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 […]

Healdsburg is one of those places I keep coming back to, and I’ve written before about why familiar destinations often reward return visits more than new ones do. The town has a certain quality to it — the square, the walkability, the wineries close enough that a morning tasting and a long lunch don’t require […]

In late June last year, on a hillside above the Adda River valley in northern Italy, Greg and I spent an afternoon walking through vineyards with a man named Luigi who spoke not a word of English. Valtellina isn’t a place most travelers have on their list. It’s a beautiful, narrow alpine valley in Lombardy, […]

There’s a version of cruising most people have experienced, or heard enough about to have written it off entirely.  The ships that carry five, six, seven thousand passengers. The bars with lines at any hour. The pool deck that feels like a waiting room. The dining room food that declined year by year until the […]

If you’ve been reading along for a while, you may remember me mentioning Little Palm Island. I’ve referenced it more than once as one of those places that belongs to its location in a way few resorts do — small, intimate, adults only, accessible only by boat, with no televisions, no phones in the rooms, […]

There’s a moment on every trip when you stop traveling and actually arrive. Not when the wheels touch down, but something subtler — a shift in your nervous system when the weight of everything you left behind stops competing with where you are.  That moment doesn’t happen automatically. And how quickly it happens — or […]

I’m writing this from my seat in front of a fireplace at Roche Harbor, on the northwest side of San Juan Island, with a glass of wine and a view of the marina as the sun sets behind the trees. This week’s newsletter is a little different. Instead of writing about how to think about […]

Most people start planning a trip by picking a destination. It seems logical. But I’ve found that destination is rarely the decision that actually determines how a trip feels.  There are five decisions that shape every journey — and most travelers only think consciously about one of them. The other four happen by default.  How […]

People often ask me how to plan the “perfect” trip — as if there’s one formula that works for everyone. There isn’t. Because travel preferences don’t change because people lose interest. They change because life changes.  What felt exciting at one stage of life — packed itineraries, constant movement, doing everything — can feel exhausting […]

There’s a question I hear constantly: “When is the best time to visit?” It’s reasonable. And almost always unanswerable — not because I don’t know the answer, but because there isn’t one single answer that works for everyone.  The best time depends entirely on how you like to travel.  Some people thrive on energy and […]