Gerard Guide: Tuscany, Italy Recommendations & Advice


Gerard Guide: Tuscany, Italy Recommendations & Advice

By Steve and Sam Gerard (still being edited / have photos to add!)

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Important Notes About This Guide

  • The majority of this guide is about the area surrounding the villa in Tuscany we stay at, as well as cities you’d fly into and out of (Rome & Florence) and some smaller cities to visit around Tuscany. If you’re looking for more advice on another city not listed or more in-depth on Rome or Florence, let us know! This guide is focused on staying in/around the villa itself in Tuscany.
  • We stay at the same villa every time we go to Tuscany – it is a part of a larger group of villas that also has a hotel – they’re all spread out throughout the hills of the large property. The hotel itself is beautiful and referenced in places to eat, get a drink, stay (there are single rooms in addition to the villas), etc.
  • In this guide, the villa/hotel may be referred to as CdC (Castello di Casole)
    • Address: Castello di Casole, Localita Quercerto, Casole d’Elsa, Siena 53031
    • Villa Name: La Fonte di Barben
  • Happy traveling – ENJOY and eat a lot of pasta, drink a lot of wine, and put your phone down 🙂
  • After your visit, please add anything not on this list as a comment in specific section so we can add it and share with others traveling there! 🙂

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General Tips

  • If you have Verizon, sign up for Travel Pass. You just call customer service and ask for it – it’s $10 a day and auto charges you when you arrive in foreign country and stops when you leave. So once you set it up the first time you travel abroad, you never have to call again – really convenient. Good to have internet not for things like social media or email – but to use Google maps and Waze and be able to call places to ask questions!
  • If you are on a connecting flight (1-2 stops), make sure to bring a change-of-clothes and essentials WITH you on the plane, as our bags have gotten lost/delayed a few times. Have enough stuff in your carry-on so that you are not inconvenienced for a day or two if your bags are delayed
  • Italy uses Euro’s – many places will not take American dollars, bring a Visa card and get Euro’s from bank MAC machines to get best rate. You can get change for Euro’s in the airport (or your local bank). The exchange rates at the airport and fees are not good at all – total rip off
  • If you get a rental car: CHECK YOUR NAVIGATION SYSTEM BEFORE YOU LEAVE THE RENTAL CAR PLACE (for use, language, etc) – I have had my NAV not work a number of times, and on one occasion it was in Russian and I could not change it myself. Noawadays you do not even need a NAV if you have WAZE or GOOGLE MAPS and a car charger AND free cell phone or car wifi. If those do not work, make sure to get a navigation system in the car, or a portable one from the rental car company. If you need to charge it, make sure the cigarette lighter IN the car works, or that you can charge it at your hotel or villa. Many companies disable the cigarette lighter – therefore making it impossible to charge your phone or navigation system. Make sure wipers work, fluid, tires and lights are okay – some roads in tuscany don’t have street lights and get very dark at night. There are many toll roads – and the rental cars do not come with an EZ Pass (electronic toll payer). When driving and coming to a toll booth(s) – look for the lane(s) that has the sign for using Euro’s – carry Euro’s (see below). There is usually a person/toll-taker in the booth and when you hand them your biglietto (ticket) – the charge will appear electronically for you to pay with Euro’s. Many rental cars in Europe are manual transmission … be aware of what you need/rent! Also, be aware of the size of the cars and their trunks – they can be very small!
  • Specific to traveling to the villa (Cdc), it is sometimes tricky to get the CdC address to come up on the navigation —- so you can put the town of Mensano or Casole D’Elsa into the navigation system, and it will get you into the area of CdC.

