We went to Florence this past October. Took the train easy trip. We hired a private driver to take us to several cities in Tuscany including Volterra and San Gimignano. Well worth it.
Any progress on your trip planning? I’m missing Italy and need to live vicariously through you. 
I don’t think anyone has mentioned Lake Como. If at all possible, try to get to Lake Como where George Clooney has his villa. One of the most beautiful spots in all the world. Montecatini is a spa town that’s a lot of fun, if you can also get there or pass through. I love Roma, not a huge fan of Florence, but oh well, to each her own.
DH and I are also going to Italy, late August. We’re just doing an organized tour (Venice, Florence, Rome) – I don’t travel well, and I would be the one organizing it all, which I don’t care to do. I was there about 55 years ago and, for some reason, I really don’t remember too much! DH has never been but he really wants to see the artwork in Florence.
It’s an expensive tour, but it will be our 40th anniversary and my 70th birthday, so we’re doing it.
I’ll second the use of google.com/flights to monitor and to purchase airline tickets. Just used it for the first time, and I’m happy that I did.
While true, it’s also 3-4 hours from Florence - too far for a day trip.
^^Make it your whole trip. Definitely worth a whole trip visit, now or in the future.
We went to Rome, Florence and Sorrento two years ago (3 days in each). I would recommend two days in Florence if you can. We went by bus from Florence to San Gimangnano and then Siena and wine
We did Rome and Florence last March - I can’t tell you how jealous I am that you are going!! I know it is not cheap, but the best thing we did was hire a driver and/or guide for certain things. We used a company called Italy Chauffeur Service (after much research) and I highly recommend them! If you use them beg for Mikayla as your driver (she took us from Rome to Florence then was our driver all over Florence) - she was amazing. If you use them in Rome and need a guide beg for Marco - he is not always around because he is an archaeologist and is often away for that job, we got so lucky that he was there because he was so passionate and knowledgeable about everything we saw. I’ll put the prices we paid at the end of this, although most of yours would be cheaper since we had so many people and usually needed a big van or sprinter.
We hired a driver to take us from the Rome airport to Florence with a two hour stop in a town called Orvieto which we loved. It was our first time traveling abroad and I wanted to make the first day nice and easy.
We spent about 5 days in Florence and used them to do day trips for wine tasting (2 wineries plus a lunch stop - you could probably do more but we specifically wanted to go to Montelpuciano and Montalcino and they were kind of far apart) and one day we did Pisa and Cinque Terre. I would suggest skipping Pisa, we only went because the kids really wanted to see the tower.
Cinque Terre was great - the drive there is spectacular - but since we had done Pisa first we did not have enough time to see it properly. I think if you did only CT you could probably see two towns on a day trip. Our driver was great and since she knew we didn’t have enough time to really get from town to town she suggested we just see Rio Maggiore and then head to Portovenere. This was a great suggestion - Potrovenere was very cool.
When it was time to head back to Rome we took the train then a cab to our Air BnB. We used the same company for two half day tours in Rome. One we went to see the Colosseum, the Catacombs and a little bit of the Apian Way the other was for the Vatican.
Rome to Florence with 2 hour stop - 2 people - 685 euros
Pisa/Cinque Terre driver only (although we got lucky and Mikayla was basically a tour guide as well) - 7 people/11 hours - 705 euros
Wineries - 7 people/ 9 hours - 535 euros
1/2 day Rome with guide - 7 people/ 4 hours - 220 driver/ 250 tour guide
In Rome we committed to Five Gelato Days, which were basically days walking from sight to sight in Rome and every time one of us got cranky we ate a gelato. It’s a great way to do Rome.
Outside of Rome you might want to go see Ostia Antica – the original port of the city.
Similarly if you want to see Pompeii, an easier and very similar site is Herculaneum – destroyed in the same volcanic eruption, still be excavated, but much much less touristy. I went to both and Herculaneum was much more satisfying and mysterious seeming. Pompeii is larger, is set up for tourism, and certainly worth the effort. I’d bring an umbrella as a shading device when and if you go. The sun can be bright.
Agree Venice is too far for a day. I love Siena. Assissi is a two hour drive - gorgeous hill town, Giotto frescoes and Saint Francis. Ostia has great Roman ruins. I did Pompeii as a day trip from Rome many eons ago. Took a bus.
We went to Rome last fall to celebrate our 25th anniversary last year. We toured most of Rome on our own as we found the public transportation and taxis easy to use and affordable. We used Context tours to see a lot of the historical places (Coliseum, Vatican, toured a current excavation site in the city). Most of our tour guides were Art History, Classics, or Archaeology trained tour guides holding a PhD or Masters degree in their field. We love in depth tours. The only thing I wish I would have done but ran out of time is to take a food tour. We did this in Barcelona (my husband thought I was wasting time and money when I booked it) and it ended up being one of the best things we did. The 5 hours flew by with food dishes, wines, and different restaurants that we may not have tried on our own and met some wonderful people.
We went to Florence for a day and found that it was not enough time. I would have spent at least 2 days there to see it all and shop.
