Distinct Trails of Italy Tour: An Active Exploration of Cinque Terre & Tuscany

Vernazza town on Cinque Terre, Italy

What to expect on this itinerary

The landscape and history of Italy hint of adventure hidden in the hills of Tuscany and along the trails of Cinque Terre. Your custom tailored tour will introduce you to the everyday beauty of La Dolce Vita on the paths that crisscross the countryside. Uncover seductive wines in secluded vineyards and wander through shaded olive groves to reach pristine views of the Ligurian coast. Explore preserved medieval villages and climb to the top of antique towers as your active tour will embody the pleasures found in the rolling hills and the seaside precipices.

Countries Visited

Italy

Places Visited

Volterra, Siena, Colle, San Gimignano, Fonterutoli, Riomaggiore, Vernazza, Corniglia, Manarola, Monterosso, Ulignano, Portofino

Suggested Duration

8 Days

Customizable Itinerary

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Day 1

Volterra – Welcome to the Charming and Historical Town of Volterra

Tuscany is famous for its lush rolling hills, vast vineyards, and towering cypress trees as country roads lead to enchanting preserved medieval towns. Your flight will arrive at Florence International Airport, and your private transfer will meet you at baggage claim to escort you into the Tuscan countryside. The sunlight spreads across the verdant olive trees as emerald vineyards blanket the hills as the scent of succulent oaks and herbaceous plains fill the air. Your guide will meet you at the head of a small trail that leads to Volterra as your transfer continues to town with your luggage. You will continue on the trail for an easy walk that will allow you to bask in the beauty of the landscape and stretch your legs after the flight.

Stone farmhouses rise out of the growing stalks, and your guide will have you grab a dangling olive to feel its plumpness and coarse texture. The town of Volterra rises above the cypress and oak trees on the hillside as you will reach the imposing walls that protect the medieval city, a structure matched in drama only by the remaining historical towers that create a stone skyline. Etruscans settled the province before the Romans overtook Tuscany in the 3rd century BC as the cobblestone lanes and studded walls were built between the 14th and 16th centuries. Wander through the Etruscan Museum for perspective on the 3,000-year-old history of settlements on the hillside with galleries that exhibit funerary urns, ceramics, and gold jewelry.

What's Included:

Accommodation
Transfer
Tour
Day 2

Volterra – Delight in a Hike around the Tuscan Olive Groves and Vineyards

Day 3

Riomaggiore – Arrive in Cinque Terre and Venture along the Famous Paths

Day 4

Riomaggiore – Traverse the Trails of Portofino National Park and Portofino

Day 5

Colle – Enjoy the Village of Colle and the Towers of San Gimignano

Day 6

Siena – Discover Siena and Wander along Chianti during a Wine Tour

Day 7

Siena – Follow Via Romea around the Tuscan Countryside to Fonterutoli

Day 8

Siena – Depart for Home

Trip Highlights

  • Relish the fresh air and the enchanting landscape during magnificent hikes across the hills of Tuscany and coastal promontories of Cinque Terre
  • Trek the paths of Portofino National Park to discover a lavish array of wild flora, from asparagus to strawberries, growing near the coastal cliffs
  • Indulge in the creamy texture and abundant flavor of gelato on a private gelato tour in the historical town center of Siena
  • Sample Tuscan wines on a private estate outside the city walls of Siena during a walking tour of city center and bordering countryside
  • Enjoy the serene preserved medieval streets of Volterra and San Gimignano
  • Delight in the sea breeze during a private boat ride along the Mediterranean Sea
  • Trek portions of the historical Via Romea, a pilgrimage route that connects France to Rome
  • Enjoy the stunning natural beauty of Tuscany when walking along the banks of the Cecina River
  • Climb to the top of Torre Grossa in San Gimignano for an unadulterated panoramic view of central Tuscany

Detailed Description

Tuscany and Liguria entice visitors from across Italy and around the world with promises of ancient relics, medieval charms, and inspiring nature. Your 8-day tour will combine hiking and culture in a way that is perfect for explorers, adventurers, and history lovers. The journey will begin as your flight lands at Florence International Airport. Your private transfer will escort you to a trailhead to meet your guide. Stretch your legs and enjoy the fresh Tuscan air with an easy introductory walk along the countryside to the medieval hill town of Volterra, which enchants visitors with its ancient foundations and preserved antique district.