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  • Rental companies in airport: Hertz, Avis, SIXT, Maggiore, EuroCar, Budget, Fox
  • Hertz is what we typically use – it’s in Terminal A, Level 1
    • When you exit Customs, getting to Terminal A is to the LEFT. The counter on Level  1 in Terminal A (if you are gold or platinum) and go right there.
    • When you exit the luggage area, elevators are on the left – to the left of the cafe
  • Specific to Gerard Villa: It is a 3 hour car ride from Rome to Castello di Casole (middle of Tuscany). Not a bad ride, all highways and tolls, and pretty easy with a navigation system. Plenty of toll roads and speed traps (see below)


  • There is a Hilton at the airport if you’re staying over before an early flight or after a flight getting in very late – it’s easy to find, and you can walk to just about any of the terminals
  • Hotel Adriano – good price in an older section of Rome – good spot to walk to places (stayed here with Cindy & Henry – Via di Pallacorda, 2  39.06.6880245
  • 1 Hotel Rafael – expensive and amazing rooftop bar
  • The First Luxury Art Hotel
  • Hotel Forum – overlooks the Forum (American Bar)
  • FortySeven Hotel (rooftop bar)
  • Hotel Eden

Places to Eat

  • Ristorante la Campana – oldest restaurant in Rome – great place to eat with locals and very small  (Vicolo Della Campana 18
  • Pierluigi – in a really quaint square with great food and wine list. If the weather is nice it is a great place to eat outside

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General Tips

  • The city of Florence is about a one hour drive from CdC (the villa), and while it can be a little tricky, there is ample parking in one of a few lots that you can be directed to.
  • I would advise getting a guide to take you on a walking tour and to one/two of the museums. Having a guide can get you into the shorter line also!
  • The Uffizi is amazing (and huge) and the Gallerie dell’ Accademia, is where the actual statue of David is, as well as a number of other statues and versions of the David are.
  • Doing a walk on/around the Ponte Vecchio bridge and along all the side streets and piazzas is great. You can easily spend a day or two walking/exploring Florence.
  • Getting a tour of the Duomo’s (churches) is also amazing, but can get crowded.

Transportation/Rental Cars

  • Florence Airport – I have not found direct flights from NY/NJ to Florence … but there are numerous connections (i.e. thru Paris, Germany, etc).
  • Plenty of rental car places outside the Florence airport – short shuttle ride. The shuttle bus for rental cars is right outside the airport – which is very small.
  • If you are staying in Florence – there is a train right at the airport that will take you into Florence city center.

Things to Do

  • David at the Galleria dell’Accademia – we took a guided tour which was nice to get some of the background of the statue.  Must do in Florence.
  • The Duomo – Try to go to top of the dome which is cool.  Something like 500 steps up a winding stone staircase. Not for the claustrophobic.
  • Michelangelo – don’t miss this – fantastic views of all of Florence.  You can walk to it but is it is quite a hike up a hill.
  • If you have a science geek in the group we went into the Galileo museum which is pretty cool.   Lots of old telescopes, clocks and other scientific equipment.
  • Pisa – there are direct flights in the high season to Pisa – which is ~2 hours to Castello di Casole (Villa is one hour south of Florence)

Places to Eat

  • For a great view and place to eat/drink – The Westin Excelsior rooftop has a great rooftop deck that is amazing. Going to a chain hotel seems touristy, but going there for sunset is special! (it is right along the ARNO river – across from St Regis)
  • Trattoria 4 Leoni – really nice inventive pastas and a good wine list.
  • Lungarno Bistro – very nice restaurant on a piazza right on the river with great food with a focus on fish and seafood.
  • Mamma Gina – traditional Tuscan cooking – not as refined as the other two
  • Ristorante Parione – great atmosphere with a really nice staff.  Food was excellent. They were featuring truffles when we were there and we had a primi of fried eggs with shaved truffles over the top.  It was excellent.
  • The best gelato we had in all of Italy was at La Carraia in Florence. Right across the Ponte alla Carraia.

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Things to Do / Places to Visit

