We've traveled to Italy twice: our first trip was several days in Rome and then a week near Montepulciano and our most recent was 3 days in Venice, a week in the Chianti region outside Florence and then a second week at a villa near Cortona in Tuscany. I'll describe both trips for you with information on where we stayed, as well as recommendations on how to find accommodations. My restaurant recommendations will be on a separate page.
For both of these trips, we traveled in June because we had our children with us. If you have to travel in the summer due to school schedules, I'd recommend as early in June as possible. It only gets more crowded and hot as the summer goes on!
We rented our car through AutoEurope on our first trip. We picked the car up at the Rome airport, after we had completed our Rome vacation. You do NOT want a car in Rome! It is easy to get to the airport and rent the car from there. It is outside the city and the major autoroutes are easily accessible. Driving from Rome to Tuscany was easy; we stopped in Orvieto on the way, to break up the trip, explore and have lunch. The roads in southern Tuscany are easy to navigate. Once you are off the highway, they are generally well paved two lane roads. This is not the case in northern Tuscany/Chianti! It seemed kind of counter intuitive, but when we stayed outside of Florence on our most recent trip (about 30 minute drive from downtown Florence), the roads were much more of an adventure; part of it is the terrain, it is more mountainous but also the area is less touristy and the roads are narrower.
The train system in Italy is excellent. I booked the tickets from the USA and printed off the tickets before we left. I was able to get an excellent rate by booking a few months ahead of time using Rail Europe http://www.raileurope.com/index.html. When I travel in France I usually use the French rail systems booking site directly but had trouble doing this in Italy.
A word on finding places to rent in Europe. On most of our trips we have rented apartments in cities or houses/apartments in the countryside and rarely been disappointed. When going to someplace new, I spend a lot of time cruising the internet, often starting with sites I've had success with such as Slow Travel, or Trip Advisor, but I often will just type what I'm looking for into Google search and see what sites I'm taken to. Many times houses are listed on more than one site and you can cross reference to make sure the information is consistent. I do pay a lot of attention to the reviews and am more hesitant to rent a place that has not been reviewed.
Lastly a tip on cell phone use in Italy. I highly recommend you either pick up a cheap cellphone when you arrive or if you have an iPhone or newer Droid, you can pick up a SIM card at a Vodaphone store and use your existing phone there. You may need to get your phone unlocked by your wireless carrier before you leave and make sure you know whether you need a regular SIM or microSIM card when you go to the store. My iPhone 4S required a microSIM and we had to go to a larger store to get it.
Rome and Southern Tuscany:
For my first visit to Italy (back in 2005), I used the Slow Travel Italy website (http://www.slowtrav.com/italy/) to find the properties in both Rome and in Tuscany and found the reviews on the website to be accurate and very helpful.I think less people are using this site now and using TripAdvisor.
The apartment we rented was through Dolce Roma (http://www.dolceroma.it/) and was near the Colosseum, which I'm not sure is still available but the company in general was excellent. It looks like their current apartment is in the same neighborhood, which we loved because it was still in the thick of things but not overly touristy. As a result, the restaurants in the neighborhood were reasonably priced and we felt we were able to experience Rome more as a local would. We made it our personal quest to have gelato every day!
While in Rome we hired a guide, David Lown, to take us on a tour of the ancient sites (Colosseum, Forum, Pantheon and everything in between). His website is http://www.aguidetorome.com/ and I highly recommend him. He made the history come alive for us and took us places we would never have found for ourselves. He also gave us the tip to visit the Vatican Museum later in the day as the crowds were much more manageable. He also taught us to use the bus system in Rome, which was an adventure in and of itself! We loved him so much we hired him again this year and had him give us a tour of Florence. One useful tip he gave us, was that all those lovely water fountains spread all over Rome are full of clean water and so buy one water bottle in the morning and keep filling it up at the fountains for the rest of the day! They also have some of these fountains in other Italian cities (Venice) but they are not as ubiquitous as they are in Rome.
Our week in Tuscany was wonderful. We stayed at Sant' Antonio (http://www.santantonio.it/), charming place that had been a monastery and was converted into apartments. We stayed in Casa Francheca, which was lovely. It had absolutely beautiful original frescos on the walls and a perfect kitchen.
At this time, our boys were 10 and 13 and by this time were experienced travelers. We would generally tour the local towns (Pienza for cheese, Siena, Cortona and Montalcino for wine) in the morning and over lunch, and then relax in the later afternoon by the pool. Sometimes we would go out for dinner and other times we'd pick up salami, tomatoes, bread and pasta for a relaxing dinner at home.
