Planning a trip to Italy is not hard, but there are a few things to keep in mind, which I will share with you as you read down the list of tips I've selected to make your planning easier. Yes, I know, there are TOO many resources out there, so many books, so many websites... how confusing!! But don't be scared! Asking yourself the right questions will help you figure out the answers, therefore allowing you to put together an outline for your trip plan. Having a plan will prevent that you go way out of your budget, that you are not left without hotel reservations, that you don't lose time trying to figure out what is worth seeing, and how to get there. You don't need too much information, just the right kind so you can be off to a buon viaggio!

1. What is the purpose of this trip?

2. Who Is Going on the trip?

3. How Much Are You Prepared to Spend?

4. How Long Is Your Vacation?

5. When Do You Want to Travel?

6. What are the top 3 places you 'have' to see?

7. What Types of Things Do You Like to Do?

8. What Type of accomodations do you want/need?

9. How will you get around? Will you be renting a car/taking the train/ hiring a private driver?

10. Do you need custom services (a private guide, etc.)? Do you require special attention (diet, health, etc.)?

What is the purpose of this trip?
What is the purpose of your trip? Are you looking for R&R in the countryside while sipping on fine 'vino'? Are you craving art & architecture and want to see as many churches as possible? Are you a history buff, wanting to see museums, ruins, and the Renaissance cradle of the world? Or, are you one of those "please don't call me a tourist" traveler, who wants to "blend with the locals" and explore the off-the-beaten-path towns where hardly anyone speaks English? Either way, deciding your purpose for the trip will be the first step and help you in the long run while planning what to see and do. One of the most common mistakes people make when planning a trip is they try to see EVERYTHING, do EVERYTHING, experience EVERYTHING. This is virtually impossible, it's just not going to happen in one single trip. Italy is a small country (about the size of the states of Georgia and Florida combined), but it is super-packed with things to do and to see. If you pack too much in one single trip (unless you're planning on staying over a year), you're going to end up over-doing it and not enjoying your trip as much as you would if you just took it easy, relaxed, and took in the culture, sites, food, on a more leisurely pace.

Who Is Going on the trip?
Family and friends often get together to discuss where they want to travel or vacation next. If someone has already been to Italy, chances are they will be talking about their trip, and maybe proposing one to the group. Getting people excited about Italy is not difficult, but going from a person exclamating "Oh, that's definitely where I want to go!" to actually getting them to nail down dates on the calendar and reserve their flight is a whole different story. So, as much as getting a group of friends together to travel with you may be a fun idea, you should really make a decision for yourself first, and if Italy is where you want to go, plan your trip and your dates. If others are seriously interested, they will join you in no time. A big mistake would be to wait on them to make a decision, which may eventually result in you not finding availability if you delay too long (and then also hitting yourself in the head).
Italy is great for all age groups, but it does take a little extra effort if you're traveling with children and are planning on taking public transportation. Sometimes keeping a small group together in a very crowded train station can be challenging. Italy is more crowded on a regular basis than most American cities, there just isn't much room to move around in. If you think about it, Italy's cities and towns were built thousands of years ago, long before the use of cars and buses. Nowadays, you'll find city streets as an urban jungle setting, where busses, cars, mopeds, motorcycles, bicycles.. oh, and yes, pedestrians intertwine in a ferocious race, with no time for delaying or stopping. Children love Italy because of the marvelous sites they've been seeing on their school books, while adults love it not only for the sites, but the wonderful cuisine and wine, among many other things. Unfortunately Italy is not well-equiped, or very handicap-friendly. The reason for this is quite unknown, but perhaps it's the topography itself of the cities (as I said before) that makes it difficult to make wider, more even sidewalks. If a person has any type of problem with mobility, such as being on a wheelchair, Venice can be more of an inconvenience to travel to, than a pleasure. Being on water, Venice has small streets which connect to other islands through a series of small elevated bridges, sometimes without a railing.

