Honeymoons, anniversaries and big birthdays in Italy, Portugal and Greece. Fewer hotel changes, more long dinners, and the surprises arranged before you land.
Couples, 7 to 14 days
Best in May, June and September
Planning from $500
What it can look like
Three nights in Positano, then four on a quiet Greek island
A private boat day with a swim stop nobody else knows
The table at sunset, booked months ahead
A driver waiting at every arrival, so you never drag a suitcase up a hill
What I plan for you
Hotels I’ve stayed in myself, an order of travel that keeps you from packing every two days, and the small moments: flowers in the room, a cooking class for two, a late checkout on the last day.
A week, roughly
Arrive in Naples, driver to Positano. Two slow days on the coast, one of them by boat. Ferry to Capri for a night. Fly to Santorini for a sunset dinner in Imerovigli, a day on a sailing boat and a last morning with nowhere to be.
Good to know
Planning is $500 and comes off your booking. For June and September, reach out eight to twelve months ahead.
Plan a trip like this
Planning from $500
Send me a Trip Brief with your dates and who’s coming. I reply within one business day.
