderful time to visit, with excellent wildlife sightings and comfortable temperatures.

On the way home, we found business class seats through Istanbul on Turkish Airlines for 115,000 points each — a wonderful way to end the trip and an excuse to enjoy the Turkish Airlines lounge, which we’d loved on a previous visit.

This was, without question, one of the best trips we have ever taken.

All thanks to a few million Marriott points and a brother-in-law who finally decided to use them.