Wedding Anniversary trip - May 2018
 

Hello all, my wife and I are taking a 10 day trip at the beginning of May to Italy to celebrate our 10th wedding anniversary. Dates are not flexible as I already have the flights. We have some idea on what we want to see, and have some tentative hotels reserved, but those can be moved around. For the places I do not have hotel, need some recommendations as well. Please provide feedback and suggestions on additions/changes. We are renting a car the whole trip. Thanks for your help!

May 2-4: Florence (already have hotel)
We arrive to FLR on 5/2 evening. Planning on staying all day on 5/3 and can leave early 5/4 spend the day in Sienna (on our way to Pienza)

May 4-6: Pienza (already have hotel)
Spend a full day in Pienza an potential another day in Montepulciano

May 6-10: Need advice here
From Pienza go up northeast towards Cinque Terre. Stop in Lucca and spend the night there (6th), then go towards Forte dei Marmi and spend another night there (7th). Then go to to Cinque Terre, but stay in La Spezia two nights (8th-9th). Leave on the 10th early in the morning and stop in Parma and Piacenza, on our way to Milan.

May 10-12: Milan (already have hotel)
Arrive late night on the 10th, spend all day on the 11th and leave early morning on the 12th.

Just a small comment. In Italy, CT generally and officially stands for, and everybody understands, the province and the city of Catania in Sicily when using this, especially in travel-related texts. So be careful with the FT-wide habit of using acronyms, as you may find yourself in the opposite direction. :cool:

Thank you, edited the post to reflect this.

You have 8.5-9 days. You can't count the May 2nd when you arrive in the evening. You don't even have a full day on May 11, because for an early morning flight it is almost an imperative to stay at an airport hotel (the Sheraton) So you have something in the range of 8.5 days, and you want to see 10 cities? Actually, that itinerary guarantees that you aren't going to be seeing any cities.

Other than renting a car in Florence, which is the second worst way to ruin your trip to Italy, the number one way to ruin a trip to Italy is pretty well described the article linked to below called, "The Biggest Mistake People Make When Planning a Trip to Italy," published in Walks of Italy, written by Gina Mussio. I'll provide a link to the full article below.

"The main problem for anyone planning a trip to Italy is that it’s impossible to see everything you want in one trip! This leads to the biggest travel planning mistake that most people make in Italy: They try to see too many things in too short a time. We hate to be the bearers of bad news but overloading your itinerary is a recipe for stress.

We understand why you do it and we sympathize, but let us repeat: rushing your Italian vacation is a surefire way to ruin it. Luckily, the solution is easier than you think: narrow down your focus and divide your time accordingly.

The rhythm of any trip to Italy, that is, how long you spend seeing what you came to see and experiencing what you came to experience, is just as important as what you see and experience. In fact, you could simply book a trip to Rome and spend two weeks hanging out there without ever getting bored. In order to help you get an idea of how to budget your time in some of Italy’s most popular regions, we have written three sample itineraries. After many years of traveling in Italy and interacting with other travelers, we have honed the rhythm of these itineraries to perfection. Feel free to crib them as is, or use them as a base to create your own custom itinerary. In this case, the where isn’t important; it’s the when that matters. As always, we’ll be waiting in the comments sections for anyone with questions."

According to this article, from a respected source, that is pretty well agreed to by people who travel to Italy a lot is that on an 8-9 day trip you only have time to visit three cities, for example for Rome, Florence or Venice, and maybe one other city. You can't visit 11 places in 8-9 days, or else you won't have time to see any of them.

The full link is here. https://www.walksofitaly.com/blog/al...anning-mistake

Remember, that when you try to squeeze in too many places, you spend a lot of time packing, traveling, checking in, and unpacking, not actually seeing the place you are traveling to. That is why many people consider a day during which you are traveling as only half a day. With all that is involved in trying to see 10 places in 9 days, it really becomes more like a five day trip where you are actually visiting a place.

Thank you for the advice and reference article