Relaxed Trails of Tuscany
- Easy-going hikes through classic Tuscan landscapes with rows of iconic Cypress trees
- A relaxed itinerary with time to experience this region's vibrant history and culture
- The iconic hilltowns of Volterra, San Gimignano and Monteriggioni
- Enjoy Siena, a medieval masterpiece and home to the famed Palio horse race
- Indulge in lazy lunches and take pleasure in this region's mouth-watering cuisine
Gallery
Itinerary
Day 1 Arrive Pisa or Florence. Transfer to VolterraUpon arrival either in Pisa or Florence Airports, you will be picked up and transferred to the exquisite hill top town of Volterra, which has an Etruscan, Roman and medieval history. Its location at 1,770 feet above sea level makes for amazing views across the surrounding countryside. Settle in to your centrally located, hand-picked accommodation and stroll the narrow picturesque streets as you familiarize yourself.Â
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.
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.
This morning offers the chance to stroll around the town and explore using our Macs Adventure smartphone app. Simply follow the track which takes you around all the major sights of Volterra, including the Romanesque 12th century cathedral that has very impressive interior art, the Medici Fortress, and the Mario Guarnacci Etruscan Museum, with very impressive ancient pottery and sculpture. Although this city walk is only just over 2km/1.5mi it can take you a few hours to take everything in, visit the museums and places of interest and get distracted too by the stunning panoramas every time you pass a viewpoint.Â
With a plethora of restaurants and bars to choose from, dine al fresco on delicious local pasta and wine, a satisfying end to a delightful day.Â
Elevation Gain and Loss:Â 58m/190ft
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.
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.
Today, after a leisurely breakfast, you will be picked up from your accommodation and taken to the start of your hike in the little hamlet of San Donato, a beautiful Romanesque parish with outstanding views over the vineyards. Here you will find the San Donato Winery, a family-run business offering wine-tasting, which you can sign up for with 24-hour advance notice (all the details on that are in your Information Pack). Or simply set off on the route in the app which takes you through the wonderful countryside to San Gimignano. En route you will hike past local agriturismos, farmhouses, and olive groves and as you walk closer towards San Gimignano enjoy great views of the town set atop a ridge.Â
Upon arrival in the town walk through the medieval stone streets to your delightful accommodation where you will be warmly welcomed. Â
Elevation Gain:Â 298m/978ft
Elevation Loss:Â 332m/1090ft
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. Now 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 either set off for your hike bright and early after breakfast, or take the time to explore the town first. The choice is yours! This pretty and historic town is encircled by 13th century walls and is best known for its medieval towers which were a symbol of power for the local gentry and merchants. A competition existed to see who could build the highest tower, but which led to many collapsing because of engineering inexpertise! They have left a legacy, however, as 14 towers still remain. Visiting the civic museums inside the walls give a good insight to the history of the town. The first one is the Palazzo Comunale with its Torre Grossa, which means 'Big Tower' and which you can climb up to the top of. Also check out the Pinacoteca, where the city's collection of painted panels by Sienese and Florentine artists from the 13th to 15th century is housed.Â
There are plenty of places to chill out and relax if you wish to have a break from all the sightseeing. Grab a spot at an outdoor cafe with a glass of local wine, beer, or a cold beverage and gaze out at the surrounding scenery of olive groves, vineyards, typical Tuscan rows of Cypress trees and honey-colored stone houses.Â
Your hike today takes you in a loop out to the north of the town and around it, coming back in from the south. With great views of San Gimignano constantly on view this hike is a really great leg stretcher and enables you to see the town from another perspective.Â
Elevation Gain:Â 231m/757ft
Elevation Loss:Â 232m/761ft
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. Now 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.
Today's adventure begins with a transfer to Strove, a small hamlet on the Via Francigena, Italy's popular long-distance trail and camino. It's an easy and relaxing hike, which first brings you to Abbadia Isola, a small village where you'll find a 1,000 year-old Benedectine Monastery that houses MAM, the Archaeological Museum of Monteriggioni. Not only can you visit the church and the cloisters of this ancient monastery, but within the museum itself you can view great ancient ceramics, sculptures and even jewelry.Â
After a visit here hike on to one of the most best-known and recognized villages in all of Italy, Monteriggioni. While it's a steep climb to reach inside the town walls, it is well-worth it. Here you can walk on top of its 13th century walls, visit the Arme Museum and enjoy browsing in the little shops. We recommend buying a ticket, which will get you into the MAM, the Arme Museum and also the entrance for walking around the walls.Â
A transfer to your accommodation in Siena completes this great day, full of typical Tuscan views, ancient towns, sites and relaxation in Monteriggioni's town piazza where you can enjoy a coffee and a delicious local cake, Castagnaccio.
