Countryside to Coast Hike and Bike Adventure

About the Experience

Diane Lane made us all swoon over the idea of impulsively purchasing  a rural Tuscan villa and living happily ever after. The golden film footage based on Frances Mayes memoir, Under the Tuscan Sun, unspooled a timeless landscape that was tempting, rapturous and all-encompassing. Tidy vineyards and robust reds. Plates of handmade pasta noodles and staggering coastline views. Dripping gelatos.

With a little sweat equity, you can experience a slice of Frances’ Italy by bike or better yet, by e-bike! The views and rewards at every turn (and downhill) are well-deserved. Ride the undulating cypress-fringed hills peppered with poppies from one enchanting village to the next. Follow cobbled streets and crooked alleys past time-worn churches and through medieval villages. Dozens of wine cellars offer free wine tastings and the al fresco tastings are always a cherished and animated exchange with locals.

It’s easy to fall under the spell of afternoon siestas, lingering dinners and unexpected conversations over espresso. This hiking and biking journey visits the famed Cinque Terre (and the secret ‘sixth town’) and its rainbow cluster of cliffside buildings. Hiking this magical stretch of coastline will sink deep into your memory bank. Steeped in history and resilience, the pastel towns of the Riviera will colour your mind and leave permanent warmth of the Tuscan sun on your shoulders.

This is a big taste of the ‘La Dolce Vita‘ modus operandi of Italians. Bonus: If you’re feeling a little more wild at heart than totally wild, this trip has been made more accessible with the addition of e-bikes! 

 

Click here to see the full itinerary!
Countryside to Coast Hike and Bike Adventure

About the Experience

Diane Lane made us all swoon over the idea of impulsively purchasing  a rural Tuscan villa and living happily ever after. The golden film footage based on Frances Mayes memoir, Under the Tuscan Sun, unspooled a timeless landscape that was tempting, rapturous and all-encompassing. Tidy vineyards and robust reds. Plates of handmade pasta noodles and staggering coastline views. Dripping gelatos.

With a little sweat equity, you can experience a slice of Frances’ Italy by bike or better yet, by e-bike! The views and rewards at every turn (and downhill) are well-deserved. Ride the undulating cypress-fringed hills peppered with poppies from one enchanting village to the next. Follow cobbled streets and crooked alleys past time-worn churches and through medieval villages. Dozens of wine cellars offer free wine tastings and the al fresco tastings are always a cherished and animated exchange with locals.

It’s easy to fall under the spell of afternoon siestas, lingering dinners and unexpected conversations over espresso. This hiking and biking journey visits the famed Cinque Terre (and the secret ‘sixth town’) and its rainbow cluster of cliffside buildings. Hiking this magical stretch of coastline will sink deep into your memory bank. Steeped in history and resilience, the pastel towns of the Riviera will colour your mind and leave permanent warmth of the Tuscan sun on your shoulders.

This is a big taste of the ‘La Dolce Vita‘ modus operandi of Italians. Bonus: If you’re feeling a little more wild at heart than totally wild, this trip has been made more accessible with the addition of e-bikes! 

 

DAY ONE: UNDER THE TUSCAN SUN

Plan to arrive in Cortona (by train from Rome or Florence) before 6 PM. Cortona is one of the most famous villages in Tuscany–it was featured prominently in the film Under the Tuscan Sun. If you arrive early, the agenda is simple: take in the stunning hilltop views, wander the streets and absorb the pizzas and piazzas! The Town Hall is quickly recognized by its clock tower and the dramatic staircase to the facade, and the imposing Palazzo del Capitano del Popolo (also known as Palazzo Passerini) tower above the square. The Renaissance buildings, tiny artisan shops and first sweet fix of gelato are just the beginning.

Before our decadent welcome dinner and introductory taste of Italy’s sumptuous flavours, our guide will walk us through our cycling days ahead and what we can expect.

 

DAY TWO: MONTEPULCIANO

We’ll immediately get into the groove and go for a scenic spin on a 48km (30 miles) magical bike loop that will take us from the hilltop perch of Cortona to the medieval town of Montepulciano. We’ll cycle past the Renaissance palaces, ancient churches and cinematic squares that were the backdrop for the vampire saga Twilight (and its sequel). 

Expansive panoramas unfold the verdant valleys of Val d’Orcia and Val di Chiana that surround it. The hillsides are neat quilt patches of vineyards–these grapes produce the famous red vino Nobile, one of Tuscany’s most renowned Sangiovese-based reds.

If the length of this first day’s ride seems daunting, here’s some reassurance: the first 4km (2.5 miles) are downhill with knock-out views as you whir down the elevation from Cortona. The 35km (22 miles) that follow are flat. Bonus: You can opt for an e-bike and rely on a boost when you need it. Or, take advantage of the optional van shuttle to our hotel in Montepulciano to avoid the climb altogether. For those who are eager for a challenge and want to feel the burn, this route will have your Fitbit purring.

Extra bonus: Every challenge deserves a reward after–hello vino rosso and vino Nobile!

