I don't agree that it would be heretical...depends on your interests. E have travelled to Italy 6 times over 8 weeks and still haven't been to Florence! Pick places you are interested in, no one place is better Han any other, it's all great!

Enjoy!

All of these suggestions are great! And yes Dayle, you are right, my husband and I would love a mixture that would include seeing the countryside!
I have printed out everything posted here. I've stacked all of my books, articles, etc. and am going to start seriously mapping out our September trip!
I thank all of you for your help, and if anyone has any other ideas they will be most appreciated!

Have you considered a cruise? For example, the new ship Carnival Breeze has 12 day itineraries that would take you to all of those places and more. You unpack once, and travel while you sleep.

Well guys I'm still researching....but to book an independent trip (rather than a bus tour) is looking much more expensive considering the airfare out of Houston!
And....I hate to admit it, but the thought of someone else driving is very enticing! Especially considering I want to try all the Italian wines! LOL!
The beautiful hotels (alberghi)? and the bed and breakfasts I've looked at tho, seem sooo much better than what they offer on the bus tours.
Still researching....and going thru everything that has been posted here.
Thanks again Everyone!!!!! And yes, it's definitely going to take more than one trip! Just got to get a start!!! e

Look carefully at those tours. Add all the extra costs. I've taken two to Italy, and have never seen one that is actually less than an independent trip of equal quality food and hotels. You don't have to take a tour to have someone else drive. Use trains.

THANK YOU Sassafrass!
Since I'm feeling absolutely lost. think I might be better off just going thru a travel agent for this first trip?

No, I do not think you would be better off with a travel agent unles she/he has spent lots and lots of time in Italy, has an interest in art and architecture, has driven through Tuscany, etc., etc., There are many people on this board who have traveled far more than most travel agents and can give you better advice based on your personal interests.

You already know you have about two weeks max. You said you want relaxing, not moving from hotel to hotel. You already know you want to go to Rome. You love Art, and Florence is the birthplace of the Renaissance. You enjoy wine tasting, so Tuscany/Florence makes sense, and you like water/seaside, so Venice, the lakes, CT or AC are good starts. Simply starting with that:

Venice, 4 days with day trip to one of the islands and day trip to Padua or Vicenza for art

Florence, 3/4 days w/day trip for wine tour or to visit Sienna

Rome, 4/5 days and if you are tired of the city, day trip to Orvieto or Ostia Antica

or trade Venice for the
AC 4/5 days with trips to Positano, Pompeii & Capri.

See how easy it can be.

Decide on your major bases. Honestly, you can't go wrong with any place you choose. If you have more time, don't add more bases, just do more day trips. You could easily spend weeks at any of these bases and see something new and wonderful every day.

Then get flights - open jaw, into first city and depart from last base.

Then book hotels. Lots of help here on Fodors for that once you have selected bases.

Get train tickets when you arrive in Italy.

What you decide to see/do once you are there is your personal choice. Example: I will go miles out of my way to see one painting in one church and spend hours at an archeological site while others research to find the best restaurant every place they go. I love taking boats from place to place along the AC. Others enjoy the cliffside drives. No travel agent can really say what is best for you, only what they like.

Venice versus the AC - tough call. You can't do both this trip. I say see Venice now because it is most unique and take a vacation to the AC some time.

Agree with whoever said to go in (late?) September rather than November.

Don't give up on making this your personal trip.

Since I think there are TA among the posters, I would need to be more obtuse. I am not sure how long you have been traveling. Over the deregulation since the 80's, I think the travel agents' role has changed significantly. Before the deregulation, they obtained commissions in many different ways to be able to recommend many options for the clients. Now, with limited commission sources and competitions from DIY resources, I feel more push to take commissioned hotels, transports, tours, etc. The only time I use TAs these days are for very complicated itineraries using resources not bookable online but accessible only through TAs business partners in target countries. If your TA is your friend, that person my do a favor in using suppliers that do not pay commissions, but nevertheless is relevant to you. However, in current business environment, the TA cannot stay in business without choosing sufficient number of commission/fee producing bookings. Consequently, if you want to maximize your benefit at an acceptable price, you have to do your own homework anyway to be able to tell the TA what you accept what you don't.

I think one reason you might be lost is that there is no starting point - any starting point. Dayle has offered some itinerary ideas. Once some options are put on table, others can comment how well the itineraries are meeting your initial requirements.

However, at this time, there is none on the table to start a discussion.

Hi eb,

Been very busy at work and planning my own vacation for July!

I happen to work with a young woman who has been planning her first trip to Europe with her fiance. I have been giving her lots of the practical advice and suggestions about how to spend their 3 weeks.

At first they were looking at a "package" from a local travel agent. I told her to check out venere.it and italyby.com and see what kind and location for hotels/b&bs they could get by booking their own trip! You can sort by stars, price, location, it's great.

She came back the next day and said they decided NOT to do the travel agent's "package". I convinced her to stay in central hotels and find their own food.

They did get a very good airfare thru the agent and I'm sure the agent used an air consolidator. $500+ some odd bucks with just one stop to Amsterdam and back from Rome is pretty great!

I'll try and email you tomorrow. Don't be overwhelmed. Tell us what you are thinking as far as itinerary goes.
You can do it!

Ciao, Dayle