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My summer 2020 road trip along the Italian Riviera

Travelling in the midst of a global pandemic isn't necessarily the smartest of ideas. But we'd had enough of being cooped up, living within one square mile. This is the story of our two week Italian road trip. I hope you enjoy.

Scott Taylor
Scott Taylor
- 19 min read
My summer 2020 road trip along the Italian Riviera

I write this as I look out the window of my Airbnb at the enticing landscapes and azure seas of Liguria. It's enough to make anyone fall in love, and want to move here. This narrow, seaside crescent in northwest Italy, sheltered by the Maritime Alps and overlooking the rugged coastline of the Ligurian Sea, is one of the most beautiful destinations in the Mediterranean. Of all the places I could have been writing from (because of COVID), I'm glad it ended up being here.

But first, let me rewind a couple of months. It's June 2020 and COVID infections are dropping throughout Europe. Restrictions are easing. My girlfriend and I make the decision that we want to book a holiday. We convince ourselves it's worth the risk. Lockdown had made the norm monotonous. We'd been stuck at home, and in one city, for months. Leaving us yearning to jump on a plane to somewhere. Somewhere with good weather, good food and turquoise water —and not a conference call within earshot!

Our destination shortlist had been whittled down for us. We had to go somewhere within Europe. And even though we had two weeks to play with, most of the far-flung places still had quarantine measures in place. Furthermore, we couldn't risk somewhere too far off the beaten track. What if one of us ended up catching COVID? We'd want reliable healthcare facilities. And finally, it had to be cheap enough to rebook a flight with a different airline if someone cancelled on us last minute (yeah, that happened —thanks a lot British Airways!).

So we were left with the usual suspects: France, Spain, Greece, and Italy.

By the way... It's now July, and we still haven't decided.

My initial preference was to drive from London, down through France, and end up on the French Riviera. Free to roam around and explore the likes of Monaco, Antibes, Cannes, etc. However, that notion was quickly upset when France started to see an increase in daily COVID infections. The Transport Secretary never too far behind, started reneging on travel corridors. "If you arrive back in England after 4am in two days time, you'll have to self-isolate for 14 days" was the increasingly repetitive chorus on the news, as countries around Europe started spiking.

We then thought about Spain. But the same thing happened. And Greece.

The only country that seemed to have a handle on infections was Italy. Perhaps due to the fact they had quite a fitting proverb "La gatta frettolosa ha fatto i gattini ciechi." With the most literal translation being “The hasty cat gave birth to blind kittens.” In other words, doing something too quickly can result in less-than-perfect results. Whilst all of its neighbour nations had quickly abandoned masks and other precautionary measures, Italians showed a steadfast solidarity. Perhaps because they got hit so badly at the start. They were in no rush to succumb to an increasing R-rate again.

So with that, we put all our eggs in one basket and started trawling and Airbnb for hotels and hosts that had gracious last minute cancellation policies. Should the stats turn against us.

Eventually we'd decided upon the towns and areas that we wanted to visit (more on that soon) in addition to the most logical order in which to visit them. Being pedantic, we also took into account the latest weather forecasts. We booked the hotels and Airbnbs. The only thing that remained was the car rental — a Fiat 500, of course.

Now for the wait.

A period of time where everything seemingly grinds to a halt. All we could do was spectate and stress about Italy's handle on COVID (and England's for that matter). Too many days of increasing infections and the government would echo those words that had become all too familiar, ""If you arrive back in England after 4am...." And vice versa, if our numbers went up too much, Italy could potentially ban entry.

"65 days remaining", the holiday countdown app on my phone told me.

It's going to be a long couple of months, I thought.

Finally, the day had come 🛫

It's now early September, out-of-office set, suitcase packed. Masks and disinfectant, check. Thankfully nothing imposed by either country in the way of bans or quarantines. We'd made it —somehow. Phew.

It was now time to venture out of the one square mile that we'd been confined to for the best part of the last six months!


But, it was tinged with a slight unease.

