Words by Issa Breibish // Photography by Nita Breibish

It doesn’t take long for the skies to open up and the rain to start falling. Luckily for us the days ride is incredibly short – it’s less than an hour to Livorno – an unexpected stop from Vicopisano – but with a mix of rain and snow we’re happy to have a quick outing today. Originally, we’d set aside fives days between Vicopisano and Rome with the intent of heading inland to Arezzo and Siena to camp. Unfortunately our timing proves to be off as winter weather continues to move through the region. The forecast for Livorno holds the promise of warmer days and at least a bit of sun and so a new plan is laid.

The roads give us a good taste of the countryside and we ride next to the raised highways that seem to bruise an otherwise lovely view. Why the autostrada hovers like a bridge over endless miles of farmland is a bit of a mystery. If there’s an expensive way to build a road, this has to be it!

We roll through miles of oil processing plants and, for a moment, wonder aloud about our decision to stay in Livorno but after twenty minutes of industrial parks we enter the main part of the city and are immediately impressed by it’s beautiful board walk and plentiful caffè. We pull up to our hotel for the next couple of nights – the Grand Hotel Palazzo – a deal through hotels.com has gotten us great rates for what appears to be a pretty classy affair, a nice perk to travelling off-season. Unfortunately, we’re not entirely classy and strolling up to the front desk in our dirty gear and squeaky boots is an affront to our proudly distant concierge. To make matters worse, we’re very early and he makes it obvious that booking through a discount website clearly makes us second-class here. Early check-in is not an option, so an afternoon in our gear it is.

We grab a caffè at a small bar next door and sit with the locals around a group of tables all set to face each other in a circle. An older man looks up from his paper and delivers a friendly “Ciao” while a young man sits facing the water, sipping his macchiato and deep in thought. After some impromptu Italian lessons from the owner, we stroll the boardwalk along the sea; the skies have cleared and, for now at least, the sun is beating down over the water. It’s incredible how warm the sun is here. As soon as it disappears behind a cloud the temperature seems instantly cooler, but the clouds passing brings with it a wonderful warmth. The beach is lined with restaurants and a grand square with a beautiful checkered promenade unfolds out towards the water. With a little bite still lingering in the air, the boardwalk is almost completely deserted and we take our time watching the ships line the horizon while waiting for a pilot to take them safely into port.

Livorno also goes by the name of Leghorn, given to it by English sailors when the city was called Ligorno, and while we never hear anyone use it by that name, our GPS’ seem to only refer to it in old sailor parlance (“Arg matey, turn ye olde keffal port-side at Leghorn”). While this example of English-language renaming is surely one of the most ridiculous it seems strange that so many places I’ve grown up calling one name, are actually named something else entirely!

Soon enough it’s time to check-in and we’re suitably impressed with the room – we can see the “grand” in this hotel. There’s tons of room and a view of the sea which we truly appreciate. The new man at the front desk is much friendlier and happily chats with us as we head out, freed from our riding gear. With hours to go before dinner, we grab a late lunch at a boardwalk caffè and watch the rain roll back in; our timing with the weather is great – we seem to find a place to hunker down just before the torrents start to flow. Today, the rain is coming in sheets. Our waiter is a man we met on our first walkabout earlier in the day and his friendly demeanour has convinced us to return – and we’re glad we do. He’s a genuinely lovely guy and our late lunch is a great way to ease into a new city. From our vantage point we can relax and watch people go about their business which is a favourite pastime of ours. A brief break in the weather gives us a chance to bolt back to the hotel and we spend the remainder of the afternoon watching the storms roll in over the water.

From the hotel bar on the top floor we watch the sun move lower in the sky, while shards of lightning light up the boats waiting on the water. George Michaels greatest hits are drifting over the speakers and, once completed, the CD begins again. Nita seems to be reverting to junior high school before my eyes and even I’m feeling nostalgic for big hair and shoulder-pads. The dark clouds have closed in around us and it’s hard to tell if the sun has completely disappeared or if the storms have simply blocked it out. With the rain reduced to a drizzle, we set out for a dinner close-by and have a truly terrible meal of luke-warm lasagna and a repulsive calzone. Unable to finish the slop in front of us, we head back to the hotel and turn in for the night – our confidence in Italian cooking being slightly rocked.

The next days sun brings the people to the streets of Livorno. Far from the empty boardwalk of the previous day, today it’s bustling. Young and old alike seem to be reveling in it’s warm, golden rays. We spend the day walking the city, taking in the beach and writing. We’ve warmed to Livorno and, other than our original concierge, the folks we meet are warm and kind.

Fearing a repeat of our dinner from the previous day, we find a lovely little restaurant off of the boardwalk and enjoy a truly fabulous meal. A family restaurant, the photos behind the bar resemble a mechanics shop more than a family eatery, though to be fair the content doesn’t favour any particular sex. In between pictures of relatives celebrating team wins and restaurant parties are pictures of genitals enjoying a nice cigarette and other dubious explorations of body parts as people. Somehow though, it doesn’t seem out of place at all – in fact the very opposite. It makes us feel as if we’re a little up tight back home!

