Portugal to Italy ideas

Hi Wendy,

You have some really exciting tours ahead for 2020. The destinations are excellent. I noticed you have a gap between Sept 18 to Sept 22. What are you planning to do between those open dates?

Aug 14-24 Tour of Portugal. I have given myself two extra days at the start of the tour in Lisbon and one additional day in Porto at the end of the tour.

Aug 25 Porto to Salamanca

Aug 26 Salamanca

Aug 27-Salamanca to Madrid

Aug 28-Sep 1 Madrid including day trips (Day trip to Toledo)

Sept 2 Madrid to Barcelona

Sept 3-7 Barcelona including day trip (Day trips to Montserrat or Girona)

Sept 8-Barcelona to Milan

Sept 9-11 Milan (Day trip to Lugano and Bellinzona)

Sept 12 Milan to Florence

Sept 13-16 Florence - (Day trip to Pisa and Lucca)

Sept 17-18 Sienna
Ideas welcomed.

Sept 22-25 Venice/Verona/ Padua

September 25-October 2 Food Tour-Venice, Bologna, San Germino, Rome

October 3-6 Rome (Day trip to Orvieto or Ostia Antica)

Looking for ideas need to be in Sicily October 11. I have been to Naples and Sorrento on a previous trip
October 11-18 Sicily Tour Explore (Palermo, Catania, Agrigento, Syracuse, Cefalù, and Taormina)

Oct 20 Flight to Toronto

Not a bad plan.
It is a bit busy, but doable.

Porto and the Douro Valley are amazing, you don't seem to plan anything for the Douro Valley. We did a wonderful 7 day river cruise in 2016 and loved it. Consider taking the train and spending a day or two in the valley. Toledo is a must see city, you can do it on a day trip from Madrid.
You mentioned doing Seville. Seville is wonderful and you should probably plan to see it as well as the Alhambra at Granada.
If you do, you will need to eliminate something on your itinerary. Don't cut any days in Rome, since you don't have enough time there anyway. You need at least 5 days in Rome.
Milan is good, but you might just head to Florence from Barcelona. Do Siena on a day trip from Florence, unless you stop in Pisa and Lucca for a day.
Venice is great, but skip Verona and Padua, you have three days for those three and need three days in Venice.

Most important from my perspective: Your tour of Sicily isn't anywhere near long enough to see the island well. I don't know exactly what it does and does not cover, but I'd head to Sicily straight from Rome to fill in some of the gaps. Even that will not be long enough.

It's a long bus ride from Porto to Salamanca. I'd suggest planning an afternoon departure for Madrid so you'll have enough time to enjoy Salamanca, which has a large historic area.

I'd drop Milan completely and add that time to Sicily if you could, but given the timing of the tours I guess that's not going to work. I think 3 full days in Milan is rather a lot. The main sights I'm aware of are The Last Supper, the Duomo, the Galleria Vittorio Emanuele II shopping arcade and the Brera District, all of which could be seen in one day. I'm sure there's a good art museum; that would need part of another day.

I agree that the time for Venice, Verona and Padua seems short. Padua is a very interesting city with quite a lot of actual sights (pre-book the Scrovegni Chapel). I'd say Padua itself needs more than one full day. And there's Vicenza nearby as well. Plus a side-trip to Ravenna if you haven't already seen the mosaics. So for me, this is another area that's more important than Milan. This is where I'd use the unallocated post-Siena days. I'd also skip the side-trip to Pisa to have more time for Venice/Verona/Padua/Vicenza/Ravenna. Or at least substitute Lucca for Pisa.