9 days - Rome, Assisi, Siena, Florence - balance the days

You will get some good responses to your questions! First trip? Everything will be new to you, and dare I say, exciting and different.

With 5 people traveling the car is a good idea, I think. Am I correct that you land in Rome and fly out of Florence? You can do plenty in Rome but be aware that it will be hot and very humid. I suggest plan your days around a couple hour afternoon break to rest and shower.

Assisi is very special to me. I am part of an international music festival that occurs there every July. One night? Ok, but get out your RS book - there's plenty to see in Assisi. Siena is only about 1 1/2 hour drive from Assisi. One night there too? Have you thought about staying longer in Florence and day tripping to Siena? Also, Florence is in the bottom of a bowl - that means humidity (and lots of people). Remember that each time you change hotels is basically a day off your vacation.

There is plenty to see and do in each city you have chosen. May I suggest using the RS Italy and prioritize your 'must see' list. In Florence you have the big help of making timed entry reservations for almost all of the main sites. Sorry Rick Steves but I usually add at least an hour to your suggested times.

On the flight home you can do what I bet most of us do: plan your next visit!!!!

Roberto, as usual, has given excellent advice. I also recommend staying the night in Assisi- there's much to see there. As for Siena, I'd be tempted to add a day to Florence and day trip to Siena, just to reduce one one night hotel stay.

If this is your first time in Europe, don't forget to get an International Drivers Permit for each of the drivers (you'll need it in addition to your regular DL). Available at AAA offices. They can also take the photos that are required. And most importantly, familiarize yourself with Italian driving laws and road/traffic signage. Learn about ZTLs and traffic/speed cameras to avoid a costly ticket that could arrive at your home a few months after you return.

Realize that you should not include your arrival and departure days in your vacation. In actuality you have 7 days (possibly another half day if your arrival is early and everyone has recovered from the flight). There is so much to see in both Rome and Florence that you should first plan what you want to see in those cities and estimate the amount of time it might take to do it. A lot of time can be lost - especially with 5 travelers - checking in and out of hotels and locating parking while avoiding ZTL’s.

I love both Assisi and Siena but would only take a side trip to one. My suggestion would be to drop Assisi on this trip, go from Rome to Florence by train and take a day trip to Siena by bus. To save additional time, purchase tickets to sites you want to visit on line to avoid long lines at the sites. It will most likely be uncomfortably hot in August and you don’t want to wait an hour to buy a ticket. If you buy saver tickets early, you can get rail tickets for about €33 per person and the trip from Rome to Florence takes less than an hour and a half.

The down side of the travel forum is it gets me thinking and planning not only for others but also for myself! Let's talk Siena! The Duomo (along with the Baptistery and the Duomo Museum) are well worth while. You don't need a guide but you do need tickets to get in (as you face the church, the ticket place is on the right side). The Piazza del Campo (main piazza in Siena) is an amazing place to sit with a drink (they'll also bring snack food, which is traditional in Italy). Great people watching! However, I do not recommend eating a meal there. Too touristy for my liking. My usual method of finding food in a new place: walk around, read menus, avoid any place that has a 'tourist menu', and above all, you want a place that's crowded and not too quiet. Remember, in Italy you own the table for the entire evening. Relax, enjoy and don't be offended if it takes a long time to get the bill! It's called 'il conto' in Italian - catch your waiter's eye and draw a check symbol in the air. He'll say yes but that doesn't mean he's going to do it right away. If you have a schedule to keep, please tell them when you sit down. You deserve this, after all. I'm not a wine snob so I order the house wine (vino rosso [ or 'bianca'] della casa). This is the wine they are proud to serve, sometimes because it's their family's own. Yes, a 1/2 litre is cheap!

Ready for Assisi? Parking in Assisi is difficult. The city is on the side of a mountain (Subasio). You park on one level and ride (the sometimes working) escalator to a higher level. Your at the ancient Roman gate to the city. The first church you come to on your left is Santa Chiara (St. Clair). Can't miss it - it's very big! Worth a walk through, especially the basement where you'll see her and several items from St. Francis. The view from the piazza of the valley is really beautiful. Keep walking (the next gate is also an ancient Roman gate and is attached to the hotel I stay in every year for 2 weeks during the music festival - Hotel Sole). The Piazza Comune is directly in front of you. Your RS book will describe the history. What he doesn't tell you is something more recently discovered - underneath all the Roman ruins there are Etruscan ruins that were found after the 1997 earthquake. 2700 years of history! The little cafe right next to the temple (Santa Maria sopra Minerva - Holy Mary built on Top of a Temple to the goddess Minerva) is my favorite hangout. Try Campari and orange juice - best thing for a hot afternoon! Keep walking but as you pass Minerva stay to the right. The views are spectacular. The Panoramica is a great place to eat with a view. Keep walking - you'll come to another ancient Roman gate. Make a sharp left and there's the Basilica of San Francesco down the hill. There are actually 3 churches built on top of each other. Some of the most important art in the world is inside!
OK, I'm almost out of space. Real quick: food in Florence - the Mercato Centrale (center market) is both great shopping and great eating. You can each select your own dinner from dozens of choices and still eat together.
Remember: YOU deserve this!

Thank you for all of the advice. Many of you mentioned the loss of time due to check in/check out. I may change our itinerary to another night in Florence and a day trip to Siena to eliminate one transaction, but I believe in Rick's book I read that night is so special in Siena, I didn't want to miss the evening. Any opinions on the benefits of an entire evening in Siena (less tourists, etc.) I am also considering trying Air bnb rather than hotels to get a more 'Italian' experience especially in Assisi and Siena if we were to spend the night. Would you concur? I appreciate your suggestions! This is a wonderful resource for an inexperienced (but eager) traveler!

Siena in the evening is magical. If it works for your travel needs and so you can relax and enjoy it, then stay overnight.

Assisi has some wonderful apartments. Check vrbo,com - last time I looked for some of our musicians that site had more and better. You want to be on the level with Piazza Comune for the best access to everything. Do not expect airconditioning - it can be quite cool at night on the side of the mountain. Just make sure your apartment has a view of the valley (where the breeze will come from, and the best view!).

Car rental? The places you are going to have excellent train service. The summer schedule is up so I'd suggest looking at trenitalia.com