The father often stops by the table to make sure we’re enjoying ourselves, and the bartenders and wait-staff easily throw smiles our way. This may be the first time we’ve had a proper night out with other people in the restaurant; it seems that our bodies are finally getting accustomed to the after-eight dinner time in Italy. Following our pasta failure from the previous night, we opt for the carne mista (for two) and verdure grilliate – basically just a grilled selection of meats and vegetables – and it’s beautifully made. It’s simple preparation reminds us both of the barbecues at home. This is the restaurant meal we’ve been waiting for, atmosphere and all.The meal is followed with a round of homemade Limoncello courtesy of our barman and we make our way back to the hotel feeling very satisfied with our last night in Livorno. In the hallways George Michael is still playing softly over the speakers and we realize that it’s the only music that’s been playing here since we arrived! All the hits after Wham! leave Nita and me stuck in the eighties which brings on a mild case of hysterical laughter. This is a totally good night. Like, totally.

The next morning we load the bikes for Orbetello which will be our home for the next three nights. We’re excited to see this medieval town as our friend Stefano claims it’s the best place to stop between Vicopisano and Rome. The day starts with glorious blue skies and it seems that the sun we’ve been promised for the next four days is finally here.Our route takes us away from the water and winds us inland through farming country. In contrast to the sharp hills and twisty roads we’ve mostly ridden in Italy, these are long sweeping highways that occasionally offer up a road hazard in the form of a slow moving tractor.

Our lodgings at Il Cacciatore are the closest thing to a motel we’ve seen in a long time. Sitting right along the highway, the rooms are sparse and entirely practical. The owners are a nice couple with a young daughter who speak little English, which makes for a great opportunity to practice some Italian. We quickly unpack the bikes and head into Orbetello two-up to take advantage of the sun, which is still shining brightly. It’s a short distance into town and soon we’re riding down the main street and under the giant stone gate that delivers us through the ancient stone walls and into the old town. We briefly scan for a place to stop but decide to continue over a narrow spine of land that connects Orbetello to Argentario.

As we cross the water, we pass a stone windmill standing alone with a lagoon surrounding it and silently wonder if structures like this have had their land consumed by the water over time, or if they’ve been intentionally built this way. Considering that Argentario was once an island with two land bridges forming over time, it seems likely that this remarkable windmill was engineered to take advantage of the wind blowing across the water.

Soon we’re on wonderfully twisting roads along the Islands north coast that eventually deliver us to Porto Santo Stefano, a beautiful town built into the hills on this natural inlet. Famously, it’s the home to the ferries that take travellers to Giglio, the island whose coastline has been scarred by the ongoing Costa Concordia cruise ship disaster, but there’s no sign of that here. The water is still, the sun is shining and the only action at this port is a lone fisherman making his way back to the beach carrying the days catch. We grab a caffè and sit quietly watching this world go about it’s business.

As the sun drops lower in the sky, we make our way back to the hotel and chat with the owner about the area. He mentions a dirt road on the far side of Argentario that’s very difficult to travel but offers spectacular views of the Tyrrhenian Sea – a part of the Mediterranean comprised of the area between Italy, Corsica and Sardinia down to the north shores of Sicily. He thinks the route may be possible by bike, but not by car since it’s too rough and narrow. Looking at Nita I see a look of excitement in her eyes and I know she’s stoked!

The sky turns a deep red as the owner pours us some very stiff drinks from the bar and we join our bikes by the patio outside. I take a seat on my bike with a pipe and a scotch and Nita takes advantage of the fading light to shoot some photographs before the red finally gives into black. The nights are chilly and the fireplace in the dining room is calling our names. Dinner at the hotel restaurant is fantastic. The food is made by the family and definitely tastes like home-cooking. They hunt boar and rabbit in the region so the meat dishes are usually one or the other. I try a rabbit Papardelle and it’s uncomplicated tastes are incredibly satisfying.

We wake up the next morning filled with excitement and energy for the days ride. It doesn’t take long to get everything ready, grab a small bite and head out towards Argentario. Instead of taking the road north to Porto Santo Stefano, we head south through Porto Ercole which turns out to be another beautiful town. Once through town we navigate some tight switchbacks before finding the beginning of Via Panoramica – the road that will take us around the island. For the first few kilometers the road is just a beautiful sweeping ride that does offer beautiful views of the sea and the small islands that dot the water. The sky is clear and almost as blue as the rippling waves below, but not quite. The road takes us up for a while before a steep descent begins towards the sea. Signage is rare and the few we do come across have nothing more than an exclamation mark on them. As the road surface begins to deteriorate we begin to question if we’re on the right road at all. The road narrows into a single lane and begins to offer up some fierce switchbacks with steep cambers until we finally we stop to get our bearings.

