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Cycling Through History: Florence to Rome on the Pennell Trail
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Bicycle Tours in Italy: Cycling Through History: Florence to Rome on the Pennell Trail

Joseph and Elizabeth Robins Pennell were among the first touring cyclists in Italy. In October of 1884 they pedaled from Florence to Rome on a tandem tricycle. They accomplished this on tires made of metal and hard rubber, with only one gear and a questionable braking system at their disposal-if you are over 45, think about your first bike! The Pennells' route followed a major Roman road, a primary trade route during the medieval and renaissance periods. We'll parallel their historic route, which is now a highway, by taking small country roads through some of the most beautiful landscapes in central Italy.

Day 1: Arrive in Florence

The Ponte Vecchio over the Arno River in Florence.

Highlights: Bike fitting, welcome dinner

Welcome to Florence! We'll fit bicycles this afternoon and then get acquainted over refreshments before going to dinner together this evening.

What the Pennells did: After a three-day train ride straight from London in October of 1884 the Pennells spent several days in Florence, where Joseph had already been for his work as an illustrator. They stayed in Hotel Minerva near in Piazza Santa Maria Novella near the train station. For our tour we'll stay in the same hotel, now called Grand Hotel Minerva!

Day 2: Florence to Castelfiorentino

Joseph and Elizabeth Pennell cross the Ponte Vecchio in Florence on their tandem tricycle.

Highlights: Florence, Ponte Vecchio, pottery in Montelupo, Castelfiorentino

We leave Florence as a group this morning, walking across the historic Ponte Vecchio bridge on our way out of town. We follow the Pennell's route, at least partially, taking detours into the olive-clad hills to avoid the main roads along the Arno River. We'll pass through the pottery town of Montelupo and continue on to Castelfiorentino for the night. Dinner is together tonight. Distance: About 60 km (37 miles).

What the Pennells did: They bicycled across the Ponte Vecchio and out of Florence to the west following the Arno River through Lastra and Montelupo to Empoli, where they spent the night. The Pennells rode about 40 kilometers today.

Day 3: Bicycle Castelfiorentino to Siena

The famous Medieval towers of San Gimignano, Italy.

Highlights: Certaldo, San Gimignano, Colle Val d'Elsa and Siena

We ride up the Elsa River valley to Certaldo this morning and then on to San Gimignano, famous for its beautiful towers. The Pennells could see the towers from the valley below but they chose not to pedal up to them on their one speed trike. After our stop in San Gimignano we continue on through Colle Val d'Elsa to Siena where we spend the night. Dinner is on your own tonight. Distance: About 78 km (49 miles).

What the Pennells did: Crossed the Elsa at Ponte d'Elsa near Empoli and followed the river to Poggibonsi, stopping for lunch in Boccaccio's native town of Certaldo. They continued on to Siena the following day.

Day 4: Siena to Pienza

Highlights: Abbey of Monte Oliveto Maggiore, Le Crete, Pienza

We pedal south from Siena today into a different type of Tuscan landscape. As Elizabeth wrote in her account of the journey "the country through which we rode was sad and desolate. On either side were low rolling hills, bare as the English moors, and of every shade of gray and brown and purple." This is the Tuscany of dry-land wheat and sheep grazing, the Tuscany marked by lone cypress trees on the ridge and only occasional vineyards at the tops of hills capped by volcanic soils. We visit the Abbey of Monte Oliveto Maggiore today on our way to the wonderful renaissance town of Pienza. Dinner is on your own tonight. Distance: 84 km (52 miles).

What the Pennells did: The Pennells spent two rest days in Siena and then continued on to Monte Oliveto Maggiore, which offered lodging to artists. They spent several "golden days" relaxing at the Abbey, ". . . a green place in the midst of barrenness." After their stay at Monte Oliveto Maggiore the Pennells went on to Montepulciano.

Day 5: Bicycle from Pienza to Cortona by way of Montepulciano

Close up view of the Pennells on their tandem tricycle in Perugia in October 1884.

Highlights: Landscapes of the Val d'Orcia, Montepulciano and Cortona

We pedal this morning through a portion of the Val d'Orcia, a UNESCO World Heritage Landscape. Then we pass through the wine town of Montepulciano and head on across the Val di Chiana to the hilltop city of Cortona where we spend the night. You'll want to visit the Etruscan museum while we are in Cortona. Dinner is together tonight. Distance: 65 km (40 miles).

What the Pennells did: Upon leaving Monte Oliveto Maggiore they headed to San Quirico d'Orcia, Pienza and Montepulciano where they both fell ill. The couple rested for two days before continuing on to Cortona by way of Castiglione del Lago on Lake Trasimeno.

Day 6: Cortona to Assisi

Joseph and Elizabeth Pennell arrive in Assisi on their bicycle ride from Florence to Rome.

Highlights: Lake Trasimeno, Deruta ceramics and Assisi

Our route today takes us from Tuscany to Umbria, around the large hilltop city of Perugia. We'll also ride by Lake Trasimeno, site of one of the most famous battles in Roman history (against Hannibal in June, 217 BC). We'll pass through the famous ceramics town of Deruta on our way to Assisi, where we'll spend two nights. Dinner is together tonight. Distance: 105 km (65 miles).