Nobile tasting notes: Tobacco, leather, and candied fruit flavors

Fitbit notes: Biking–48km (30 miles) with a 750m (2,461ft) elevation gain

 

DAY THREE: CHIANCIANO CYCLING

After a protein and carb kickstart, we’ll strike off and bike a 31km (19 mile) loop through Chianciano and back to the walled hilltop town of Montepulciano. Chianciano (dubbed the “city of health”) is one of Europe’s most beloved thermal spa destinations. In the large thermal parks of Fucoli and Acqua Santa, mineral rich waters full of bicarbonate, sulphate and calcium attract those seeking a restorative soak. The city is full of shady holm oaks and chestnut trees. It’s also close to Pietrapociana Nature Reserve, where an all-consuming centuries-old beech forest is preserved. 

Views from Chianciano’s hilly roost are endless–be sure to figure out that panorama feature on your iPhone before this trip! The fertile agricultural hinterland of Val D’Orcia (one of Tuscany’s six UNESCO World Heritage sites) and the flat envelope of Valdichiana are the stuff of laptop screensavers. We’ll be overlooking historic abbeys, blooming ornate gardens and cypress-lined strada biancas (‘white roads’ in Italian).From Chianciano you can also see the Cetona and Amiata mountain peaks, Chiusi Lake, Montepulciano and Trasimeno Lake. 

In the afternoon, we’ll embrace the culinary side of Italy with a lively cooking class. We will learn all the cucina secrets to preparing a perfect pici, a typical pasta that originates in the province of Siena in Tuscany. Naturally, this will involve a taste test afterwards. Are you a pici eater? You will be after this informative and edible class!

Fitbit notes: Biking– 31km (19 miles) with a 660m (2,165ft) gain

Tasting notes: Squisito! (Exquisite!)

 

DAY FOUR: CYCLE PIENZA

Today we’ll cycle through the narrow streets of Pienza. Not surprisingly, it’s also situated on a hilltop. Are you sensing a theme here?

Once called Corsignano, the city was completely HGTV-restored by Enea Silvio Piccolomini, a humanist who later became Pope Pio II. Ambitiously, the restoration of his birthplace village began in 1459 with a laser focus on early urban planning concepts.The central square was harmoniously and conveniently surrounded by buildings of importance–the Cathedral, the Papal or Piccolomini Palace and the Town Hall. Dog lovers will appreciate the travertine “well of the dogs.”

In 1996, Pienza was designated a UNESCO World Heritage Site for its cultural significance in urban planning. Urbanist Jane Jacobs would have bought the Pope a pint in gratitude! 

Pienza is also the city of cacio, which means cheese (and not for the camera)! The well-loved (worldwide even) Pecorino of Pienza is a mmmm-inducing cheese made from sheep’s milk. We’ll see several shops selling various types of fresh and aged pecorino.

After reaching Pienza, you can choose to jump in the van or double-down on some pecorino and keep riding onwards to San Giovanni d’Asso, home to just a few hundred people and an annual fall truffle festival. It’s also home to Italy’s only truffle museum. 

Highlights of this area include two impressive churches: San Giovanni Battista (est. 1492) and San Pietro in Villore (first built in the 700s and restored in the 1300s). There’s also a dominating 12th-century castle (where the Truffle Museum is located) and its dreamy hanging garden.  

San Giovanni d’Asso is also designated as a “citta’ dell’olio” (olive oil town) and citta’ del Vino Orcia DOC. The wine zone is sandwiched between the two most acclaimed wine districts of Tuscany: Montalcino and Montepulciano. Saluti!

We’ll depart San Giovanni armed with newfound truffle IQ and travel by van (one hour) to our luxe stay at Bosco Della Spina, a traditional farm in Val di Merse that has been drop-dead-gorgeously renovated into a hotel. Bosco Della Spina is a turning point of the trip as we leave the undulating Tuscan hills (and our bikes) and shift to the all-enveloping seaside hamlets of Cinque Terre.

Tonight we will be privy to an elegant wine tasting before dinner, featuring wines produced by the Meoni family, owners of the country house hotel where we will be well-pampered. The restaurant is actually in the farm’s former wine cellar.

Fitbit notes: Biking–22km (14 miles) with 400m (1,312ft) elevation gain. The optional ride to San Giovanni d’Asso is a total of 40km (25 miles) with 600m (1,969ft) elevation gain PLUS huge personal gain.

Tasting notes: Everything is going to taste incredible in tonight’s setting with the snap crackle of the fireplace (seasonal) or the mesmerizing terrace view (also seasonal!).

 

DAY FIVE: CINQUE TERRE

Today we recalibrate our GPS for the Mediterranean sea. The scenery is staggering and startling–don’t fret, we’ll make several stops on our way to the fabled Cinque Terre. Steeped in history (and steep cliffs) the five tiny villages that Cinque Terre’s name is derived from, appear like a child’s whimsical drawing. Pastel-coloured buildings and houses are neatly stacked along the harbours and hills.  Cinque Terre National Park is Italy’s first and smallest! The area was protected in 1999 and includes five (cinque!) darling seaside villages (Monterosso, Vernazza, Corniglia, Manarola, and Riomaggiore) that cling to the rocky Mediterranean coastline. The villages are a marvel of Benedictine monasteries, Roman villas and ancient churches, all dwarfed by sharp cliffs.