For our return out of Rome, we stayed at a hotel, the Holiday Inn near the Rome airport. I honestly can't remember much about it but I think it was fine and very convenient. We drove down from Tuscany, leaving in the morning, dropped our bags at the hotel and then drove to Ostia Antica, the harbor of ancient Rome http://www.ostia-antica.org/ for one last bit of sight seeing before getting rid of the car.
Venice, Chianti and south-eastern Tuscany:
For our second trip, just this summer (2013), we traveled again with our boys (now 18 and 22!) but also joined up part way through the trip with two other families. So by the end of the vacation, there were 13 of us staying in the villa near Cortona.
We started our vacation in Venice, staying at the Hotel Palazzo Vitturi (http://www.hotelpalazzovitturi.com/) at the Campo Santa Maria Formosa. This was a good 3 star hotel, very clean, with helpful staff, in a great location. Not luxurious but very comfortable for the 4 of us and reasonably priced for Venice.
I loved Venice! I loved the lack of cars, exploring the city on foot till we dropped, the narrow alleys, the churches, the canals, the food...everything. We hired a private water taxi, arranged for us by the hotel, to pick us up from the airport and I highly recommend this! We were arriving from an overnight flight from the States, and it was wonderful to have door to door service in a charming speed boat. The ride woke us up and I felt like Katherine Hepburn, riding across the lagoon and through the canals!
From Venice we took a train to Florence. It was a two hour or so trip in a very nice train. We rented a car from EuropCar which was about a 4 block walk from the Santa Maria Novella train station. Once we picked up the car we were off!
We stayed this next week at an agritourism farm called Corzano e Paterno http://corzanoepaterno.com/ a wonderful vineyard, cheese maker and olive oil producer. Mirella runs the agritourism for the family and is a wonderful resource. She gets you settled, makes great recommendations for restaurants and sights to see and she even came to the local doctor's with us when my youngest son came down with strep throat! We had a wonderful time here. All their products were fabulous (you get a tasting of it all included when you stay) and we loaded up on everything (cheese, wine and olive oil) when we headed to our next location. We stayed in Il Corzanello, which was a 7 bedroom farm house. It is not a villa, there is no air conditioning, but it was a lovely house with plenty of space, breath taking views and a great farm house kitchen. There are shared pools on the property which were very pleasant as well. Mirella arranged for Lucia to come and cook 2 meals for us and these were spectacular. Lucia did EVERYTHING...from unloading her car of supplies (she wouldn't let us help!) to all the preparation, setting the table and cleaning up. Her food was incredibly delicious and very reasonably priced. I would highly recommend using her for several nights!
While we were at this location, we drove into Florence for a day, having David Lown (mentioned earlier) give us the "back-alley" tour of Florence. This was great, getting off the major streets and seeing the back streets of Florence while still navigating to the major sites. It was an ungodly hot day (100 degrees F) and so the wandering through shaded alleys and into cool churches was crucial! One of the stops he took us to was this amazing apothecary shop, the Pharmacy of Santa Maria Novella http://www.smnovella.it/?lang=en. It is an unbelievably beautiful place filled with amazing scents and products. I highly recommend a stop there and it happens to be on the same street as the rental car companies.
While we were in the Chianti region, we did quite a bit of wine tasting as there were vineyards everywhere. One thing to keep in mind: this driving in this area is not for the faint of heart! Some of the roads near the farm were practically one lane and there were even some dirt roads we traveled on. Important to keep this in mind while tasting wine! One of our trips was to Panzano, a town reached by going over hill and dale. We found a charming wine shop, Accademia del buon gusto, http://www.accademiadelbuongusto.com/, owned by Stefano. He was entertaining as well as knowledgeable.
After a week in Chianti, we headed south to our villa near Cortona. This was a decadent, over the top place that had ample room for 14 of us and included a game room, work out room, sauna, steam room and massage room, none of which we used! It was a lovely place, though we couldn't drink the water which was a bit of a surprise when we arrived. I've never had a problem with the drinking water anywhere else in Italy. We rented the place through Emma Villas http://www.emmavillas.com and the house was Casale Dei Girasoli. The property manager was excellent and very responsive. It was incredible with a great pool area, billiard room, huge kitchen and three living rooms plus a study.
For this week we visited Cortona, went to the lake nearby, Lago Tresimeno, and took a book trip to an island as well as explored the lakeside village of Castiglione del Lago which was filled with food/cooking shops. We also had a wonderful lunch at Podere il Casale, a lovely cheese producer. http://www.podereilcasale.it/contact, stopping at Montepulciano, on the way. Cortona was the closest "tourist" town and was where "Under the Tuscan Sun" took place. It was full of shops and restaurants and worth a stop.
