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Itinerary

A few days on the Ligurian coast are all we need: pastel villages stacked over turquoise coves, vineyard trails above the sea, and easy evenings on sun-splashed piazzette. We’ll start in Milan for a quick hit of city energy, then base ourselves in Monterosso: swim if it’s warm, stroll if it’s not, and refuel on focaccia the size of your face. From there we hop between the Cinque Terre by scenic trains and coastal paths: Vernazza’s postcard harbor, Corniglia’s terraces, Manarola’s vineyard viewpoints, and Riomaggiore’s cliffside lanes. We wrap in Pisa, under the Leaning Tower, with a final round of photos and plates of pasta that actually earn the carbs.

There’s a special kind of magic on the Italian Riviera: the scent of lemons, the flash of fishing boats, the clink of glasses at sunset. This express route keeps logistics light and leaves room for what matters: good walks, cold dips, strong coffee, cold gelato and a couple of late-night spritzes. Hike the iconic Sentiero Azzurro, boat-hop if the seas are calm, and lean into the vibe whether you’re chasing steps, views, or your next espresso. Expect simple connections, big scenery, and zero travel faff. By the time we roll into Pisa, you’ll have a camera roll full of colors, a pocket full of sand, and a crew you actually want to keep.

A map of Italy showing a travel route with a starting point in Milan and an ending point in Pisa.
A small boat floats on a city canal as people walk across a bridge adorned with string lights against a sunset sky.

Check-in: our adventure starts in Milan

Arrive and take an easy stroll through the center before officially meeting the group. We'll enjoy getting to know each other by the Navigli canals during the golden hour, and follow to our first dinner together. We will keep it simple: drop the bags, stretch our legs, share a aperitivo and... kick things off!

A high-angle view of a crowded beach filled with orange umbrellas, with people swimming in the turquoise sea next to a coastal town.

From Milan to La Spezia

We'll make the most of Milan: Duomo and Galleria in the morning, Brera or Sempione after lunch, and a last espresso before rolling our bags to the station. In the late afternoon/early evening, we'll take the train to La Spezia. Check in, stretch your legs with a stroll to the waterfront or Via del Prione, and grab dinner, think pesto trofie or seafood, then early night ahead of the Cinque Terre push!

A view through a stone archway of a colorful hillside village with a church and terraced vineyards in the background.

A hike through Cinque Terre

Boots on for the most iconic sections of the Sentiero Azzurro (Blue Trail). Hike from Monterosso to Vernazza first (~3.5 km/ 1.5-2 hours) for beautiful trails and views. Coffee/photos in Vernazza, then continue to Corniglia (~1.5-2 hours) through terraces and sea panoramas). If energy remains, we'll drop to Corniglia station first for a quick look at the cove before heading back for showers, gelato, and a relaxed dinner.

A high-angle view of a crowded pebble beach lined with rows of orange umbrellas, with people swimming in the turquoise sea.

Bye Cinque Terre, Ciao Tuscany!

Ride the train down-coast and focus on the southern trio. Explore Manarola first, for vineyard viewpoints and the small port, then continue to Riomaggiore. If Via dell’Amore trail allows, stroll its cliff but easy path; if not, take a short train or the steeper Beccara trail. In the afternoon, catch the train heading to Tuscany, we're going to Pisa. We'll wonder around the city and explore Piazza dei Miracoli for the classic Leaning Tower shots, before having our very well deserved farewell dinner.

The Leaning Tower of Pisa stands on a green lawn next to a large cathedral under a bright blue sky, with people strolling nearby.

See you soon!

Our final morning is unhurried: perhaps one last espresso, a gentle stroll by Pisa’s riverside, or a final look at the Leaning Tower before we go. We will swap photos and contacts, trade favorite moments, and promise to meet again. Check-out, transfers, and heartfelt arrivederci from Tuscany until the next WeRoad adventure!

What's included

What's not included

Roundtrip flight to/from destination
  • Food and beverages when not specified
  • 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.


  • Cinque Terre Sunset Cruise - approx. USD76

  • Campo dei Miracoli (Piazza dei Miracoli) - approx. USD22

  • Via dell'Amore trail - approx. USD12

  • Duomo di Milano (Cathedral + Roof Terrace) - approx USD31

Additional info

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

ArrivalMilan (MIL)
ReturnPisa (PSA)
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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
$ 810
Book with $ 0
Free trip change
Interest-free installments