Road Trip: Italy from Top to Bottom

Road Trip: Italy from Top to Bottom


We began our trip by flying into Venice
and grabbing a shared water taxi (€30pp) to the city. We visited in
the height of tourist season. The weather was hot but it didn’t
matter; seeing Venice for the first time was truly magical. The
canals, the buildings, the tiny piazzas and towering churches. You
could get lost for hours wandering the narrow streets.

We stayed at Boscolo Venezia in the
Cannaregio, Venice’s 16th-century Jewish ghetto. Casual canal-side
restaurants and bars line nearby Fondamenta della Misericordia and
Fondamenta dei Ormesini which make a perfect escape from the
tourist-heavy areas. It feels good to sit among locals in the local
bars in the evenings. A favourite was La Caravella, a vine-strung courtyard which does
excellent seafood. Among the hundred tourist “musts” to tick off
your list, don’t miss the Peggy Guggenheim Collection for timeless
exhibitions tucked away down a pretty street.


Our chosen pitstop was Sfoglia Rina, a contemporary and
charming fresh pasta café where, of course, we had to have
spaghetti bolognese – and it did not disappoint. After lunch, we
wandered the city and visited the Two Towers, impressive medieval
structures dating back to the 12th century. Then it was time to get
back on the road.


If it’s your first time in Florence, book as much as possible
online in advance. Otherwise, there are uniformed hustlers offering
tours and queue jump tickets outside the major tourist sights – for
about €30 per person we got an excellent guide, and you can leave
at any point if it’s not your thing.

One of the main draws of Tuscany is the food, and we happily
spent our days in Florence sampling as much of it as we could.
Mercato Centrale is a vibrant market, great for a quick lunch.
Alternatively, All’Antico Vinaio sells hefty
sandwiches overflowing with Italian fare – there’s always a queue
of hungry Florentines but it moves quickly and is well worth it, so
grab a coffee from Ditta Artigianale just down the road and get in

If you’re after a sit-down lunch, 4LEONI
is my favourite trattoria in town, tucked away on a tiny square
with both indoor and outdoor seating, perfect for a long lazy
affair which will probably roll into dinner. For evening drinks,
head to Piazza Santo Spirito and sit on the steps in front of the
Basilica di Santo Spirito – ideal for people watching.

You can’t leave without trying some proper gelato; at Gelateria la Carraia they put chocolate mousse on top
of ice cream in a cone – enough said. Gelateria Dei Neri is also
incredible; go for the caramel, the most intensely rich

I don’t need to tell you about the obvious tourist spots, but
absolutely do not miss paying a visit to the statue of David at
Galleria dell’Accademia – having
seen so many photographs of it, to see it in real life is pretty
incredible. We also stumbled upon a fantastic leather factory
behind Santa Croce called Scuola del Cuoio. It was a real
insight to watch how Italian leather is carefully handcrafted at
this traditional family-run establishment.

For an afternoon pick me up between sightseeing, head to
Procacci, a shop with a small bar which sells
high-quality Italian produce such as olive oil and truffles – the
perfect place to pick up a souvenir.


Next, we drove to the tiny town of Pienza, famous for pecorino
cheese and picturesque walking trails.
was everything I imagined; adorable towns nestled among
rolling hills and roads lined with cypress trees.

We stayed at La Bandita Townhouse Hotel, a
modern townhouse which has the added benefit of a sister a property
about 25-minute drive away, out in the Tuscan
. We spent a leisurely day by the pool – exactly
what we needed after all the walking over the past week.

Pienza has lots of little shops and restaurants and a couple of
churches – and that’s about it. It was extremely peaceful and one
of the most beautiful places I’ve visited; if Nancy Meyers was to
create a Tuscan village, I think this might be it. Be sure to stop
by one of the delis to sample some local cheeses and meats, and go
for cocktails overlooking the city walls.

Of course, we had to do a cooking class while
in Italy, and we found a fantastic one at Le Pietre Vive di Montaperti, a
farm 10km outside of Siena. Our teacher, Valeria, taught us how to
cook traditional Italian plates using ingredients from the
surrounding land. Most importantly, we learned how to make fresh
pasta from scratch – incomparable to the stuff you get at home.


is where I found my favourite restaurant in Italy; Pierluigi. Nestled in a beautiful square with outdoor
seating and white tablecloths, they serve the freshest seafood with
an unparalleled wine list to match. After a long, lazy lunch you’ll
need an espresso to pep you up, so head to Sant’Eustachio il Caffè, a proper Roman coffee bar
where the waiters are suited and booted. If you have room, they do
particularly good pastries too. For ice cream, seek out Gelateria Come il Latte, where melted chocolate is
poured from chocolate taps (yes, really) into the bottom of y0ur


Getting into Ravello can be confusing because it’s set back in
the cliffs on the Amalfi Coast. You’ll need to liaise with your
hotel about where to meet, and typically they will take your car
and luggage before you walk into the tiny town. Like something out
of a story book, there are no cars and stray cats wander the
cobbled, leafy streets. Be sure to peak your head into the local
football pitch, which balances precariously on the side of the

We stayed at Villa Maria, a boutique hotel in
the hills of Ravello, which has a gorgeous lunchtime restaurant and
a pool just down the road. I also recommend visiting Cumpa Cosimo – and preferably
more than once. This small, family-run restaurant under the
watchful eye of Nonna doesn’t look like much, but the food is
outstanding; the five-dish pasta sampler menu is a winner. Spend an
afternoon wandering the gardens at Villa Cimbrone, where you’ll
find a hidden bar among the trees – the perfect place to debrief on
your Italian road trip over late-afternoon Aperol.

Tips for Living La Dolce Vita

– Always order the house wine (it will be local and is usually
the best)

– Bring comfortable shoes and a good data plan

– Walk everywhere

– Poke your head into every church you stumble across

– Be prepared for tollbooth charges on the main roads

– If you pick up a car in Venice and drop it in Rome, you’ll
never drive for more than three hours, even when taking more scenic

To view the full series visit and to purchase fine-art prints
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think we might have found the perfect Italian road trip,
taking you from labyrinthine Venice
down to the cliffs of Ravello. Our truffle hunters have sought out
the insider
– all you need is a Sat Nav and an appetite.

The beautiful small town of Orta San Giulio in Piedmont, Italy

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