The next day, you will traverse the country trails outside of Volterra to visit the farmhouses, olive groves, cypress trees, and oak forests near the hamlet of Ulignano before returning to Volterra to enjoy the town’s traditions. The following day, you have a private transfer to the coastal town of Riomaggiore, one of the five towns of Cinque Terre. Explore the medieval seaside streets before you embark on the trails that connect each town along the shoreline. Board a private boat the next morning to reach the secluded Abbey of San Fruttuoso located inside Portofino National Park.

Wander the trails through the national park to enjoy the glorious views and wild flora before you reach the beautiful Italian Riviera town of Portofino. Continue the next day as you return to Tuscany to visit the town of towers at San Gimignano for a stroll along the medieval streets. Enjoy a panoramic view from Torre Grossa before you take the ancient trail Via Francigena to the town of Colle. The next day, you will venture to Siena for a full day tour of the medieval streets, the lavish Cathedral, the charming churches, and the delectable vineyards found on the outskirts of town.

Explore the Chianti Hills around the ancient pilgrimage route of Via Romea the next day and stop in the villages, hamlets, and towns that rise out of the countryside before you return to Siena. To conclude, your private transfer will meet you at your hotel in Siena ready to take you to Florence International Airport for your flight home. You could also extend your stay and continue your adventure through Italy at a pace that allows you to indulge in the sweet life of Italian culture and tradition.

Starting Price

$3,600 per person (excluding international flights)

Your Zicasso trip is fully customizable, and this sample itinerary is a starting place for your travel plans. Actual costs are dynamic, and your selection of accommodations and activities, your season of travel, and other such variables will bring this budget guideline up or down. Throughout your planning experience with your Zicasso specialist, your itinerary is designed around your budget. You can book your trip when you are satisfied with every detail. Planning your trip with a Zicasso travel specialist is a free service.

What's Included

  • Accommodations
  • In-country transportation
  • Some or all activities and tours
  • Expert trip planning
  • 24x7 support during your trip

Your final trip cost will vary based on your selected accommodations, activities, meals, and other trip elements that you opt to include.

4.9

Verified Traveler Reviews

Based on 1528 reviews

Travel Review: Memorable Vacation to Italy, Florence, Tuscany, Siena, Antinori Winery Tour, Rome, Vatican Tour
Giuliana of this Italy travel company guided us every step of the way and created one of our most memorable vacations. The most impressive thing at the outset was how quickly she responded to our initial inquiry. We had never been to Italy, had not done a great deal of research, and had only a general idea of what we wanted beyond the dates (mid-May) and the cities we wanted to visit (Florence and Rome). Within a day, Giuliana submitted a detailed proposed itinerary based on a recent client request similar to ours. The proposal included various options that provided a great starting point for further discussion. She asked many questions, including our hotel preferences (small boutique, high-rise, how many stars, etc.) and suggested a number of venues that would expose us to Italy’s remarkable history and culture. The result was a vacation specifically suited to our personal tastes and interests. We spent four days in Florence and three in Rome. In Florence, we stayed at the Hotel Lungarno on the Arno River, a lovely small hotel in the heart of the city within walking distance to everything of interest, including the Uffizi and Academy museums, and the famous Duomo. It rained two nights, but we didn’t have far to go for a great dinner. The hotel restaurant was superb. One of the highlights of the Florence leg of the trip was a day tour of the Tuscany wine region that included a stopover in the historic town of Siena. We had lunch at the Osteria di Passignano, a restaurant at the Antinori vineyards where we were treated to a four course lunch and wine tasting and a tour of the winery. Fabulous. In Rome, we stayed at the Hotel Saint George. Another small, well appointed, boutique hotel, centrally located near the Tiber River, it provided access to all the essential venues, including the Vatican, Coliseum, Spanish Steps, etc. As in Florence, everything was in walking distance, including fine dining restaurants, pizzerias, espresso bars, and gelateria—and lots of places to shop. The hotel was comfortable, attractive, with a friendly and efficient staff, but we would not recommend the hotel restaurant. It was nice enough (although too brightly lit) but was virtually empty the night we were there and the food was just O.K. That wasn’t Giuliana’s fault since the hotel restaurant was not on her recommended list. We were just tired (it was our first night) and thought we’d give it a try. The hotel concierge made up for it, however, by recommending two great nearby restaurants for the remaining two nights. Neither was on Guiliana’s list, but they were terrific. A word about the logistical aspects of the trip: we viewed this as critical to the success of a customized tour with multiple venues and connections. We couldn’t have been more pleased. On arriving at Rome’s Fiumicino Airport, we were greeted by Aldo who drove us to the high-speed train to Florence. After sharing an espresso with us in the station café, he made sure we got on the right train, helped us with our bags, and took us to our seats. Similar service greeted us at every connection point during the trip. Our personal tour guides, Enza (Florence), Andrea (Tuscany), and Sylvia (Rome), were exceptionally knowledgeable, personable, and fluent in English. Giuliana telephoned us at several points during the trip to confirm that we had arrived at our destination, that the drivers were on time, and that the accommodations met our expectations. Very reassuring to know she was keeping such close tabs on things. In short, all elements of transportation and personal service were impeccable. Would we visit Italy again? Without doubt. The trip simply whetted our appetites. Would we use this company? We wouldn’t consider any other service. Next time, however, we’ll make more of an effort to visit the restaurants recommended by Giuliana.

