Itinerary
- Day 1
Abbadia a Isola to Colle Val d'Elsa
You'll start with a welcome briefing from your CEO and group, then head to the medieval village of San Gimignano where you can look at its Gothic and Romanesque architecture. After grabbing lunch in town, the trek begins along the ancient Via Francigena through the Tuscan countryside. You'll walk past cypress-lined paths and stone farmhouses on your way to Colle Val d'Elsa.
- Meals
- Dinner
Included Activities
- Welcome Moment - Meet Your CEO and Group
- San Gimignano Guided Tour
- Walk Abbadia a Isola to Colle Val d'Elsa
Landmarks/POIs San Gimignano Abbadia a Isola Colle Val d'Elsa - Day 2
Colle Val d'Elsa to Monteriggioni
From Colle Val d'Elsa, you'll hike along part of the ancient Francigena way to reach the medieval walled village of Monteriggioni. The charming streets and well-preserved medieval walls are worth exploring, and you'll have lunch featuring local flavors. Afterward, you return to Colle Val d'Elsa where the rest of the afternoon is yours to wander around at your own pace.
- Meals
- Breakfast, Lunch (Local flavors at a relaxed setting)
Included Activities
- Hike to Monteriggioni
Landmarks/POIs Monteriggioni - Day 3
Montefioralle to Greve in Chianti
Starting from Montefioralle, a small town built around a historic castle, you'll take a scenic walk through rolling Chianti countryside with views of vineyards and olive groves. Lunch happens at a traditional farmhouse where you'll try rustic Tuscan flavors, then you continue to Greve in Chianti. The triangular piazza is worth exploring, and you'll finish the day relaxing with a cold drink at your Tuscan villa overlooking the vineyards.
- Meals
- Breakfast, Lunch (Rustic lunch at a traditional farmhouse with local Tuscan flavors), Dinner
Included Activities
- Stroll around Montefioralle
- Walk from Montefioralle to Panzano
- Molino di Grace Visit & Lunch
- Greve In Chianti Visit
Landmarks/POIs Montefioralle Greve in Chianti Molino di Grace - Day 4
Greve in Chianti to Siena
You'll transfer to Siena and walk through the historic medieval city with a local guide, checking out Piazza del Campo and the Duomo. Lunch at a local restaurant brings authentic Tuscan food, and the afternoon gives you free time to soak in the atmosphere or browse shops. Later, you'll sample four varieties of wine from local Tuscan estates and learn about winemaking in Chianti, finishing with a special wine pairing dinner.
- Meals
- Breakfast, Lunch (Authentic Tuscan flavors at a local restaurant), Dinner (Special wine pairing dinner)
Included Activities
- Siena Walking Tour
- Wine Pairing Dinner
Landmarks/POIs Siena Piazza del Campo Siena Duomo - Day 5
Siena to Val d'Orcia to Cittá della Pieve
You'll walk the Pienza loop trail in the UNESCO World Heritage Val d'Orcia, beginning in the Renaissance city of Pienza. Along the way, you pass the Romanesque parish church of Corsignano and walk through hillsides dotted with cypress trees, including the panoramic Strada dei Gladiatori landscape. A tasting of locally produced pecorino and ricotta cheeses paired with Montepulciano wine happens next, then a local guide leads you through the ancient hilltop town of Montepulciano before you head into Umbria to Città della Pieve.
- Meals
- Breakfast
Included Activities
- Walk The Pienza loop
- Pecorino Cheese Tasting
- Montepuliciano Visit
Landmarks/POIs Val d'Orcia Pienza Corsignano Montepulciano Cittá della Pieve - Day 6
Cittá della Pieve
This morning, you'll work with a local chef learning to prepare classic Italian dishes like tagliatelle with ragù or creamy tiramisu. You'll enjoy what you've cooked with glasses of wine, then have a leisurely afternoon. A local guide takes you on a walking tour of Città della Pieve, known as the birthplace of Renaissance painter Pietro Vannucci.
- Meals
- Breakfast, Lunch (Lunch following cooking class with prepared dishes and wine)
Included Activities
- Guided Walking Tour of Cittá della Pieve
- Cooking Class - Cittá della Pieve
Landmarks/POIs Cittá della Pieve - Day 7
Cittá della Pieve to Rome
You'll transfer to Rome and do a short orientation walk with your CEO. Then choose your own adventure: either a walking tour exploring the historical centre including Piazza Barberini, Piazza di Spagna, Trevi Fountain, and Piazza Navona, or hop on the back of a Vespa with a professional driver for an adrenaline-filled tour from Trastevere to the Colosseum and beyond. Breakfast and dinner are included.
- Meals
- Breakfast, Dinner
Included Activities
- Rome Orientation Walk With CEO
- Rome Walking Tour or Fully Guided Vespa Tour
Landmarks/POIs Rome Piazza Barberini Piazza di Spagna Trevi Fountain Piazza Navona Trastevere Colosseum - Day 8
Rome
Your adventure wraps up today. You can depart at whatever time works best for you.
- Meals
- Breakfast