How Much Are You Prepared to Spend?
Keep in mind that Italy is not a cheap country to travel to, not just for the actual cost of hotels, food, etc, but also for the terrible Euro-US dollar exchange rate, which will easily add 50% to all your expenses. Plan accordingly and have plenty of extra cash in your checking account for unexpected expenses. Any credit card or bank will also add an international fee, which is usually a percentage of the transaction (ranging between 2%-5%). If you are on a seriously limited budget, perhaps you should try looking into large-group tours, such as Trafalgar, Globus, Perillo Tours, among many others. Going with a large tour may give you a discounted rate and the advantage of not having to plan things yourself, such as meals, transportation, guided visits, etc. Most tours are all-inclusive, which means you won't have unexpected expenses and you may get into better hotels at a lower price than if you went on your own. If you are traveling 'solo', being with a group may also give you that extra sense of safety, because somebody would be getting worried if you didn't get back to the bus by a certain time. Traveling with a small-size group can be more expensive, but will also take the "unexpected factor" away from your planning, therefore enabling you to respect your budget before and during travel.
Waiting until the last minute and taking the opportunity of a last-minute deal may also save you a few bucks, but of course there is a risk for doing that, especially when you've already planned your days off work. Another big issue is the fact that hotels in Italy are rated by a 1-5 star system, but it really does not matter to the quality of the accomodation, nor the services or location. Some 3-star hotels are just as nice, if not better than many 4-star hotels. So how do you pick one? This is where you actually have to sit down and do some research. The best judges for hotels are their previous customers.. so start going to websites like www.tripadvisor.com and www.venere.com and base your decision on the reviews people have posted, rather than the star rating. As a general rule, a clean, 3-star centrally located, decent hotel room with its own bathroom in major cities such as Florence, Venice, and Rome, should run you between 180-250 Euros a night.

How Long Is Your Vacation?
This is a decision that will also strongly impact your budget, and vice-versa. If you have a week or less, you are probably restricted to visiting 2 or 3 major cities. Keep in mind that you may feel quite tired for the first couple of days from the long trip overseas, as well as the time change (jetlag). You will lose 2 days for travel anyway, so a short trip is great when you go to visit a major city such as Rome and focus all your time on that one city. If you can squeeze out ten days to two weeks, you will have many more options, including major cities as well as some of the countryside towns, allowing yourself more time to site-see on a leisurely schedule.
If you're on a go-go-go schedule, you may end up exhausting yourself and not remembering a thing of what you saw! As a general recommendation, try to spend 1-2 nights for each city you wish to visit. Moving from one hotel to the next is itself going to be exhausting for you, and in the end, no fun.

When Do You Want to Travel?
Another important deciding factor for your budget is the season you will be traveling in. Visit the page relative to the question "When is the best time to go to Italy?" on the previous page to determine when is the more appropriate time for you to travel. Nowadays the "high season" is considered late spring (May & June) and early fall (September & October), this is when most hotels will offer their highest rates. July and August are also considered fairly high-season because schools are out and most Europeans, including Italians take their vacation at this time. The weather can be very hot with temperatures in the high 90's. Not so pleasant when you consider that you will be walking outdoors most of the time. From November to mid-April, hotel rates as well as airfare prices will often drop drastically, but there is a reason for this: it's cold, rainy, and it is dark by 5:30pm. If walking and site-seeing in bad weather doesn't bother you, this would be the best time to travel, especially for the budget-oriented. Many hotels will be open to bargaining at this time and cities and small towns aren't as crowded as the rest of the year. Ideally, you should pick the time that works best for you and the schedule of those traveling with you. Just remember that during the "high season" rooms are scarce, therefore you should give yourself a good 6 months to submit hotel & flight reservations prior to the trip, to ensure availability.

What are the top 3 places you 'have' to see?
This should be your rule of thumb for any place you visit. The truth of the matter is that you will come up with a long list of things that you and your partner/friend/husband will want to experience during your trip, but try to limit 3 things per person. With so many things to see and do in Italy, this will keep your priorities where they need to be and it will keep you from getting distracted and not getting to see what's important. If you're going on a 2-3 week trip, you could litterally sit in front of a small map of Italy and circle the areas that most interest you. This may require some reading ahead of time, some research on what are the most popular destinations, what areas tickle your interest. Purchase a good book on Italy and mark the sections that grab your attention. Then, take your map out and start circling. As a general advice, the best thing is to pick one or two regions at the most for your trip. As it was mentioned before, there are 20 regions in Italy, and as small of a country as it is, there are so many things to see that even if you moved there, it would take you more than a lifetime to see them all. Concentrate instead on 1 or 2 regions, so that you can savor the local culture and learn about traditions in that particular area.
There are many guidebooks specifically on the various regions of Italy, which are all incredibly diverse and unique.
An easy solution for first-time travelers includes: 3 days in Venice, 3 days in Florence, 3 days in Rome. They're easy cities to visit on your own, public transportation is readily availably, and you'll get a feel for what you want to go back to.