What the Pennells did: Elizabeth managed to pedal to Cortona though, she was tired and "in no humor for riding." She opted to take the train on to Perugia while Joseph took the opportunity to test the tricycle on Italian roads without luggage. Joseph dropped Elizabeth at the train station at the bottom of the hill in Cortona and continued on to Perugia, arriving there before she did.

Day 7: Rest day in Assisi

The cathedral and monastery in Assisi, Italy.


Today is a rest day for us in Assisi, the village of Saint Francis. This is one of the most delightful hill towns in central Italy. You'll want to visit the Basilica of Saint Francis and the hermitage just east of town where Saint Francis went to meditate. This is a remarkable place to stroll and simply absorb the atmosphere. If you'd like, we'll recommend a hill or flat ride for you. Distance: Your choice of mileage 0 - 100 km (0 -65 miles).

What the Pennells did: They had taken just a short ride to Assisi from Perugia, arriving at about noon. The waiter at their inn had never seen a "velocipede" with three wheels and delighted in suggesting a route to Rome for them (the same route, it turns, out, that they had planned to do).

Day 8: Bicycle from Assisi to Terni

The Pennells encounter an obstruction on their tandem tricycle in Italy in October 1884.

Highlights: Villages of Bevagna, Montefalco, Virgil's Spring at Clitumnus, Spoleto

We continue pedaling today through the ancient lake basin that forms the heart of Umbria. We visit Bevagna, the hill town of Montefalco, and the source of the River Clitumnus, famous in Roman times and celebrated by the poet Virgil. We'll continue on to Terni with more luck than the Pennells had and we'll ride "through lively streets and piazza to the hotel, to supper, and to bed!" Dinner is together tonight. Distance: About 70 km (43 miles).

What the Pennells did: A steep climb out of the Umbrian basin challenged them but they looked forward to the downhill into Terni. The road up was rough and they ended up walking. Joseph tied a rope to the trike and pulled while Elizabeth pushed. Their luck worsened when they reached the top and faced a precipitous descent. Their brake lever came loose, and in attempting to fix it Joseph snapped it in two parts. So, after walking uphill for miles, they had to walk the full eight miles into Terni in the dark.

Day 9: Terni to Civita' Castellana

Joseph and Elizabeth Pennell meet a carabiniere upon their arrival in Rome on their tandem tricycle.

Highlights: Tiber River, Umbria and Latium, hill towns of Amelia and Civita' Castellana

We leave Umbria today, crossing the Tiber River into Latium, north of Rome. We intersect the ancient Roman road, the Via Flaminia, in Civita' Castellana tonight but our route is much longer than the Pennell's since they followed the more direct Via Flaminia. Dinner together tonight. Distance: About 75 km (46 miles).

What the Pennells did: After a late start from Terni the Pennells covered the twelve kilometers to Narni for lunch. They then continued on the Via Flaminia across the Tiber River valley and climbed to Civita Castellana, covering a total of about 46 kilometers.

Day 10: Civita' Castellana to Rome

Highlights: Rome!

We follow the Pennell's route along the Via Flaminia for about twenty kilometers this morning before turning onto secondary roads into the heart of the Regional Park of Veio. This park protects early Etruscan ruins close to Rome, the remains of Roman villas and related archeological sites and the historic landscapes of the Roman "campagna" north of Rome. We will replicate the Pennell?s entry into Rome as best we can while trying to avoid traffic. What the Pennells did: After sustaining a broken rear rack on the bumpy descent into Rome they pedaled across the Tiber River and into the Piazza del Popolo where they took a wrong turn on their way to Piazza di Spagna. They corrected for the wrong turn and pedaled into the Piazza where a crowd of onlookers surrounded them to watch as the carabinieri took their names and related information.

Day 11: Tour ends in Rome

Highlights: Rome!

Our tour ends after breakfast this morning. Of course you don't need to be reminded that a few days in Rome would be just the ticket after such a bicycle ride! Enjoy your stay.

What the Pennells did: They spent several weeks in Rome before heading back to London. Two months after arriving, they were summoned before a police magistrate where they paid a fine of 10 francs for "furious riding on the Corso" and for "refusing to descend when ordered" on the day they arrived in Rome. Thus ended their tricycle ride to Rome. Thanks for tracing their path with us!
  • Highlights
    Florence, Boccaccio's native town of Certaldo, San Gimignano, The monastery at Monte Oliveto Maggiore, Assisi, Rome, Pienza, Cortona, Siena, Virgil's country, Montepulciano
  • Includes
    10 nights accommodation, 11 days, 10 breakfasts, 7 dinners
  • Countries
  • Begin/End
  • Arrive/Depart
  • Total Distance
    537 - 637 km (332 - 397 miles)
  • Daily Distance
    0 -105 km (0 - 65 miles)
  • What to Expect
    Hills and ridge rides through central Tuscany and Umbria. No long mountain climbs but some hills every day.
  • Rating
  • Notes
  • Terms
Please call 1-800-685-4565 or e-mail us for the dates for this tour.

Click on the "pins" for details about each day's highlights.

Map Key

Green pinStart
Yellow pinCity (on route)
Red pinEnd
Other city dotCity (not part of route, provided for reference)

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