Elevation Gain:Â 92m/301ft
Elevation Loss:Â 112m/367m
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.
Located just outside the old city walls of Siena, La Villa consists of 17 rooms, including some attic rooms which boast their originally ceilings. All decorated in Liberty style, many with their own balconies, all our rooms are replete with modern comforts. All rooms have en-suite bathrooms and free Wi-Fi access. Breakfast is served from 07:30 until 10:00am.
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.
Today you have the whole day to explore this gem of a city in the heart of Tuscany. Once again you can use the Macs Adventure smartphone app, which links up all the major sights. Start and finish in the Piazza del Campo, scene of the yearly famous Palio Horse Race. Discover Siena's historic streets, savor the local cuisine, and experience the vibrant culture.Â
Enter the Il Palazzo Pubblico located at the edge of the Piazza del Campo and explore the Museo Civico to see the stunning frescoes. The Cathedral of Siena is also another must-see, renowned for its Gothic and Romanesque architecture. Admire its marble floor, stained-glass windows, frescoes and paintings. This city has so much to offer and you can spend the whole day exploring it!Â
Elevation Gain and Loss:Â 43m/141ft
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.
Located just outside the old city walls of Siena, La Villa consists of 17 rooms, including some attic rooms which boast their originally ceilings. All decorated in Liberty style, many with their own balconies, all our rooms are replete with modern comforts. All rooms have en-suite bathrooms and free Wi-Fi access. Breakfast is served from 07:30 until 10:00am.
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.
Today you can make your onward journey home at your leisure.Â
Other Information
Is it for me?At Macs Adventure we have different trip types, Classic, Slower Adventures, Pilgrimages, In Style and Discovery. This tour is the epitome of a Slower Adventure, with relaxed hikes and plenty of time for cultural immersion and sightseeing. Its easy-going pace allows you to really experience this very impressive part of Tuscany in depth. The hikes are easy to moderate, with views over outstanding and iconic Tuscan countryside. There are also a couple of easy town/city walks, so that you can see all the major sights in both Volterra and Siena. The hikes are all fairly short, which translates to more time for discovery of these idyllic towns and villages. Visit the museums, churches and cathedrals that will educate you on this historic region and enjoy long lazy lunches and dinners offering some of the best food that you have ever tasted!
Slower Adventures | Where walking and cycling meet easy-going exploring, our Slower Adventures are the perfect combination. Most days are filled with picturesque journeys with some free time to dive into the destination and experience the people, local food and culture as you go.
Multi Centre Walking | With a mix of loop and point-to-point walks stay 2 or 3 nights in one place which offers the chance to slow down and really explore a destination.
Solo Travellers, Groups > 10
The minimum age for this tour is: 9 Years
This trip is graded easy to moderate and the hikes in the countryside are between 7km/4.35mi and 10km/6.2mi. The elevation gains are between 112-300m (367-984ft) and the elevation losses between 112-332m (367-1,089ft). The city walks are rated easy and are at most only 2.8km/1.75mi.Â
The terrain is a combination of countryside gravel paths, and trails, which can be a bit rocky at times. Occasionally, in order to link up the countryside trails, it's necessary to walk along a tarmac road for short periods. Generally the terrain is easy to navigate. Since you are hiking from and up to hill top towns there are some inclines and declines, but we have tried to limit this as much as possible.Â
Since this is an easy to moderate hiking trip it is not necessary to be super fit. The hikes are relatively short and are suited to those who like to hike, but they are not considered challenging. While there are some up and downs, you have all day to do the hikes, so you can take your time and take a breather too now and again if you wish, especially if it is a hot day. It would be beneficial to train a bit before taking the trip, but it's definitely doable for anyone who is an enthusiastic hiker.
We’ve carefully selected and hand-picked our accommodations which will be family-run hotels and agriturismos, all charming lodgings with character that will make your stay in Tuscany extra memorable. They are located in the historic village centers or just a short walk away. You can add on extra nights in any of the overnight locations on this tour.
Accommodation Upgrade
If you wish you can pay a supplement for upgraded hotels.Â
Single Rooms & Solo Hikers
This trip is available to solo hikers 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 also payable.
Meals
Tuscany’s tempting food and wine is a highlight of this trip. 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.
Generally the hikes on this tour are not reliably or consistently waymarked (except for some sections where you will be hiking on the pilgrimage route the Via Francigena). However 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 trip will be made simple. You will find more information on downloading the app in your Macs Adventure Account. Rest assured that by downloading the route maps in our app, this will continue to work even in areas without any mobile or internet reception.