What Types of Things Do You Like to Do?
One of the best things about traveling to Italy is the wide variety of activities available. You can do everything from sitting at a cafe' and enjoying the view to more strenuous activities like hiking, exploring the cities, visiting museums, shopping, etc. You can be as lazy or as active as you wish. To have a happy and satisfying vacation, you should ask yourself what you'd like to do during this trip, not just for you, but for everyone that is traveling with you. People are different, and so are the things they like to do while on a trip. To avoid misunderstandings, go over the activities you are mostly interested in. If you like to shop, you should save at least an afternoon to do just that. If you enjoy wine and food, perhaps you can visit a local vineyard and/or take a cooking class.
Don't underestimate the services a hotel can give you. Once you have booked with a certain hotel, they are usually very helpful in telling you about organized tours, information on train schedules, museum reservations & tickets, wine tours, and further third-party services that they can suggest, including activities that can be booked directly through the hotel.

What Type of Accomodations Do You Want/Need?
Accomodation selection is normally a function of how much you want to spend. Many travelers will book the cheapest room available at the time of booking, preferring to save their money for shopping or other activites once they get to Italy. As previously mentioned, your selection for a hotel in Italy should not be based on its star rating. Unless you are sure you want to be in total luxury (and pay top price for it), stay away from 5-star hotels, which most of the time over-charge and often do not offer the high-quality service that is expected from a 5-star hotel. If you are looking for a quaint, clean, fairly-priced accomodation, 3-star is usually the best way to go, because these are moderately priced hotels, often located in old historical palazzos. But again, base your decision on the reviews of previous customers and how they would rate the hotel. Choosing a cheap accomodation with the excuse "I'll be out of my room most of the time anyway" is fine, but you still want a clean place to sleep in, a little larger than a closet so you can get your clothes out of your suitcase, and maybe not on the 5th floor with no elevator, right? For more tips on finding the right accomodation, go to the "Finding the perfect Accomodation" page on my website.

How will you get around? Will you be renting a car/taking the train/ hiring a private driver?
Getting there is important, but how to get around once your there is just as important. When planning your flight, keep in mind that the best deals are not always the ones you get a year ahead of time, nor the last-minute. Obviously, the more time you have before your trip, the more time you can simply "observe" the fluctuations in ticket prices.. and when the moment is right, strike! If you have airmiles you'd like to use, you should inquire about this matter as soon as you decide to go. Tickets purchased with miles can sell out as much as a year ahead of time, so make sure to look into this as soon as you can. The airline may impose black-out dates which may limit your time to travel. If you are booked on a tour, getting there one day before the tour begins may be a good option to prevent any airline strikes, delays, missed connections, or possibilities for lost luggage.
If you decide to plan the whole trip on your own, figuring out how to get around is an essential part of your trip, which needs not to be taken lightly. Big mistakes can be made at this time if you do not give transportation enough thought and adequate planning. Depending on which areas you chose to visit, renting a car may or may not be the best solution. You should consider several options before commiting to anything. If you are only traveling to the major cities (Rome, Milan, Venice, Florence, Bologna, Naples, Verona, etc.) then the train will be the quickest, easiest, cheapest solution. If you are including small, off-the-beaten path town, which aren't always easy to reach by train, you may think of renting a car or hiring a private driver for segments of your trip. Read the article on "Renting and driving a Car in Italy" on this website to learn more about renting a car in Italy. The best transportation will be dictated also by how many are in your group, and in the end, it may be a combination of private and public means. Moving an entire family (and its luggage) on and off busy trains can be difficult, but driving around in two or more vehicles (Italy's cars are generally smaller than in the USA) can also be stressful without knowing the roads, especially for those not fluent in Italian. Research distances well, or you'll end up saying "It looked so close on the map!", after being in the car for hours, because you didn't realize that the only way to get to your destination was by a regional country road in the middle of nowhere. Even if you are booked on a tour, ask if the transfers from and to the airport are included and if there is any other transportation you need to take care of on your own.

Do you need custom services (a private guide, etc.)? Do you require special attention (diet, health, etc.)?
Do you take insulin? Are you a vegetarian or vegan? Do you have celiac disease or food allergies? Are you hypoglycemic? What about the people you will be traveling with? Do you or someone in your party have a mobility problem or has a hard time standing and walking for long periods of time? Any kind of special attention should be addressed as you are planning the trip. Although this tip is number 10, it could also be number 1, because your health condition may determine how much you can and cannot do in one single trip, as well as limit you in selecting which cities to visit. You should definitely learn the few Italian words relative to your condition, if a situation should arise in which you need help. Also, learn how to say the foods you cannot eat, so you know what to order in a restaurant.
Besides health conditions, you may establish a need for other customize services, such as a private guide in a particular city or museum, or transfers from and to the airport, and so on. Just write down all the things you will need during your trip to avoid any problems and misunderstandings later. If you are unsure regarding a particular topic, you can research it online (chances are, you're not the first person to have that particular doubt) or contact your hotel, tour operator, or travel agent.