Classic Tuscany
- Walking in Tuscany; Volterra, San Gimignano, Colle Val D’Elsa, Siena
- Quintessential hilltop towns and villages amidst vineyards and farmland
- Indulge in the fresh organic produce —olive oil, pasta, cheeses & wines
- Relaxing over night stays in classic medieval centres
- Wine! Red Chianti Colli Senesi, Sangiovese, chilled Vernaccia San Gimignano
Gallery
Itinerary
Day 1 Arrive Poggibonsi/Pontedera, transfer to VolterraSlow down and savour a week of walking through quintessential Tuscany—starting in the classic Etruscan city of Volterra, perched 1770ft above sea level, with its 1120 Duomo (cathedral), and fascinating ruins.
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, just 100m from the famous Piazza dei Priori. The property dates from 1700 and has 18 hotel rooms. There is a lovely garden for guests to relax. This Etruria is run by the owners who can suggest excursions, museum trips and the best restaurants nearby. The buffet breakfast is made with fresh, high quality ingredients.
You can admire beautiful views across the Tuscan hills at Albergo Villa Nencini, located just 550 yards from the centre of Volterra. It offers a large garden with swimming pool. The grand dining room at Villa Nencini is used for banquets but is also where a breakfast is served each morning.
Located within the historic hilltown of Volterra. The Roman Theatre and Porta Fiorentina Gate are a short walk away. Breakfast is buffet style, with a selection of cold meats, cheeses and cakes. The property's restaurant is 100 metres away, and serves local food and wines.
This accommodation can be booked as an upgrade. Please do not hesitate to contact us.
Start with a transfer to the trailhead, then set off on a rewarding walk which explores the gently undulating landscapes north west of Volterra, dotted with picturesque villas and poker-straight cyprus trees. Follow strada bianche (gravelled roads) and footpaths across rolling farmland.
Ascent/Descent: 450m/150m
Albergo Etruria is found in the historic center of Volterra, just 100m from the famous Piazza dei Priori. The property dates from 1700 and has 18 hotel rooms. There is a lovely garden for guests to relax. This Etruria is run by the owners who can suggest excursions, museum trips and the best restaurants nearby. The buffet breakfast is made with fresh, high quality ingredients.
You can admire beautiful views across the Tuscan hills at Albergo Villa Nencini, located just 550 yards from the centre of Volterra. It offers a large garden with swimming pool. The grand dining room at Villa Nencini is used for banquets but is also where a breakfast is served each morning.
Located within the historic hilltown of Volterra. The Roman Theatre and Porta Fiorentina Gate are a short walk away. Breakfast is buffet style, with a selection of cold meats, cheeses and cakes. The property's restaurant is 100 metres away, and serves local food and wines.
This accommodation can be booked as an upgrade. Please do not hesitate to contact us.
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.
Ascent/Descent: 450m/510m
Centrally located in Piazza Cisterna the hotel is ideal for exploring the winding streets of San Gimignano in the evening. The hotel used to welcome pilgrims to San Gimignano. The hotel has all the modern amenities you require for a lovely overnight stay and an evening menu bursting with traditional Tuscan options. There is also a private library and reading room to relax in and a selection of spa treatments.
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 Hotel Villa Belvedere offers you peace and relaxation. There is also an outdoor swimming pool. Ideal for cooling off on the warm Tuscan days.
Palazzo al Torrione is a 100 year old building that has been carefully restored with rooms using original materials to keep the unique characteristics. It is located along the wall of San Gimignano and one side faces the panorama of the city and the other the gentle rolling hills around San Gimignano. The property is managed by Vanna Poli and Francesco Indiani, who come from a family of the Bed & Breakfast owners.
You can choose to explore San Gimignano’s medieval walls, piazzas and climb its towers, or venture into the patchwork landscape of vineyards and woodland for a rewarding 17km loop walk.
A lovely place to stop for a ‘light lunch’ is the rural farmhouse at Fattoria Poggio Alloro. Relax and soak up the views of San Gimignano from the terrace as you feast on bruschetta, pasta, fresh green salad, pecorino cheese, prosciutto, salami, red and white wine, rounding off with a sweet taste of vin santo and cantuccini biscuits. Take your time winding back to San Gimignano.
Ascent/Descent: +-500m
Centrally located in Piazza Cisterna the hotel is ideal for exploring the winding streets of San Gimignano in the evening. The hotel used to welcome pilgrims to San Gimignano. The hotel has all the modern amenities you require for a lovely overnight stay and an evening menu bursting with traditional Tuscan options. There is also a private library and reading room to relax in and a selection of spa treatments.
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 Hotel Villa Belvedere offers you peace and relaxation. There is also an outdoor swimming pool. Ideal for cooling off on the warm Tuscan days.
Palazzo al Torrione is a 100 year old building that has been carefully restored with rooms using original materials to keep the unique characteristics. It is located along the wall of San Gimignano and one side faces the panorama of the city and the other the gentle rolling hills around San Gimignano. The property is managed by Vanna Poli and Francesco Indiani, who come from a family of the Bed & Breakfast owners.
