The Mid-Lifers

Some places are trips. Italy is our love story.

Our first visit was with our boys, just 13 and 8. A few unforgettable nights in Rome, wandering streets where ancient ruins sit casually beside busy cafés. We then rented a car and settled into a Tuscan villa in Sovicille for five golden days — mornings exploring hill towns, afternoons by the pool, and evenings cooking simple meals together in our own kitchen with fresh local ingredients. Long drives along winding roads lined with iconic cypress trees became part of the rhythm of our days. It was family travel at its best: cultural, relaxed, and beautifully unhurried.

We loved it so much we returned two years later — Rome again (because how could you not?), then the high-speed train to Florence and on to Venice.

When the world began to  cautiously reopen after COVID, I went back once more for five indulgent nights in Rome with a girlfriend. Same country. Fewer playgrounds, more lingering dinners. Just as magical.

I love the ancient architecture, the unapologetically great food, and the wine that somehow tastes better simply because you’re there. You don’t just see the history — you feel it.

Italy comes alive in a way few places ever have for us. It’s familiar. Almost like home.  We’re so comfortable and enthralled by Italy that we find ourselves simply strolling the streets, soaking in the culture, stopping for coffee, or lingering over wine and people-watching. Here, we don’t feel the need to schedule tours — Italy speaks for itself.

All I know is this: every time we leave, we’re already thinking about going back. We even had Sicily and Malta booked at one point — hotels reserved, transport secured, plans half-dreamed — before life pivoted us toward Thailand instead. Italy will wait. It always does - it knows we’ll be back.

Our itinerary at a glance:

Trip One:

Rome - 3 nights

Stay: Hotel Condotti

Tuscany - 5 nights

Stay: Costello Poggiarello, Sovicille

Cinque Terre - 3 nights

Hotel Pasquale, Monterosso al Mare, Cinque Terre

Trip Two:

Rome - 4 nights

Stay: Hotel Condotti

Tours: Vatican and Sistine Chapel Tour (withdrew)

Florence - 3 nights

Our stay is no longer open

Venice -  3 nights

Stay: Airbnb

Tours: Gondola ride

Trip Three:

Rome - 5nights

Stay: Airbnb