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Travel/Study
An active exploration of what makes Italy "Italia"

Tuscany Walk

A jaunt through the rolling hills to experience quintessential Italy: world-class wines, luscious cuisine, and medieval villages filled with history.

Overview

A walk through the Tuscan wonderland

This walking trip truly has it all—vineyard strolls, delicious picnics, medieval castles, and, of course, some of the most delectable wines the world has to offer. Delve deep into Italian history, stroll through medieval villages that were once home to Popes and nobles, and engage with one another in meaningful conversations against the backdrop of some of Europe's most enchanting scenery.

We explore the birthplace of Chianti wine, wander among the Sangiovese vineyards of Brunello, and explore Tuscany's least known region, the Maremma. In addition to hilly hikes along cypress-lined paths, we also meander cobbled streets during visits to medieval hill towns and renaissance villages such as San Gimignano, Siena, and Montalcino.

Dates

May 23–June 1, 2026

Duration

10 days

Price

From $11,795 per person

Trip size

30 participants
Reserve(opens new window)

Faculty leader

A different kind of classroom

With renowned Stanford faculty and scholars leading the way, every Travel/Study trip is a one-of-a-kind educational experience.

Roberto D'Alimonte

LUISS Guido Carli University, Rome



A professor of political science and noted Italian political journalist, Roberto brings his unique understanding of modern European politics to Stanford travelers.

Learn more about Roberto

“Roberto was the highlight of the trip—personable, charming, incredibly knowledgeable and a great communicator.”

—Pamela Phillips

Meet our walking guide

Peter Watson has led the way for Stanford travelers across Western Europe since 1996. His carefully crafted itineraries reflect his passion for the culture and history of the regions we visit. A graduate of Oxford University in French and Spanish literature, Peter provides insightful commentary along our walks, adding to the trip’s educational experience.

Itinerary

Chart your course of discovery

Walk through some of the most scenic landscapes of Italy, where Romanesque churches, medieval castles, and monasteries filled with beautiful frescoes dot the rolling hills and cypress trees and olive groves line our routes. Along the way, sample the region’s pastas, aromatic olive oils, and famous wines during picnic lunches and dinners in superb restaurants.

  • Florence, Italy / Gaiole in Chianti

    Upon arrival in Florence’s Amerigo Vespucci Airport, meet fellow travelers and transfer to our hotel, a restored medieval monastery located in the heart of Chianti. Gather this evening for a welcome wine reception and dinner.

    Accommodations:

    Castello di Spaltenna

    Included meal: Dinner

  • Monti del Chianti

    Our first walk begins on the eastern slopes of the Monti del Chianti. Meander through isolated farming villages with breathtaking views over the Arno Valley and visit the imposing Castello di Brolio, situated on the Ricasoli estate and first among wineries of the Chianti Classico DOCG.

    Accommodations:

    Castello di Spaltenna

    Included meals: Breakfast, lunch and dinner

  • Strada dei Castelli del Chianti

    Today, we walk along the Strada dei Castelli del Chianti, a route that takes us past Romanesque churches and medieval castles nestled in the thick woods. Stop to visit the  Castello di San Polo, then continue to the medieval hilltop town of Radda in Chianti before turning back to our hotel by road.

    Accommodations:

    Castello di Spaltenna

    Included meals: Breakfast, lunch and dinner

  • Gaiole in Chianti / Siena

    Depart this morning for the Tuscan village of Colle di Val d'Elsa to begin our walk through scenic hill country to San Gimignano. After a stroll through the town with its 13th-century walls and numerous medieval towers, continue by road to Siena.

    Accommodations:

    Grand Hotel Continental

    Included meals: Breakfast, lunch and dinner

  • Siena

    Today, we discover the many art treasures of Siena and enjoy some time to wander its cobbled alleys and historic streets. Take in the shell-shaped Campo, Siena's famous main piazza—site of the biannual Palio horse race and locale of the magnificent Palazzo Pubblico.

    Accommodations:

    Grand Hotel Continental

    Included meal: Breakfast

  • Siena / Bagno Vignoni

    After breakfast, travel south to the medieval Benedictine abbey of Monte Oliveto Maggiore, stopping in to see the exquisite frescoes by Sodoma and Signorelli that line the monastery cloisters. Then, walk down to the walled town of Buonconvento through the dramatic landscape of the Crete Senesi. After lunch, we drive to the medieval village of Bagno Vignoni and check in to our hotel, built over the ancient spa.