Ahead lies a long but enjoyable day of walking along the famous Via Francigena, the ancient pilgrimage route which stretches from Canterbury to Rome.
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. Rooms come either with wood-beamed ceilings or bare-stone walls. There is a guest lounge/reading room with internet access and a small garden. Breakfast is available every morning and, during summer, it can be served in the furnished garden.
In Colle Val D’Elsa, in the heart of Tuscany, La Vecchia Cartiera Hotel with its 38 rooms welcomes you in a discreet and familiar atmosphere. Set in the centre of Colle Val d'Elsa, La Vecchia Cartiera was once a paper mill. Now it offers air-conditioned rooms and a fine restaurant specialising in traditional Tuscan cuisine for lunch and dinner. Each morning at La Vecchia Cartiera a large continental breakfast is available buffet style.
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. The area is popular for hiking and cycling, in addition, bike hire is available at this hotel.
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.
Ascent/Descent: 280m/220m
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. Offering a garden and a terrace, La Chicca Siena is located in Siena, a 5 mins walk from the Piazza Campo and a 15-minute walk from the Cathedral.
Set in a 13th-century building, Hotel Alma Domus offers rooms in the historic centre of Siena, a 2-minute walk from Basilica Cateriniana San Domenico Church. Many of the rooms have balconies offering city views and they are all stylishly decorated.
Hotel Minerva is one of the most historic 3-star hotels in the city of Siena. The hotel is located within the ancient city walls of Siena, in the north of the city, just a few steps away from Piazza Campo: the heart of the historic city center, famous throughout the world as the City of the Palio.
You’re free to explore all that Siena has to offer today. The Campo, or main square, is at the very core of the city. Shaped like a scallop-shell, the Campo is the setting for the famous Palio horse race.
Built on a Y-shaped ridge, immerse yourself in Siena’s steep and narrow ancient streets, scattered with architectural gems; amongst them the Gothic Duomo and Palazzo Pubblico, as well as numerous churches.
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. Offering a garden and a terrace, La Chicca Siena is located in Siena, a 5 mins walk from the Piazza Campo and a 15-minute walk from the Cathedral.
Set in a 13th-century building, Hotel Alma Domus offers rooms in the historic centre of Siena, a 2-minute walk from Basilica Cateriniana San Domenico Church. Many of the rooms have balconies offering city views and they are all stylishly decorated.
Hotel Minerva is one of the most historic 3-star hotels in the city of Siena. The hotel is located within the ancient city walls of Siena, in the north of the city, just a few steps away from Piazza Campo: the heart of the historic city center, famous throughout the world as the City of the Palio.
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.
This trip has a carbon score of 13kg per person per night, meaning it’s one of our best trips! For comparison, a carbon count of 13kg is equivalent to 3 full English breakfasts. Here at Macs, we pride ourselves on being a responsible travel company and continue to adopt, develop and innovate ways to positively impact the environment. Find out more information on how we've carbon counted our trips.
Other Information
Is it for me?Walking, classic must-see hilltop towns and a smorgasboard of organic Italian cuisine and wine combine over a week of soaking up the sights, tastes and ambience of stunning Tuscany. 2 Night stays in Volterra, San Gimignano, and Siena mean you can choose to kick back and relax, sightsee, or enjoy lovely loop walks.
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&Bs, inns, and guesthouses.
Solo Travellers, Families with Teens
The minimum age for this tour is: 16 Years
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).
We’ve carefully selected our ‘comfort’ properties; charming lodgings of character, small family-run agriturismo, and charming village B&Bs 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.
Accommodation Upgrade
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.
Meals
Tuscany’s tempting food and wine are 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 be more than happy to provide a packed lunch on request and this can be booked on arrival.
The route is not waymarked (with the exception of some sections where you will be walking on the pilgrimage route the Via Francigena), but navigation is straightforward using the Macs Adventure App which has maps, GPS tracks and daily route information. Simply download the GPS tracks for offline use and follow the route on your phone with the assurance that navigation on this tour will be made simple. You will find more information on downloading the app in your Macs Adventure Account.
- Overnights in traditional B&Bs and guesthouses
- Breakfasts included
- Baggage transfers between accommodation
- Taxi transfers as per itinerary
- Access to maps, GPX tracks and daily route information with the Macs Adventure app
- All your trip documents provided digitally through your online Macs “My Account”
- 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
This tour is available to start anytime between March and October.
Peak Season Availability
As Tuscany is a very popular destination, we suggest booking as soon as possible to ensure availability for specific dates. Availability in Siena is very difficult around the times of the 'Palio' horse races held annually normally in early July and then again in mid-August.
Time of Year
The springs months offer warm sunshine, fewer crowds, and pleasant walking conditions. May is when most wildflowers are coming into bloom. The autumn months of September and October are also a favourable time of year, boasting cooler weather and a striking landscape made up of autumnal colours. July and August are good months to go but can be very hot for walking and therefore aren’t best suited for everyone. You will have to start early to miss the heat of the day and carry a lot of water (additional weight) with you. Although the towns and villages are buzzing at this time of year which is great to see.
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.
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/44lbs per person.
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.
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.
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.
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