Italy: Tuscany & Cinque Terre Hiking & Biking Adventure

October 4 - 10, 2020

“You may have the universe if I may have Italy.” 

 Giuseppe Verdi

From the lush, rolling hills of Tuscany to the breathtakingly blue waters of the Cinque Terre coastline; from the mouthwatering cuisine to the exquisite wines; from the incredible architecture to the stunning natural scenery; it’s easy to see why Italy is one of the world’s top destinations.

We visit the beautiful regions of Tuscany and Cinque Terre in the fashion of the locals – by bike in Tuscany and on foot in Cinque Terre, allowing us to experience both areas via “human-powered” transportation, by far the best way to immerse ourselves in the Italian culture.  Tuscany’s lovely wheat-covered rolling hills are beautiful to behold and even better to bicycle, as we make our way from one of our favorite cities (Florence) all the way to the Ligurian coast. What a wonderful backdrop for cycling this astonishing countryside, from one medieval town to another, and with many opportunities to talk to the locals and sample the flavors of the area (particularly the gelatos and vinos!).

Cinque Terre means “the five lands” – it is not just one destination, but five small fishing and wine-making villages dramatically perched along a stretch of the Italian Riviera. They are mostly pedestrian-only, which is a big part of their charm and allure, and hiking paths link the five villages. Dating back to the 11th century, the inhabitants of Cinque Terre have carefully built out terraces and buildings on the steep, rugged landscape right to the edge of the cliffs that overlook the sea. They’re spectacular! The rocky coves, dramatic cliffs, terraced vineyards and olive groves that climb straight out of the sea are a sight to behold as we hike between the wonderful villages of Monterosso, Vernazza, Corniglia, Manarola, and Riomaggiore.

Trip Favorite Moments & Reviews

“Fantastico! Loved the first 3 days of hiking to not only enjoy the landscape but also to enjoy getting to know everyone on the trip! Perfect amount of km’s offered per day/activity. The food, wine & special events were outstanding… Hotel choices great — loved how each one was completely different. Guides couldn’t have been more attentive and helpful!”

Sue M.

“Excellent, I was a little worried about a group tour but the leaders were wonderful and the organized events interesting, not to mention the great backdrop of Italy.”

Nina S.


  • Dates: October 4 - 10, 2020
  • Cost Per Person: $3,900
  • Single Supplement: $600
  • Activities: Hiking & Biking
  • Difficulty: Moderate
  • Guides: Giovanni Ramaccioni

Other Info: Bicycle Rental €100 (e-bikes available for an additional charge of €100).

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Trip Highlights

  • Beautiful landscapes of rolling hills, sea views, quaint villages, and waving wheat fields
  • Incredible cuisine: pastas, pizza, and bruschetta...Pecorino cheese...olive oil like you have never tasted before...all capped with a little gelato or limoncello!
  • The picturesque “jewel box” hilltop towns of Cinque Terre embedded with history throughout their winding streets and inviting shops
  • Seeing this amazing country the way the locals do – by foot and by bike!
Day 1

We begin our adventure in the legendary city of Florence, considered by some to be the “cradle of the Renaissance” due to its stunning museums, palaces, and churches that house some of the greatest artistic treasures in the world. Our guides meet you in the morning and whisk you away to meet our bikes, have our safety talk and start pedaling to the historic and captivating town of Lucca. Here we’ll find almost perfectly preserved medieval architecture and monuments, including the stunning city walls and elegant town center. This ride is mostly flat with one long climb (long route only). We’ll pass through the vineyard hills of Carmignano, descending to Vinci (hometown of the most famous Leonardo), and on to the gentle hills of Cerreto Guidi and the wetlands of the Padule di Fucecchio, finally reaching the iconic Tuscan scenery of the charming boroughs. Biking Distance Options: 40 KM, 65 KM, 94 KM

Day 2

Today, we ride from Lucca to the renowned town of Pisa. We’ll stop to explore the Piazza dei Miracoli and snap a photo or two of our crew "holding up" the iconic leaning tower. From here, you’ll have the choice to ride or shuttle back to Lucca. Riders will bike back to Lucca on a pleasant and easy route through the forested coastal areas of San Rossore reserve. Once everyone has returned from our day’s journey, we’ll meet up back at the hotel before heading out for an aperitif and lovely outdoor Puccini concert.  Tonight's dinner is on your own and we'll give you recommendations on where you might want to go. Biking Distance Options: 35 KM, 60 KM

Day 3

We’ll say farewell to Lucca and pedal to the next fantastic town: Viareggio. Today’s route will be hilly but we promise it is worth the views! We will be riding along the hills that separate the coast and the Garfagnana mountain district. We’ll take in the beautiful countryside vistas of olive groves and fields as far as the eye can see until we reach the majestic forests of San Rossore and Migliarino. During the ride, we will pass through the village of Pietrasanta; attended often by artists and sculptors of the famous Carrara marble. Our destination is situated between Massacciuccoli Lake and the elegant Tuscan coast.  Viareggio was the home of opera composer Giacomo Puccini and where the famous Summer Opera Festival is held. After checking into our hotel, we’ll gather in the lobby to walk to another delectable Italian meal. Biking Distance Options: 35 KM, 60 KM

