Itinerary
Italy is a dream, and this trip keeps it real! Fast trains, explorer days, and nine backpacker-style moments stitched from Renaissance rooftops to cliffside trails, Roman ruins to street pizza in Naples. This is a flexible and affordable ride down the spine of Italy, starting in Florence, cutting west to the Cinque Terre, and then dropping south through Rome, Naples, and the Amalfi Coast.
We move with curiosity, riding local trains, walking coastal paths, and choosing spritz spots based on sun position. We'll also have space to pause, swim, nap, journal, or just watch the sky shift color above a piazza. We’ll hike the iconic Sentiero Azzurro, toast in a boat at sunset, and cross off Rome's heavyweights before heading south to Pompeii and a ridge hike to Positano.
This is Italy in motion, on rails, on foot, and on our own terms. A backpack, a flexible mindset, and a willingness to share limoncello with strangers? That’s all you need!


Welcome to Italy!
1 night: Florence
Florence, let's begin
We'll meet in Florence in the afternoon: drop the bags and meet the rest of the WeRoad crew for sunset. We’ll gather for a casual welcome meeting, learn each other’s names, and toast with our first aperitivo in a lively piazza. Maybe we’ll head to a cozy trattoria, or keep it street-style with pizza slices and beers by the river. No pressure to go big, just time to settle in, share travel stories, and get into the rhythm of Italy.

Florence Classics & Renaissance
1 night: Florence
Exploring the capital of Tuscany
Today, Florence will be our playground. We'll wake up with the scent of espresso and fresh cornetti in the air. For art, we'll head to the Uffizi and go face-to-face with Michelangelo’s David. For views, we'll climb the Duomo and hike up to Piazzale Michelangelo with a picnic; and if we energy remains, get lost among the artisan shops in Santo Spirito, hidden gardens, local markets. The vibe will be ours to choose, but for sure we'll enjoy a lazy aperitivo of wine in hand and shoes dusty from stone streets.

Arriving to Cinque Terre
1 night: La Spezia
Riomaggiore and Manarola
We'll hop on a morning train to the Ligurian coast and arrive in the Cinque Terre before the crowds. First stop: Manarola, where colorful buildings tumble into the sea. We'll walk up to the vineyard terraces, take a photo (or ten), and slow down over a seaside lunch. Later, we'll ride to Riomaggiore for golden-hour exploration and a laid-back spritz at sunset, maybe from a local boat bobbing off the shore, if the sea's calm and the mood is right.

Sentiero Azzurro through Monterosso, Vernazza & Corniglia
1 night: La Spezia
Conquering Cinque Terre Trails
Time to hike the trail that made Cinque Terre famous. We'll kick off in Monterosso and follow the Sentiero Azzurro through craggy cliffs and coastal terraces. First stop: Vernazza, for photos, coffee, and maybe a dip. Then we'll hit the path to Corniglia, perched high above the water with a peaceful vibe. Views will be pure magic: vineyards, waves, lemon trees, and tiny villages in the distance. Whether we're hiking the way or tagging out early for a scenic train ride, it’s our day to connect with nature and earn that pasta dinner.

Rome Arrival & Hidden Corners
1 night: Rome
Arriving to the Capital
We'll roll out early and ride south to Rome, the Eternal City. Bags down, sneakers on, and into the streets. We’ll toss a coin in the Trevi Fountain, and sit in awe under the Pantheon dome. We'll head to the Jewish Ghetto for history and the best fried artichokes in town, and climb Aventine Hill for skyline views and a hidden keyhole perspective of the Vatican. Rome can be wild and overwhelming, but also peaceful and poetic.

Ancient Rome
1 night: Rome
Rome wasn't built in a day
We'll decide how to spend the day: ancient Rome, papal power, or both! If gladiators are calling, tour the Colosseum, walk through the Forum, and stand on the ruins of empire. If you’re chasing art and awe, hit the Vatican Museums, marvel at the Sistine Chapel, and enter St. Peter’s Basilica. No fixed times, just good advice and flexible options. In the evening, most likely we'll grab pizza or carbonara in Trastevere, relax by the Tiber River, or sip espresso at a bar older than your hometown.

Naples & Pompeii
1 night: Naples
Southbound to Naples + Pompeii Ruins
This morning, we board'll a fast train to Naples, a city with more energy than espresso. After dropping bags, explore the chaotic beauty: Spaccanapoli street slices the city in two, while murals, markets, and scooters race past. In the afternoon, we jump a local train to Pompeii and walk among the frozen ruins of a Roman city. It’s powerful and eerie, in the best way. Back in Naples, it’s all about pizza: the real deal, where it was born. Eat it hot, folded, and unapologetically messy.

Amalfi Coast & Positano
1 night: Naples
Path of the Gods
Another full day that will begin early but, this time, into the mountains above the Amalfi Coast. From Agerola, we'll hike the legendary Path of the Gods, a ridge trail with jaw-dropping views over cliffs, sea, and tiny whitewashed towns. We'll descend into Positano, where steep staircases lead to beach cafés and pastel houses. Swim if you like, snack if you must. If energy remains, we'll catch a ferry to Sorrento, the perfect place to linger with a lemon granita or check out artisan shops. One last journey back to Naples for a farewell dinner. We’ll be tired, but glowing.

Farewells
See you soon!
We pack, hug, and say our goodbyes. Some head home, some keep going. But the group chat is alive, your shoes are scuffed, your phone is full, and your appetite for the world is wide open. Italy’s behind us—but the journey’s still rolling.
What's included
All accommodations in shared rooms
Entrance tickets to Colosseum, Roman Forum, and Palatine Hill
Entrance tickets to Roman Baths of Caracalla
Train ticket to Cinque Terre
Train ticket to Rome
Medical and baggage insurance - (coverage limits by destination country/region - €10,000 Italy, €20,000 Europe, €30,000 World, €50,000 USA/Canada)
What's not included
- Food and beverages when not specified
Cinque Terre Trekking Card - approx. USD 8
Pompeii Tickets - approx. USD 26
Train Tickets to Pompeii - approx. USD 19
Transfer to Agerola - approx. USD 19
Ferry Positano - Sorrento + Sorrento - Naples + train - approx. USD 35
Public transport (bus, metro, taxis, trains, Uber)
- All the extras you'll be able to fit in your backpack
- Anything not mentioned in the "What's included" section
Optional activities
Please see below extra optional activities that you can experience during your trip. Your Group Leader will be happy to assist with organizing these activities for the group. Availability may vary depending on location and group preferences.
Please note these activities are provided by third party suppliers and liability rests exclusively with these third party suppliers.
Duomo Complex - Brunelleschi Pass - approx. USD 36
Uffizi Gallery - approx. USD35
Guided Tour in Rome - approx. USD 16
Pompeii Private Tour - approx. USD 26
Additional info
All accommodations in shared rooms (private rooms available upon request)
- Info on private roomsShow all details
Why WeRoad
Small groups, on average 11 people
Move or change your trip for free up to 31 days before departure
Book with $ 0. Pay the $ 100 deposit only once the trip is confirmed
The Group Leaders
Find your flight
For this trip, we recommend arriving and departing from these airports.
This is a WeRoadX
A trip designed and created entirely by an experienced WeRoad Travel Group Leader.
This is a trip designed and created entirely by an experienced WeRoad Travel Group Leader. They organise the whole trip: from defining the itinerary to selecting accommodation and on-site experiences. On the WeRoad website you can book the trip and manage it in MyWeRoad, just like any other WeRoad.



























