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Out 'Fifteen Favourite' Things To Do Around Gaiole

Here a few notes on no less than fifteen things which we hope will help keep our guests entertained through their holiday, and there are are loads more!  We've tried and enjoyed them all and  you'll notice a certain theme on food - but that's all part of being on holiday!


  1. Visiting Firenze by Train:  We suggest going by train as Florence can be a drivers nightmare.  Trains run regularly from Montevarchi, which is about a 25 minute drive from Gaiole.  As you approach Montevarchi, at the first roundabout, take the first (slightly right) exit to the station, (not left towards the town).  The station car park is about 500m down, on your right adjacent the subway that leads to the station.  Parking is free; if full, there is an overflow car park, just 100m past the roundabout where you left the main road, on the left hand side, and a three or four minute walk back. Purchase tickets from the office reached through the waiting room off platform 1.  A return ticket is around 8-9 euros pp.  (‘biglietti a andare a ritornare a Firenze’). Trains run regularly from platform 2 through to the terminus at Firenze SMN, a slow train taking around an hour, and the fast train around 30 mins.  Note: there is a frustratingly long gap between trains from around 9.30 to around 11.00.  Evening returns seem easier with more regular fast trains.  The Santa Maria Novella terminus (SMN) takes you right into the old part of town, with the Basilica and Piazza di Santa Maria Novella just a subway away.

  2. A Drive to Siena:  It’s about a 35 min drive to Siena.  Your first ‘landmark’ is going under the railway bridge; take the first exit at the roundabout immediately after the bridge, and at the next roundabout turn LEFT (second exit)  towards ‘centro’ and Porta Ovile.  Follow the main road up the hill all the way to the Porta Ovile (gate), where the main road turns sharp LEFT; follow it round (don’t go through the gate), and past the petrol station on your left you will see the San Francesco car park.  There is an upper and below ground level, both are 1.60 euros per hour.  After parking, walk back towards the petrol station and Porta Ovile and cross the road about 150m on to enter ‘The Elevators’ to Piazza di San Francesco. The ticket machines/booth for the car park are in the foyer here at the bottom of the escalators.  Five escalators later you emerge at the walkway through to the Piazza, from which all of the main locations (Campo, Duomo etc) are clearly signed.

  3. Castello di Brolio Terrace:  This has to be one of the finest views in Chianti.  It will cost you 5 euros, and try and pick a clear day (closed Mondays).  The gardens are pleasant enough, but nothing special; however the view from the terrace over to Siena is worth every cent!  There is an interesting little museum in the tower which will cost an extra 3 euros, guided tours only.  Your ticket allows you a ‘free’ wine tasting at the wine shop at the bottom of the hill.  (it’s worth trying the desert wine, Grenello; and the rose, L’Albia, as well as the chiantis).  The restaurant is also very nice (closed Thursdays).  You can park near the restaurant and take the very pleasant walk up to the Castello, though you can also drive up!  Brolio is a 10-15 min drive from the Borgo, head towards Siena, look for the left turn after about 3-4km and follow the signs.

  4. Cook Your Own Lunch:  If this takes your fancy, I recommend you book in advance through the website link on our 'About Us' page.  Malborghetto in Lecchi is a lovely little restaurant with excellent food and in Simone, an equally charming host and teacher.  A half day course including your lunch and wine tasting will cost around 90 euros (bear in mind that a lunch of this quality with wine would have cost you 35-40 euros anyway!).  Family and friends can join you for lunch to sample your dishes and join in the wine tasting for around 35 euros a head.  Lecchi is about 10mins by car, turning right off the road to Siena shortly after the Brolio turning.  As you enter the village, turn a ‘hairpin’ right to get to the restaurant.

  5. A Sunset Presecco:  There are lots of places to see a lovely sunset, but if you will enjoy it all the more with a glass of wine, then try the newly opened Café Bar in Radda off the road that runs under the wall (to the west facing side!).  I think it’s called Forchetta di Chianti – but the views are great here anyway.  Radda is only 15 mins or so by car – head out to Siena, take the first right and follow the main road, all signed.

  6. The Perfect Hilltop Village: There are lots!  Here are two suggestions.  Vertine is walkable; about 45 mins up hill from the Borgo, turning right and right again.  Lovely views and a little café open from late morning.  Or try Volpaia; about 20-25 mins by car; head for Radda, go straight on at the roundabout and under the bridge (towards Lucarelle) and turn right after a further 2-3km.  This is a beautiful spot, enhanced by a very nice restaurant (La Bottega) with great views from the terrace, and a café and a wine shop.

  7. Wine Tasting: There are literally dozens and dozens of places, some within walking distance.  These are two suggestions at different ends of the business scale.  For a small family size business, try Riecine. ​​​ it’s all very low key, but the staff there are directly involved and very knowledgeable.  This year (2013) they are undergoing a major building expansion project, and they have moved their office down into the village piazza where you can buy their excellent organic wines.  For something more sophisticated in the tasting experience department, try Rocca di Castagnoli in Castagnoli village, about 10 mins drive from Gaiole along the Siena road, taking the first left and then to the top of the ridge.  Turn left in the village for the wine shop.  A wide range of wines can be tasted here in nice surroundings.  There may be a modest charge, but unlikely if you buy something.

