Thank you in advance for your advice on our itinerary.
Three adults will be traveling together on this trip in June 2016.
Two of us have been to Italy twice before and visited Rome, Venice, Verona and the Amalfi Coast.
One of us has never been to Italy and they would really like to do a quick day tour of Rome.
We are using mostly hotel points for free nights and we are basing our itinerary on the free nights in the hotels.
Priorities for places to visit are Bernina Express over Alps to Switzerland, Cinque Terre, Lake Como, Tuscany hill towns(siena, Montepulciano, San Gimignano.
Day 1- 2 The current plan is fly into Rome from the US and arrive in the morning. We would drop our bags at the hotel and do a quick one day tour of Rome and then spend one night in Rome. I realize we will be tired after having flown all night, but this is just a quick look at Rome for the traveler that has never been there. If we didn't fly into Rome where should we fly into for the one night before our reservation in Florence?
Day 3 - Day 7 we will travel to Florence and stay at the Westin Excelsior Florence for 5 nights on hotel points. Florence is new to us all.
On two of the days we are based in Florence we are thinking of doing day trips. Any suggestions for day trips? I love Brunello wines and really want to go to the Montalcino area for wine tasting. Suggestions? I have seen suggestions on this forum for Best of Tuscany day trips.
Day 8- When we leave Florence, we have a free night that we were considering to go spend the night at Cinque Terre. Do you suggest more than one night at Cinque Terre? We will need to travel to Lake Como from this location.
Day 9 - 13 The plan was to go to Lake Como to stay at the Sheraton Lake Como for 5 nights on points. Sometime during this stay we wanted to do a day trip and travel on the Bernina Express train (panoramic coaches) to St. Moritz and back. We are having difficulty figuring out the logistics of this. I have emailed the hotel, but have not heard back from them on how to go about this.
I posted another thread about the Bernina Express from Como, Italy and it doesn't sound like you can easily get there from the Sheraton, so we will probably need to shorten this stay from 5 nights. community.ricksteves.com/travel-forum/italy/como-italy-to-bernina-express
Day 14 and 15 - we are thinking of going to Milan or Venice and spending one or two nights there and then flying home on Day 16. Any other suggestions of where to go after Lake Como? We've never been to Milan, but I've never really had a big desire to go there other than to see The Last Supper. I really don't care if I ever go to Venice again.
Maybe we should fly home out of Rome and spend the last few nights there? Another option is to take the Bernina Express at the end of our Italy trip and fly home from Zurich. I have read zurich isn't all that spectacular though.
I have never had such a hard time putting an itinerary together. Thanks again for your advice and help.
Suggestions on how to make this work? Any advice would be greatly appreciated.