Classic Tuscany Short Break5 Days & 4 Nights 4.7 Read 26 reviews
- 3 Days of walking in Tuscany; Volterra, San Gimignano, Colle Val D’Elsa, Siena
- Rolling landscapes of vineyards, villas, woodland and medieval hilltop towns
- Gourmet Tuscany— local olive oils, hand-made pasta, pecorino cheeses
- Cobbled streets with medieval, Romanesque & Gothic churches & palazzos
- Robust Chianti Colli Senesi, Sangiovese, chilled Vernaccia San Gimignano
Self Guided | Go at your own pace on an independent tour.
Multi Center Walking | You will spend multiple nights in one or more of the locations on this walking tour
This trip is suitable for:
Groups > 10
Ideal if you have an interest in:
- Foodie Adventures
- Wine, Whiskey & More...
- Historical Journeys
Activity Level & Terrain
This trip is graded ‘moderate’ overall, as the terrain is hilly. Most of the route follows gravel and farm tracks and trails, and you will be following minor roads from time to time. You’ll be walking up to between 17-25.5km each day, and on 2 days the loop walks are optional. Should you wish to skip a walk between towns then (with prior notice) you can travel in the taxi (luggage transfer).
The route is not waymarked (with the exception of some sections where you will be walking on the pilgrimage route the Via Francigena), and we supply detailed 1:50 000 Kompass maps and route notes so you will have no problem finding your way.
We’ve carefully selected our ‘comfort’ properties; charming lodgings of character, small family-run agriturismo, and charming village B&B’s that will make your stay in Tuscany extra memorable. The accommodation we normally use is detailed below and on our website, however are subject to availability and therefore alternatives of an equal standard may be offered. You can add on extra nights in any of the overnight locations on this tour.
Alternatively, you can pay a supplement for ‘superior’ properties which include former convents, monasteries and stylish villas.
Single Rooms & Solo Walkers
This trip is available to solo walkers and a supplement is payable as some of the costs (such as transfers) are not shared. Single rooms are on request and a supplement is payable.
Tuscany’s tempting food and wine is a highlight of this trip. There are countless fantastic restaurants throughout the region, and on the walks you’ll come across some real gems in the form of fattoria and agriturismo (farms making olive oil, cheese, pasta, saffron and wine), just begging for you to stop and enjoy their local produce.
In order to keep things flexible, dinners and lunches are not included, as you will be spoilt for choice!
The price of your tour includes 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.
- 4 Nights in traditional B&Bs and guesthouses (3-star standard)
- 4 Breakfasts
- Baggage transfers between accommodation
- Taxi transfers as per itinerary (days 1, 2, 4)
- Route notes, maps and detailed information pack
- 24-7 Emergency telephone support
- Travel insurance (required)
- Travel to Pontedera/Poggibonsi and from Siena
- Lunches, dinners, drinks and snacks
- Personal equipment
- Additional nights before, during or after the walk
- Supplement to upgrade to 4-star properties
- Transfers from Pisa/Florence/Rome
When To Go
You can start this walking tour anytime between May and October. Tuscany is very popular so it’s best to book as far in advance as you are able to. Please bear in mind that July and August can be hot for walking. Availability in Siena is very difficult around the times of the 'Palio' horse races held each year on the 2nd of July and the 16th of August.
Getting to the Start
By Air: We recommend flying to Florence or Pisa and then you can catch the train from the city centre to Pontedera (train from Florence approx. 45mins, Pisa 15mins) or Poggibonsi (train from Florence or Pisa approx. 1h15).
A taxi transfer from either Poggibonsi or Pontedera train station to Volterra is included in your trip arrangements. Train timetables are available at Trenitalia; www.trenitalia.com.
Getting from the End
From Siena you can take the train back to Pisa (1h45), Florence (1h30) or Rome (3hrs). Again, please see Trenitalia’s website for timetable planning.
Your bags will be transferred from your accommodation as per your itinerary and moved onto your next overnight stay. We ask you to limit your luggage to one bag of up to 20kg per person.
The distances and ascent/descents are approximations of the recommended routes. Please be prepared by packing all necessary items, for example, proper rain gear (jacket and pants), sun hat, sunscreen. Your information pack has a detailed equipment list which includes standard walking gear such as good walking boots or shoes, warm and waterproof clothes for the cooler months and lightweight clothing for summer, and a day pack.
