So you’ve decided to go to Italy.. now what? Are you going on a tour or are you going to try and pull the whole thing off relying solely on your own organizational skills and bits of time spent “casually browsing the internet” at work? It’s a common dilemma that many travelers have, it appears sometimes that the choice is a hard one to make: doing the “tourist thing” on a big cattle bus or ending up lost on the crazy winding roads of Italy without an English-speaker in sight. Well rest assured, the choice isn’t so dramatic after all. Many travelers disdain any hint of being shepherded around, the “We’re not tour people” syndrome. But at the same time, many are afraid that if they go alone they may be right next door to something that they should see but miss it because nobody told them about it.
Some operators specialize geographically, by country or region. Others focus on special interests, such as artist tours, adventure, opera, cooking and wine tours. There are infinite options to look into, so let’s take a look at some of these together starting with the pros and cons of going on your own versus going on a tour:

GOING ON A TOUR Vs. GOING ON YOUR OWN

THE PURPOSE:
The first thing you want to do when planning a trip is to ask yourself “What do I want from this vacation?”. Are you craving a week of relaxation on the porch of a villa overlooking the gentle hills of Tuscany enjoying the breeze and sipping on some local red wine? Or are you looking to see as much as possible in the limited time you have, on a journey through the most well-known historical sites and cathedrals of Italy with knowledgeable tourguides explaining details bit by bit? Or do you want a combination of both? What is important to you? What do you expect from your trip? Are you looking for a particular level of comfort or luxury? Or are you on a shoe-string budget? What type of vacation is right for you? What sounds better for you: a budget-saving escorted tour, a special interest trip with few individuals, or an independent, on-your-own vacation? These are the decisions you need to worry about before you let the experts take over.
The first choices that you'll be making when deciding which service will better fit your needs will ultimately determine whether your trip is a once-in-a-lifetime experience or a waste of time and money.
How much activity do you want? Some people want to see everything; others prefer a casual day relaxing by a café in the piazza. On an escorted tour, find out how much actual travel there is, versus time to be free, explore, shop, etc.
Are your expectations realistic? Remember, you usually get what you pay for. Are you willing to compromise in order to save money? If you're trying to save money, decide whether it matters that your hotel room faces the back or that you are on a bus with 60+ people eating a tourist menu.
A determining factor in deciding whether an organized tour is better for you instead of an independent choicel, will also be determined by how long is your vacation time. Tours take out the hesitation and time lost while figuring out where to go and how to get there, therefore a traveler can squeeze in more sites and activities. If you have plenty of time available, than discovering sites on your own can be a pleasant adventure and challenge for you and your travel mates.

THE ITINERARY:
Obviously when you choose an organized tour, you leave the planning to the tour operator, so there is no need for you to scout the best places to see, because they are already chosen for you.  You do not have as much flexibility on a tour, so make sure you like the destinations that are going to be covered, as you may not be able to wander off and see other cities. A good idea is to research several tour catalogs so you can look at each one’s itinerary and pick the one that best fits your needs. Keep in mind that itineraries are subject to change based on weather conditions and other situations that may occur beyond the organizer’s control. Still, most serious tour companies will make sure to substitute a destination with another one of equal cultural interest if the situation should arise. When you have driven for hours trying to reach the cathedral you were dying to see, only to realize it is completely covered with scaffolding, sometimes it may be hard to quickly come up with another site to visit. Tour companies take this sort of “stress” away from you so you can fully enjoy your trip and not even notice the “speed bumps” along the way. Someone else is concerned with all your transportation, getting you to and from airports and on and off buses, cruise ships and trains, providing you a room with bath and many if not all meals, carrying and keeping track of your luggage, making sure you see all the must-see sights, steering you toward the best shops, providing museum tickets, and in some cases, allowing travelers to enjoy plenty of free time.
When you travel on your own you can just decide what to do with your day on “the fly”, but you may also miss out on things you wouldn’t normally be able to get to. Italy’s roads can be very confusing, so put aside extra time during your daytrips for “getting lost”. It’s something that happens to everyone, especially on unfamiliar roads, even more so in a foreign country. So always give yourself extra time to get to each destination, as well as to return back to your accommodation.
If you are looking at a tour, grab a map of Italy (or print one out from the internet) and mark each city that will be touched during the stay. Also, keep track of how many cities will be visited on any given day. Whatever city you visit, you should be able to spend at least 3 hours in it. Less than that will likely get you exhausted and stressed out from moving around too much. Take a look at the distances between towns, how long do you really want to spend sitting on a bus every day? The busier the schedule, the more time you will spend getting on and off the bus. How much free time do you have? How cruel would it be for you to float along as the group meanders through the city streets and suddenly catch a glimpse of that perfect item you’ve been looking for in a side store window... only to be swiftly tugged away by your travel companion, to keep you from being left behind. At the same time, you don’t want to be funneled into a store selected by a tourguide who will make commission on your purchases. Ask about alternative activities, what happens if you opt to skip a daytrip during the tour to get some rest? In most cases you will forfeit the cost of that daytrip, but will you still have something to do, walk to some stores, and be able to get some food?
Assess your physical fitness, capability of walking uphill, and standing for extended periods of time with objectivity. How much do you walk on a daily basis? Even the most low-activity itineraries will require that you do more walking than you are generally used to. If you have any doubt as to whether you're up for a given trip, call the tour company. If they are professionals, they will be honest with you and let you know upfront if the trip is right for you. Be honest with them about your health, if you have any sort of allergy, dietary need, illness or health condition that may prevent you from participating in certain activities or which will require that you follow a specific nutrition, not only may you run into extra expenses that the company will not cover, but also in serious situations that may prevent you from participating in the tour.

