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A cypress-lined gravel road leading to a hilltop stone estate, Val d’Orcia, Tuscany

Sample journey · 12–16 days

Italy — a journey through food, culture & place

Bologna and Emilia-Romagna, Florence, the Tuscan countryside and Puglia — mostly by train

Photo: Kristof Van Rentergem / Unsplash

Illustrative journey ideas — not bookable packages. No prices, dates or accommodation are implied.

Italy feels familiar — which is exactly why it’s worth knowing more deeply. This journey begins in Bologna, a city many pass by, though it’s one of the country’s great food capitals. From there, by train to Florence, then slower days in the Tuscan countryside, and finally the southern sun and olive groves of Puglia.

It’s also a reminder that a journey doesn’t have to be far away to deserve careful planning. Closer to home, the details — where to stay, when to reach the market, which day for a farm and which for a museum — are often what separate a good trip from one you’ll remember for a long time.

The route

The journey

  1. Bologna
  2. Modena & Parma
  3. Florence
  4. Val d’Orcia
  5. Puglia
  1. Bologna’s towers and red rooftops, with the San Luca sanctuary on the hill beyond

    01Days 1–3 · Bologna

    Arcades, markets and fresh-pasta workshops

    Bologna’s old town is miles of covered porticoes, medieval towers and the market lanes of the Quadrilatero, hung with hams and stacked with wheels of cheese. It’s worth learning to make tortellini with a local cook, walking the arcades up to the San Luca sanctuary and spending an evening in a small osteria.

  2. Rows of small wooden barrels where balsamic vinegar is aged, Modena

    02Days 4–5 · Modena & Parma

    Where Parmigiano and balsamic are made

    Short train rides from Bologna lead to Modena and Parma. Mornings might mean a dairy making Parmigiano Reggiano, afternoons a family acetaia where balsamic vinegar ages in wooden barrels for decades. In between, Romanesque cathedrals and quiet piazzas.

  3. The dome of Florence Cathedral above terracotta rooftops in evening light

    03Days 6–8 · Florence

    The Renaissance, unhurried

    The fast train from Bologna to Florence takes under an hour. Here it’s worth choosing a few things and knowing them well: the Uffizi with a guide early in the day, artisan workshops in the Oltrarno, the San Lorenzo market and sunset over the domes from the hill of San Miniato.

  4. The view from Montepulciano over vineyards, olive groves and the San Biagio sanctuary, Tuscany

    04Days 9–11 · The Tuscan countryside

    Hills, vineyards and a farm stay

    This is easiest with a car or a driver. A farm stay in the Val d’Orcia or Chianti, breakfast with the estate’s own olive oil, a wine tasting in Montalcino or Montepulciano and walks through Pienza’s stone lanes. The pace is slow — and that’s exactly the point.

  5. The white old town of Ostuni and olive groves stretching towards the sea, Puglia

    05Days 12–16 · Puglia

    White towns and olive groves

    South by a longer train ride down the Adriatic coast or a short flight to Bari or Brindisi. In Puglia you stay in a masseria — a restored farmhouse among centuries-old olive trees. From here it’s easy to reach white Ostuni, the trulli of Alberobello, baroque Lecce and, if you wish, Matera in neighbouring Basilicata.

Experience highlights

  1. 01

    Handmade pasta in Bologna

    A class with a local cook — from rolling the dough to folding tortellini.

  2. 02

    A morning at a dairy and an acetaia

    Seeing how Parmigiano Reggiano and traditional balsamic vinegar of Modena are made.

  3. 03

    The Uffizi with a guide

    A morning with a guide turns Botticelli and Leonardo into far more than textbook images.

  4. 04

    Dinner at a masseria

    Orecchiette, burrata and local wine beneath the olive trees on a warm Puglian evening.

First, we listen. Then, we explore what's possible.

Make it your own

  • The Amalfi Coast instead of Puglia

    From Florence by train to Naples, then Pompeii, Sorrento and the coastal towns. A busier but spectacular finale.

  • A shorter week-long version

    Bologna and Florence with a day in the Tuscan countryside — all by train, no car needed.

  • As a family

    Pasta classes, a farm stay with a pool and animals, and in Puglia, shallow Adriatic beaches.

  • In another season

    Spring and autumn are often the most pleasant; autumn brings the grape and olive harvests, while summer in Puglia is hot and busy.

Practical considerations

  • Between the big cities, fast trains are usually easier than a car; in the countryside, the reverse is true.
  • Popular museums such as the Uffizi are worth reserving ahead in the busy season.
  • Many historic centres have restricted traffic zones, so a car is best collected only when heading into the countryside.
  • Summer can be very hot, especially in the south — a midday rest is worth planning in.

General guidance only. Seasons, weather and wildlife are never guaranteed, and travel requirements are always worth checking before you go.

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