Caribbean: The Cruise and the Keynote

Our friend Haresh turned 50 and celebrated by chartering a cruise from Antigua to St. Lucia and inviting about 60 of his closest friends. G and I flew into Antigua the day before and spent the night at Hodges Bay Resort & Spa, about ten minutes from the airport. Modern resort, good pool, the kind of place that makes you briefly consider not getting on the ship the next day. We got on the ship.

Six days on the Emerald Sakara, a yacht-style ship small enough that you know everyone on board and large enough that you can find a quiet corner when you need one.

I gave a keynote on the ship. Haresh had asked me to speak at one of the evening events and the topic was something I'd been developing about how people update the operating systems on their phones every month but never update the operating system running their own lives. I called it "The Operating System Update." I delivered it in the ship's main lounge to about 50 people, most of whom had a drink in hand and all of whom were on vacation, which is either the best or the worst audience for a keynote. It went well. The drinks helped. People came up afterward and continued the conversation, which is always the sign that something landed.

The ship itself was beautiful. The Emerald Sakara is a newer vessel with a pool on the top deck, multiple restaurants, and suites that felt more like hotel rooms than cruise cabins. Our room had a balcony overlooking the water and I'd wake up every morning to the sound of the ocean and the sight of a different island on the horizon. The Caribbean from a ship is a different experience than the Caribbean from a resort. You see the islands from the water, approaching them slowly, watching the green mountains rise out of the blue, and it gives you a sense of scale and geography that you don't get when you fly in and go straight to the pool.

We stopped at a few islands along the route. St. Barts was the standout. We had dinner at Le Petit Plage right on the beach in St. Jean, feet in the sand, rosé in hand, grilled fish that was fresh off the boat. The whole table ordered the same thing and nobody regretted it. St. Barts has that effortless French Caribbean energy where everything is expensive and beautiful and nobody seems to be working very hard.

One of the most memorable moments of the entire cruise was the Holi party Haresh organized on one of the beach stops. Colored powder, music, the entire group of 60 people throwing color at each other on a Caribbean beach in the afternoon sun. G was purple and yellow and laughing harder than I'd seen her laugh in months. I was every color. The photos from that afternoon are some of the best we have from any trip. It wasn't planned or polished. It was just joy, the kind that happens when someone cares enough to create the conditions for it.

The other days on shore were spent walking small towns, eating at beachside restaurants where the fish was pulled from the water that morning. On one of the island stops we rented a jeep and drove to a beach on the windward side that the crew had recommended. The road was unpaved and the beach was empty except for us and a fisherman repairing a net. We swam in water so clear you could see your feet on the sand ten feet down. G floated on her back with her eyes closed for about 20 minutes and didn't say a word. That's her version of meditation. No app required.

G and I found a rum bar on another stop that was literally a shack with a plywood counter and a guy making drinks from bottles with handwritten labels. There was no menu. You told him what you liked and he made something. The rum punch was the strongest thing I've tasted since the mezcal in Scottsdale and G drank two and became very friendly with a parrot that lived on the bar's railing. The parrot was not friendly back. G was undeterred. She named him Gerald. Gerald did not acknowledge the naming.

The evenings on the ship had their own rhythm. Dinner was communal, long tables, Haresh's friends mixing and reconnecting. The conversations ranged from business to travel to personal stories that only come out after the second bottle of wine on a boat in the Caribbean. G and I met a couple from London who knew Nora (small world, smaller when you're on a boat with 60 people) and we spent three evenings in a row talking with them on the top deck after dinner, watching the stars and the phosphorescence in the wake of the ship.

We ended in St. Lucia, where we spent two nights at the Rabot Hotel from Hotel Chocolat in Soufriere. The hotel sits on a cacao estate with views of the Pitons, the two volcanic peaks that are the most iconic image of St. Lucia. The rooms are open-air with louvered walls instead of glass windows, which means the jungle comes inside: sounds of birds and insects and rain on leaves. The restaurant uses cacao in nearly everything, including savory dishes, which sounds gimmicky and isn't. The cacao-rubbed steak was one of the more interesting things I've eaten.

The Pitons from the hotel terrace at sunset are something I'll carry with me. Two green spires rising straight out of the Caribbean, the water between them catching the last light. G sat on the terrace with a glass of wine and said "I could stay here for a month." She said the same thing about the Heuriger in Vienna and the pool in Scottsdale and the bridge in Reynosa. She says it about every place that stops her brain. I've stopped pointing this out. She's right every time.

We flew home from St. Lucia tanned and full of rum and carrying a bag of cacao nibs from the estate that we've been putting in smoothies ever since.