One of our favorite routines was for my husband and I to go out early and get our espressos in the morning and pick up breakfast pastries for everyone. We discovered, a charming little pastry and gelato cafe called Gelateria Pasticceria Santamaria in Foiano Della Chiana, which was a quick drive from our house. The address is Via di Cortona 9. The brothers who own it are so fun and charming and the pastries and gelato were fabulous. We became regulars and by the end of our trip were given espresso cups as farewell gifts!
Just a note, that my family doesn't eat light...we love our food and generally will have multiple courses, though not always dessert and ALWAYS wine. So for the places mentioned below, assume we had at least two courses and wine and prices unless noted are for 4 people. Service is included in the bill in Italy. All of these restaurants were visited on our most recent trip, in June 2013.
VeniceUn Mondo Divino: Tapas, 46.8 euros, including wine. In Venice, they have bars similar to Spanish tapas bars, with a variety of hot and cold items (bite sized portions) that are excellent. We discovered this one the first afternoon we were there and loved it. http://www.tripadvisor.com/Restaurant_Review-g187870-d1886705-Reviews-Un_Mondo_Di_Vino-Venice_Veneto.html
Ristorante Al Barbacani: Dinner, 161.2 euros. This was a small, charming, informal place that is canal side and near our hotel. The dinners ranged from good to excellent. My older son made the best choice by ordering the black ink squid dish...absolutely fabulous. The prices were reasonable byVenetian standards. I didn't list the trip advisor link since the reviews are all in Italian or French! Which tells you this isn't too touristy a place. http://www.ristoranteaibarbacani.com/home-en.html
L'Osteria di Santa Marina: Dinner/Seafood, 262.5 euros. My husband and I discovered this Osteria as we were walking back from the Vodaphone store. We had to wait an extra night to get in because it has a loyal following. The food was excellent. I had fish encrusted in salt (one of my favorites) and I loved it. http://www.tripadvisor.com/Restaurant_Review-g187870-d716271-Reviews-L_Osteria_di_Santa_Marina-Venice_Veneto.html
One thing you might want to try while you are in Florence or Chianti is the Florentine steak. I don't usually attribute good beef to Europe but this area is the exception. The beef was incredible; much fresher than we ever get it in the US, simply served and great. Other dishes I highly recommend you try are squash blossoms, wild boar stew, and any type of pasta with truffles. This area is known for truffles as well and I was astounded by the huge quantity they use: sauteed in olive oil and covering the pasta.Unbelievably scrumptous!
Osteria Cinque di Vino, in San Casciano: Dinner, 157 euros. I found this restaurant on Tripadvisor where it got excellent reviews. Our meal was excellent though a bit oversalted. I had my favorite, fried squash blossoms (if you've never tried these, you HAVE to), and they also featured fried sage alongside the blossoms. I've never had sage or any herb prepared this way (lightly breaded and fried) but WOW, I am a convert! My husband had very rare house ground beef (almost an Italian beef tartare) that was melt in his mouth tender and fresh. http://www.tripadvisor.com/ShowUserReviews-g652039-d1458075-r176859377-Cinque_di_Vino-San_Casciano_in_Val_di_Pesa_Tuscany.html
Southern TuscanyWe did not eat out as much during our week in the villa near Cortona as we again had a chef, Tonino and his wife Ruth, who cooked for us three evenings. His food was amazing: homemade pasta and fresh mussels that was to die for. To contact them, use Ruth's email: email@example.com
Poggio Sant Angelo: We discovered this lovely place early in our week in southern Tuscany. We were looking for a good pizzeria one night and this lovely B&B had a pizzeria sign out front so we stopped to investigate. It ended up that they weren't actually a pizzeria, but the B&B had a lovely restaurant. They explained that they were just re-doing their menu so weren't officially open for dinner. We described our group of 13 and they offered to create a family style, multi-course dinner just for us. It was a wonderful experience! The food was delicious, served by the whole family. We ended up playing the piano, singing and having a once in a life time evening. The B&B gets excellent reviews on Trip Advisor and based upon the service and kindness we experienced, I'm betting it is a wonderful place to stay. Plus the location is excellent and the building and grounds looked lovely. http://www.tripadvisor.com/Hotel_Review-g187894-d664727-Reviews-B_B_Poggio_Sant_Angelo-Cortona_Province_of_Arezzo_Tuscany.html