Italy,
the Classic Route

The shape of your weeks

Fourteen days, and how they fall

Every confirmation number, train ticket, and tour voucher is safely stored in your itinerary document in the TravelJoy app. I am keeping a close eye on all of it.

1. Sep 19Sat

   Arriving in Rome

   Your driver will meet you right outside baggage claim holding a sign with your name. They will take you directly to your hotel so you can drop your bags and shake off the jet lag.

2. Sep 23Wed

   Rome to Florence

   Your first train day! I booked this mid-morning to avoid the heaviest commuter rushes. Once in Florence, you’ll be diving into the Renaissance, including your combo tour of the Accademia and Uffizi galleries.

3. Sep 26Sat

   Florence to the Cinque Terre

   You’ll take the train from Florence to Vernazza. It’s a bit of a travel day, but you are staying right near the station in Vernazza, making arrival a breeze.

4. Sep 29Tue

   Levanto to Venice

   This is your longest train journey, requiring a couple of stops, but the payoff is worth it. When you walk out of the Santa Lucia station in Venice, your private water taxi will be waiting to sweep you directly to your hotel—the most spectacular way to arrive after a long travel day.

5. Oct 2Fri

   Home

   This last leg I am leaving in the concierge’s capable hands, since that is what you would rather do — just ask the desk the night before to arrange your car or water taxi to the airport. If you change your mind and would rather I book it directly, say the word and I will take it off your plate instead.

Practical things

A few things to know

Currency

The euro. Cards work almost everywhere, especially for meals and shopping. Carry about 50 to 100 euros in smaller bills for quick coffees, gelatos, small tips, and public restrooms.

Language

Italian. English is widely spoken in all the areas you are visiting. Two phrases to know: buongiorno for good morning or day, grazie for thank you.

Weather

Late September into early October is Italy’s sweet spot. Highs in the mid-70s, cooler evenings. Perfect sightseeing weather.

Trains

Italian train platforms, binari, are usually only announced 10 to 15 minutes before departure. Find the big digital board, look for your train number (not just the destination, as yours might be terminating further down the line), and head to the platform when the number pops up. Your seats are reserved, so there is no need to rush.

Tipping

Not strictly required in Italy like it is in the US. If you sit down for a meal, a service charge (coperto) is often included. If service is exceptional, leaving a few extra euros on the table is appreciated.

Power

230V. Bring a Type C, F, or L adapter, the ones with two or three round pins.

Water

Free, cold, safe drinking water flows from public fountains, nasoni, all over Rome and Florence. Bring a refillable bottle.

What to pack

The suitcase

Documents

Entry requirements

A quick two-minute read, then you’re done.

Questions people ask

Before you Google it

Is it safe?

Yes. Violent crime is incredibly rare. The only thing you need to practice is standard city awareness regarding pickpockets in crowded areas like train stations, around the Colosseum, or on the Vaporetto (water bus) in Venice. Keep your bags zipped and cross-body.

Will the train stations be chaotic?

They are busy, but they are highly organized. Because I’ve booked reserved seats on the fast trains, you are guaranteed a spot. You just wait for the platform to be called, board, and find your carriage.

What if I get lost in Venice?

You will, and that is the best part. Venice is an island; you can only wander so far before you hit the water. Use Google Maps, but don’t be afraid to just follow the yellow signs pointing to “San Marco” or “Rialto” when you want to find your way back to the main areas.

Before you go

Watch, listen, read

Dinner party material

Six things about your cities

1. i

   Around €3,000 is thrown into Rome’s Trevi Fountain every single day. The city collects it nightly and donates it to a charity that runs a supermarket for Rome’s needy.

2. ii

   Gelato isn’t just Italian; it’s Florentine. It was invented in Florence during the Renaissance by an architect named Bernardo Buontalenti to impress guests at a Medici banquet.

3. iii

   The Cinque Terre villages are so steep that local winemakers use tiny, rollercoaster-like monorails, called trenini, to carry baskets of grapes down the cliffs during harvest.

4. iv

   Venice isn’t a single landmass. You will actually be walking across 118 separate small islands, stitched together by more than 400 bridges.

5. v

   By a 16th-century Venetian law still in effect today, all authentic passenger gondolas must be painted black. It was originally passed to stop wealthy nobles from competing with overly flashy, bedazzled boats.

6. vi

   The dome of the Florence Cathedral, Il Duomo, remains the largest masonry dome in the world. It was built over 500 years ago without modern technology, cranes, or even scaffolding.