We have booked our flights in and out of Florence. We haven’t booked tours yet. Am I too late? Splurging on private tours is part of the plan, but which ones? Thanks to the specific suggestion above!
Good move to fly into Florence. You will save yourself time and hassle.
As you plan your excursions out into Tuscany, check on which days are market days. http://www.tuscanyitaly.info/marketdaysintuscany/marketdaysintuscany.htm#.WoNQ_2JMHYU You will get exposure to genuine local living.
Has been been suggested already to day trip to Lucca?
No. I know nothing of Lucca. Do tell.
The ancient city walls are wide and act like green space. They even rent bikes for going around on it. Should be about an hour from Florence. My sister loved it and it’s untouched medieval core. I was planning on going this fall but my dates coincided with a massive comic con type event there and that is not my scene.
Edited to add: my sister is a hot springs fan. I know on one trip she went to a hot springs spa. It was very popular with Italians. This website lists a couple but with some internet digging you could find more. https://www.discovertuscany.com/what-to-do-in-tuscany/thermal-baths/
I am going to send you a PM because I am not sure about the rules about links to private businesses.
The food tour in Rome was a highlight. The Travestere Twighlight Tour was fantastic.
https://www.eatingitalyfoodtours.com/rome/tours/twilight-trastevere/
I second the suggestion of a side trip to Ostia Antica from Rome. It is a short train trip (30 minutes or so), connected to the main Metro. I believe you leave from the Pyramide station. Very fascinating ruins with interesting mosaics and a clear lay-out of the old port city.
In Rome, some of the sites I have enjoyed most (aside from the stand-bys, the Forum, the Pantheon, St. Peter’s Basilica, the Coliseum, Piazza Navona, the Trevi Fountain, the Spanish Steps) are the Ara Pacis Museum (stunning!) and the Capitoline Museum (also stunning!). I have wanted to go to the Antico Caffe Greco for a long time–you can check the Wikipedia list of famous historical figures who have been there–but it is not open in August, when I have usually been in Rome. Actually, quite a lot is not open in August. Babington’s Tea Room, quite near the Spanish Steps, has also hosted famous historical figures. My daughter and I had tea there in the midst of a rainstorm, and it is one of the coziest and most memorable experiences I have had. There is also a Ferrari souvenir-type shop nearby. The Largo di Torre Argentina is somewhat less known, but quite interesting–it’s located about a story below the current street level, and serves as a home to many cats.
Climbing as far up as you can go at St. Peter’s Basilica is extremely rewarding, and well worth all the effort plus the slight sense of claustrophobia on the inside as you approach the top and the interior curve of the dome is right beside you, plus vertigo on the outside at the top, as you look out over Rome. A number of popes are buried in the crypt and there is a grave there that may possibly be the grave of St. Peter. It is remarkable.
The Villa d’Este is also a very interesting side trip from Rome. Great interconnected fountain and pool system!
I stayed once at the Waldorf-Astoria in Rome–could only afford it once, but what an incredible experience!
The Via Veneto was apparently fashionable in the 1960’s and not so much now, but there are some interesting places there. The Hard Rock Cafe Rome is on that street–often crowded, good if you go in off hours–and there are some quite nice restaurants (from my viewpoint, anyway) that feature large Lucite enclosures–maybe about 4 to 6 times as large as a bus–so they can be air conditioned, and they are very pleasant.
I will try to come up with other recollections. I have not yet been to the Borghese Gardens, but they are definitely on my list for future visits.
I did not like the catacombs, though I am a Christian. (Would not go back.)
The city tour by bus is worthwhile, for a first- or second-time visitor, to become oriented to the city, and identify places you would like to see for a longer time. One of the great things about Rome is that practically everywhere you go, there are sights that will leave you gasping! I think Amazon has a paperback guide to the cafes in Rome, which I enjoy just reading–have visited 2 or 3 of them so far.
One tip: You know the old saying that there are no atheists in foxholes? My daughter remarked that there are no atheists in the restrooms at the Coliseum. Another tip: Do watch out for pick-pockets. They are astonishingly skillful. Some are on motorcycles, come up beside you, and grab a purse. Others are just amazingly agile, especially the ones at Termini Station. Luckily, I have managed to avoid problems on trips, but I wear one of those zippered waist cases under my clothes. My daughter: “That’s not a good look for you, Mom.” It is not! But it’s worth it.
We enjoyed Florence quite a lot, though the number of tourists there did not seem to be very much smaller than the number in Rome, on a per square foot basis. Venice was well worth seeing, though it is not a day trip. I regret not buying one of the large glass balloons from a shop on St. Mark’s square, and also regret not buying one of the Carnival masks sold nearby. (But both were quite expensive.)
I have asthma so I am a little limited in what I can do. My sister did day hikes from Florence and thought the countryside was fabulous. http://www.travelandleisure.com/local-experts/tuscany/best-day-hikes-in-tuscany
http://italywithgusto.com/hiking-near-florence-italy/ your friends will need to help you translate the link in the article to a hiking trails map
I think this may be a blog - google word press Florence For Free The Castle Hike. the blog seems to have a lot of good ideas.