Our pre-departure information pack has detailed advice and a kit list on what to take with you to Tuscany. This includes warm and cold weather gear, hiking boots, and lots of other useful bits and bobs.
It is a requirement of booking this tour with Macs Adventure that you have suitable travel insurance which covers you for the activity and emergency evacuation and hospital care.
This trip is graded ‘moderate’ overall, as the terrain is hilly. Most of the route follows gravel and farm tracks and trails, and you will be following minor roads only occasionally. You’ll be walking up to between 17-25.5km each day, and on 2 days the loop walks are optional. Should you wish to skip a walk between towns then (with prior notice) you can travel in the taxi (luggage transfer). You should have a good level of fitness, to make the most of this trip.
We suggest you book as soon as your plans are finalised as the region is extremely popular. The accommodations mentioned on our website are those that we normally use and are subject to availability at the time of booking, however we will always try and accommodate your plans.
You will need good walking shoes/boots (ideally waterproof), comfortable walking clothes, and dependent on when you are travelling; waterproof jacket and trousers, a daypack and hats/gloves etc. Our info packs have a list of all equipement to bring on your walk.
If you prefer to walk in cooler months then May and September/October will be perfect for you. The autumnal colours are spectacular in Tuscany. The summer months (June, July, August) can be very hot.
You can (with prior notice) join the taxi which is transferring your luggage, and therefore avoid walking between hotels if you wish. Alternatively, you can use public transport or local taxis to move you to the next overnight stop. There are three walks where youll be walking between accommodations, but on the other days the loop walks are optional so you can choose to explore on foot or simply relax.
ItineraryDay 1 Arrive Poggibonsi/Pontedera, transfer to Volterra
Your Tuscany short break begins in the hilltop town of Volterra, its well-preserved medieval ramparts affording panoramic views to the rolling landscape and over the narrow cobbled streets inside the town’s walls. This evening, relax at an authentic trattoria, where you can take your fill of fresh pasta and pecorino, washed down with deep red sangiovese and a glass of grappa.
Arriving at either Poggibonsi or Pontedera train station (both an easy train ride from Florence or Pisa), meet your taxi driver and transfer to Volterra.
Albergo Etruria is found in the historic center of Volterra, in the main shopping street, just 100m from the famous Piazza dei Priori. The property dates from 1700 and each of the 18 hotel rooms have a private bathroom with shower, access to free Wi-Fi, TV, telephone. There is a lovely garden for guests to relax. There is no lift, but luggage service is included.
Hotel San Lino was originally built as a convent in 1480 and remained as such until 1982 when it became an hotel. The rooms facing the Via San Lino street offer guests a view of one of the most beautiful medieval streets, whilst the rooms located on the internal side of the hotel offer a view of the small garden, swimming pool and tiny church of San Lino. The accommodation is spread over three floors, and occupies the nuns’ original sleeping quarters. It is the only hotel situated within the city walls that offers a viewing terrace and pool with sunbathing terrace. Guests can dine in the I Papi restaurant.
After breakfast your driver will transfer you to the tiny hamlet of Ulignano, close to the Riserva Natural Montenero. Wander eastwards along rural woodland tracks to reach the nature reserve of Castelvecchio.
Pass through the tiny medieval village of San Donato set amidst classic green hills, and glimpse your first view of San Gimignano’s magnificent towers.
Soaring on a hilltop overlooking Valdelsa, San Gimignano once boasted 72 towers (around a dozen remain today). The town is a UNESCO World Heritage Site, boasting fine examples of Romanesque and Gothic architecture. Visit the Palazzo Comunale, the Collegiate Church and Church of Sant Agostino to see their 14th and 15th century frescoes.
Centrally located in Piazza Cisterna the hotel is very well located for exploring the winding streets of San Gimignano in the evening once the day tourists have left. Many years ago the hotel used to welcome pilgrims to San Gimignano, which was just an unknown medieval village nestled in the Siena countryside. Now the hotel has all the modern amenities you require for a lovely overnight stay. The hotel does have an evening menu bursting with traditional Tuscan options, but there are plenty of places to eat in San Gimignano. There is also a private library and reading room to relax in, a selection of spa treatments, and laundry services available.