The road isn’t mapped on GPS so it’s all a matter of gut and feel. A couple of miles back there’s a turn-off with better asphalt so we decide to check it out before continuing down this road. After finally getting the bikes turned around we find the good asphalt and follow it – right back into Porto Ercole. Damn. We retrace the original route to our turn-around spot but this time continue on. The road dives and twists before finally flattening out – and then it simply disintegrates. What’s left of the asphalt now looks like broken bits of wax – gnarled, warped and rutted – then, as it climbs up and out of sight it’s simply gravel, boulders and ruts. Now we see what our host at the hotel is talking about. By the side of the road, Nita and I talk about the plan of attack: continue or turn-back.

I volunteer to scout the road and begin the ascent – it’s bumpy and with the ruts and baby-sized boulders dotting the route, I pick a careful line. The road climbs for about 500m before breaking into a tight and steep right-hander. Finding a place to stop I let Nita know she’d be fine – but I’m too late, she’s already on her way up! Around the next corner the road returns to destroyed tarmac before once again deteriorating into some decent hard-packed gravel – though still rutted and bouldered. After about half an hour of climbing we hit a plateau and take a minute to take it in. We’re pretty happy with where we’ve ended up and decide to scout the upcoming section.

From where we are the road seems a little out of our league. After a couple of deep river crossings the already narrow road tightens up to something a little wider than our bikes and climbs steeply up, winding along the side of a 700ft cliff. After a fairly long internal debate we decide to retreat – we have no idea how long it’ll take to circumnavigate the Argentario, and the road we can see offers no way to turn around if we should find ourselves in trouble. We’ll have a bite to eat in Porto Santo Stefano and see what the roads on that side of the island have to offer.

While we sit along the water in Santo Stefano, we revisit the section of road that we managed to complete and we’re definitely feeling a high from it. That little section of road was a blast and we’re half tempted to return to it just for a laugh. Instead we feel like it’s smarter to start from this end of the Via Panoramica and see how far we can get. The road heading south from the town quickly starts winding skyward before leaving the last of the businesses that line it at the base of some tight switchbacks. The road degrades quickly as we ascend and soon the potholes and loose asphalt dominate our attention. As we crest the mountain our efforts are rewarded with an amazing view of the Tyrrhenian Sea.

A short descent into a tight corner and the road is gone; it’s been replaced with a loose, sharp gravel interspersed with more large rocks and ruts. The experience is more akin to a rollercoaster with steep descents followed by switchbacks and yet another climb up an impossibly steep line. At one point we come to a fork in the road that presents two routes that make the previous tracks seem like perfect tarmac. To the right, an unmarked road dips down and disappears around a corner. Straight ahead a sign reads “Grossetto” which we know we need to head towards. The rougher of the roads, it’s steep climb twists to the right and offers and nice rut as it’s narrowing track stretches out along the highest part of the cliff.

It’s interesting being in moments like this. Nita’s had problems in the past with being on twisty roads along the side of cliffs and I can’t help but think that she’s probably not very happy about our current route. But I’m completely wrong. As we stop halfway along the apex of the road, my helmet is filled with laughter and cheers; she’s stoked at what she’s accomplished so far. We take a moment with our bikes perched along the narrow track to take in the most amazing view we’ve seen along this coast. We’re alone, it’s silent and the warmth of the sun could have us taking a nap, undisturbed, for hours. I ask how she’s doing and it seems that her fear of cliff-side roads is now long gone.

The total route takes a few hours but it’s some of the most fun we’ve had on our bikes. Pushing ourselves mentally and physically through the technical sections of the route is not only rewarding but also incredibly fun. As our new track meets up with our old one from the morning we’re feel awash in the glow that comes from meeting a challenge. Before heading back to our room at the hotel we stop for a caffè in Porto Ercole to recount the days travels.

In fact it turns out getting to dinner is the most dangerous part of the day. Our hosts let us know that the restaurant is closed but that we can grab a bite at the hotel up the road – just along the highway. By the time we head out it’s pitch black and there’s no sidewalk to act as a buffer between us and the speeding semi’s and cars. Waiting for a small gap in traffic we bolt down the freeway and almost make it to a field before a truck passes within feet of us. Catching our breath we wait for the next gap and repeat the process until we arrive at the parking lot of the hotel. To say that we have a little bit of “pucker” from the experience would be an understatement!

Dinner is quite good though the hotel has a strange feeling about it. About halfway through the meal Nita comments that she’s the only woman in the restaurant. I look around and notice that she’s not only right, but all the men are seated facing us. Interesting. We finish up somewhat awkwardly and make our way back out to the highway and our 400m dash. With a larger gap in traffic we bolt down the road at top speed and easily make it free of any close calls with semi’s.

We spend our last day visiting the shoreline in Porto Santo Stefano and sipping a caffè in the sun. The people here are lively and we’re surrounded by plenty of animated conversations and friends meeting on the streets. We meet the hotel cat in the dining room for dinner – a surprise friend for Nita who’s allergies usually mean that cats are off-limits. This little character though has enjoyed spending breakfast and dinner sitting snugly between Nita and the back of her chair.

Our time in Orbetello has been brief but the wonderfully challenging day spent on the Via Panoramica around Argentario will be with us for many years to come. The next morning we’re met with a different kind of nervous energy; we’re heading for Rome and the madness of riding the capitals busy streets.

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