On the walk to London Liverpool Street Station, the City was empty. A reminder that the trip would bring with it risks. And that it wasn't going to be a normal holiday, not by a long shot. Once on the train, this was again confirmed. You could see everyone's furtive glances in the hope that you wouldn't sit in the set of seats next to them. Heaven forbid anyone coughs! Masks on.

Same story at the airport. I fall into the crowd that likes to enjoy a customary pint (regardless of time of departure). I reason that it's more of a signal to show the holiday has well and truly started, and that I can put my metaphorical feet up. Well the pub, much like the train, had this rather sad, quiet and dreary ambience about it. To add insult to injury, I'm not sure the lights were even working. Everyone kept to themselves. Quiet. Dark. Patiently waiting to head to their gates. But at least we had our pints of Moretti, COVID hadn't taken that from us!

A bit of a change from the normal boisterous stag dos, excited young families, business travellers, etc. I hoped to myself that this wasn't indicative of what was to come, once in Italy.

Our schedule 📆

Before we jump into the 14-day schedule, I wanted to make a special mention on what was probably the most terrifying flight of my life! You see, as you'd expect, landing in a storm doesn't quite make for that pleasant of an experience. Up until the approach to Pisa, the flight had actually been pretty perfect (ignoring the face masks). I even managed to get a beer from the in-flight service, something I thought would be cancelled.

But in the last twenty minutes the sun disappeared. Dark clouds approached fast. Next thing, the plane was bouncing all over the place.

With bolts of lightning now seemingly within reach, the pilot decided to pull a very quick U-turn, whilst accelerating. This isn't good I thought to myself. And, lo-and-behold, the stewardess announces over the PA system, "we've just had a failed approach, I'll get back to you when the pilot is less busy with more information."

Adrenaline now flowing, I glance at my girlfriend — who's normally pretty chilled through things like this — her worried look exacerbates mine. I managed to catch one of the bolts of lightning, when recording from my phone.

The pilots bring us back out to sea and circle there for a while. They're trying to predict and decide what the storm is going to do. Should we re-route to nearby Florence? Or stick with Pisa and hope it clears a bit? They decided on the latter.

Twenty or thirty minutes later, after being in a holding pattern, I see the approaching shoreline through the odd clearing in the clouds. It looks like day time when the lightning strikes. We're trying a different approach. Buckle up.

By this time everyone on the plane is bolt upright and awake, their phones pointed out of the windows. We're all collectively holding our breaths. Eerily quiet. Only the rattling of the plane to be heard.

Thankfully, the pilot manages to keep it in a straight line, progressively decreasing in altitude. And after what seemed like the longest ten minutes of my life, we touch down. Everyone claps. Something that usually annoys me, this time actually brought me some relief. Everyone's looking a bit pale. But at least we made it.

Buona sera, Italia.

The rest of the evening is a bit of a blur, we stumble up the road to our budget B&B. We book it simply because of its close proximity to the airport. Just somewhere to lay our heads down for a few hours before returning to the airport to collect our Fiat 500. As you can probably guess, not much sleep was had, the thunder and lightning continued until around 4 or 5am.

Now onto our schedule! Below is a rough outline, feel free to skip to the part that interests you the most. I realise this post is already quite long!

Day Activity
Day 1 Land in Pisa (1)
Day 2 Get hire car and head to Santa Margherita (2)
Day 3 Visit Portofino (3)
Day 4 Drive to Cinque Terre (4), new Airbnb
Day 5 Hiking at Vernazza, and dinner at Manarola
Day 6 All day at the beach at Montorosso
Day 7 All day at the beach at Montorosso
Day 8 Drive to Tuscany (5), new hotel
Day 9 Stay by the pool, and dinner in Montepulciano
Day 10 Drive to Pienza, dinner again in Montepulciano
Day 11 Wake up at 5am and drive to Positano (6), new Airbnb
Day 12 Boat and beach day
Day 13 Check-in at Belmond Caruso
Day 14 Beach club
Day 15 Fly home

Map of our route 📍

This map took a lot more work than originally anticipated, haha. I didn't want to use Google Maps as it'd be unnecessarily clunky —and most likely mess up on mobile devices. So I went for D3.js, a javascript library. It basically shows the places, in order, that we visited on our road trip.