    Accommodations:

    Le Terme

    Included meals: Breakfast, lunch and dinner

  • Val d’Orcia

    Spend today in Val d’Orcia, the quintessential Tuscan landscape filled with terraced vineyards, olive groves, cypress-capped hilltops, and wooded valleys. We walk through the medieval town of San Quirico d'Orcia and past the Ripa d’Orcia Castle, returning to our hotel on foot.

    Accommodations:

    Le Terme

    Included meals: Breakfast, lunch and dinner

  • Bagno Vignoni / Castiglione della Pescaia

    Depart Bagno Vignoni this morning, driving to Montalcino, home of Brunello, Italy’s most renowned red wine. Set out on foot through this countryside filled with ancient farms and hamlets to the Abbey of Sant’Antimo, a former Benedictine monastery. From here, travel by road to the Maremma region of Tuscany, famous for its wines and farm produce.

    Accommodations:

    L'Andana Resort

    Included meals: Breakfast, lunch and dinner

  • Maremma Regional Park

    Today, explore the Maremma Regional Park, which sits on nine thousand hectares of hills, plains, woods, and evergreen scrub inhabited by porcupines, fallow deer, roe deer, wild boars, foxes, and wolves. After our final picnic lunch, return to our hotel by road for our farewell reception and dinner.

    Accommodations:

    L'Andana Resort

    Included meals: Breakfast, lunch and dinner

  • Castiglione della Pescaia / Rome / Home

    After breakfast, transfer to Rome’s Fiumicino Airport for homebound flights.

    Included meal: Breakfast

Trip details

Start preparing for the trip of a lifetime

From top to bottom, we’ve taken care of all the details, so you can enjoy a no-stress, worry-free travel experience.

Activity level

The terrain of Tuscany is varied and includes rough hilly scenery with small paths and occasional rocky trails as well as some vehicle tracks and small roads. Paths can be rugged with sections that are uneven. They may also be wet and slippery in places and muddy at times. Travelers must commit to walking with the group for the entire day as there is no support vehicle or other opportunity to deviate from excursions. Additionally, participants must be comfortable making use of a bush, tree, rock or whatever else the terrain might provide when “nature” is the only restroom available.

On most days when walks are scheduled, we offer options at two different activity levels. Our scenic walks range from 4 to 8 miles with altitude gains and losses of up to 1,000 feet for an average of 3.5 hours on the trail each day. Strenuous walks range from 6 to 12 miles, or 4.5 hours of walking on average. These walks allow more adventurous walkers to explore the higher areas and to see the wilder parts of the countryside where trails are often rugged, rocky and steep, and have altitude gains and/or losses of up to 3,600 feet. Additional time on the trail may require skipping a site visit or spending less time in a stop on our itinerary. All walks are led by experienced leaders.

Pricing

Secure your spot today

The price of your trip covers a comprehensive educational program in addition to meals, accommodations, tours, and excursions. Continue reading for a full list of what’s included.

Price

Double occupancy:
$11,795 per person

Single occupancy:
$14,395 per person

Stanford Alumni Association nonmembers add $450 per person.

What’s included?

  • Educational program with lecture series and pre-departure materials, including an education resource list and travel information

  • Services of our professional tour manager to assist you throughout the program

  • All meals, tours, and excursions as described in the itinerary

  • Gratuities to guides and drivers for all group activities

  • 9 nights of deluxe hotel accommodations

  • Group transfers and baggage handling on program arrival and departure days

  • Minimal medical, accident, and evacuation coverage 

You are responsible for your personal travel expenses, including flights to and from the program.

Deposits, payments, and cancellations

A $2,500-per-person deposit is required to reserve space on this program. Final payment is due 150 days prior to program start. Deposits and any payments are refundable, less a $1,000-per-person cancellation fee, until 150 days prior to program start. After that date, refunds can be made only if the program is sold out and we resell your place(s), in which case a $2,500-per-person cancellation fee will apply.

Join us in Tuscany

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