Cinque Terre and Classic Tuscany ~ Cultural Walking Tour


FALL IN LOVE with the colorful fishing villages of le Cinque Terre

Explore seaside pathways and tucked away avenues – all while taking in those spectacular views of the turquoise Ligurian Sea! Spend 3 extraordinary days getting to know the treasures of the Italian Riviera, including this region’s specialities of fresh seafood and the tastiest pesto you can imagine.

Then FALL IN LOVE AGAIN with the classic Tuscan countryside

Enjoy 3 dreamy days walking through sweeping vineyards and silvery olive groves, and exploring medieval hill towns from top to bottom. From the postcard scenes of the stunning Val d’Orcia, with its winding, cypress-lined lanes, to the inviting, thermal baths of Bagno Vignoni, you’ll find yourself saying, “Pinch me, is this for real?”

Designed for first-time visitors, seasoned travelers, friends, couples or solo travelers…

Walkers’ Cinque Terre and Bella Tuscany features easy to moderate walks each day, along with other fabulous options should you prefer to take a break from walking, all with the expert guidance of a Tuscan-born trip leader who knows where to find tucked-away treasures – off the beaten path.

DATES & PRICES: 7 Days/6 Nights

  • April 28 – May 4, 2019
  • Trip Price: $4,195. Price is per person, based on double occupancy.
  • Deposit of $500 plus 5 monthly payments automatically charged to the same credit card
  • Single Supplement $495 USD solo traveler, single occupancy


WALKING RATING: Our walks are rated as easy to moderate, with durations on average of 1.5 – 3 hours and distances of 5-10 kilometers (3-7 miles). Although most routes are relatively short, you will encounter cobblestones, rugged pathways, uneven steps and steep ascents and descents in order to reach stunning views and hilltop villages. Our walks ideal for active travelers. No hiking experience is necessary, but we do recommend walking regularly before your trip, including up hills, whenever you can. Although non-walking options are provided throughout the tour, we caution that this trip is not the right fit for those who have difficulty walking or have a health-related condition that would limit participation and/or impede or inconvenience others.

REVIEWS: What People Are Saying

“Off the beaten strada is exactly what Pam’s tours are all about! Of course we enjoyed the wine and the food and the sites, but having access to such amazing, welcoming Italians was far more than we expected. Thank you so much, Pam!” —Rebecca and Larry H. – Ann Arbor, MI

“I cannot say enough about how wonderful the whole experience was for me! Every experience was so special due to Pamela’s great planning and connections, whether is was hotels, the villa or the fabulous foods that you introduced us all to. Thanks so much, Pamela and everyone for such a wonderful time off the beaten strada.” —Virginia H. – Vancouver, BC

DAY 1 – April 28: Arrival Florence Airport, Monterosso al Mare

  • Group transport from Florence Peretola Airport, trip orientation, village/seaside walk, welcome dinner
  • Dinner

Sit back and relax – we’ve got you! After you’re rendezvous with the group at Florence Peretola Airport, our private driver will be transporting you to the spectacular Ligurian coast, also know as the Italian Riviera. You’ll soon be exploring the breathtaking coastline by foot and getting to know the winding avenues and delectable cuisine of le Cinque Terre. 

AFTERNOON: After check-in at our characteristic Hotel Souvenir, we’ll meet up for a vigorous village and seaside walk. As you get to know charming Monterosso al Mare – the northern-most village of le Cinque Terre – you’ll notice how it has maintained its authenticity as a simple, colorful, fishing village. 

EVENING: This evening you’ll enjoy our signature, complimentary aperitivo hour, followed by a delectable welcome dinner featuring Ligurian specialities.

DAY 2 Cinque Terre

  • Manarola panoramic ring walk,  limoncello tasting, Riomaggiore ring walk (optional)
  • Breakfast, dinner

MORNING: This morning we’re up early and on our way, so put on your walking shoes and grab your camera. You’ll take a short train ride to our first stop –  Vernazza – the only village of le Cinque Terre with a natural harbor. It’s nearly impossible to imagine the beauty of this area, so we head up to Castle Doria for a better look. Then it’s off to colorful Manarola to enjoy a panoramic, vineyard ring walk before heading to Corniglia where you can enjoy lunch on your own.  

LUNCH: On your own in Corniglia


OPTION 1: Continue by train to the village of Riomaggiore to walk the less-frequented, but splendid, Riomaggiore ring walk – about 1.5 hours and nothing but gorgeous. You’ll ascend the trail to the Sanctuary of Montenero, which was a parish church till the 11th century, then reconstructed in the 18th century. Inside is a beautifully decorated ceiling and outside are views that stretch across the azure Mediterranean Sea. 

OPTION 2: Explore and shop your way through le Cinque Terre villages at your own pace. Pesto, lemons and anchovies are all specialties here, along with linen clothing shops and plenty of quaint bars where you can sip a glass of the local white and take in the views. Take the inter-village train back to Levanto at your leisure.