THE PRICE:
Many tour companies sell a “fixed rate” so that you are not subject to the exchange rate fluctuations, which have been cause of serious concern recently for many who travel overseas. Unfortunately the exchange rate is very disadvantageous, so having a fixed rate will save you a lot of money in the long run, as you may not know where the Euro may be up to 12 months from now. Generally speaking, if you are budget-conscious, taking a tour will cost you much less than going at it on your own, because groups get better rates on hotels, restaurants, and transportation.
Check the fine print carefully for extra charges. The big tour companies are known for promoting “unbelievable deals” for vacationers. Unfortunately the promotional price hides behind a cluster of conditions, black-out periods, and optional extra services and daytrips that are essential to going on the tour. So make sure to check exactly what’s included and to add up all the extras before you decide to sign up (i.e. luggage handling fees, transfers, hotels, taxes, processing fees, airport taxes, fuel surcharges, daytrips, bilingual guide service, exchange rate adjustments, gratuities, meals, beverages, etc.).
Also ask about the cancellation policy: how much do they require as a deposit per person? How much of that is refundable? What are the deadlines for balance? How much do you get back if you need to cancel? Does the tour company offer cancellation insurance and other personal travel insurance (for lost luggage, delayed flights, personal damage, etc.)? Sometimes it’s best to purchase travel insurance from a third-party that is not associated with the tour company, such as AAA, TravelGuard, among others, if you're willing to spend a little extra money in exchange for peace of mind.

THE TOUR COMPANY:
If it’s a big company you are dealing with, getting to speak with customer service may become a challenge. Often times brokers can find you a good deal, but full-service companies typically provide their own guides, personally tested accommodations,  and thorough pre-trip information, all of which leads to tighter quality control. If you have questions about your trip and itinerary, sometimes having a local neighborhood travel agent plan the trip for you may be a solution. If you sign up for a tour offered by a small company, it is often possible to talk to the organizer directly through phone or email, that way they can answer in detail to any question or concern you may have, including what to pack, weather information, services offered, etc.

BIG TOUR, SMALL TOUR:
Usually, the bigger the number of people going on the tour, the smaller the price of it. This follows the logic of getting better deals on hotels, flights, and other services when traveling in a large group. At the same time, ask yourself if you want to be with so many people at any given moment. The larger the group, the larger the bus being used. This is not always a good thing, because it will take longer for the group to get on and off the bus, and also longer times to check in and out of hotels. The logistics become a tad more complicated. The larger buses will not be able to access most of the historical centers of the Italian cities, simply because the streets are not able to fit the large vehicles, so may end up walking more than you had anticipated with the group to get to the town from the bus, and back. Small groups usually give you more of a “family” feel and use smaller vehicles that often carry special permits that allow them to get in and out of the historical heart of each town, just like a taxi.
So ask how big is the group before signing up. Ask if there is a minimum and maximum group size. Ask about the age range for the participants and if it’s more couples or singles. You want to make sure you’re making the best choice for you. In addition, have you thought about a special interest tour? Is your dream to be able to paint the landscape of Tuscany with an Italian master painter? Are you very active and want to be cycling from town to town with a new challenge around each turn? Are you a wine afficionado who wants to know all about the regional vineyards?

GETTING THERE:
If you are on a tour-booked flight, there will probably be other travelers on your plane. The more of you who are on the same flight, the more likely the tour’s departure will be delayed if your flight is late arriving.
If you do choose to use frequent-flyer miles for a flight or want to book independently, you might want to get to the departure city a day early to avoid the stress of worrying about flight problems, whether they be weather, mechanical or strike-related. Always make sure to stay the last night of the trip in the city you are flying out of. This will relieve you from having to get up in the middle of the night to take the train/taxi/car to the departure city to make sure you get to the airport on time.