Winter time is the very best time to appreciate the history and culture of Tuscany without the crowds. If you are staying for a short break the city of Florence is a must, however it is still almost invariably cheaper and easier to fly in to Pisa than Florence airport and take the train or a cheap bus transfer into Florence (about an hour). Whilst accommodation is cheaper in Florence during the winter, it is still expensive compared to the surrounding regions. If you are staying for more than a couple of days it is better value and more fun to rent a car and a holiday home in Pisa or one of the surrounding villages. Bear in mind the evenings are longer in the winter so consider renting a home with a real fire, and well equipped kitchen where you can try out your culinary skills with fresh local ingredients.
Between November and March it rains heavily in region, although rainy days are usually punctuated with fresh clear chilly days. Check the weather forecast regularly and be prepared to be flexible with your itinerary.
Florence
The Uffizi gallery holds one of the finest collections of paintings in the world. Book well in advance online and exchange your online voucher for a ticket at a separate booth before you join the queue. Allow a day for a first time visit. A cafe is conveniently situated half way round as your feet will need a break.
The Galleria dell'Accademia houses Michelangelo's David and a collection of other paintings less grand than the Uffizi, but still impressive. Again book well in advance online and exchange your online voucher for a ticket before you get into the queue.
The Cathedral
The Cathedral is free to enter. Check the opening times online in advance (no tourist visits are permitted during mass). Take the time to appreciate the unique grand exterior before joining the short tourist queue. The interior is surprisingly plain contrasting the grand exterior. Look up as you leave for the one handed liturgical clock. If you are fortunate the organist may be playing.
In addition to the Cathedral you can visit the Dome, the Bell Tower, the Baptistery, the Crypt and the Opera Museum for a combined ticket price of Ten Euros (At the time of writing the Opera Museum is closed for refurbishment). The Bell Tower and the Dome require the visitor to climb a lot of stairs. Since all must be visited within 24 hours for the combined ticket to be valid, start early and consider packing some provisions which you can eat in the square, since restaurants around the Cathedral are mostly over priced and aimed squarely at the tourist.
Museo Galileo
The history of science museum is a worthwhile visit although likely to appeal to the more technically minded and contains a vast collection of priceless ancient technical instruments in superb condition.
Ponte Vecchio
One of the most iconic sights in Florence; take some time to view the bridge from the side before you cross and appreciate the intriguing construction of the shops, dangling over the water.
Piazzale Michelangelo
If the weather is fine an impressive view of the city is available from Michaelangelo square. The Piazza is visible from the riverside. Cross one of the many bridges and the route is signposted. The walk is steep but should be possible if undertaken slowly by all by the most unfit. At the top is a viewpoint and café. If you are on a budget take your own food since prices are steep.
Pisa is famous for its tower but the accompanying Cathedral is much under-rated. Whilst the outside is less glamorous than the Cathedral in Florence, is it arguably more sublime and the inside is truly spectacular. Visiting the site on a clear evening is particularly romantic since the white stone glistens in the moonlight and since the site is not a throughfare like Florence, in the evenings it is almost free of tourists.
It is possible to visit just the Cathedral for free, but if you have a bit more time you have options to visit four other monuments: Baptistery, the Monumental Cemetery, the Opera del Duomo Museum and the Sinopie Museum. You can climb the leaning tower for 18 Euros (book ahead) but you may feel that, given the price, viewing from outside is sufficient. The other monuments can be booked on a more reasonably priced combined ticket. Simply indicate at the office which monuments you wish to visit. The cemetery and the baptistery are particularly impressive.
The Jewish cemetery lies just outside the walls, a short walk from the Tower and is one of the most ancient burial grounds still in use. It is open Monday mornings and Wednesday afternoons.
On the other side of wall beyond the Cathedral site is a cluster of restaurants designed with tourists in mind. Unless you are truly famished, save your money for some of the excellent restaurants in the center of Pisa, bear in mind however that most local restaurants have well defined opening hours - for lunch about 12-2 and for an evening meal from 7-10. Outside of these hours snacks are available but any meals served are likely to be aimed squarely at tourists.
Marina di Pisa
The Pisa Marina, set some distance from the town and best reached by car is deserted during the winter, although you will find one or two cafes and a restaurant on the front open at lunchtime serving local workers. On windy days the front is lashed with spectacular waves which, combined with the wide empty streets of attractive shuttered houses make it an atmospheric spot for contemplation.
Viareggio
Viareggio, Tuscany's seaside resort, holds a Carnival on diverse days in February and has a good range of clothes stores which make it worth a visit just for shopping, even in the rain. In January the sales are very aggressive and it is possible to get a bargain on quality winter wear since Italians want to look stylish even when wrapped up warm. The wide promenade is well populated even in the winter and a walk on the beach can be pleasantly bracing.
San Giuliano Terme
If the weather is truly awful, a day spent at the thermal baths between Pisa and Lucca is a good choice. You can choose from afternoon (30 euro) or evening sessions (40 euro), the afternoon sessions tend to be less crowded.
Basilica of San Piero a Grado
The church is held to be on the site where the Apostle Peter landed on his trip from Antioch to Rome and where the first altar on Italian soil was built. Numerous frescos can be seen inside. It contains a rebuilt altar to Saint Peter.
Villages
Take a drive through the villages of Buti, Calci, Cascina, Vecchiano and Vicopisano, situated a short drive from Pisa. Each has beautiful and ancient architecture. You can visit all of the villages in one or two days, but they are best seen in clear weather.
Cinque Terre
A day trip out of Pisa is the cinque terre, 5 picturesque costal villages, built into the hillside. The villages are unreachable by road – either take a train from Pisa, or park at La Spezia and take a train. It is possible to hike above the villages but only recommended in good weather. The whole area is a UNESCO world heritage site.
General tips for your trip to Tuscany in the winter:
-Check the weather reports regularly and plan inside and plan your itinerary accordingly.
-Wrap up warm and bring an umbrella
-Drink Italian thick hot chocolate which is truly superb.
-Remember that it will get dark early, so plan your evenings in advance.
-Bring a good camera
-Remember that good Italian restaurants tend to be open 12-2 and 7-10, anywhere open outside these hours is likely to be for tourists.