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Luxury Italy Group Tour Review: Rome, Tuscany, Chianti, Montepulciano, Montalcino, Siena, Florence, Pisa, Lucca, San Gimignano

THE BEST VACATION EVER!!!!

I must admit that I was somewhat uncomfortable arranging a group tour to Italy with someone I communicated with only via the Internet and telephone.  However, after my first communication with our agent -- I knew that she “had it.”  She understood exactly what we wanted to do.  She was right-on in both concept and execution.

Our ten-day adventure in Italy began with a private transfer with an English speaking local driver from the Rome airport to our fantastic 3 star boutique hotel located right in the historical center of Rome.  During our three days in Rome, we had fantastic private tours of Ancient Rome, the Coliseum, and the Vatican Museums.  Extremely knowledgeable, English-speaking guides led all of our tours.  Sense of Italy had arranged for VIP, skip the line, priority entrance for all tours -- saving us from long waits in long lines.

After our busy 3 days in Rome, we departed via private van transfer from our hotel in Rome to the Chianti Region of Tuscany.  The transfer included stops on the Val D’ Orcia to visit the amazing Villages of Montalcino and Montepulciano.  The “light lunch” and wine tasting we enjoyed in Montalcino was one of the highlights of our trip.  In Tuscany we stayed 7 Nights in a beautiful, historic villa located on one of the best wine estates of Chianti (Villa Le Corti near San Casciano) where we were met with a fantastic welcome dinner. During our time in Tuscany we were transported by private van from our villa to private tours of Siena, San Gimignano, Florence, Pisa and Lucca.  On each of our stops we were met by knowledgeable English speaking guides that clearly were proud of the history of their country, and were anxious to share it.  Interspersed in all of this activity were numerous exceptional meals with opportunities to taste (and drink) very fine Italian wines.

When we finally were forced to leave Italy, our agent arranged for private transport accommodating our varying departure times from the Florence airport and train station.

Thanks to this travel company and our agent for designing the perfect vacation for our group.  The only complaint that I heard was that we ate too much — wow was all the food delicious.  I really don’t know how she did it.  All of the tours were great — the van drivers friendly and helpful, the guides knowledgeable, and the sites spectacular.  Our stay in the villa was a great experience.  We were treated royally everywhere.  We all marveled at our agent's ability to get us, the vans, the guides, the food and wine, etc. all at the right place at the right time.  She is a genius!!!!