As you can see, most of the places are quite close to one another. We actually only needed the car on a few key days —the rest of the time it was parked. But it was nice to have the reassurance that if we wanted to jump into it and drive somewhere, we could. Plus, in COVID times, we didn't want to start risking taking a lot of public transport or taxis. I think overall it cost around £700 for the two weeks. When we were in the North, everywhere was only a couple of hours drive from one another. The longest drive was between Montepulciano and Positano, five or six hours I think.

So back to Day 2, we've just picked up our rental car from Pisa Airport, and decide to head into town to see The Leaning Tower of Pisa. The storm continued to hang around, putting a bit of a dampener on the morning —but checking out the tower was only ever going to be a nice bonus. The weather also made getting used left hand drive a little more interesting! I might have driven on the wrong side on a couple of occasions.

Our main mission of the morning was heading north 137km to Santa Margherita, to our first Airbnb. We picked a town near to Portofino, rather than staying in it, as we heard Portofino was a little small, and overpriced (for accommodation). Also, apparently there wasn't a huge amount to do beyond eat, drink and shop around the harbour —although that sounded good to me, to be honest.

Two hours later and I was already becoming more Italian in my driving. "Vaffanculo!" coming from my window when a moped got in my way or cut me off!

We drove around in circles for the best part of an hour in Santa Margherita, trying to find some parking. Getting my first taster of the narrow, one way, streets of the Italian Riviera.

That said, the majority of the time was spent trying to understand the Italian parking signs. No English at all. And the illustrations harder to decipher than hieroglyphics. We eventually found a multi-story car park. It would be our Fiat's home for the next few days.

We left our luggage at the Airbnb.

The Airbnb was nice. Simple. Good sized balcony, modern bathroom.

And then it was time... lunch. Finally. My first taste of authentic Italian pasta. My tastebuds were tingling. We found a cosy little restaurant about two minutes walk from the Airbnb. It had seats outside in a small alleyway with a view of the harbour. Perfecto! The furtive glances on the train, the overhang of COVID, the near death flight... it was all starting to subside and become a distant memory. Relaxation level: increasing.

Portofino 🛥

After lunch the plan was to get a ferry from Santa Margherita to Portofino, but the sea was a little rough. Maybe it was our good 'ol friend 'Storm Pisa' heading up the coast to disrupt us even more, haha! So the ferries were cancelled, and the options were: either walk for 45 minutes or get a 15 minute bus.

We elected for the bus.

We were so exhausted from all the travel that we'd rather risk contracting COVID on an overpopulated bus than have to walk for 45 minutes in 30 degree heat.

Once in Portofino, it was easy to understand what all the fuss was about. It was a picture postcard town. So much so that the main buildings in the harbour actually have their fancy arches and architecture painted on!

Maybe the local council was onto something, Instagramify your town. They were basically using photoshop to attract visitors to their idyllic hideaway. Genius.

We stayed there all day. Embracing the culture of Italian aperitifs and people watching. We were eagerly awaiting dinner. We'd booked Da ö Batti - a restaurant famous for its seafood, specifically its shrimp. And wow, it lived up to the hype. I'm already planning a weekend trip back to Portofino, simply for Da ö Batti.

I'm not sure what more I can say about Portofino and Santa Margherita. We returned to Portofino the next day. This time doing the 45 minute walk, stopping off at the two or three little coves that were along the way. The landscape, the huge colourful villas sprawling over the coastal rocks, the turquoise sea, the views... it's all really as you'd expect. I do think a couple of days is enough in this part of the Riviera. Oh, we also walked up to the lighthouse at Portofino and saw a couple of whales out at sea!

Cinque Terre 🏘

It's now Day 4, and we're driving to Cinque Terre. Specifically, Riomaggiore. It will be our base whilst we're there.

The sun is out, we've just had breakfast and the coastal drive is beautiful. It's about an hour back toward Pisa. And again, we'd have to ditch the car. Cinque Terre is a set of five (duh!) villages along the coast which are connected by train. We park at La Spezia Train Station, not quite sure what the daily rate is. I guess we'd find out in four days time!

