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First Italy Trip: tour versus independent?

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I would like to travel in Italy for 4weeks (sept 2014). I have looked at guided tours to name a few ( ie GateOne, Rick Steves,etc). I have been researching thru travel guide books,websites and this forum for past 8weeks. Needless to say now I'm getting confused and find myself procrastinating about whats the best choice for me. Hence the reason I'm here. I'm drawn to the experience of independent travel. I have only done it in United States (mainland,Hawaii and PuertoRico). I have never done guided tour travel. I will be traveling solo. This is my first experience with European travel. I am a healthy,active,attractive,middle age working professional female with one carryon piece of luggage. I've seen several tours that hit most of the places I'd like to visit. However there seems to be a lot of time spent on bus travel vs train travel to destinations along the guided tours. I don't speak Italian therefore have concerns about getting lost on trains (little apprehensive about first time European independent/solo travel)since limited travel time. I am not interested in renting a car. I am interested in train travel, if it gets me to my destination quicker than a bus. I realize this also requires additional planning/scheduling re; alternative transportation(after looking at sites in Italian ...I'm really clueless how to arrange tickets). I would like to travel North to South flying into Milan and departing from Naples. I'm drawn to the Italian culture in general especially their architecture,art,history and cuisine/agriculture. People and how they live are very inspiring to me. Side-note my maternal grandparents were from Southern Italy( island of Ischia and a small remote town outside of Avillino). I enjoy people but I'm particular about travel mates hence attraction to solo travel. (I prefer to be responsible for my own happiness vs. the disappointment of others). This is sort of a life celebration trip for me approaching empty-nesterhood, (3 kids off to college/graduating).Ive been dreaming of going to Italy for some time.
Therefore I'm seeking info to finalize my travel tour choice and anything else that would benefit a solo independent traveler like myself thru Italy.
Questions:
1.What's the best tour choice for this trip: independent/guided/combination guided n independent?
2. Is this 4 week tentative plan (local/length of stay) realistic?

Milan/2days
Varenna/Lake Como/ Verona /3ays
Dolomites/2days
Venice/2days
Florence/2days
Cinque Terre/2days
Siena/Assisi/2days
Umbria/Orvieto / 2days
Rome/3days
Southern Italy / 7days
would like to include/experience:
*The Costiera Amalfitana/An amalfi coastal drive (private driver).
*visit one of the quaint towns in that local to experience an evening of cuisine and music.(?positano/suggestions) ?base location vs.
*sorrento(as base location ?) with day boat trip to capri
*Ischia / to relax 3 days at thermal mineral healing pools
*end in naples with a day visit Pompeii/museum in naples/then depart next day.
Again I truly appreciate the time anyone has taken to read/reply to any part of this lengthy inquiry.. This site is so amazin thanks to all the insightful contributions that are shared here... I have learned so much about Italy/European travel in general as a result of my frequent visits here.
Peaceful travels to all!

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