Day 4

Today’s ride will be the last biking day of the tour.  We make our way out of Tuscany and head toward the coast. The first half of our route will be a relaxing, flat ride along a coastal road and through several charming waterfront towns. The second half gradually gets hillier as we leave Tuscany for Liguria and enter gorgeous Bocca di Magra, well-known as a place where writers and intellectuals meet. From there the road climbs the steep terrain typical of the Liguria region, giving way to stunning views of the rocky coast, providing a preview of our next destination, Cinque Terre. Biking Distance Options: 34 KM, 50 KM

Day 5

This morning we’ll ditch our biking gear for a sturdy pair of walking shoes as we set out to explore. We’ll board a boat to Portovenere and thus begin the Cinque Terre portion of our tour. Along our path from Portovenere, we’re treated with incredible vistas overlooking the coast and the Palmaria and Tino islands. As we climb up to reach the ridge, we’ll enter the classic Mediterranean woods that cover the mountaintops, including an area of cork oak wood when we reach the ridges of Monti dei Fraschi and Telegrafo. From there, we’ll start our descent into the most eastern village of Cinque Terre, Riomaggiore. Once at the bottom, we’ll take a short train ride to our hotel for the next two nights in Levanto. Hiking Distance Options: Up to 14 KM

Day 6

Today we will take a “walk in the elements” as we mix the blue of the Ligurian sea with the green of the Mediterranean bush. We visit the incredible overlook point of the Mesco Promontory and views of the Corsica island and Riviera. Our walk will also pass through the famous villages of Monterosso, Vernazza, and Corniglia, where there will be plenty of opportunities to sample the focaccia, the garbanzo bean pizza (farinata), and the local pesto. Once we’ve had our fill of the local delights, we’ll hop on a train back to Levanto for the night. Hiking Distance Options: 7 – 15 KM

Day 7

On our final day, we meet after breakfast to walk west to another village of Cinque Terre, Bonassola, along the La Francesca footpath. This path follows the layout of the ancient railway line from 1874, along the rocky coast. It has since been stabilized with wooden steps and fencing to make our final jaunt less precarious. Before departing Bonassola, make sure to stop in a local café to try their famous focaccia! Once back in Levanto, we’ll say our goodbyes and shuttle to the train station so you can start your journey home or, if you’re extending your stay, head to your next destination. Hiking Distance Options: flexible

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Trip Accommodations


This old-world comfortable hotel is located in the heart of the picturesque old city within easy walking distance of shops, restaurants, and beautiful historic monuments.


The Sina Astor is just a two-minute walk to the beach and is at the centre of Viareggio's seafront promenade. It also has a wonderful sea-view rooftop terrace, as well as an indoor pool and hot tub.


With stunning views of the bay, this tranquil hotel is the ideal place to rest after a long day of exploring.


A lovely and small family run hotel located only a few minutes away from the harbor, shopping, restaurants and train station.  A perfect base for our last two nights!

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Arrival & Departure

We meet you in Florence in the lobby of a designated centrally located hotel the first morning of the trip. On the last day of the tour, we transport you to the Levanto train station, where you can easily return to Florence or continue on to Rome. We highly recommend arriving at least a day early and also extending your vacation in Italy if possible! We will provide more specific travel information upon your booking.

What's Included
  • Two Zephyr guides accompany each trip, with a third added as necessary.
  • Double occupancy lodging is included. If you are traveling solo, we will match you with another traveler of the same gender. However, you may pay a single supplement to have your own room.
  • All of your dinners (except one night in Lucca where we substitute a Puccini concert) and breakfasts are included. Gratuity for these meals is also included. In general, we leave lunches open so that you have time to explore and enjoy the local flavors en route.
  • All your transportation is included once you meet your guides on the first day.
  • All group activities are included.
  • NOT INCLUDED Beverages, desserts, lunches, gratuities to your guides, personal expenses and travel to and from the destination.

We like the shoulder seasons in Italy because they tend to have the best weather and fewer crowds. We typically plan our tours there in the spring and the fall when the temperatures are quite comfortable and usually stay in the low 70s. Evenings are nice, with low temperatures at an average of 55 degrees.

Extending Your Vacation

Wow. Italy has so many things to do it is hard to choose. If you are interested in ancient monuments, visit Rome for sure.  If you are interested in art, arrive early or stay after the tour in Florence and see Michelangelo’s David sculpture (and much more!).  If you want to do a little more hiking, head north to the Dolomites.

Route Directions

It’s all about the adventure! (It’s even in our name) We wouldn’t want to disappoint by providing a guide with you the entire way, holding your hand. We will provide detailed route directions before each day’s ride as well as GPS units to show you the way. Our guides will be available in case anything comes up but you won’t need to worry about staying with the pack or keeping up with faster riders.

Ability Level

This trip is rated as Moderate which means we’ll be on slightly harder routes, including going up and down a good number of hills. Though not every route will be tough, you will need to have a base level of fitness and have the basic skills of riding a bike.  If you are concerned about hills, e-bikes are a great option to assist!

Pedals & Seats

We have available for rent excellent 27-speed bikes that are designed to handle the mix of pavement and short sections on gravel roads we use on this tour. You can bring your own pedals, shoes, and bike seat if you wish to “personalize” your bike with what you are used to at home. Additionally, we offer e-bikes for an additional charge.

Type of Person Who Would Enjoy This Trip

Cyclists! Food lovers! Wine lovers! Actually, we can recommend this trip for almost everyone. If you are a serious cyclist, we have plenty of distance for you. If you prefer hanging out in towns and sampling the wines, we have more than enough of that to satisfy as well.

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