Walking Trips featuring Historic Towns
This selection includes ATG Independent and Escorted trips which visit major historic towns or cities as part of the itinerary, where you’ll find stunning architecture, significant historical landmarks or famous works of art; discover the cultural centres of Florence, Rome, Orvieto, Santiago de Compostela, Porto and many more.
Our routes also journey through a variety of smaller historic towns – medieval settlements, whitewashed seaside villages and isolated mountain habitations. Like open-air museums, each town tells its own unique story through its architecture, culture and traditions. Walking through and staying in these towns offers more than just scenic beauty – it’s a chance to slow down and connect with local life, past and present, whichever trip you choose.
Italy
Insight into the lives and works of some of the greatest artists of the Renaissance and their frescos still in their idyllic original locations.
• Evening presentations on Renaissance frescoes and technique
• Visits to frescoes in Siena, Florence, Assisi & Perugia
• Nights, with time to explore, in delightful Orvieto & Perugia
• 5 nights at Pieve a Castello, ATG’s Tuscan retreat
Escorted
Easy Walking
Duration: 8 days
Trip dates:
03 - 10 Nov 2026
30 Mar - 6 Apr 2027
02 - 09 Nov 2027
Price: from £3,760 per person
Italy
Journey through ever-changing, wide open, rolling landscapes punctuated by hilltop towns, cypress trees, vineyards, olive groves and ancient forest.
• Enjoy timeless scenery as seen in medieval paintings
• Walk a section of the Via Francigena, an ancient pilgrim route
• Perfectly preserved medieval towns including San Gimignano & Siena
• First stage of a three-part, continuous 225-mile route to Rome
Independent
Moderate Walking
Duration: 8 days
Route Open:April, May, June, July, August, September, October
Price: from £1,420 per person
Italy
Starting in Viterbo, walk between historic towns along ancient paths, wooded trails and tracks, passing a variety of unspoilt landscapes, all the way to Rome.
• Walk the medieval ‘Via Francigena’ and the Roman ‘Via Cassia’
• Remarkable Roman & Etruscan remains at Sutri
• Impressive finish in the ‘Eternal City’ of Rome
• Third stage of a three-part, continuous 225-mile route to Rome
Independent
Moderate Walking
Duration: 7 or 8 days
Route Open:April, May, June, July, August, September, October, November
Price: from £1,280 per person
Spain
Join ATG along one of the greatest medieval pilgrim routes, walking the best and most historic sections, from the Pyrenees across northern Spain.
• Great cathedrals at Burgos, Leon & Santiago de Compostela
• A delightful succession of legends, histories & narratives
• Days at leisure to enjoy Burgos & Santiago de Compostela
• Variety of regional cuisines & notable wine regions
Escorted
Moderate to Challenging Walking
Duration: 15 days
Trip dates:
23 May - 06 Jun 2027
Price: from £7,380 per person
Italy
Walk through classic Tuscan scenery of cypress trees, olive groves, vineyards and high forested hills between the two art capitals of Siena and Florence.
• Art & architecture of Renaissance rivals, Siena and Florence
• Picturesque, fortified villages
• Walk through the renowned wine estates of Chianti
• Optional complimentary extra night at the finish in Florence
Escorted
Moderate to Challenging Walking
Duration: 8 days
Trip dates:
25 Sep - 02 Oct 2026 - No longer available
Price: from £4,800 per person
Italy
Walk from Florence, art capital of the Western world, along ancient paths through timeless Tuscan landscapes, to iconic medieval San Gimignano and Etruscan Volterra.
• Famed Renaissance art & architecture of Florence
• Discover San Gimignano, a ‘medieval Manhattan’ with its iconic towers
• Explore the ancient Etruscan and Roman sites of Volterra
• Stay on a wine estate in the Chianti Classico region
Independent
Moderate to Challenging Walking
Duration: 5, 6, 7, 8 or 9 days
Route Open:April, May, June, September, October
Price: from £780 per person
Italy
Follow paths through olive groves and wonderful high pastures with spectacular views from historic Spoleto to Assisi, birthplace of St Francis.
• Castles, monasteries, hilltop towns & superlative frescoes
• Flower-filled pastures of Monte Subasio in spring
• Memorable approach to Assisi along path used by St Francis
• Delicious Umbrian cuisine & fine wines
Escorted
Moderate to Challenging Walking
Duration: 8 days
Trip dates:
15 - 22 May 2027
25 Sep - 2 Oct 2027
Price: from £4,360 per person
Italy
Walk pilgrim trails from Spoleto to Assisi, birthplace of St Francis, passing age-old olive groves, hilltop villages, castles and monasteries rich in art and history.
• Walk from Spoleto to Assisi, the birthplace of St Francis
• 4* and 5* hotels in historic and period buildings
• Pilgrim paths along the ancient olive grove route - spectacular views!
• Castles and hilltop villages rich in history and art (wonderful frescoes!)
Independent
Moderate to Challenging Walking
Duration: 8 or 9 days
Route Open:April, May, June, July, August, September, October, November
Price: from £1,560 per person
Italy
Walk in the footsteps of Federico da Montefeltro across the picturesque Montefeltro hills from crag-top San Leo to Renaissance triumph in Urbino.
• Reach high points with magnificent panoramas
• 15th-century ducal palace of Federico da Montefeltro
• Fine churches, monasteries & fortified villages
• Wildflowers in spring; mushrooms & truffles in autumn
Independent
Moderate to Challenging Walking
Duration: 8 or 9 days
Route Open:April, May, June, July, August, September, October
Price: from £1240 per person
Italy
From medieval Siena, traverse the forested Chianti hills to Renaissance Florence, following paths and tracks through vineyards and olive groves.
• See some of the greatest artworks in the Western world
• Chianti hills – crested with castles, cypress trees, and fortified villages
• Stay at an elegant wine estate with gardens & pool
• Wine tasting opportunities on route
Independent
Moderate to Challenging Walking
Duration: 8 days
Route Open:April, May, June, July, August, September, October
Price: from £1,660 per person