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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

Five days on the Italian Riviera built around the Cinque Terre, from Milan to Pisa. Scenic trains and coastal paths link Monterosso, Vernazza, Corniglia, Manarola and Riomaggiore, with the Sentiero Azzurro on foot, a swim if it is warm and boat-hopping if the seas are calm. Nights in Milan, La Spezia and Pisa, plus pastel villages, focaccia, pesto, gelato, piazzette and the Leaning Tower.

A map of a travel route in Italy, showing a path that starts in Milan and ends 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

We arrive in Milan and take an easy stroll through the centre before the group officially meets.

  • We get to know each other by the Navigli canals in the golden hour, bags dropped, legs stretched, aperitivo in hand.

  • Then a first dinner together, kept simple, and the trip is under way.

 

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

One more morning in the city, then we swap Milan for the Ligurian coast by train.

  • We make the most of Milan: Duomo and Galleria in the morning, Brera or Sempione after lunch, a last espresso before the station.

  • Late afternoon the train reaches La Spezia: check in, walk the waterfront or Via del Prione, dinner of pesto trofie or seafood, then an early night before the Cinque Terre.

 

 

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 Blue Trail: today we walk.

  • We hike the Sentiero Azzurro from Monterosso to Vernazza first, about 3.5 km and 1.5 to 2 hours of trail and sea views, with coffee and photos on arrival.

  • Then on to Corniglia, another 1.5 to 2 hours through terraces and sea panoramas, and if energy remains a look at the cove by Corniglia station before showers, gelato and 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!

The train runs down-coast to the southern trio, and by evening Liguria becomes Tuscany.

  • Manarola comes first, for vineyard viewpoints and the small port, then Riomaggiore, reached along Via dell'Amore if the trail allows, otherwise by a short train or the steeper Beccara trail.

  • In the afternoon we catch the train to Pisa, wander the city and reach Piazza dei Miracoli for the classic Leaning Tower shots, then the 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!

The final morning is unhurried, with nothing to catch before check-out and transfers.

  • One last espresso, a gentle stroll along Pisa's riverside, maybe a final look at the Leaning Tower.

  • We swap photos and contacts, trade favourite moments, and say arrivederci until the next WeRoad trip.

 

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