9 great ways to see Tuscany Paul Rickard, Inntravel | Posted: 21 February 2018

Inntravel’s Paul Rickard is based in Italy, and is familiar with nearly all of our Italian holidays. So who better to guide you through all the different ways you can see Tuscany?

It’s great that Inntravel provides such a wide selection of holidays to Tuscany, one of Italy’s favourite regions. But this means that it can sometimes be tricky to choose the one that’s right for you! So here’s my perspective on each of the trips we offer, which should help you to narrow down the choice.


Walking in Tuscany

1. Hill-top Towns of Tuscany (grade 1-2 hotel-to-hotel walking; 7 nights)

An absolute classic and the first of Inntravel’s walking holidays in Tuscany, in fact in all of Italian-speaking Italy, this leisurely route has remained more-or-less unchanged since the mid-90s. Taking in the iconic sights of San Gimignano and Siena, it provides a hugely enjoyable introduction to the region. Or choose Strolling Through Tuscany, a shorter version of this holiday, for a great first experience of Tuscany and the concept of a walking holiday – we guarantee you will soon come back for more!

Walking in Tuscany

2. Essence of Tuscany (grade 2 hotel-to-hotel walking; 7 nights)

Taking you through evocative landscapes to the south of Siena, amid waves of open rolling farmland and the stupendously beautiful ‘Val d’Orcia’ (one of Tuscany’s most picturesque valleys), this is a truly poetic landscape that helps you explore away from the beaten track. Visit the timeless hill-top towns of Montalcino and Pienza, and don't forget to sample some of the renowned local red wines!

Walking in Tuscany

3. Bologna to Florence (grade 2-3 hotel-to-hotel walking; 10 nights)

Starting in Emilia-Romagna, this long-distance route (more suitable for experienced walkers) heads south to reach the regional capital of Florence. You enter Tuscany via the little-visited Mugello Hills and cross the magical hillsides of Fiesole, where you stay overlooking Florence, before a final push into the magnificent Piazza della Signoria. A shorter, 4-night version, Through the Mugello Hills to Florence, is also available (grade 1-2).

Walking in Tuscany

4. Florence to Siena (grade 2 hotel-to-hotel walking; 8 nights)

Connecting two major art cities and crossing the glorious Chianti Hills in between, (with stops en route in the charming villages of Greve & Radda-in-Chianti), this trip gives you a unique perspective on one of the region’s most renowned landscapes.

Walking in Tuscany

5. Etruscan Hills to the SeaNEW  for 2018 (grade 1-2 hotel-to-hotel walking; 7 nights)

The hauntingly beautiful Maremma in western Tuscany is the quieter side of the region, offering a real sense of freedom and space. In fact, you can walk for miles here without meeting another soul. The accommodation is particularly stylish, and you finish by the glistening coast at Baratti Bay.

Walking in Tuscany

6. A Stroll through History (grade 2 hotel-to-hotel walking; 7 nights)

Set deep in Tuscany’s southern reaches – and criss-crossing into Umbria & northern Lazio – this is an extraordinary and lesser-trodden route, taking you along Etruscan sunken paths and cart tracks via a string of stone-built villages set in splendid isolation.

Cycling in Tuscany

7. Tuscany on Two Wheels (grade 2 hotel-to-hotel cycling; 7 nights)

This is classic Tuscany on a bike, taking you across rolling landscapes via some of the region’s must-see sights, such as San Gimignano and Siena. The last couple of days take you south into the remote Crete Senese, along some of the most glorious (and traffic-free) backroads in the entire region. The route, while inevitably hilly, is packed with interest, and the daily distances are not long. Our 4-night cycling break, A Flavour of Tuscany, is a shorter version of this holiday.

Cycling in Tuscany

8. The Quiet Side of Tuscany (grade 1 hotel-to-hotel cycling; 7 nights)

This is our two-wheeled exploration of The Maremma – the quieter, western side of Tuscany, where you are never far from the sea. One of the coastal rides leads to the remote-feeling Baratti Bay, with its sandy beach and vast Etruscan archaeological park to explore. This is an ideal choice for those wishing to enjoy Tuscany’s sublime scenery, but with fewer hills!

Cycling in Tuscany

9. Or take a pick’n’mix approach

Remember that our holidays are highly flexible, so it’s possible to combine itineraries for a more in-depth exploration of the region if you wish. You could walk all the way from Bologna to Siena over 16 nights; or combine no’s 1 & 2 above for a classic, two-week north-to-south journey encompassing some of the finest scenery – and wines – the region has to offer. You can add extra nights to any of the itineraries I have outlined, and I would highly recommend a short stay in Pisa or Lucca for sightseeing, especially if you are flying via Pisa. Buon viaggio !


Related Holidays

Walking in Tuscany

For a holiday combining culture, gastronomy and walking, Tuscany is the perfect choice. Take your pick from the itineraries described by Paul above, browse our website and give us a call if you would like to know more.

More about our walking holidays in Tuscany >

Cycling in Tuscany

Offering an appealing mix of history, great art and delicious cuisine, Tuscany is the ideal destination for a fascinating and varied holiday on two wheels.

More about our cycling holidays in Tuscany >


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