Packing for a week on a catamaran is strange compared to other types of warm weather vacations. You need swimsuits, a cover-up, some t-shirts and comfortable shorts. That’s nearly the whole list. After three newsletters this month built around logistics, access, and the kind of planning that takes months, this one starts with the opposite: almost nothing to decide.

Greg and I spent a week sailing the US Virgin Islands with my aunt and uncle, Kathy and John, aboard a 52-foot catamaran called Grace. We’d hoped to sail the BVI, but this was not long after COVID, and the boat was US-registered, which kept us on the American side. It turned out not to matter. St. Thomas and St. John gave us more than enough — Maho Bay, Christmas Cove, Magens Bay, a string of anchorages that showed us Caribbean beauty and required nothing of us beyond showing up.

Before we ever stepped aboard, I had one phone call with Joseph, our captain. We talked through food preferences, wine, and whether we wanted to dive. That was the entire planning process. No itinerary to build, no reservations to chase. Compared to the moving parts of a trip like the one I wrote about last week in Kenya, this was almost nothing. And that contrast is the point of this blog post.

Joseph and Britta

Joseph is Captain and Chef who was classically trained at the Western Culinary Institute in Portland, OR, where he completed dual degrees in both Culinary Arts and Patisserie & Baking. He then moved to the Caribbean and spent five years as private chef aboard a 120-foot motor yacht, where he further trained in the French approach of mise en place — everything prepped, in its place, before service begins. That discipline is what makes the ease possible. He is moving constantly, mapping the next anchorage, managing the boat, prepping the next meal, all so that none of it shows.

Britta is his wife, First Mate and dive instructor — PADI-certified since 2005. Greg and I are certified divers but hadn’t been in the water in a few years, so she ran us through a refresher before our first dive. We had a second dive planned later in the week, but conditions weren’t right — so we simply didn’t go. Nobody scrambled to rebook. It just wasn’t the day for it, and that was fine.

And then there’s Zoe, their small terrier mix, who clearly ran the show and found her way into everyone’s heart. Britta paddleboarded her ashore a few times a day for potty breaks. Kathy, who has a soft spot for little dogs, became Zoe’s favorite by day two.

Egg Station

Every morning before we were even properly awake, Joseph had something waiting — fresh-baked bread, muffins, pastries, always with fruit and coffee. We’re early risers, so this was the first thing we saw most days, and on the first morning, we assumed it was breakfast.

It wasn’t. Breakfast came a couple of hours later: a full plate of scrambled eggs, perfect bacon, sausage, and something else freshly made — waffles one day, crepes another. The eggs looked like ordinary scrambled eggs. They were not. Fluffy, properly seasoned, cooked exactly enough and no more. At some point that week, one of us asked Joseph how he got them so right, and he mentioned spending a lot of time on “egg station” in culinary school. The name stuck and we still joke about it today.

Lunch and dinner kept the same rhythm — full courses, properly plated, paired with wine Joseph had stocked based on our one phone call before the trip. Old World, mostly French and Italian, whites and reds with the occasional glass of something sparkling. Nothing extravagant, but every bottle chosen with real intention, and matched thoughtfully to whatever was on the plate.

By the end of the week, Greg and I needed a few days to recalibrate (or as we jokingly call it, “diet and detox”). Nothing was wrong — we’d just spent seven days eating and drinking better and more than we do in normal life.

What This Trip Asked of Me

I’d be leaving something out if I didn’t mention why I needed this particular week. I was deep in the stress of a demanding job at the time, and my father had recently been diagnosed with cancer. I didn’t need adventure or complex logistics. I needed to be near water, surrounded by great people, and someone else to carry the mental load for a few days.

That’s what this trip gave me, almost without my noticing it was happening at the time. There was no itinerary for me to manage, no reservations to track, not even meals to choose. Joseph and Britta had already worked all of that out from our one call before we arrived — what we liked, what we didn’t, how we wanted to spend our days. Joseph managed the rest of it too — reading the weather, checking which moorings were crowded, adjusting the plan before we’d even thought to ask. Britta, meanwhile, made sure we had everything we needed and somehow cleaned and made up our cabins without any of us ever noticing. We just woke up and were somewhere beautiful, with no idea how much had already been decided on our behalf.

Africa was a trip built on logistics — camps, transfers, small planes, a level of coordination that only works with the right people managing it behind the scenes. This was the opposite kind of complexity. There was nothing to manage at all. But the advisory value here is just as real, even if it looks different. It starts with knowing this category of travel exists — a fully crewed, private sailing charter, the kind of trip most people don’t know to ask for. It doesn’t end there. A simple search will turn up dozens of crewed charters, and they are not all the same. 

There’s a real difference between a boat run with the kind of training and intention Joseph and Britta bring and one where the crew simply gets you from one anchorage to the next. Knowing which is which, and who is actually behind the boat you’re booking, is not something most people can sort out from a listing page. For a trip at this price point, that’s exactly the kind of decision worth putting in an expert’s hands.

One Thing I’d Tell Anyone Considering This

The price catches people off guard. It’s not inexpensive, and I won’t pretend otherwise. At the occupancy we sailed, four guests, it landed in the same range as a base suite on a luxury cruise line for a comparable week. What changes the equation is what that money buys. On even the best ships, you’re still one of several hundred guests, sharing restaurants, reservations, and crew attention with everyone else aboard. On Grace, every meal, every dive, every stop was built entirely around the four of us. And the math improves the more people you bring. Grace held up to eight, and the per-person cost drops meaningfully as those extra cabins fill.

What I remember most, though, isn’t the food or the wine or even the water. It’s how little I had to hold onto for that week. No decisions, no logistics, nothing to manage, just permission to be present. I came home rested in a way I hadn’t been in a long time, steadier for whatever was waiting when I got back. That feeling is exactly what I try to build for other people now, every time I design a trip.

These charters book out well in advance, often more than a year. Joseph and Britta have since retired the Grace we sailed on and have purchased a larger boat, still called Grace, for the 2027 season, which means more room and a higher price point, but also more guests to share the cost across. If a week of genuinely doing nothing, while eating better than you would at most restaurants, sounds appealing — this is worth planning for early.

Our next post will close out June with a preview of what’s ahead — Greg and I board the Scenic Eclipse I in July for an Iceland and Norway expedition cruise, and that kind of trip asks for an entirely different sort of preparation than a week sailing the Caribbean did.