I was not looking forward to dragging the best part of 40kg of luggage solely uphill. The train journey was only 10 minutes, but then steep inclines by foot. Note: our next Airbnb was at the top of the town. Brilliant.

Yup, I'm exhausted. To put it mildly. Steps, steps and more steps. Why did I pack so much? Clothes now soaked in sweat. I swear the Airbnb host might think I've got COVID. This makes me even more worried, making it harder to recover and cool down.

My girlfriend nailed it on the accommodation. The apartment is beautiful. Another massive balcony. Comfortable bed and modern decor. Somehow though, as if the steps in the town weren't enough —this apartment had steps down, then up, then down —just to get to the front door. Maybe they just like steps?

We spend the majority of our time in a nearby town, Monterosso —famous for its beaches. It took a bit of negotiation with the beach clubs, who seemed to favour their fellow Italians, in terms of booking sun loungers. But my Irish charm must have won them over, haha. I couldn't wait to jump into the sea. It looked so welcoming, especially with the hot midday sun blazing down.

The next day we do one of the famous hikes. Starting early, to avoid the heat. We do the one that connects to Vernazza (which you can see in the photo above). Highly recommended, even if I did get stung by something.

One restaurant that I want to pay kudos to is Da Eraldo. Ranking highly in my overall top meals in Italy. P.S. Do all the restaurants begin with Da? Da ö Batti, Da Eraldo, I'm starting to notice a trend...

Onwards to the tuscan hills.

Tuscany 🌳

Good news, car survived. No dents. And it was only around 100 EUR to park for four days. We now had a longer drive ahead, around three hours in total. Mostly highway. The destination —Montepulciano. A town that shares its name with a type of wine from the region. I'm already excited - a town whose name is a wine. We've just spent the last 8 days with seafood and white wine, now it was time to switch it up. Meat, ham and red wine —yes, please.

I'd heard all of the hype regarding the tuscan landscape, but nothing does quite prepare you for the wow factor when you first see it. Photos just don't do it justice. I spent a good ten or twenty minutes trying to capture it on my phone and fancy camera —but I couldn't. The colours simply wouldn't translate. So I guess my advice would be: head to Tuscany whenever you get the chance. As it's about 100x better than what you see on Instagram, even with saturation set high.

We had booked a boutique hotel, set in an old villa. It was beautiful. Like something out of a movie. Lightly coloured pebbles lining the well kept grounds. A lot of greenery, and a lot of fountains. Creaky floorboards as you walk up to your room. Huge four-poster bed and equally characterful bathroom. The infinity pool (seen in the photos at the bottom) was everything we'd hoped for —and more.

Note to self: I'm soon going to run out of superlatives in this blog post!

During the daytime whilst in Tuscany we mostly explored the landscapes we'd seen so much on Instagram. The treelined roads, the vineyards, the hills. We were a far cry from the hustle and bustle of central London. We loved it. We also spent a good amount of time lounging by the pool. Portofino and Cinque Terre had been quite active, it was nice to slow the pace a little.

I also wanted an excuse to get my drone up in the air, I'd missed using it ever since I thought it died when it crash landed in our swimming pool in Thailand last year. Reluctant to fork out another £2k, I just let it dry —for a long time. And eight months later, it finally turned back on! Woohoo.

Probably our most memorable meal of the trip was in Montepulciano. Ristorante Degli Archi. The food was great, but the owner even better. This old school elderly guy (spoke no english) and seemed to just fumble around the restaurant, making sure his patrons were enjoying themselves —you could tell he loved it. Now and again he would shout at his already flustered staff, if something needed attention. Then a flurry of activity with them all running around the place. The owner obviously had a thing for showing all of the celebrities that had dinned there over the years. The walls plastered with photos of him alongside them.

It was time to say goodbye to Tuscany, and make our way south.

Day 11.