  • A good day trip that we’ve done multiple times is to take a drive and stop in a number of great Tuscan hill towns – all are doable in half a day or at most, one day (listed below)
  • Monteriggioni – about 15-20 minute ride from CdC and a wonderful example of a walled Tuscan hill town …. Good place for lunch and/or dinner also … just a few shops in the town. Monteriggioni is also at the ‘bottom’ of the Chianti Road (see below)
  • San Gimignano – another great ‘town/city’ to go spend a few hours walking around … not too big, and can be done nicely in a few hours. Plenty of shops and places to eat/café’s ….. Parking is all around the walled city in lots where you grab a ticket when entering, and pay when you leave.
  • Casole D’Elsa – right across the “hill” from CdC is the small town of Casole D’Elsa. If you are interested in the Etruscan history of the area – great little museum there. Not much to “do” in town, but another one of those places you can walk around, grab a lite-bite and just experience Tuscany and it’s beautiful atmosphere. Wonderful old church from the 1400-1500’s in town. Dry cleaners and bank in town.
  • Volterra – about an hour from CdC and a nice hill-top town. This is the place to buy alabaster if you like it. Personally, if I were to “skip” one town – this would be it. While it was nice, there was nothing “too” special about it for us.
  • Castiglione della Pescaia – One of the closest beach / seashore towns – if you want to get a taste of beach-life in Tuscany – about a 90-120 minute drive from CdC. We went there for a day, rented a ‘cabana/umbrella/chairs’ on the beach, and had a great day people watching and eating and drinking (places to eat on the beach with seafood and wine you can bring to your chairs or sit there). It’s a bit of a drive, but if you want to get a taste of beach-life, this was very convenient.
  • Forte de Marmi (about 2.5 hours from house) – great beach area (like LBI) – You can rent bikes and bop around. Great views of the Carrara marble mines!
  • The Chianti Road
    • There is a road in Tuscany referred to as the Chianti Road (Strada Regionale SR-222), and technically takes you from Siena to/from Florence. For the “best” part, it starts about 15 minutes from CdC, and takes you thru gorgeous Tuscan hill towns and vineyards … truly a great day/trip. The towns we like to hit are:
  • Castellina in Chianti – small town, but a nice place to walk around and experience daily life in Tuscany. Nice little shops and café’s
  • Penzano – a little ‘dot’ of a town, but if you have time, you can park and walk up the hill/street and see some nice little shops and the church at the top of the hill/street. Beware of the wine shop near the top of the hill (before the church) and the man-with-the-red-hat. Tells great stories and sells you a lot of wine.
  • Greve – another nice small town with a nice town square and shops. Once again – not very big …. But nice. There is an amazing butcher/cheese shop there, run by Dario-the-Butcher – a legend in Italy. Great place to buy stuff if you want food for your villa/hotel.
  • Radda – also a cute little Tuscan town where you can walk around, hit some shops and grab a bite.
  • Ceramic Shop à Rampini Ceramiche – Casa Beretone Di Vistareni, Radda 53017 Tele 0577-738037 (between Radda and Giaole)
  • Gaole – maybe it was just us, but this town had nothing !!!
  • Val D Orca – Montepulcino Wine region
  • Town of Montalcino and Montepulcino
    • These are nice towns with many wine shops and places to buy food and local artwork. About 1.5 – 2 hours from Villa.
    • Lucce Winery – great wines and a good tour
  • Shopping: The Mall Outlet is located about an hour and a half hour by car from the Villa, and 30 minutes from Florence. If you are dying to shop and get some great stuff – at good prices – then this is it. They’re open daily from 10 a.m. to 7 p.m. Brands include Italian and international labels Agnona, Alexander McQueen, Balenciaga, Bottega Veneta, Burberry, etc.

