Thoughts on Italy Itinerary

When are you going? That might determine if it's worth for you to travel 3 long hours on the train to the Cinque Terre from Florence.

Siena and San Gimignano to me are both worth it. I generally take people to both on the same day, however I always have a car. Not sure how feasible it is with buses to do both on the same day.

For train schedules to Salzburg, check www.bahn.com

Florence main station is: FIRENZE S.M.N.
Salzburg main station is: SALZBURG Hbf

We arrive in Rome on May 29th so will be in Florence May 31st through June 4th when we leave for Salzburg. Would it be better to rent a car and go to Siena and San Gimignano or perhaps overnight in one of those places? Or in Cinque Terre? I've heard CT is really crowded. Do you have tips to avoid big crowds i.e. times of day/days of the week? thanks!

Since you've already been to Florence, I would consider making Siena your home base in Tuscany on this trip.

Siena is not like the other hill towns of Tuscany. It was a major cultural center, the capital of a republic that lasted for 400 years before the plague in the 14th century and then the defeat by the Florentines in the 16th century. There is much to see there, and it is a lovely place to spend the evening. It is also a good base for day trips to some of the Tuscan hill towns to the south: Pienza, Montalcino, Montepulciano, and others.

I think Florence to CT is too long of a trip to do in one day, though I know many people do it.

And I know lots of people love San Gimignano, and it is pretty with all the towers, but to me it felt like a Disney set. All that charming architecture served as nothing but a backdrop for the sale of cheap souvenirs. Volterra, not too far away, is a far more compelling town to visit.

Thanks! We'll take a look at Siena as a base. Since we have 5 days, we could consider splitting them b/w Florence and Siena. Would it be helpful to rent a car from Rome then spend a couple of days in Siena and surrounding area before moving to Florence and spending couple of days there (we would drop off the car before Florence)?

Intrepid, I agree with the others that Florence (or Siena) to CT is too far for a day trip, especially because during the middle of the day the area will be very crowded with cruise passengers and other day trippers, like yourself. Go to CT next trip, when you might have time to spend a couple nights. Siena is a great day trip or place to spend a night or two. There are various sites to visit. It too is crowded during the day, but magical in the evening when it is quieter and the lights come on, including illuminating the public buildings. If you go for a day, try to stay into the evening and for dinner, then catch a late evening bus back to Siena. San Gimignano is also lovely. The main street uphill from the gate to the main piazza is very busy, commercial and touristy during the middle of the day, but you are rewarded at the piazza with two excellent and competing gelaterias. Then walking beyond and away from that piazza, the town is really very quiet, scenic and pleasant.

I visited San Gimignano last summer and it was fantastic! We only spent a few hours there and that seemed enough. It has the most breathtaking views I have ever witnessed and I highly recommend it.

On other thought, Salzburg was probably my favorite travel place yet! Such a cool city with a rich history.

Have you considered spending a night or two in Verona - it's a lovely town with lots of sights (google Verona Card) and great ambiance in the evenings.

Tuscany - I'd stay in Siena, day trip by bus to San Gimignano and Florence.

I am definitely a fan of renting a car to see Tuscany, especially with adult kids. Since you have already seen the big cities I would stay in an agriturismo somewhere in the countryside and explore the area by car. You can visit lots of small villages and vineyards that would take so much longer by train. I would not stay in Siena with a car... parking is very difficult. You can just take off in your car and have some roadside picnics, do wine tastings, watch sunsets over the tuscan hills. So much more freedom to travel on your own.

One thought - if you rent a car, make sure it's big enough so everyone will be comfortable. It's worth the extra money. 3 adults in the back seat, even small adults . . . .

Day 1 - Arrive in Rome. Since you have been there before no need to stay. Head to Termini Station and board a train to Monterosso. You can get direct high speed trains during the day. Sleep in Monterosso

Day 2 - Monterosso / Cinque Terra. Get place to get over Jet Lag.
Day 3 - Monteross in the AM. Take a late train into Florence.
4,5,6 - Florence

Thanks so much for your suggestions. We've revised the itinerary per your suggestion, Roberto -

Day 1 - Arrive in Italy (Rome or Milan) and go directly to Monterosso
Day 2 - Cinque Terre
Day 3 - Morning in CT and then afternoon train to Florence
Day 4, 5 and 6 - Florence
Day 7 - Leave for Salzburg

Couple of questions - since we haven't booked yet, would it be better to fly into Milan or Rome (fare is roughly the same) to get to CT by train? Also, of the 3 days in Florence should we rent a car for a day and just drive through Tuscany or would it be better to do a day trip to Siena?

Additionally, does anyone have recommendations for a hotel in CT/Monterosso?

It looks to me like the train trip is about an hour shorter from Milan than from Rome, and there are direct trains from Milan to Monterosso every two hours. That seems like a better option.

Check out Rome2Rio.

Milan is closer to Monterosso than Rome (1 hr less on avg).

However the closest airports to Monterosso are Pisa (PSA) or Genoa (GOA) (both about 1 - 1.5 hr away) and both are connected to Munich, Germany (MUC) with Lufthansa.

If you live in DC, then your home airport, Dulles (IAD), is a United/Lufthansa hub, Lufthansa is a United codeshare partner (Star Alliance) and both fly to MUC from your airport. The fastest and most efficient way (and maybe the cheapest), therefore, might be:

Lufthansa (or United/Lufthansa combination)
IAD > MUC > PSA (or GOA)

I would be looking at this flight option first. Lufthansa is great to fly with, Munich is the most efficient and easy to use airport I've used in Europe, and maybe around the world (and I travel enough). Plus the train trip from either Genoa or Pisa to Monterosso (which is between the two cities) is short and super-cheap. Even if the airfare might be a bit more than to Milan, however you'd save on train fare and on time (and hassle) and time is money,

Italy Itinerary is awesome. As of those friends of mine who went there, replied same - awesome city of loving people. I would love to go there.