It was 5am in an old creaky, echoey, Tuscan villa. On the top floor. I'm sure the other guests loved us. My friend, Mr. 40kg luggage, making another appearance —trying to kill me on the slanted ornate granite stairs, as we pack our Fiat 500 to the gills. Time for the longest drive yet, six hours down past Rome to Positano. It's still dark, and I still don't really understand the Italian speed cameras. Let's go.

Amalfi Coast 🏖

If I thought I had a handle on the Italian way of driving all the way back in Santa Margherita, just imagine me now. Confidence was high. I'm sure people must have thought some sort of emergency was occurring as they saw a tiny Fiat 500 in the outside lane of the highway barrelling its way toward them in their rearview mirrors. Needless to say, we squeezed every bit of horsepower out of it. Making record time. We didn't want to waste our day —time was fleeting, with less than five full days remaining.

We'd been most apprehensive about the parking situation in Positano. Our Airbnb host recommended we use one of the local parking garages. But a quick google highlighted the fact the attendants must park the cars with their eyes closed, as most people complained about new dents and bashes upon collection. This is fine if you paid for the bumper car, zero excess, insurance. We hadn't. It doubled the price. Reading online: apparently finding a space on the street (at 3 EUR per hour) was the ultimate win. But they were rarer than hen's teeth. All this advice seemed to be written in non-COVID times, because we lucked out. A perfect solo spot right beside our Airbnb. One that no one else could try and squeeze behind or in front of. Result. We'd just have to keep coming out to top it up every 24 hours —getting a ticket for 50 EUR and displaying it on the front dashboard.

We were excited. We knew we had left the best to last, and initial thoughts of Positano didn't disappoint. It was beautiful. We could see the lines of umbrellas at the beach club from our balcony. And even though it was only 10am, we could already see people in the ocean swimming. We were eager to get down there.

We weren't eager for the steps. We knew they would be something. And we had mentally prepared, somewhat. But half way down, my legs started to shake for no apparent reason other than probably the weight of my body and the impact of 300 steps. Yes, I was counting.

At the bottom — 600 steps later —it took about ten minutes to feel human again. Back in London, I had pre-booked the front row at L'Incanto Beach Club —the only one in Positano. Today was going to be a beach day, with an evening meal at Villa Tre Ville.

The next day we had booked a boat for five hours. We wanted to tour the coast, dive from some cliffs, and see the Amalfi Coast from where it's best viewed —the ocean. Amongst all the billionaire's yachts. This was probably one of the highlights of the trip. We'd splashed out a bit and got a reasonably sized boat for the two of us. Francesco, the Captain, was an excellent tour guide. In the evening we ate at Le Sirenuse. Which was actually a bit of a let down —a rarity on the trip. For the best part of 300 EUR, the food and service could have been better.

Maybe we drank too much wine or had too much sun, but that evening we took the plunge and booked a bucket list hotel of ours —Belmond Hotel Caruso. So the next day had to get up early to get the ferry from Positano to Amalfi, as the roads were shut due to forest fires. Belmond did not disappoint. It was probably the best stay at a hotel I've ever had. Everything from the service, to the scenery, to the attention to detail was perfect. We also got an upgrade to one of their exclusive suites. This was basically a small house. Actually, a large house. The bathroom was over three floors —crazy. Of course, what it is probably most famous for is its incredible infinity pool, seemingly in the heavens looking down. You can see me in the photo above.

We enjoyed ourselves so much at Belmond, that we've made it a life goal to try and stay in all of their hotels around the world. And it seems our travel bug continues, as I think next week we're heading to Sicily.

And that's really it. The next day we went to Arienzo Beach Club for the whole day, and then ate at a local restaurant in the evening. Packing our bags, sad that our road trip had come to an end.

Ending note 📝

It probably goes without say that both my girlfriend and I fell in love with Italy. The holiday was once in a lifetime, and thoroughly enjoyable. Just what we needed to gain some semblance of normality through 2020. I could definitely see us living for half a year or longer in Positano at some point in our life. We just need to unbuckle from our City lives.

Some more photos 📷


Scott Taylor

Started and sold a few companies. My aim is to make sense of the world, constantly improve and become increasingly empathetic. Sharing what I learn along the way.