- Overnights in charming locally-owned and hand-picked hotels
- Daily Breakfasts
- Transfer from either Pisa or Florence Airports to Volterra on Day 1
- Transfers as mentioned in the itinerary
- Luggage Transfers
- Access to maps, GPX tracks and daily route information with the Macs Adventure Smartphone App
- 24/7 Emergency Telephone Support
- Travel insurance (recommended)
- Travel to Pisa/Florence and from Siena
- Lunches, dinners, drinks and snacks
- Personal Equipment
- Italian City Taxes (need to be paid locally and are between €2-5 per night
- San Donato Wine Tasting (optional activity)
- Museum entrances, etc
- Additional nights before, during or after the tour
- Single Room Supplement
- Solo Traveller Supplement
This tour is bookable anytime between the months of March and November.
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 challenging around the times of the 'Palio' horse races which are held annually on July 2nd and August 16th and lasts for about 4 days around those dates.Â
Time of Year
The spring months offer warm sunshine, fewer crowds, pleasant hiking conditions and is when most wildflowers are coming into bloom. The autumn months of September and October are also a favorable time of year, boasting cooler weather and a striking landscape made up of fall colors. The towns and villages are very vibrant at any time of year, which makes for a great atmosphere, yet as soon as you get on the hikes, it's relatively quiet and peaceful.
November has pleasant temperatures and less crowds and is a delightful time of year to be there as you will be sharing the region with the locals, rather than other tourists! Some restaurants in Volterra and San Gimignano maybe closed, but there will still be enough options to choose from.Â
July and August are good months to go but can be very hot for hiking and therefore aren’t best suited for everyone. You will have to start early to miss the heat of the day, wear a hat and carry a lot of water with you.
This trip starts in Volterra. It includes a transfer to your hotel from either the Pisa (PSA) Airport, which takes approx. 1 hour or the Florence (FLR) Airport, which takes approx. 1H30.
Once your trip is confirmed please share your flight information with us, including your arrival time, as soon as you have booked your flights, so that we have those details well in advance and we can arrange the transfer for you ahead of time.Â
It's easy to travel from Siena by train to the major airports of Florence, Pisa, and Rome.
The Siena Train Station and Bus Station are located in the valley below the city center. (about a 2km/1.25mi walk from the majority of accommodations we use). To make your way to the station you have a few options (each payable locally): 1) take the escalators 2) take a bus or 3) take a taxi.
Approx. total journey times from Siena are:
To Florence 2H15 – 3H15
- The train to Florence Santa Maria Novella station is usually a direct train that goes via Empoli and takes around 1H30. Some trains are direct whereas others go via Empoli.
To Rome 2H15 – 3H20
- To Roma Termini Train Station it’s normally necessary to change trains in Florence or Chiusi-Chianciano Terme and takes around 3H30.
To Pisa 2H00 – 3H15
- To Pisa’s Train Station there is usually a train that departs approx. every 30min that goes via Empoli and takes around 1H45.
Once again it will be necessary to travel from the central train stations in these cities back to the airports (see ‘Getting to the Start’ for further information about this).
Alternatively, we can arrange a taxi from Siena to your departure city or airport. Please let us know in advance if you wish to include this option for an additional fee.
Please check the Trenitalia website for timetable planning. There are also local buses that you can take for your onward travel and you can find the information here. Please note that not all buses/trains run on a Sunday, or they may have a reduced timetable.
Your bags will be transferred from your accommodation as per your itinerary and moved onto your next overnight stay. This will happen twice on this particular trip and both times you will be transferred along with your bags to the beginning of the walk, then once you are dropped off, your bags will be taken on to the next accommodation. We ask you to limit your luggage to one suitcase/bag of up to 20kg/44lbs per person. This luggage restriction can be a challenge, especially as airlines generally have limits that are higher. However, these limits are there for a reason and we must respect these rules which are usually due to Health & Safety reasons of luggage transfer company employees.Â
If you wish, you can book a wine tasting at the San Donato Winery on the morning of Day 3. They will accept requests 24-hours in advance. More information on this maybe found in your Information Pack.
Your Information Pack has a detailed equipment list, which includes standard hiking gear such as good shoes, sun hat and a day pack.
It is strongly recommended that you secure adequate travel insurance.
For the Start of your trip, the closest airports are Pisa (PSA) and Florence (FLR).
Upon arrival in either of these locations, you will be picked up by your private transfer and taken directly to your accommodation in Volterra. Once your trip is confirmed, you will need to provide us with your flights details as soon as possible so that we can book and confirm this transfer.
At the End of your trip, you depart from Siena at your leisure. There are buses or trains from Siena back to Pisa or Florence Airports, which take 1H and 1H30 respectively. Please note that both the Siena bus and train terminals are a good 2km/1.25miles walk from the center of town. We therefore recommend a taxi to get you to these locations from your hotel. You can ask your hotel to arrange that for you. Alternately we can arrange a taxi for you in advance (at an additional fee). Please inquire about this at time of booking.
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