La Collegiata is located in a peaceful location. The property has a fascinating history; In 1587 the people of the village decided to build a monastery in honour of the Cappuccini monks who helped the population during the difficult times. The monastery was onsacrated in 1599. It was occupied then abandoned in Napoleon’s era, and eventually became a hotel in 1988. All 20 rooms are beautifully furnished with echoes of the past. There is a lovely pool and a fantastic restaurant L’Eco Divino (closed Mondays). There is also a small wine bar overlooking the cloister.
Hotel Villa Belvedere is a splendid late 19th century property, surrounded by a verdant garden. The building has been renovated internally to provide comfortable bedrooms while still keeping in harmony with the elegance of the external structure. The rooms are decorated with elegant furniture and all have private bathrooms, TVs, refrigerator bar and air conditioning. The Hotel Villa Belvedere offers you peace and relaxation, only a few steps away from San Gimignano. There is also an outdoor swimming pool. Ideal for cooling off on the warm Tuscan days.
Ahead lies a long but enjoyable day of walking along the famous Via Francigena, the ancient pilgrimage route which stretches from Canterbury to Rome. You can shorten the walk to 21km by taking a bus for the final 4.5km.
Pass by vineyards and honey-hued stone hamlets to approach Colle di Val D’Elsa through the ancient Porta Nova, passing fine 16th- and 17th-century noble houses to arrive at the Palazzo Campana, and the castle.
Colle di Val D’Elsa retains a proud history of creating exquisite crystal glassware and you can browse the artisan workshops and pick up a memento to take home.
The Arnolfo B&B, next to the ponte di Campana, is a comfortable B&B, divided into three apartments wth a total of 10 rooms - each with own bathroom with shower, Wi-Fi and satellite TV. There is a guest lounge/reading room with internet access and a small garden.
Situated in the old part of Colle Val d'Elsa, the Hotel Palazzo Pacini Residence offers a welcoming atmosphere of elegant grace and charm, in the peace and quiet of Colle's “Borgo” neighbourhood. Guests can enjoy a complimentary 1-hour wine tasting at Enoteca Il Salotto in Colle Val D’Elsa. Rooms have Wi-Fi access, air-conditioning, flat screen plasma TV, safe, minibar and private bathroom.
The Relais Della Rovere is a charming location created from the conversion of an ancient Benedictine abbey and a papal villa of the Renaissance period. It owes its name to its most illustrious owner: Cardinal Giuliano Della Rovere, who later became Pope Julius II, remembered as the patron of artists of the calibre of Michelangelo and Raphael.
Monteriggioni is a short transfer away, set amidst the gentle Sienese hills and a rare example of medieval military architecture, with its 14 square towers.
Leaving Monteriggigoni on foot, follow in the pilgrims footsteps along the Via Francigena to Siena. Siena’s layout is still as it was in its heyday of the 14th century, when Sienese art and economy rivalled that of Florence. With so much to see, this is the ideal spot to spend your final 2 nights in Tuscany.
La Chicca B&B is run by the Garavini family. The accommodation is situated in an old villa in the San Prospero area, just outside of the historic Siena’s walls. It’s just a 5 mins walk from the Piazza Campo. The B&B has 6 spacious double rooms (3 are ensuite, 2 have an external shared bathroom) with fans and central heating.
The Hotel Duomo is located in an antique mansion, whose history can be traced to the 12th century and it was originally the home of the noble family Loli. It was restored on the old foundations in 1726 with the façade in the Renaissance style. The furniture of the hotel is modern, with some traces of the past still visible in the wood beams and the brickwork in the breakfast room. On the terrace, above the sienese roofs, you can sun yourself in total relaxation, immersed in the romantic atmosphere of the mediaeval town, in one of the most beautiful regions of Italy, Tuscany.
Hotel Alma Domus enjoys the privilege of being in the heart of Siena’s historic city centre. Many of the rooms have balconies over looking city views and they are all stylishly decorated.
Bid a fond ‘arrivederci’ to Tuscany after breakfast. From Siena you can catch the train to Florence or on to Pisa, or perhaps continue your journey further within Italy; Tuscany combines perfectly with our coastal walks of the Cinque Terre or Amalfi Coast.
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