Jeff E

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Italy Tour Review: Bologna, Parma, Modena, Balsamic Vinegar Factory, Wine Tasting, Cuisine, Cooking Class, 2 Weeks
"We set out to experience culture and food, and Zicasso’s travel agency did not disappoint."

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Travel Review: Italy Vacation, Rome, Venice, Tuscany, Puglia, Orvieto, San Gimignano, Siena, Bologna, Food Tour, Ferrari Museum

Trip was very good.  Everything was well coordinated and only a couple of hiccups.  

Overall comments:Rome: 4 days in room was perfect, wouldn't want to do more.  Can't trust taxis so happy we had drivers and guides.  The private guides are the only way to go.  We saved hours in lines, had personal feedback and was very cordial and polite.  Rome itself is great but it is disappointing to see how much better it could be if the city invested in a few things (toilets!).  Again - I'll mention that taxis were there to steal your money.  No issues at all with the travel plans and the plans made by zicasso were very good. The boutique hotel was a great choice.  Location was excellent, rooms very clean and new.  Breakfast was excellent there.  In general, all of the hotels we stayed at had a very good breakfast, this is the only way to go as it just takes that meal out of your schedule and starts the day out right.  Our biggest snafu was the car rental, we were supposed to have an Audi A3 or equivalent and all the car rental could offer was a ford fiesta... it really took away from our experience in Tuscany to have such a poor automobile on those roads.  Again - not zicasso's fault - car rentals are terrible everywhere and in Rome it was very poor service.  Our drive and trip to Tuscany was great, we stopped in Orvieto as zicasso recommended and had lunch there - one of the best restaurants during our whole trip.  We stayed at the hotel and it was excellent, the food and wine there was excellent - worth staying just for that.  It was a little difficult to get to - and a bit of a drive to anywhere from there - but no real complaints and it was worth it to stay there.  In all of Tuscany we enjoyed San Gimignano and Pienza the best.  We found Siena great but overcrowded, Pienza and San Gimagnano were just as (more) scenic and less hectic.  The day trip and guide in Florence was very good but we were glad we only spent 1 day in Florence.  This is a personal thing as I understand most people prefer more time in Florence.  We really enjoyed Bologna - the food tour was probably the highlight of our trip (the downside is we can no longer eat Parmigiano, Balsamic Vinegar or Prosciutto from any other place, it was THAT much better than anywhere else).   We took a day to go to Modena, see the Duomo there (best in all of Italy in our opinion), and we enjoyed the Ferrari museum.  I would highly recommend adding Bologna, the food tour and Modena to everyone's trip suggestions.. It is less crowded than the main touristy cities - and just as enjoyable... Loved this  part of the trip.  The hotel in Bologna was perfectly placed and very very nice, excellent choice.The train to Venice was perfect.  The pickup and ride to the hotel was good also.  The hotel was ok - but probably the least nice of all the places we stayed.  It was very good, just not as nice, more cramped and the breakfast was by far the worst.  I equate this to Venice as everything was more expensive and more cramped in Venice.    We loved Venice - more than I thought we would.  I could see 1 more day in Venice and 1 day less in Rome.  Just walking the streets - wonderful!Getting from hotel to airport was good - though it was much further than we'd thought. The airline we used sucks... no way around that - not Zicasso's problem - but flight was 1.5 hours delayed and well - as an airline it isn't very good.  I'm still not so sure that taking a full day train ride to get to Puglia wouldn't have been better?  (Venice to Naples to Puglia?) Pick up at airport in Puglia was good.  The driving service was good - same driver for all our trips in Puglia - but he didn't speak a word of English so that was a challenge.  Thank goodness for Google Translate!  We had a mix up where we interpreted the itinerary as us having a guide in Alberobello (see itinerary - says private tour - so we were confused).  The driver had a friend who gave us a personal private tour of the Trullo homes and some history - that was very nice he arranged that.  But it was a little embarrassing and confusing. It could have all been avoided if the driver spoke English as well as the itinerary being more clear.Ostuni and the guide were great.  We loved Ostuni as well as Alberobello and the caves.  We probably enjoyed those areas more than the renaissance areas of Florence, but that is just us.  Note: once we got to Ostuni we told our guide no more going inside churches... at some point - its just another beautiful church - but there is one on every corner in Italy!   The Hotel in Puglia is awesome.  Seriously this place is amazing.  The food was amazing the spa was amazing the service was over the top.  What a beautiful part of Italy...   We changed our schedule to spend the morning in Bari before catching the train to Rome - we could have easily spent more time there.  I probably liked the food in Puglia the best.  The focaccia is amazing (just like Grandma made!).  In general we loved Puglia though we'd probably have been better served to have a rental car as we were a long way from anything and it would likely have been less expensive than a dedicated driver.  We would have had much more flexibility in our schedule and planning if we had our own car.   Train back to the Rome train station and pickup was very good - though the Rome train station and driving out of Rome - is never a good experience.  The hotel we stayed at our last night was very nice but probably overkill since all we needed was a bed before we caught a flight out.  All in all - highly recommend zicasso, they did a great job for this trip.  Having guides and drivers on our first trip to Italy - priceless!

