From rowing a boat through Venice’s quiet canals to sipping wine high above the cliffs of Vernazza, our 17-day Italy adventure was a whirlwind of breathtaking views, unforgettable flavors, and rich history. We hiked the cliffside trails of Cinque Terre, refueling with pesto pizza in the region where it was born, and wandered through Pisa, climbing the Leaning Tower. In Florence, we immersed ourselves in Renaissance brilliance—admiring Michelangelo’s David, exploring hidden passages in the Palazzo Vecchio, and ending our days with sunset gelato at Piazzale Michelangelo.We slowed down in Tuscany, tasting our way through Chianti and Val d’Orcia, where vineyard-covered hills and cypress-lined roads made every drive feel like a dream. Our agriturismo stays were the heart of this leg—from the cozy, cat-filled Castellinuzza in Chianti to the medieval Castello di Spedaletto near Pienza. We explored Montalcino, Pienza, Montepulciano, Monticchiello, and Siena, sampling local wines (including Brunello), pecorino cheese, and plenty of pici pasta along the way. Before heading south, we made a quick stop in Orvieto, a stunning hill town perched on volcanic rock, where we enjoyed wine with views of the striped Gothic Duomo. Then it was on to Naples, where the chaotic energy of the city was no match for the pure pleasure of a pizza from the legendary L’Antica Pizzeria da Michele. The trip ended with a bang on the Amalfi Coast, where we ferried to Capri, (survived a scooter mishap), and soaked in the coastal views of Positano and Ravello, followed by a final few days in Rome. There, we walked in the footsteps of emperors at the Colosseum, took in the grandeur of St. Peter’s Basilica, and tossed a coin into the Trevi Fountain, hoping to return someday. Seventeen days, countless scoops of gelato, and one unforgettable journey through the heart of Italy.

17 Day Italy Adventure

Our 2016 Italy trip was filled with many memories! Check out each regional blog for detailed itineraries, travel tips, and highlights from every stop.

• 🛶 Venice – 2 days (Aug 27–29, morning train out on 29th)
• 🥾 Cinque Terre (Monterosso) – 1.5 days (Aug 29–31 morning)
• 🏛️ Pisa – Half day (Aug 31 morning)
• 🎨 Florence – 2.5 days (Aug 31 afternoon – Sept 2 morning)
• 🍷 Tuscany – 3 days (Sept 2 – 4)
  • Greve in Chianti – 1 day (Sept 2)
  • Monteriggioni, Siena & Montalcino – 1 day (Sept 3)
  • Pienza, Monticchiello & Montepulciano – 1 day (Sept 4)
• 🍷 Orvieto – Half day (Sept 5 morning)
• 🍕 Naples – Half day (Sept 5 dinner)
• 🌊 Capri – 1.5 days (Sept 5 night – Sept 7 morning)
• ☀️ Amalfi Coast (Positano) – 2 days (Sept 7–9 morning)
• 🏛️ Rome – 3 days (Sept 9 night – Sept 12)

Pictures

See our Italy 50 Favorite Photos.

Italy Tips and Tricks

🧳 Packing & Prep

• Pack light—but pack smart – Italy has lots of cobblestone streets, stairs, and steep hills (looking at you, Positano and Corniglia!). A carry-on-size suitcase or backpack is ideal.
• Bring versatile, comfortable shoes – You’ll walk more than you think—from museum halls to vineyard trails and cliffside villages.
• Bring modest dress for churches – Shoulders and knees covered for places like St. Peter’s Basilica and the Duomo in Pisa.
• Carry cash – Some places (especially small towns, churches, or tasting rooms) are cash-only or charge for card use.
• Check for strikes – Planned train strikes are a real thing in Italy (RIP, Pompeii plan). Check ahead and have a backup.

🚆 Trains & Transportation

• Trains are fast and efficient – Use them between major cities (e.g. Florence to Rome), but reserve in advance for peace of mind and better prices.
• Validate regional train tickets – If it’s not a pre-assigned seat ticket (like Trenitalia’s regional routes), you’ll need to validate it at a little green or yellow machine before boarding.
• Skip scooters unless you’re super confident – Especially in places like Capri. Curvy roads + no guardrails + questionable hospital care = regrets (and a fractured fibula).

🏛️ Tours & Sightseeing

• Pre-book big attractions – The Vatican, Colosseum, Uffizi, Accademia, and Leaning Tower of Pisa all benefit from advance reservations to skip the long lines.
• Use Rick Steves’ audio guides – Free, surprisingly fun, and perfect for DIY touring in places like the Rome, Florence, and Venice.
• Look for the secrets – From the Inferno tour in Florence to underground cellars in Montepulciano, some of Italy’s best stories are hidden in plain sight.
• Expect stairs – Elevators aren’t always a thing. Pack accordingly (and stretch those quads).

🍕 Food & Drink

• Try the regional specialties – From pesto in Cinque Terre to pici in Siena, and pizza in Naples, each region has its own iconic flavors. Order accordingly!
• Drink your coffee at the bar for better prices – Especially in places like Caffè Florian in Venice. If you sit at a table, you’ll be charged extra. Besides, you’ll gulp down that espresso shot in no time!
• Slow down and savor – Italians linger over meals, and you should too. A good dinner can last hours—and be unforgettable.

🏨 Staying & Sleeping

• Don’t skip the agriturismos – Our stays in Castellinuzza (Chianti), Castello di Spedaletto (Pienza), and Buranco (Monterosso) were some of the most peaceful and memorable places we’ve ever stayed. Local wine + homegrown food + stunning views = heaven.
• City center stays save time – In big cities like Florence, Rome, and Venice, staying close to the historic core makes early tours and late-night walks easier.

🌋 Pompeii Itinerary

• 🛥️ 9:15 AM – 9:55 AM: Ferry to Sorrento
• 🚆 10:37 AM – 11:07 AM: Circumvesuviana to Pompeii (💡Be sure to check for any planned train strikes and plan around them.)
• 🏛️ 11:00 AM – 2:00 PM: Tour Pompeii (🎟️ Buy at station)
• We originally planned to tour Pompeii but there was a train strike and had to cancel because we couldn’t get transportation there.

Pompeii No Way: That Time a Train Strike Ruined Our Ruins

Pompeii was supposed to be a highlight—ancient ruins, eerie ash-covered streets, dramatic volcano views… We had it all planned to stroll through 2,000 years of perfectly preserved tragedy, and be back in time for pizza in Naples. What could go wrong?

Cue the Italian train strike (sciopero ferroviario). Apparently, the only thing more predictable than Vesuvius erupting in 79 AD is a last-minute transport protest. The Circumvesuviana wasn’t running, private transfers were booked solid, and unless we wanted to walk to Pompeii in 90-degree heat with luggage in tow… it wasn’t happening.

💡 Travel Tip: Always—always—check for scheduled train strikes in Italy. They’re like surprise plot twists in your itinerary, except no one claps at the end. If Pompeii is high on your list, consider building in a little flexibility or booking a guided tour that handles transport.

We didn’t make it to the ruins, but we did make it to lunch—because even when plans fall apart in Italy, there’s always pizza and gelato to emotionally recover. Pompeii, we’ll get you next time. Probably.