Route: Siena – Monteriggioni ~16 mile roundtrip

Bike Rental: DF Bikes Siena

Month: August (Summer)

There is something special about scenery earned – the landscapes you take in after a long hike, bike ride, or trying journey. These are the rare moments when in a foreign land, I feel like I take some ownership of the scenery, as if at that particular moment in time, the view is all mine. In this way, 8 miles of road in Tuscany became mine for a day. 

Tuscany’s vineyards – orderly lines of lush leaves shading large purple grapes, and olive groves full of silvery fronds set along rolling hills compose the perfect romantic and rustic landscape.  The scenery from vineyard to villa, farm to medieval fortress is best done al fresco from the seat of a bike – also a great way to earn an extra piece of pizza and another glass of prosecco at dinner.

The landscape surrounding Siena inspired us to hit the saddle and bike to the nearby medieval fortress town of Monteriggioni despite the heat of the Italian summer. We opted for the freedom of going it together without the restrictions of the many tours offered in the area.

Our day started at D.F. Bike in Siena where the store attendant picked the perfect bikes for our experience level and the route which is 8 almost completely paved miles. We were able to take the Via Francigena for some of the trip – an ancient pilgrimage route from Canterbury to Rome.

On the outskirts of Siena we drank in the scenic views of local villas, vineyards and olive groves. We also discovered that what look like gently rolling hills, are definitely butt busters when you’re experiencing them on a bike in the middle of a Tuscan summer! We ran out of water halfway through the ride and stopped at a roadside cafe to join the local Italian farmers and their sons enjoying lunch and respite from the sun.

Two hours of pedaling brought us to the gates of the Monteriggioni fortress enclosing a quaint little town taken straight from the pages of a fairy tale! We strolled it’s perfect cobblestone alleys  full of flowering vines and window boxes and popped into tiny handicraft shops before enjoying some extremely well-deserved pizza and rosé before riding into the sunset to return our bikes before dark. Despite being what my mostly sedentary lifestyle considered to be a strenuous journey. It was one of the most rewarding and beautiful ways to see Tuscany!