We’ll head to Siena first, and take in the buzz of the central piazza known as Il Campo or Piazza del Campo. It’s known worldwide for the famous Palio di Siena. The wildly popular bareback horse race is held twice each year (July 2 and August 16). Ten horses and riders are dressed in appropriate colours, representing ten of the seventeen city wards. We’ll explore the old city on a walking tour, minus the bareback ride!

After the tour, we’ll continue our drive closer to Manarola (which we will reach by foot). The walk is approximately 6km (3.7 miles) along the predictably hilly and sculpted coast. The van will carry our luggage onward, while we make our way down the steep, rocky path into town. 

Fitbit notes: Hiking: 6km (3.7 miles)/ 1,600m (5,249ft) gain

Netflix notes: Get a sneak preview of Siena and the Palio in the James Bond movie, Quantum of Solace.

 

DAY SIX: HIKE TO PORTOVENERE

Today we’ll set off on a 13km (7.4 mile) hike from Manarola to Riomaggiore (affectionately known as Lover’s Lane or Way of Love) and continue on to Telegrafo. There are actually 120 km (74 miles) of hiking trails inside Cinque Terre National Park  but the most popular hike is along Sentiero Azzurro–also known as The Blue Pathway or Blue Trail which can be hiked in one day. The trails have been affected by erosion and flooding over the years but where there’s a will, there’s a way and the Way of Love persists!

We’ll follow the storied, serpentine track that leads to Porto Venere (or Portovenere), a photogenic coastal fishing village. This trail reaches the tiptop of the mountains, 650 meters above sea level and your heartbeat will remind you of your efforts! Porto Venere is Cinque Terre’s “sixth town” but who’s counting?

This shiny Riviera jewel overlooks the Gulf of La Spezia or Golfo dei Poeti–the “Gulf of Poets.” It’s a romantic nod to the literary giants who fell under the spell of the area’s natural beauty and curves. You may go home with a poem of your own!

Two kilometres (1.2 miles) before Porto Venere, the trail passes through Fort Muzzerone, which is now used by the Italian army for training. This area is a magnet for sinewy climbers who love the scale the multi-pitch craggy pillar.

After, we’ll hopin a boat to return to Manarola’s marina–we don’t have to Spiderwoman our way to our next glass of wine or Spritz!

Fitbit notes: Hiking– 13.5km (7.4 miles)/ 616m (2,021ft) gain/ 616m (2,021ft) descent

Tasting notes: An Aperol Spritz sundowner is highly recommended to properly enjoy the marmalade-tinted Manaroloa sunset. Aperol is an Italian bitter apéritif made of gentian, rhubarb, and cinchona (a type of tree bark–don’t go barkin’ up the wrong tree!).

 

DAY SEVEN: TRAIL TO VERNAZZA

Our final day concludes with another monumental hike from Manarola to Corniglia. If our crew is ambitious, we can walk further to Vernazza, covering 8 kilometres (5 miles). This hike offers extraordinary panoramic views and one very tall tale.

The first part of this trail connects Manarola to Volastra where we will hike past the sanctuary of Our Lady of Health. To reach the sanctuary, the road climbs upward and consists of about 1,200 steps. Your Fitbit might look for a new career!

As for tall tales, legend has it that during the historic Saracen raids, the wealthiest inhabitants of Volastra hid the village’s church bells underground, to prevent the gleam and flitter of the metal from attracting the pirates. Despite this proactive and genius idea, the pirates still attacked the village. Disgruntled and empty-handed, they destroyed the area instead. Much later (*tall tale does not include specific time references), an elderly man appeared in Volastra. He spoke with an Asian accent and claimed to be one of the escapees and survivors of the Saracen raid. He was back to unearth the treasure of the church bells–however he died the exact same day without revealing the exact location of the bells. Now here’s the spooky bit: the bells still ring on stormy nights!

We’ll then take a boat or train back to Manarola, where we’ll gather for a memorable farewell (arrivederci, sigh) dinner together. 

Fitbit notes: Hiking–Approximately 8 km (5 miles), give or take a few selfies, with a 450m (1,476ft) gain/450m (1,476ft) descent. Also, 1,200 steps to reach the sanctuary alone!

Tasting notes: Bittersweet of course, it’s our last night together.

 

DAY EIGHT: ARRIVEDERCI ITALY

We’ll have a leisurely morning to linger over coffee or wander a little before taking the train from Manarola onwards to Florence, Rome, Genoa, or wherever you decide to continue your edible adventure in Italy.

Hug your Wild Women pack goodbye, decide where you’ll meet again and be sure to squeeze in one last gelato. It’s a la dolce vita mandate!

 

 

 

 

 

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