Milestone travel, designed
A honeymoon isn't a destination. It's a piece of memory you're building on purpose. Anniversaries, 50ths, retirements, elopements, second marriages — same principle. These are the trips couples still talk about twenty years later. I plan them that way: slowly, specifically, and with enough room in the pacing that the moment has space to land.
What I plan
Five milestones, one philosophy — build the trip around the moment.
Honeymoons
From 10-day Italy-and-the-islands classics to month-long round-the-world itineraries. See also the honeymoon planning timeline.
Anniversaries & Vow Renewals
A return to where it began, or something new for the twenty-fifth.
Milestone Birthdays
40, 50, 60, 75 — trips structured around the person, not just the number. See also milestone birthday trips.
Retirement Journeys
The long one. Transatlantic crossings, round-the-world cruises, the 60-day stretch you've earned.
Second-Chapter Weddings & Elopements
Destination celebrations sized for 6, 16, or 60. See also Groups & Celebrations.
Trip shapes I'm planning right now
Five milestones in motion this season — pick the one that sounds like yours, take the quiz if it doesn't.
Italy in Five Itineraries
Five shapes for the same country, depending on how you want to travel. Pick the week that matches you — not the one in the magazine.
Read the dispatch →︎ Honeymoon · 7–10 nights · May–SepSwitzerland for Two
Lauterbrunnen Valley, Zermatt, the Bernese Oberland by train. The country I keep sending honeymoons to — the proposal trips, the second-decade returns, the just-because-they-asked.
Open the guide →︎ Milestone · 7–14 nights · Year-roundA Milestone on the Water
A 40th, a 50th, a 70th — celebrated on a ship that throws the party without making it the staff's project. The Cunard transatlantic is the load-bearing example.
Read the dispatch →︎ Destination wedding · 5–10 nights · May–OctA Wedding in Tuscany
Villa, vows, the people you actually want at the table. The guide for couples doing it small and to taste.
Read the dispatch →︎What I do for the moment
I ask what the day is for.
Before I book anything, I ask what you're celebrating, what you already know you want, and what you're quietly hoping the trip will do. The itinerary follows from that — not the other way around.
I put real money where it matters.
Suite upgrades, private transfers, the cabin on the bow instead of the stern, the table at the window. I know which hotel's "honeymoon amenity" is a bottle of prosecco and which is a private beach dinner — and which one you'll actually remember.
The quiet enhancements add up.
The relationships behind these trips include amenities that don't appear on public rates and aren't bookable directly. They're calibrated to your specific stay — and the best of them tend to land at check-in, not on the proposal. A trip planned this way feels elevated, not engineered.
Many of the properties I anchor honeymoons around sit in the Belmond Hotels collection →︎
The transatlantic crossing I keep coming back to is Cunard →︎
Trips like these are planned on a fee that scales with their complexity — here's what it actually buys →︎
For the longer version of how I think about all this — the manifesto →︎
Who this is for
Couples planning a first honeymoon and wanting it done beautifully. Same-sex couples who want to celebrate without thinking about where they can and can't. Interfaith couples designing a honeymoon that weaves both traditions. Parents whose kids are finally old enough to leave behind. Second-chapter couples doing it smaller, smarter, and more to taste. Anyone marking a number worth marking.