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This is a Backpack trip: backpack on your shoulders, adaptable spirit, and a desire for discovery! You might have to give up a few comforts, but you’ll enjoy authentic experiences.

Is this trip for me?

Party and nightlife
Relax
Nature and adventure
City and cultures
Monuments and history
Physical effort
Trip type
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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!

A map of Italy showing a travel route starting in Florence and ending in Naples.
An illuminated stone bridge crosses a river in a dense cityscape at dusk, its lights reflecting on the water.

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.

The large, red-tiled dome of a cathedral overlooks a cityscape of red-roofed buildings and distant mountains.

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.

A crowded pebble beach viewed from above, filled with people relaxing under orange umbrellas next to turquoise water.

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.

A village of colorful houses built into a rocky cliffside overlooking a turquoise sea under a blue sky with white clouds.

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.

A woman with curly hair and a denim jacket stands on a cobblestone street, looking up at a large, ancient stone amphitheater under a clear sky.

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.

A large, ornate fountain in a cobblestone square, with tourists gathered around and a souvenir stand in the foreground.

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.

Two Neapolitan pizzas topped with fresh mozzarella and basil resting on a restaurant table with glasses of water.

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.

A high-angle view of a coastal village on a cliffside overlooking the sea, with vibrant pink flowers in the foreground.

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.

A white scooter is parked on a cobblestone street in front of an outdoor restaurant stand with two large wooden barrels.

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

What's not included

Roundtrip flight to/from destination
  • 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

Learn more about accommodation, transport, and other useful travel information.
  • 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

Our Group Leaders are chosen because they’re people just like you: passionate travelers who share the experience authentically, while having the skills to take care of the organisation, and help you get the most out of every moment of the trip.

Find your flight

For this trip, we recommend arriving and departing from these airports.

ArrivalFirenze (FLR)
ReturnNápoli (NAP)
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WeRoadX

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.

FAQs – Frequently Asked Questions

About this trip

About WeRoad

About Italy

From$ 1,599
-7%
$ 1,484
Book with $ 0
Free trip change
Interest-free installments