Classic Tuscany Short Break
- 3 Days of active hiking in Tuscany: Stay in Volterra, San Gimignano, Colle Val D’Elsa, Siena
- Immerse yourself in rolling landscapes: vineyards, villas, woodland & medieval hilltop towns
- Gourmet Tuscany at your fingertips: try local olive oils, hand-made pasta, pecorino cheeses
- Stroll cobbled streets with medieval, Romanesque & Gothic churches & palazzos
- Sip robust Chianti Colli Senesi, Sangiovese, chilled Vernaccia San Gimignano
Gallery
Itinerary
Day 1 Arrive Poggibonsi/Pontedera, transfer to VolterraSlow down and savour several days hiking through quintessential Tuscany—starting in the classic Etruscan city of Volterra, perched 1770ft above sea level, with its 1120 Duomo (cathedral), and fascinating ruins.Â
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.Â
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.
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.Â
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. Â
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.
Elevation Ascent/Descent: 450m/510m (1,476ft/1,673ft)
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.
Ahead lies a long but enjoyable day of hiking along the famous Via Francigena, the ancient pilgrimage route that stretches from Canterbury to Rome. You can shorten the hike by taking a bus for the final leg.
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.
Longer hike option, 23km/14.3mi Ascent/Descent: 330m/490m (1,083ft/1,608ft)
Shorter hike option, 13km/8.8mi  Ascent/Descent: 270m/380m (886ft/1,247ft)
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 amid the gentle Sienese hills and a rare example of medieval military architecture, with its 14 square towers.
Leaving Monteriggigoni on foot, follow in 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 rivaled that of Florence. With so much to see, this is the ideal spot to spend your final 2 nights in Tuscany.
Ascent/Descent:Â 280m/220m (919ft/722ft)Â
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.
Located inside Siena's historic walls, this family-run hotel has a restaurant, bar, and terrace with views over the city and the surrounding valley. They follow the philosophy of the GoGreen brand of environmental sustainability and low-energy impact. Their energy comes from 100% renewable sources. Their spacious bedrooms are decorated in a traditional style with warm colour schemes and tiled floors.
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 hikes of the Cinque Terre or Amalfi Coast.
This trip has a carbon score of 15kg per person per night, meaning it’s one of our best trips! For comparison, a carbon count of 15kg is equivalent to 88.5 candy bars. 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 about how we've carbon counted our trips.
Other Information
Is it for me?This is a 4-night active hiking adventure in Tuscany: enjoy 3 days of exploring Tuscany on foot, hiking between classic hill-top towns and villages brimming with atmosphere. Explore Volterra, San Gimignano, Colle Val D’ Elsa and Siena by night, with plenty of opportunities to indulge in Chianti wine, organic aged pecorino cheese and home-made pasta.
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 in Scotland, the world renown Tour Du Mont Blanc and Germany's Moselle 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 occasionally. You’ll be hiking up to 22km/13.7mi each day. Should you wish to skip a hike between towns then (with prior notice) you can travel in the taxi (luggage transfer).Â
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 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 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 hikes 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 spoiled 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 (except for some sections where you will be hiking 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 smartphone 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. 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. Â
- 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)
- 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 (recommended)
- 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 challenging around the times of the 'Palio' horse races, which are held annually in early July and then again in mid-August over the course of 4 days each month.
Time of Year
The Spring months offer warm sunshine, fewer crowds, and pleasant hiking conditions. May 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. 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. 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 its relatively quiet and peaceful.
This trip starts in Volterra and includes a transfer from either Pontedera or Poggibonsi, where an included taxi will transfer you directly to your hotel in Volterra.
To reach Pontedera or Pogginbonsi, we recommend flying into Pisa Airport (PSA) or Florence (FLR), however, flights in and out of this airport are limited.
If arriving in Florence: There’s a tram that departs approx. every 10min that will take you to Florence’s main railway station – the Santa Maria Novella (takes 20min). From there it's a 45min train ride to Pontedera or 1H15 to Poggibonsi.
If arriving in Pisa: From the airport take the PisaMover that departs approx. every 10min to the Pisa Centrale Train Station (takes 5 minutes). After exiting Arrivals, follow the signs for the PisaMover, turning left and walking along the passageway to the little Pisamover station at the end of this passageway. You can either take the stairs up or go up to the platform with the elevator. Once upstairs you can buy a ticket from the machine. From Pisa Centrale Train Station, trains to Pontedera take 15mins or 1H15 to Poggibonsi.
Please check the Trenitalia website for timetable planning. Please note that not all buses/trains run on a Sunday, or they may have a reduced timetable.
If you’d prefer to avoid public transport from the airport, a private transfer can be requested. Please let us know at the time of booking if you would like to add this option (additional costs apply). 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. We ask you to limit your luggage to one bag of up to 20kg/44lbs per person.
It is strongly recommended that you secure adequate travel insurance.
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 occasionally. You’ll be hiking between 17-25.5km (10.5-16mi) each day, and on 2 days the loop hikes are optional. Should you wish to skip a hike 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 finalized 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 hiking shoes/boots (ideally waterproof), comfortable walking clothes, and depending on when you are travelling: waterproof jacket and trousers, a daypack, hats/gloves, etc. Our Info Pack has a list of all equipment to bring on your hike.
If you prefer to hike in cooler months then May and September/October will be perfect for you. The fall colors are spectacular in Tuscany. The summer months (June, July, August) can be very hot.Â
You can (with prior notice) join the taxi which is transferring your luggage, and therefore avoid hiking between hotels if you wish. Alternatively, you can use public transport or local taxis to move to the next overnight stop. There are three hikes where youll be hiking between accommodations, but on the other days the loop hikes are optional so you can choose to explore on foot or simply relax.
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