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Tuscany: Lucca to Siena

8 Days & 7 Nights 3.3 Read 3 reviews
  • Walk across the heart of Tuscany from the walled city of Lucca to Siena
  • Follow the ancient Via Francigena through vineyards and rolling hills
  • An extra day to enjoy the lively piazzas and street-side restaurants of Lucca
  • San Gimignano and Siena, recognised by UNESCO as World Heritage Sites
  • Sample fresh truffle pasta, Chianti wine and Italy's finest cured meats
Walk one of the most popular stretches of the Via Francigena in Tuscany, between rolling vineyards and Etruscan villages that are perched on hilltops. This trip seamlessly combines culture with history and excellent gastronomy. The scenery is varied with quiet stretches through green woodland and walks between rows of cypress trees, an iconic sight when walking in rural settings. Reaching the “City of Towers”, San Gimignano, is a sight to behold, much like a walk around Lucca’s city walls that once protected its historic heart. One of the best places to try white truffles is the sleepy village of San Miniato as this delicacy grows in the surrounding hills. Sample ‘tagliolini al tartufo bianco’, fresh pasta with white truffles, and be sure to treat yourself to a refreshing gelato when reaching Siena’s city gates!
This classic Italian adventure is ideal for regular walkers that are looking to combine moderate walks with culture and sightseeing. One of the highlights is the well-known Tuscan villages that you stay in such as Lucca, San Miniato, San Gimignano and Siena. It gives you the opportunity to live like a local, dining 'al fresco' on the medieval piazzas. Furthermore, this trip is suitable for children aged 12+, solo walkers, and small groups.

Tour Type:

Classic Routes | If you’re the active, outdoorsy type, who’s interested in taking on the great routes of the world or looking for a challenge, then our Classic Routes are for you. We’re talking the West Highland Way, Tour Du Mont Blanc and the Passau to Vienna Danube Cycle Path, to name but a few!


Inn to Inn Walking | Walk from place-to-place changing accommodations each night. Generally staying in B&B’s, inns, and guesthouses.

This trip is suitable for:

Solo Travellers

As a guide, we would suggest that the minimum age of traveler this tour would be suitable for is: 12 Years

Ideal if you have an interest in:

  • Foodie
  • Wine

Activity Level & Terrain

This walking trip is graded moderate overall. The daily distances range from 14 to 30 km and the terrain can be described as hilly with regular ascents and descents. Depending on your fitness level and preferred distance it is possible to shorten the longest day of 30 km (Altopascio - San Miniato). Please view the itinerary for more details. It should also be noted that the walk from San Miniato to Gambassi can be experienced as more challenging in terms of ascent/descent. This walking holiday is ideal for regular walkers with a good level of fitness or beginners looking for a challenge. We always advise you to set off early especially during summer to avoid the heat of the day and to allow plenty of time for small breaks to reach your next location.


The route is well waymarked as you are largely following the Via Francigena pilgrimage trail. The Tuscan sections of the trail are among the most popular and the paths are known to be well signposted and maintained. To make sure that you have no problems finding your way we will be supplying you with detailed route notes, GPS tracks, and access to the Macs Adventure smartphone app. You will also have 24/7 assistance from our local partner as well as our office.


You will stay in lovely 3-star hotels and B&Bs. We carefully select small and friendly accommodations that offer a warm welcome and great food so you enjoy every minute of your stay. Many of our walkers choose to add extra nights along the walk to sample more of the wonderful walking and attractions available in Tuscany. If you choose to extend your holiday we would recommend spending extra nights in Lucca, San Gimignano, or Siena.

Single Rooms

This independent walking holiday is available to solo walkers. If you require single rooms for your booking party we will try our best to accommodate your request, subject to availability.


The delicious Tuscan food and wine available locally is undoubtedly a highlight of this holiday. The price of your holiday includes a hearty breakfast each morning. Lunch and dinner are not included so you are free to choose from the available options. Most of your accommodations will more than happy to provide a packed lunch on request and this can be booked on arrival. Alternatively, your route includes details of local shops and convenient lunch stops on the way. Dinner is available either at your accommodation or nearby restaurants.

  • 7 Nights in hand-picked B&B's, guesthouses and small hotels
  • 7 Breakfasts
  • Baggage transfers
  • Transfer from Lucca to Valpromaro on Day 2
  • Transfer from San Gimignano to Abbadia Isola on Day 7
  • Macs Adventure Information Pack
  • A welcome pack on arrival in your first hotel
  • Access to detailed maps and GPS tracks
  • 24/7 Emergency telephone support from our office
  • Travel to Lucca & From Siena
  • Train journey from Lucca to Altopascio on Day 3
  • Lunches, dinners, drinks & snacks
  • Personal equipment
  • Travel insurance (required)
  • Extra nights before, during or after trip

When To Go

You can start this walking tour anytime between April and October. Tuscany is very popular so it is recommended to book as far in advance as you are able to. Please bear in mind that July and August can be hot for walking and during these months it is even more important to wear sun protection and stay hydrated. The availability in Siena is very difficult around the times of the 'Palio di Siena' horse races that are held each year on the 2nd of July and the 16th of August.

Getting to the Start

Getting to the start of your Tuscan adventure in Lucca is easy. The nearest airport is Pisa which is served by both low-cost and international carriers. You can simply take a local bus from the airport that takes you directly to Lucca (1hr - departing hourly) or if you prefer to take a taxi from Pisa Airport this should only take around 30 minutes. You could also take a local bus to the main train station Pisa Centrale (7 min - departing every 30 mins ) and then catch a train to Lucca (30 min - departing hourly).

Getting from the End

Siena is well-connected to other Italian cities and the perfect place to finish to further explore the delights that this UNESCO World Heritage city has to offer. 

If returning to Pisa Airport, simply take a train from Siena to Pisa Centrale (1hr30min) via Empoli. Then it is just a short local bus journey from the train station to the Airport (7 min). If flying from Florence Airport, a local bus takes you from Siena to Florence in 2hrs. Or it is possible to get the train to Florence (1hr20min), then another train to the airport (20 min).

Luggage Transfer

Enjoy the ease of walking with a light backpack and having your main luggage moved for you each day. Your bags will be collected from your accommodation and moved onto your next overnight accommodation. We ask you to limit your luggage to one bag of up to 20kg per person.

Travel Insurance

It is a requirement of booking this tour with Macs Adventure that you have suitable travel insurance that covers you for the activity, emergency evacuation, and hospital care.

How do the baggage transfers work?
What personal equipment do I need?
When is the best time of year?
How fit do I need to be?


Day 1 Arrival in Lucca Day 2 Walk from Valpromaro to Lucca 9 miles / 15 km Day 3 Free day in Lucca Day 4 Walk from Altopascio to San Miniato 18 miles / 29 km Day 5 Walk from San Miniato to Gambassi 15 miles / 24 km Day 6 Walk from Gambassi to San Gimignano 8 miles / 13 km Day 7 Walk from Monteriggioni to Siena 11 miles / 18 km Day 8 Onward travel from Siena

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