Help with itinerary for October 2015

Day 0 Arrive Milan and train to Como (Varenna) (2)
Day 1 Lake Como
Day 2 To Milan (1)
Day 3 To Verona (1)
Day 4 To Venice (2)
Day 5 Venice sights
Day 6 To Siena (2)
Day 7 San Gimignano day trip
Day 8 To Florence (3)
Day 8 Florence sights
Day 9 Pisa+Lucca day trip
Day 10 To Assisi (1)
Day 11 To Rome (3)
Day 12 Rome sights
Day 13 Rome sights
Day 14 Depart Rome

You have 9 locations listed for your 13 days in Italy. I would suggest you cut it down to about 4 cities that are the most important for you. From the looks of your list Tuscany (Florence and Pisa) is one location you're interested in. You'll need to decide the others.

As for "must sees", those are the sites that are the most important to you. You and your friend need to get a few guide books and make lists of what you want to see and do in each city. These will be the "must sees" for you. Without knowing you or your friend it's really just a guess as to what you may or may not like.

Donna

You already know you can't visit all these places without spending all your time traveling. Prioritize and you can probably see half. Many newbies to Italy visit the Big Three (Venice, Florence, Rome). In 13 days you might visit four without too much rushing about. By train I suggest heading to Lake Como (Varenna) for a couple of nights, then on to Venice, Florence and Rome. From Florence you could day trip to hill town and from Rome maybe visit Assisi. Allocate 2-4 nights at each stop.

Thanks so much for the quick responses! Nobody really said much about spending much (if any) time in Milan or Verona, so I'm thinking those could be places we could "cut". I saw a day tour from Florence that hits Siena, San Gimignano and Pisa. Does anyone have experience with that type of tour...would that be a good use of a full day?

Como to Milan is only 0:59 hour by train.
Milan to Verona is only 1:22 hour by train.
Verona to Venice is only 0:59 1 hour by train.
If you travel say between 5pm and 7pm you have all day beforehand to see the sights, arriving for dinner at your next destination.

Further travel times ...
Venice to Siena is 4:01 hour by train.
Siena to Florence is only 1:25 hour by train.
Florence to Assisi is only 2:31 hour by train.
Assisi to Rome is only 2:18 hour by train.

Milano can be visited as a daytrip from Varenna, or take a morning train from Varenna on your way to Venezia, check your luggage and spend most of that day in Milano.

From Venezia, or on your way out of Venezia to Firenze, stop for the day in Verona.

Siena, Arezzo, and other towns in Toscana are easy day trips from Firenze. Or spend a day on an organized tour.

Overnight in Assisi. Then continue to Roma.

This will minimize your one-night stops and give you more time to enjoy the places you are seeing.

I would take the ferry to some of the towns on Lago di Como, go to the roof of the Duomo in Milano, and see whatever is important to you.

Have a great trip!

I like Milan and we spent two nights there after flying into Milan. The cathedral is a must. We reserved online before trip to see The Last Supper. I would return to Milan. It is only an hr to Lake Como. And Varenna. We spent three nights there and took in a cooking class which was delightful. Verona is a day stop, no overnight required. Skip it unless you really need to see Juliet's balcony. As others have pointed, out, focus on Venice, Florence and Rome. There is more than enough to keep you busy for your entire stay. Be prepared for crazy crowds in Florence and Rome.

Have you considered Rick's Best of Italy tour? It is well worth the price. We added two days ahead in Milan and two nights after in Rome with a day trip to Pompeii.

Many thanks to all of you! Some really great input and will definitely help us to refine our plans. Thanks for all the help for us novices. Does anyone have advice re: "Walk About Florence" day tours? We're interested in the "Best of Tuscany" tour to get us around to Siena, San Gimignano and Pisa.

I have no experience with the company you refer to but would offer this advice.
Siena and San Gimignano in a day sounds good and easy to do.
Pisa and Lucca in a day sounds good and easy to do.
Siena and San Gimignano AND PISA in a day sounds like way too much to enjoy.

Thank you, David. We will think carefully about that!

I'd like to offer a different opinion from the earlier comment on Verona (i.e., that there's not much to see besides Juliette's fake balcony). Interesting Roman ruins, some beautiful churches and their art, and the Castelvecchio and its museum were all quite enjoyable. Consider doing it as a day excursion from Venice. You might also do Padua as a day trip from Venice – the Giotto frescoes, the Basilica of St Anthony, the university, an interesting market, etc.

You also asked about local tours. I find context travel, which operates in a number of Italian cities, to be consistently superior to any other operators I've used. Very small groups, and very well-educated guides. You might want to take a look at their website.

Siena and San Gimignano in a day sounds good and easy to do.
Pisa and Lucca in a day sounds good and easy to do.

You could easily spend the entire day in three of the 4 cities mentioned (Pisa requires several hours but not the entire day). To pair them up means you really don't have enough time in any of them to explore. The all deserve more than just a few hours unless all you plan to do it tick boxes off a list.

I suggest you get a good guide book or two and make a list a site you wish to see for each city you're interested in. I would then choose the 4 cities that have the most sites on your list. I would consider Tuscany as one area but still make a list for each town you wish to visit. If you plan to do day trips from any location add that onto that specific location such as Assisi would be a day trip from Rome so it would be considered a Rome day. This will help you organize and make the cuts necessary to make this a nice trip. If not, you'll find yourself running ragged trying to fit in every city and small town you hear of.

Donna

We took the Walkabout tour from Florence to Siena, San Gimignano, lunch at a Tuscan farm, and Pisa. We usually never take bus tours but it was excellent if you want to see all these places and don't have the time to arrange it yourself. We spent the most time in Siena with a guide. The lunch was delicious. So yes it is a good idea. Linda

We learned about WalkAbout Florence on this site - they are very well liked. They also have great reviews on TripAdvisor. We are going in October also, we are taking a bus from Florence to Siena as a DayTrip (great details on how to do this if you keep looking in the Italy Forums) . . . but we also did book a WalkAbout Florence CHIANI WINE & FOOD SAFARI TOUR. After all the research & planning we have done, I do think you have too many places for 13days. You'll spend more time traveling than EXPERIENCING ITALY. Less is sometimes MORE. You can also do an easy train trip from Rome to Orvieto as a DayTrip. If you go to the WATCH, READ, LISTEN section of this site - you can see Rick Steves Videos of several of the Tuscany and Umbria Towns - (that's how we chose Siena & Orvieto (with the help of people on this forum). We initially had way too much booked too and narrowed it down to one 'country town' in each region as a DayTrip & base ourselves out of Florence & Rome (we are going to Venice & Sorrento also, but we have 21days).... Happy Planning.

If you go to Milano, it would be a real pitty not to visit the Expo 2015. It is really worth it and it will close for ever on 31 october.
I would leave out lake Como and might do the costa amalfitana instead. You could do Como when you visit Switzerland another time along with lago di lugano and Locarno.
You would need at least 4 days in Roma, 3 days in Florence, 4 days costa amalfitana, for the other days, choose one of the following: Siena, Peruggia, Assisi, Gubbio, Lucca, San Gimignano). If you come to Italy, you will fall in love, so you will come back.

Just the expo need one full day.
Then another half to one day to stroll near the Cathedral and see the last supper.
Do not overestimate your physical capacity after a long flight.

We took the Walkabout Florence tour. It was a long day, but you had some down time on the bus between locations. I though it was a great tour and we really enjoyed our guides. We don't usually take guided tours and I was very impressed with this one. I would definitely recommend it.