Romantic Getaways

Italy, made for two.

Rome → Florence → Val d’Orcia → Pienza. Four chapters, one journey — shaped around slowing down together, not checking places off a list.

A sunset view over the Tuscan countryside in Italy

Chapter 01 · Rome

Begin where every street has a story.

Rome doesn’t need much of an introduction. But experiencing it together is different. Start with the landmarks you’ve always wanted to see, then leave room for the quieter parts: an unhurried morning, a walk through Villa Borghese, an evening wandering Trastevere, and dinner without watching the clock.

This isn’t about fitting all of Rome into a checklist. It’s about having enough time to notice it.

Little moments worth making time for

  • Early morning around Rome's historic center
  • A slow walk through Villa Borghese
  • Sunset from Pincio
  • Dinner and an evening wander through Trastevere
The Colosseum's ancient arches glowing at golden hour above a quiet cobblestone plaza in Rome
The Ponte Santa Trinita bridge reflected in the Arno river at sunset in Florence

Chapter 02 · Florence

Slow down. Florence rewards it.

Florence is compact enough to explore without turning the day into a race. Cross the Arno, wander beyond the busiest streets, stop when somewhere looks inviting, and save part of the evening simply for the view.

The art and architecture may bring you here. The pleasure of having nowhere else to be for a few hours is what makes Florence feel made for two.

Little moments worth making time for

  • A morning through Florence's historic center
  • Crossing the Arno and exploring the quieter side of the city
  • A long Tuscan lunch
  • Golden hour overlooking Florence
  • An evening walk near the river

Chapter 03 · Val d'Orcia

Then, let Tuscany change the pace.

Leave the city behind and the scenery begins to open up. Val d’Orcia is Tuscany in long, beautiful sentences: rolling hills, cypress-lined roads, vineyards, olive groves and hill towns appearing on the horizon.

Here, the journey between places matters almost as much as the places themselves. Take the slower road. Stop when the view asks you to. Stay somewhere that makes going out again feel optional.

Little moments worth making time for

  • Driving the country roads without rushing
  • A vineyard or wine-country stop
  • Long lunches overlooking the hills
  • Small villages along the way
  • An evening at an intimate countryside stay
A cluster of tall cypress trees crowning a rolling green hill in Val d'Orcia under a clear blue sky
A narrow, lantern-lit stone street in Pienza leading toward the historic clock tower at dusk

Chapter 04 · Pienza

End somewhere worth lingering.

Pienza doesn’t ask for a packed itinerary. Its Renaissance center, stone streets and views across Val d’Orcia make it the kind of place where a simple walk can become the best part of the day.

Take your time. Find a table. Wander a little more. Watch the light change over Tuscany. Sometimes the most romantic part of a journey isn’t something you booked at all.

Little moments worth making time for

  • Wandering Pienza's historic center
  • Finding Via dell'Amore
  • Pecorino di Pienza and a leisurely lunch
  • Views across Val d'Orcia
  • One last Tuscan sunset

Stay Your Way

Accommodations shaped around how you like to travel.

Essential

Beautiful & Comfortable

Well-reviewed accommodations chosen with location, comfort, and value in mind.

Signature

Boutique & Character

Distinctive stays selected for atmosphere, design, and a stronger sense of place.

Elevated

Exceptional Stays

Luxury properties, upgraded room categories, and special settings when available.

Not sure which fits you? That’s completely fine. We’ll help you find the right balance for your trip.

The Journey Is Yours

Italy doesn’t have to look the same for everyone. These four chapters are a starting point. Stay longer in Florence. Add another night in Tuscany. Change the pace completely. We’ll shape the journey around how you want to experience Italy together.

Plan Your Italy Journey

Plan Your Italy Journey

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