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Travel Review: Anniversary Trip to Italy, Rome, Florence, Pisa, San Gimignano, Positano, Truffle Hunt, Cooking Class, Food Tour

Locations Visited: Venice, Verona, Florence, San Gimignano, Siena, Pienze, Rome, Pompeii, Positano

My husband and I planned this trip for our 10-year anniversary. I’m a person with high expectation and this travel agency exceeded all my expectations. The entire trip was dream.

We opted for personalized tours and transport for 95% of our trip. All of our drivers were wonderful. They arrived on time and made sure we made it to all of our destinations without issue. They had the contact information for the tour guides we were meeting. Upon arrival to our first hotel, a local cell phone and gift were given to us. Having the iPhone during our trip made any needed communication with our agent and his team a breeze. In addition, we used the phone apps for navigation throughout the cities we visited. We made a last-minute request for an additional private transport, and our agent was able to make it happen. We greatly appreciated their customer service.

We participated in a several unique experiences while in Italy. We went truffle hunting in Pienza, which was amazing. After, we were served a meal that highlighted truffles and the cheeses made locally. In addition, we did a cooking day in Rome. This was a private cooking class where we made pasta, several sauces, and appetizers. The one disappointment is that we never received the recipes from the chef (we were told by the chef that they would be emailed to us). However, this is a knock on the chef and not our travel agent. Once the class was done, we were served a meal in a private garden area. Lastly, we did a food walking tour in Rome. This was an amazing way to find local cuisine that we wouldn’t have known about otherwise. A wonderful experience.

All of our tour guides were excellent. They were knowledgeable, friendly, and familiar with the cities. We had one guide that really went into the details and reasons for expressions in the art. We didn’t care for that, but we didn’t specify that ahead of time or to the guide. It was wonderful seeing her excitement and passion for all of the amazing working works of art and sculpture that we saw.

Overall, I would highly recommend this travel agent and his team if you are traveling to Italy!! You will not be disappointed. We gave him our wish list of activities, accommodation preferences, etc. ahead of time and he made sure we got them all! Thank you for such a wonderful and memorable trip. If we are able to return to Italy, you will be hearing from us.

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Italy Vacation Review: Florence, Bologna, San Gimignano, Siena, Cinque Terre, Rome, Monteriggioni

This is the second Italian adventure our Zicasso travel partner planned for us and it was fantastic from start to finish!

We loved returning to Florence and this time around, our agent suggested day trips to Bologna, San Gimignano, and Siena – amazing places! (We also added a stop in Monteriggioni, which was a great little spot.)

Our stay in Cinque Terre was idyllic… from the hotel to the food and even the challenging three-hour hiking tour.

We ended our trip with a couple of days in Rome. Everything from the tours to hotels and private transfers went smoothly. It was an almost perfect trip (it would have been perfect had the elevators at the Monterosso train station been working!).

Our travel agent gave us a beautiful experience!

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Customizable Itinerary

This is a sample itinerary to inspire a personalized trip designed with your travel specialist.

28,000+ Verified Traveler Reviews