When to Go
Late fall and early spring are the best times to visit Italy. Most of the tourists have gone home, and lodging and airfare might be cheaper. If you're traveling to the major cities, you might need a light jacket, but temperatures are comfortable. Those interested in winter sports should consider visiting in mid January. This is when the snow conditions are most reliable. Additionally, since the Christmas crowds have gone home, the resorts often need visitors. In some cases, this can be a good time to get affordable lodging packages.
While they may be quaint and charming, Italy's ancient cobblestone streets are not kind to a walkers feet. As such, proper walking shoes are crucial to the enjoyment of an Italian walking vacation. Avoid high-heels, clogs, flip-flops and tennis shoes. Instead, opt for a walking shoe with a thick bottom and decent ankle support. If you can afford it, consider purchasing them in Italy. Valleverde is an Italian shoe company that specializes in walking shoes. They have multiple stores in just about every Italian city. Most models cost over $100, but they are known for their durability.
Avoid short-shorts and halter tops, even if you are visiting in the summer. You can avoid over-packing by sticking to solid, interchangeable colors. Although dress codes are not always enforced, common courtesy suggests that women should wear clothing that covers their knees and arms when visiting the Vatican and other churches and cathedrals. Use a backpack for your carry-on luggage. It can double as a day-pack on walking tours, which will allow you to carry extra clothing if the weather changes.
Italian tap water is loaded with calcium. While it is not unhealthy, you might not enjoy the taste. As such, if you are taking long walks or hikes, bottled water is advisable.
Italy does not have any type of medical insurance program for visitors. As such, if you plan to engage in activities that may result in injury, purchasing travel medical insurance is advisable. Call 113 for emergencies. If you need to go to the emergency room, it is called "pronto soccorso" in Italian hospitals.
Train travel is the best way to get from city to city in Italy. If you are traveling across the country, consider taking an overnight train. You'll save money on hotels, and its a great way to meet people. You can pre-book your train travel on the English version of the Trentitalia site.
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While Italy has some famous ski resorts, consider taking the road less traveled to visit Bormio. Bormio is not a typical ski town. It's a medieval Italian town that just happens to have a ski mountain. Unlike North American ski resorts that are owned by corporations, Bormio is owned by the town. The mountain is best suited for intermediate skiers and snowboarders. In lieu of a hot tub, you can visit the town's ancient hot springs. Although Bormio is the training grounds for Italian skiing legends such as Alberto Tomba, you might be surprised to see some dated ski equipment, such as rear entry boots and straight skis. However, ski outfits are often elaborate. Expect to see expensive one piece ski suits. During apres ski, its not uncommon to see women dressed in fur coats.
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La Passeggiata is a popular Italian tradition. Every evening between 5 and 7pm, Italians dress up to walk though the center of town. Perhaps this is why they can eat they way they do and still stay so slim.
While many Italians speak English, they love it when Americans at least try to speak their language. If you plan to visit remote sections, taking an elementary Italian course prior to leaving is advisable.