Exploring Italy by bike
Cycling in Italy is a national pastime and as such "biking clothes" are acceptable attire while riding. Lycra bike shorts and bike jerseys are commonplace. However, don't be surprised if you see locals riding without helmets. Italians have a history of not wearing helmets, but this has been changing in recent years. Due to the hilly terrain and the fast drivers, helmets are highly recommended. Many cycling tours of Italy involve exploring towns along the way. If you don't enjoy wandering around a city in your bike clothes, it is advisable to carry a change of clothes. For this reason, women may prefer to wear biking shorts that are integrated into a skirt. As you would expect, road biking shoes are not the most comfortable when walking around cobbled hill top villages. With this in mind, it might be preferable to use mountain biking shoes when cycling around Italy or carry a pair of lightweight shoes when biking.
Exploring Italy's mountains and vineyards
Italy offers wonderful rugged hiking in the Italian Alps and Dolomites. It is best to wear "layers" when hiking in the mountains, as the weather can be very changeable. Hats, gloves and rain gear should be carried at all times. Trails in the Dolomites and the Italian Alps are typically rocky and uneven. With this in mind, high-top leather boots are recommended as they are waterproof and offer ankle support. Trekking poles provide additional support and are especially recommended for travelers with weak knees. A trip to Italy wouldn't be complete without walking through a couple of vineyards, especially if you are traveling to Tuscany. When walking through vineyards, be sure to wear comfortable shoes as the terrain is very uneven and often involves steep ascents and descents.
Exploring Italy's villages and cities
Comfortable walking shoes are the key to successfully enjoying Italy's cities and hilltop villages. Most travelers spend their days exploring museums, wandering around archeological sites and letting themselves get lost in the cobbled back streets. Many miles later, most travelers can't understand why their feet hurt. Cities can be more tiring than a trip to the mountains. In addition, many villages are located on the top of a hill and involve a lot of walking up and down.
Visiting a church is inevitable during your trip to Italy. Most churches require that visitors cover their shoulders and knees. Keep this in mind when planning your day. A shawl is a handy item to carry as it is light and will cover your shoulders.
Italians are known for their sense of style and fashion. They tend to dress "smarter" than most Americans when going out to dinner. For this reason, it is advisable to pack some "dressier" clothes for the evening. Dining in outdoor clothes will be frowned upon. At most places, wearing blue jeans to dinner is fine. However if you want to blend in with the locals, avoid wearing baggy jeans. Shorts are not common for women unless you are at the beach. Most Italians dress for dinner and then stroll through the old town. This ritual is called the "passeggiata" and is most common on Sunday evenings. Take a seat at a bar in the piazza and join the ritual.
If possible, avoid wearing fanny packs and money belts. Italians dress with a sense of style and fashion and these items will label you as a tourist. It is preferable to carry a leather purse or shoulder bag.
Packing for the seasons
When deciding what to wear while traveling in Italy, it is handy to know a little about the weather. Like anywhere in the world, the weather is unpredictable, so it is best to pack a little of everything. As a general rule, July and August are the hottest months with temperatures in Rome averaging in the low 80s. Most places don't have air conditioning, so lightweight materials are advisable. June and September are typically a little cooler with warm days and cooler evenings with temperatures often in the 70s. November and December are typically the rainest months, however expect a fair amount of rain in March and October. December, January and February are the coldest months. Temperatures in Rome during the winter average in mid-40s and the lows are the mid-20s. In general, Italy is a damp, cold wet place in the winter, so pack warm clothes. It doesn't begin to warm up until March when the average temperature is in the low 60s.