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San Gimignano & the Sienese Plains

San GimignanoThe Chianti Hills are as famed for their beauty as for their dark red wines. Hill-top villages crown the rolling landscapes, and every church seems to contain a fine painting. As you cycle, you will be struck by an extraordinary sense of history, from the towers of San Gimignano to Siena’s magnificent Campo, and the alluring timelessness of the countryside in between.

Nights: 7
Grade: 1-2
Terrain: lanes and strade bianche (unsurfaced roads) across wooded hills
Hotels: one 3-star hotel; three 4-star hotels
Meals: breakfast each day
Climate: average temperatures of this warm, sunny region range from 17°C in May to 25°C in July and August.

Relax and take in the views
<empty>Colle Val d'Elsa
San Gimignano
There is plenty of interest along the routes
Ride along lanes lined with cypresses

Starting point: Hotel Garden (4*), Siena. Created from the former summer home of an aristocratic family, the Hotel Garden stands on a hill to the north-west of the old town within its own attractive, shady gardens (complete with outdoor pool) and is surrounded by vineyards and olive groves. Breakfast only is included.

Day 1: you begin by cycling north-west across a gentle landscape of vineyards and cypresses, passing from the Chianti region into the Elsa Valley via fortified Monteriggioni. Formerly Siena’s northernmost bastion during the wars with Florence, it sits like a hill-top crown with 14 towers and a neat circle of walls. You continue along quiet lanes to Colle Val d’Elsa, a little-visited town dating from pre-Roman times with an atmospheric walled upper town which stretches along a ridge with its one long street lined with medieval mansions. (28km)

Accommodation: Relais della Rovere (4*), Colle Val d’Elsa. The hotel has been stylishly converted from an 11th-century abbey, and is now a handsome and beautifully decorated stone building with many original features. There is a sense of refinement, too, in the large attractive gardens where you can relax by the swimming pool and admire the views over to the town. You stay on a bed and breakfast basis, leaving you free to take your pick of the local restaurants.

Day 2: winding roads with some short ascents followed by a longer but steady climb lead you towards San Gimignano. Perhaps the best-known village in all of Italy, it provides an unmistakably dramatic skyline as you approach, with its 14 medieval towers piercing the sky. The town is immaculately preserved and boasts a fine array of museums and galleries. Admire the panoramas in all directions before returning to Colle Val d’Elsa, either along a low ridge to the east of San Gimignano which offers a different perspective of its skyline or along a longer, more demanding route through beautiful countryside. (31km or 40km) 

Accommodation: Relais della Rovere, as above.

Day 3: today’s route passes from the Elsa Valley into one of Tuscany’s least-known areas, the Merse Valley, crossing wide-open spaces and the ancient wooded hills of Montagnola. There are plenty of small villages and hamlets to discover along the way, such as Scorgiano – where it is possible to pre-arrange wine-tasting from a small local producer – and Pievescola. The day ends with a descent onto the plain to reach Stigliano. (40km)

Accommodation: Borgo di Stigliano (3*), Stigliano. A stylishly renovated country house with a swimming pool set in picturesque countryside. You stay on a bed and breakfast basis and can dine at the nearby village restaurant (closed Monday when a short taxi transfer is required to another nearby restaurant – pay locally).

Day 4: relax by the hotel’s outdoor pool, or take a gentle circuit via the historic hamlet of Torri, complete with an 11th-century abbey boasting a handsome cloister (usually open Mondays and Fridays). (17km)

Accommodation: Borgo di Stigliano, as above.

Day 5: discover changing scenery dotted with small yet captivating medieval hamlets as you leave the Merse Valley behind. The panoramic roads afford idyllic Tuscan views on the return to the Gothic cityscape of Siena. You can either deposit your bike on the outskirts of the city and take a taxi to your hotel (pay locally) or ride all the way into the centre. (22.5km or 26km)

Accommodation: Palazzo Ravizza (4*), Siena. This elegant former Renaissance palace stands in a quiet area within Siena’s historic heart, and is now a charming hotel with lovely rooms, a high-quality restaurant (pay locally if you choose to dine here) and a beautiful garden overlooking the Tuscan hills.

Day 6: you are ideally located to spend your last day wandering round on foot just soaking up the atmosphere of this great Italian city. There is a remarkably easy-going feel to Siena, and you will want to spend time simply relaxing in its great scallop-shaped plaza, Il Campo, the focus of city life and perhaps the loveliest of all Italian public squares. You should also visit the iconic and zebra-striped cathedral and the Gothic Palazzo Pubblico, not forgetting to admire the succession of beautiful vistas from the three ridges on which the city was built.

Accommodation: Palazzo Ravizza, as above.

Recommendations for extra nights: any one of the hotels would make a good choice.

Other information: if you would like to see the brochure page, you can download this (and the pages for any other holidays you are interested in) by using our brochure creation system.

Similar holidays: Siena & Southern Tuscany (grade 2), Ancient Périgord (grade 1-2), Timeless Tarn (grade 1-2), Luberon Valleys & Villages (grade 1-2)

Prices & travel 2008:

£ per person based
on 2 in a double rm
Cycle
price*
Single
room
7 nights: 29 March-12 July & 30 August-31 October 2008
29 Mar-25 Apr 768 238
26 Apr-9 May 804 238
10-23 May 830 272
24 May-12 Jul 851 274
30 Aug-10 Oct 851 274
11-16 Oct 830 272
17-31 Oct 796 272
3rd+ person saving 55  

Recommended destination airport: Pisa
Latest flight arrival time: 1630
Earliest flight departure time: 1400
*Connecting travel: return rail from Pisa (out/home 2h35) £20pp
Book your flights through us and we'll find the best route, times and price to suit you
Start: any day (best Sat-Wed to avoid restaurant closure in Stigliano)

Extra night prices 2008 (extra nights can be booked at any hotel):

Extra night (£ per person per night) Double
room
Single
room
Siena - Hotel Garden (B&B; no cycle hire) 29 Mar-30 Apr; 30-31 Aug 45 67
  1 May-30 Jun; 3-12 Jul; 1 Sep-31 Oct 50 72
  1 Jun-2 Jul 98 156
Colle Val d'Elsa (B&B) 29 Mar-23 Apr 91 125
  24 Apr-12 Jul; 30 Aug-18 Oct 103 149
  19-31 Oct 91 125
Stigliano (B&B) 29 Mar-10 May 54 79
  11 May-12 Jul; 30 Aug-10 Oct 61 86
  11-31 Oct 54 79
Siena - Palazzo Ravizza (B&B; no cycle hire) 29 Mar-12 Jul; 30 Aug-31 Oct 90 131

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