Get ready to do lots of research.

Italy is a big country with hundreds and thousands of sites visited by millions of tourists every year, so there are a lot of internet and book resources out there.

Buy or borrow a good guidebook, or two or three. Read some of the thousands of threads on here about Italy and have a look a Tripadvisor forums as well. There are lots more.

Decide on what time of year you are going and what kind of holiday you want.

Have fun - planning is as much fun as travelling.

I just noticed you said 'fall' (autumn). You can use google to find climate charts for all areas on Italy.

Trying to combine Lake como, Sorrento, Rome, Venice and Florence in two weeks is an extremely BAD idea. For a two week trip pick two, max three locations. Sorrento and Rome would be fine. Rome, Venice and Florence can be done to just see the highlights. Lake Como and Venice would work. But if you try to do all you will have your primary memories be of the inside of train stations.

For weather - google the town and 'weather averages' and you'll get sites that give you average temps for any given month.

For the highlights you could read some guidebooks. You can obviously buy them, but you can also take them out of libraries or go to B&N and read skim them there. On line most of the big guide books have most of their info available free. Here on Fodors go to destinations. Frommers and rough guides have their entire books on line as well.

I agree, there is a lot to see in Italy, and it is very varied. You need to decide what is the most important for you to see. We are doing almost 3 weeks, with 3 days each in Venice (at the beginning) and Rome (at the end), but we have already been to both of those places. The majority of the time will be spent in Bellagio (Lake Como) and in Tuscany. Venice, Bellagio, Tuscany, Rome... working our way down to Rome. If you want to just hit the big cities (Venice, Florence, Rome) you can hold down the train travel a bit and just divide it up into those cities. If you want to start adding the more outlying areas (such as Sorrento and Lake Como) then you're looking at more involved train schedules and extra travel time. Are you looking for scenery, history, art, churches, food? Make a list and go from there! Good luck!

After 17 trips to Italy we have not seen it all, so you will need to be selective in your planning.

A good starter trip is to fly into Venice and home from Rome and include a third destination between. I would prefer rural Tuscany as my third destination. Get a good guide book and do some reading---I like the Michelin Green book.

The Michelin Green guides are excellent for sites. You will also need a Fodor's or Frommer's which will have restaurants and hotels and a concise description of the Italy.

Romance and a hurried trip are usually at odds with one another. And while Florence is beautiful and interesting it is the tourist epicenter of Italy which detracts from the experience.

We travel with the idea that is better a few places well, than many poorly. Sit at a cafe, linger over lunch, you will enjoy Italy more.

I agree with the previous comments - Don't try and do too much. Staying within a region or two is best so do the North (Venice, Verona, the lakes and possibly a bit of Tuscany) or consider the Mid/South (Amalfi coast, Naples and Rome)

My last trip to Italy was just over 2 weeks on a Tuscany tour which included a lot of scenery, variety, culture, food and at least 3 days in each place. My itinerary was Bologna, Lucca, Sienna, Montepulciano, Florence and back to Bologna. Included in this were day trips to Modena, Viareggio and San Gimignano. I travelled by train and bus the whole time.

You could easily add in Rome or Venice with the fast trains from Florence or Bologna but it depends where you are flying in/out from. Check out www.trenitalia.com for timetables.


Whatever you decide to do you will enjoy Italy.

Venice, Florence, and Rome are easy to connect to one another by train, city center to city center. Traveling to Lake Como, Cinque Terre, and Sorrento each involve making a number of connections--adding just one them to the mix adds a longer travel day to get there and then to travel to the next place. I think you can pick one and have a balanced vacation, though not everyone would recommend so much moving about--but it is your vacation so you get to choose.

Itinerary 1:
Day 0: depart home (fly to Milano Malpensa)
Day 1: arrive Milan; travel to Lake Como (Bellagio? Varenna?); sleep lake Como
Day 2: Lake Como
Day 3: Lake Como
Day 4: train to Venice (Varenna Esino-Milano Centrale; Milano Centrale-Venezia SL); sleep Venice
Day 5: Venice
Day 6: Venice
Day 7: train to Florence (Venezia SL-Firenze SMN); sleep in Florence
Day 8: Florence
Day 9: Florence
Day 10: train to Rome (Firenze SMN-Roma Termini); sleep Rome
Day 11: Rome
Day 12: Rome
Day 13: Rome
Day 14: fly home

Itinerary 2:
Day 0: depart home
Day 1: arrive Venice; sleep Venice
Day 2: Venice
Day 3: Venice
Day 4: train to Florence (Venezia SL-Firenze SMN); sleep in Florence
Day 5: Florence
Day 6: Florence
Day 7: train to Sorrento Firenze SMN-Napoli Centrale; Circumvesuviana to Sorrento)
Day 8: Sorrento
Day 9: Sorrento
Day 10: train to Rome (Circumvesuviana to Napoli Garibaldi; Napoli Centrale-Roma Termini); sleep Rome
Day 11: Rome
Day 12: Rome
Day 13: Rome
Day 14: fly home

What are your exact dates? By late Oct the northern lakes will be getting chilly and some places will be closed. Also - by end Oct places will be closing on the Amalfi caost (most people don't like beach resorts off season) and ferries will run less frequently, some routes not at all.

If you don;t like cities the traditional Rome, Florence, Venice may not be for you. (I didn't see Venice until my 3rd trip to italy.) But I would get a couple of good guide books and decide what YOU really have to see - and keep the weather in mind.

then people can help you put together a plan.

Hey CC,

With 2 weeks in the Fall, I would fly into Venice: 4 nights
Train to Florence: 5 nights with visits to Siena and Cinque Terre
Train to Rome: 4 nights with a visit to Orvieto

Enjoy your visit.

I agree with nyt about the weather not being so dependable at the end of Oct. at least in the north.
Ellenem's number 2 itinerary sounds very nice for a first trip. You might take a day from Rome to stay in Florence an extra day, rent a car or take a tour and do a daytrip in the countryside, say San Gimignano and Volterra, taste some wine.
Or stay in the countryside around Florence, do daytrips from there to the hilltowns, and a daytrip to Florence.

Keep in mind that if you ever come back to Italy (and you will) you will likely fly into or out of Rome, so will have time to see more of Rome.

Rick Steves Italy is very good for first time visits, I found, since he gives so much practical information on transportation, what to see, etc.

It's nice to also have Fodor's Frommers as well, they have pictures where R Steves doesn't.

We are going to Italy for our 30th wedding anniversary this fall too! We'll be there late September - early October. Given the time of year, we're heading south for the sunshine. We live in the Pacific NW and feel desperate for some sun!

Here's our trip:
2 nights in Naples
pick up rental car, drive south to a coastal area called The Cilento, south of the Amalfi coast
3 nights in Cilento, staying 2 nights at an Agriturismo and 1 night at a hotel in Pisciotta
drive up the coast to Positano (Amalfi Coast)
4 nights relaxing and hiking in Positano
return rental car in Naples, train to Rome
4 nights in Rome at an apartment

We also have 3 nights in London at the start of our trip, and a night in Germany on the way home. So we are 2.5 weeks total. It's a mix of city excitement and splendid relaxation on the coast. Good food and wine every day. We leave in 4 months - I cannot wait!