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Places to Eat

  • Osteria del Borgoin Mensano. Our favorite. This place is close to the CdC hotel, and a 10 minute drive. You can park right outside of the village on the street that comes up to the town, park, and walk up, onto the main street. If the church is open – take a walk in and see it – beautiful. At the other end of the “one” street in town is this restaurant. GREAT food – and just have the house wine ….. We go there twice a week when we are there … and it is one of the highlights of the “food” in Tuscany …..If you get there in the daylight and can walk around – you really get a sense of life in Tuscany. You’ll sit outside on a cobblestone street that cars can barely get through. Very authentic and small-town Italy.The waiter there (Roberto) works there and his sister is the ched. Tell him we say hi – we’ve become great friends with him and email often! Note: There is another Osteria del Borgo in Tuscany because a friend went there by mistake (didn’t check to make sure it was in Mensano after typing it in the GPS!)
  • Locanda del Molino17 – place at the back entrance to CdC – very good food and wine.
  • La Esperanza – totally local place at the bottom of resort area near gas station. Great BEEF and totally local – open fire cooking.
  • La Pergola in Radicondoli – about a 25 minute switch-back hilly ride to another nice Tuscan hill town … and great thin crust pizza and truly local place.
  • Erta (Varno) – this place is a true agriturismo eatery/hotel/winery/stuff! It seats about 10-15 people, and you get the experience of a small property, and all it has to offer. Pretty “rocky” ride down the hill to the property – but so worth it!! All cash – you can buy wine and olive oil here.
  • Il Pozzo – small place in Monteriggioni (the small walled town about 20 minutes from CdC), but very good. A little expensive, but you can also see this walled-village at night – which is cool. Great wines and food and high end service.
  • La Antica Trattoria (Colle di Val d’Elsa) – really good place with great food, in town 30 minutes from CdC. Nice wine list and quaint town to see. Parking is a little tricky, in that you have to drive past the restaurant on the left (one way street – the piazza it is in), go a few blocks, and make a right for a public lot. Very safe … but tricky.
  • Badia a Passignano – A winery and restaurant – by Antinori. Their ancient cellars are located in a magnificent fortified abbey that you might be able to get a tour of – with advance notice. Badia a Passignano has an outstanding Michelin starred restaurant with great cuisine and a superb wine list. The pre-fix menu is very expensive, but if you are looking for a 3-4 our dinner and a special night —– great choice. 45-50 minutes from CdC.
  • Arnolfo – in Colle di val D’Elsa – very, very expensive and stuffy …… but, was very good. Very small place …..
  • In this village, there is a restaurant at the top of the “hill” (sort of like an old prison/jail) that was very good – I believe it is called Il Frantoio

Note: Make sure to verify these on Trip Advisor in terms of exact name and location and to verify that they’re still open / have the same hours.

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  • The Castle of Verrazano – highly recommend this! The best wine/estate and histor with /4-course lunch tour we have been on. You drink so much wine and eat such a large lunch – you may not need dinner. It is about 10 minutes NORTH from the town of Greve, roughly an hour from the house. You can get the wine in the USA —- so, no need to ship it home after you have a ‘happy-face’ from the great wine and food
  • Antinori – they just built a beautiful new winery into a mountain along the highway between CdC and Florence (45 minutes) and it is a really nice winery / tour. Also a nice place for lunch.
    • Antinori also has a restaurant in Tavernelle called Badia Passagna – and they have caves there in an ancient abbey where you can try to arrange a tour. Dinner there is also really, really good.


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Other Cities to Visit

Day Trip to Lucca

  • Great little town and they also have an extensive music festival every summer.  The venue looks like it only holds 3000 people or so and they get really great bands. Here is the web site
  • Also – plan on renting bikes for a few hours and exploring the town. The wall around the city is actually a park, in that you can walk/bike around it. Plenty of bike rental shops.


Pisa (Near Lucca)

  • Leaning Tower of Pisa is worth seeing actually – pretty amazing and a quick stop. Every time I mentioned going there – people told me to go to Lucca instead if I was going up that way … and to skip Pisa ?? It really is crazy how leaning the ‘leaning’ Tower is!


  • It’s about 30-35 minutes from CdC, and frankly, sort of tricky to get there and park (but if you rent a car in Italy – getting lost is part of the game)!
    • Take the Siena Ovest [West] exit off the highway – when driving south from the house/Florence) …. Park in the Stadio Soccer Stadium parking (follow the signs for the Stadia (soccer ball)
  • That said – taking a guided tour of the churches and streets of Siena, and learning about the twice-annual horse race (The Palio) that have had there since the 1400’s is amazing
  • Lots of really good shops/stores to buy unique things … and the main Palazzo Publico are a great place to enjoy a coffee/espresso and people watch.


  • 2 hour drive, and a nice ‘city’ to see – but not something I would do if I were only in the area for a week. Heard Cortona was better, but have not been there.

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Last but not least, if you’re REALLY lucky (or a stalker), you’ll follow Bruce to Europe – The Italians LOVE him too 🙂

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