Italy here I come

My preference would be irrelevent, since my likes and dislikes and past experiences are likely vastly different than yours. Without knowing what you will do while in Monteriggioni, and where you might want to go for your second (and/or 3rd) locations, it's impossible to say. Providing your choices of location aren't greatly distant from each other, there likely isn't a wrong choice.

I like sea and beaches, so my preference would be a week at the seaside, maybe in Sardinia or Elba, after Monteriggioni.

But I am I and you are you, so you can only decide for yourself, maybe after researching the many options Italy has to offer.

My wife and I love the sea and beaches. We are flying into Rome or Florence. Our trip must include a week in Tuscany at Monteriggioni with 10 friends. We have never been to Italy so we are looking for advice. The sites all say see Rome and Florence. My wife prefers a quiet relaxing visit to a location without hustling around everyday trying to visit every tourist stop in town.

We have never been to Italy so we are looking for advice. The sites all say see Rome and Florence.

You have a few months to reflect since your trip is in June.

Consider your interests.

• (Ancient) Roman History
• Art
• The Renaissance
• Religion or churches. (Consider that much art was made for churches and cannot move from those churches.)
• Food or cooking
• Wine
• Mountains
• Beaches
• Hiking

Since you’ll be in Tuscany consider its history. Maybe read The Agony and the Ecstacy or watch Medici Masters of Florence or Medici The Magnificent on Prime … or (for Rome) The Borgias on Paramount+ or Apple TV. Historical novels by Robert Harris, such as Imperium.

Look at multiple guidebooks - you can check them out from your local library - with your interests in mind.

Thank you Fred. Your direction was quite helpful. My wife has informed me that I did not ask the correct question the first time.

We’re here to help, that includes helping frame your question!
First course of action is to decide if you want to see Rome or Florence or not. There is no rule that you must! The smaller towns are happy to receive you.
Second: Are you going to rent a car for Monteriggioni?

Yes we will rent a car either in Siena or Florence at the appointed time when we travel to Monterggioni. We will spend the next couple of months reviewing videos, and books. My wife is a quilter and loves beautiful decor.

Mark have you booked flights yet? If so, where are you flying in and out of?

And also If you do have flights, or even just dates blocked out, when is Monteriggioni in your itinerary?

We have not booked our flights, train tickets, rental car or hotel/airBNB yet. We are trying to decide on the best plan so we know where to fly into to start our trip. We are open to hearing +/- experiences with certain airports Rome/Florence. We will be flying American Airlines.

What is your home airport you are departing from North America? That would be useful information for us to suggest flight options as Florence has only intra Europe flights.

Regarding whether to visit Rome and/or Florence that is up to you and you must do some research on that to decide for yourself. You are in Monteriggioni for a week, which is a very strategic location, therefore you will have opportunities to see Siena (a small city) as well as famous smaller villages like San Gimignano, Certaldo, Barberino Val D’Elsa, Colle Val D’Elsa, Volterra, the Chianti Hills (Castellina) all of which are within 30-40 min drive from where you are staying. Even Florence is 45 min away.
Where to pick up and return a car will depend on where you fly to and from. You should pick it up in the city where you arrive and return it in the city you depart from. If you have never been to Italy I think you should spend 3 nights in Florence and/or Rome, depending on your flight choices. If you fly out of Rome, leave Rome for the last 3 or 4 nights before the flight back. If you fly out of Florence then spend the last 3 night in Florence. Florence is only 45-50 min from Monteriggioni, so it’s closer.
You won’t need a car while you stay in Rome or in Florence. Therefore arrange your rental in such a way that you don’t have a car while staying in Rome or Florence.

Just wondering, how did you decide on Monteriggoni. It looks very beautiful, but not a lot to explore.

We will be flying American Airlines.

Flying from where?