  8. Fine Dining: Try a long lunch linked with a short tour of Baddia di Coltibuono and it’s cellars.  This is an excellent fine dining restaurant, reasonably priced for the quality.  The five course tasting menu is around 50 euros including wine.  Afterwards, take the Baddia tour for 5 euros – a very interesting short tour of the abbey and it’s cellars.  You can of course do all this in the evening.  If feeling energetic you can walk to Coltibuono by continuing up the ‘white road’ past Reicine (see above), to the main road before turning left and then right up to the abbey.  It will take you about an hour and a quarter – or just 10-15 mins by car, up the main road to Montevarchi and turn left at the crossroads.

  9. An Ice Cream in San Gimignano: You can of course buy wonderful ice-cream all over Italy, (and indeed in Gaiole at Bianchi in the Piazza), and yes, ‘Saint Jimmy’s’ is the one of the most touristy places in Tuscany – but the combination is still worth it!  About an hour and a half drive (so make it a day trip) via Poggisbonsi.  The Gelateria di Piazza is in the Piazza della Cisterna and just a ‘gelato experience’!  Don’t forget to enjoy the rest of the town!

  10. The Butcher of Panzano: A 40-45 min drive to the butchers seems a bit excessive! But Panzano is a lovely town to walk around, it’s a pretty road (via the road to Radda/Volpaia and then on through Luccarelli), and this is no ordinary butcher.  Visit Dario Cecchini for lunch and enjoy the experience (unless you are vegetarian!).  Good value and great entertainment, and maybe even buy something for the BBQ in the butchers shop!  The shop is just ‘above’ the main town visitors car park.

  11. Chianti Sculpture Park: Something a little different when you tire of food and wine (?!).  Situated near Pievasciata, it’s about a 30 min drive; out towards San Sano, turn left onto the ‘white roads’ before the village and follow them through towards Valgliagli, eventually picking up the Sculpure Park signs.  There is a very pleasant woodland walk taking you through a series of modern art installations, and then visiting the house is a must.  Beautiful items in a beautiful setting.  If you have deep pockets, some lovely things to b

  12. Castello Courtyard Dining: one of the delights of ‘chianti cuisine’ is seeking out the rustic village osterias, but for something a little different try Il Celliere in Castagnoli. Summer dining is ‘al fresco’ in an enclosed castle courtyard where you can feel the days sun warmth radiating from the walls!  Spring, autumn and chilly evenings you are in a very atmospheric grand castello dining hall.

  13. Hot Springs: Rapolano Terme is about a 40-45 minute drive situated off the main (dual carriageway) road from Siena to Arezzo/Perugia.  If you pick up the road just beyond Castelnuovo Beradenga it is the first exit heading Eastbound.  The Hot Springs resort at San Giovanni Termopolano, offers three hot pools (one indoors) in a beautiful garden park setting with fantastic views.  There are excellent facilities including a very good Bistro with buffet salads and a nice café bar.  Drive through the village of Rapoliano, and turn right following the brown signs to San Giovanni.  A day ticket is currently 14 euros.  You can hire towels etc. but feel free to take our pool towels.

  14. River Swimming & Picnic Paradise: Pick a hot day, possibly when the pool is a bit crowded and drive down to the River Merse (see separate inserts). Pack the hamper (if you are in ‘Minore’) or load up a couple of shopping bags (if in ‘Maggiore’) and off you go.  All in about 50 minutes from the Borgo.  Take the directions to Briolio castle, carry on past  -  through Castelnuovo Beredenga  - through the town go ‘straight on’ towards Siena, pick up the dual carriageway towards Siena and Grosetto and stick to the Grosetto signs (E78/S223) throughout.  After the second set of double tunnels the dual carriageway shortly ends, slow down and take the first right on the single carriageway to Orgia.  Then second left to Brenna, and in Brenna take a narrow left hand road that drops away signed ‘Alto Merse’.  Parking is just before the bridge, and then all as per ‘clipping’. There is an excellent small Pizzeria/café on right just before the car park  -  Vecchio Tinnio should you want to supplement your picnic.  Note: it is quite remote, so best not to leave valuables in your car.

  15. Opera in Siena: From April to November Siena Opera hold a series of Aria Concerts three times a week (Tues, Thurs, Sat) at 9.15pm.  Singing of the highest quality in the fromer church of Santo Stefano.  23 euros pp booked on line.  Usually twelve pieces, around 90 minutes.  Why not have pre theatre dinner around the corner at Enzo! and


Other worthwhile day trips include Volterra, Montepulciano in Le Crete and Cortona; or stay more local and walk up to Barbischio (Il Papavero is a very nice restaurant) or over the ridge to San Sano (Grotto della Rana is also a nice restaurant).



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