Florence to Rome: A Challenging but Tremendously Satisfying Bike Tour Through Italy’s Umbria Region

Embracing a little extra adventure.

I love group bike tours because I meet people who share my love for seeing countries close up, on a bicycle. I love guided bike tours because smart locals share their love for their country with us – and know secret routes, great cafes, and bathroom locations. A lot of my favorite rides have been boat and bike tours, which have groups and guides and the same bed each night.

But I recently decided to accept a challenge. My brother couldn't join me for our usual annual ride, and I needed to be in Italy for family obligations. So I signed up for a self-guided ride on which, by fluke of the marketplace, I was the only rider. It was an awesome itinerary starting and ending with nights in Florence and Rome, with six days of riding between two cities about an hour's train ride from each – Arezzo in the north and Poggio Mirteto in the south.

I realize that a solo trip is not many people’s dream vacation, but this chubby 70-year-old's experience may encourage you to consider pushing the envelope a little on your next ride. Several times on my solo 190-mile (310km) ride up and down hills in summer heat I said to myself, “This is a trip that I'll enjoy more after it's over.” But you needn't be as daring as me in order to taste a little adventure.

Italians boast that it's "hard to find a bad meal" in their country. Umbria is no exception. Not just pasta, like my all-time favorite of Wild Boar Ragù with Fettuccine. But great cheeses, beef and veal, charcuterie, and vegetables and tomatoes that have real taste, real freshness. And awesome wines.

I admit that riding alone, particularly up the steep hills and along state roads, was challenging. The tour company arranged the transport of my suitcase to my destination each day – a brilliant service. But I've compiled a little list of things that make any ride like this more comfortable and safer:

1. Study each day's route over your cappuccino and cornetto each morning. Master whatever GPS – cellphone or Garmin-type device – you're going to use. Turn off the
   automatic re-routing if you go off-course. One new route put me on roads that the tour company didn’t intend.
2. Identify places you can get water along the route – or bring enough for the day's ride. On Sundays, even restaurants and bars are closed in many towns.
3. If you have one, bring one of those bicycle rear-lights that have a radar sensor. As cars approach from behind, your GPS device warns you with beeps and a graphic representation. You won't be startled by the vehicle. It really reduces the stress of riding on roads.
4. Pace yourself as if you were with whining friends. You have all day to reach your destination, so stop and rest, drink water, smell the flowers.
5. If the terrain is hilly, go ahead and complain out loud – and remember that no hill on your route is too big to walk up.
6. Don't be shy about offering a hearty "buongiorno" to everyone you see. People are delighted to see us, and you will feel their warmth. And when you enjoy their wonderful food, they'll smile from ear to ear. If you use the bread to sop up the delicious sauce of the dish – called scarpetta – the chef will offer to adopt you.

Another bit of advice off your bike in the cities. If you take a bus or Metro, which is the second best way to get around, learn how to pay for the ride. In Rome, I saw a big, wonderful family be fined €50 ($57) each (€105 or $120 if they delay payment) because they didn't know how to pay for the bus (just tap a debit or credit card on the box). When they were caught, the officers first made them hand over their passports – not a fun experience.

I’ve visited Rome – 'The Eternal City' – several times before, but it felt even more exciting after my six days crossing Umbria. Cycling gives us a deeper appreciation for the bond between the land, the history, and the people. All of the hotels included in the tour were comfortable, but the one in Rome was the best – my just reward. My next trip will probably be in a group, but I was happy and reaped, even at my age, a sense of accomplishment.

Fulton Armstrong worked in the U.S. Government for many years and currently teaches at the American University and Syracuse University program in Washington, DC.