EVENING: Enjoy a relaxing apertivo hour along the seaside in Monterosso, followed by dinner on your own. No worries on selecting a place, as we offer plenty of suggestions.

DAY 3 Cinque Terre

  • Monterosso al Mare to Levanto seaside trail, Convento di San Francesco, exploring and shopping in Monterosso
  • Breakfast, dinner

MORNING: After a generous buffet breakfast, you’ll get an early start on the seaside trail that leads from Monterosso al Mare to Levanto – just north of the le Cinque Terre villages Here you’ll enjoy some time free time to explore, shop and grab lunch on your own. 

LUNCH: On your own in Levanto


OPTION 1: Take the inter village train with your trip leader to the village of Bonassola, then return to Levanto by foot through the evocative “old tunnel” system that runs along the spectacular coastline. 

OPTION 2: Return to Monterosso al Mare by train to explore, shop and meander on your own. 

EVENING: After returning to our accommodations in charming Monterosso, kick your feet up and enjoy some time on your own to relax or shop – later we head to our friend, Silvia’s, award-winning restaurant.

DAY 4: Tuscany, Poggio alle Trese

  • Village/seaside walk (optional), transfer by private service to Tuscany, welcome to Villa Poggio alle Trese countryside walk, pasta-making lesson
  • Breakfast, dinner


OPTION 1: Grab an early breakfast and join your trip leader for an invigorating village and seaside walk before your pick-up.

OPTION 2: Sleep in, enjoy a later breakfast and join up with the group for pick-up. 🙂

It’s off to the Tuscan countryside and your elegant villa accommodations, nestled in the heart of picturesque wine country. We’re continually amazed at how quickly and dramatically the Italian landscape changes – from one stunning scene to another – and now you’ll feel as if you’ve stepped into a postcard of winding cypress lanes and sweeping vineyards that lead to medieval hill towns and stone farmhouses.  

LUNCH: Lunch on your own in route

AFTERNOON: After check-in you’ll have time settle in before enjoying a vineyard walk followed by a delightful pasta-making lesson with Chef Doriana. 

EVENING: Aperitivo hour with sommelier Paola, followed by a delicious welcome dinner

DAY 5 Pienza, Montepulciano

  • Pienza ring walk, Pienza duomo and labyrinth, wine tasting in 15th century cantina, Montepulciano shopping and exploring
  • Breakfast, lunch, dinner

MORNING: After an abundant buffet breakfast, you’ll be transported, via our private service, into the heart of the Val d’Orcia, and the charming hill town of Pienza – famous for its ideal Renaissance layout and pecorino (sheep’s milk) cheese. Take a walk along the town’s passeggiata pathway that offers classic, panoramic views that only this part of Tuscan can offer. Your walk ends back in the historic center of town with a visit inside the Cathedral of Pienza, including its ancient labyrinth. Take time to explore your way along Pienza’s cobbled avenues, with its fine artisan shops, Pope’s palace, and pecorino cheese shops, before we head to lunch and wine tasting in the regal town of Montepulciano.

LUNCH: Lunch and wine tasting in our friends’ 15th century wine cantina


OPTION 1: After lunch, shop and explore the avenues of Montepulciano at your own pace before joining up with our private drivers to return to the villa. 

OPTION 2: Walk with your trip leader to the cathedral of San Biagio, located on the outskirts of town. Along the way, stop for a photo opt of the sweeping vineyards the surround the town before joining up with our private drivers to return to the villa. 

EVENING: Aperitivo hour with Paola, followed by dinner prepared by Chef Doriana

DAY 6 Sarteano, San Casciano 

  • Etruscan necropolis, walk to Sarteano, village visit and castle tour, visit to thermal spa (optional/extra)
  • Breakfast, lunch and dinner

MORNING: After breakfast,  you’ll enjoy a panoramic walk along a stunningly beautiful ridge-line that straddles the regions of Tuscany and Umbria, and where you’ll discover an ancient Etruscan necropolis Afterwards you may walk with your trip leader – or shuttle – to the Tuscan village of Sarteano where you’ll enjoy a delightful walking tour along the town’s winding, medieval alleyways – all the way to the its regal castle. Afterwards we continue to San Casciano dei Bagni for lunch.

LUNCH: Lunch at Daniela’s chic, Tuscan restaurant


OPTION 1: After lunch, head to the nearby thermal spa, Fonteverde, where you can soak in thermal waters and even schedule a relaxing massage, if you’d like (optional/extra)

OPTION 2: Head back to the villa to enjoy an afternoon of free time and relaxation on your own.

EVENING: Enjoy a bruschetta-making lesson with Paola, along with a friendly aperitivo hour, followed by a special farewell dinner. 

DAY 7 Departure

Alas, it’s time to say arrivederci. This morning we’ll provide private group transportation to Florence Peretola Airport.



  • Options and flexibility. You’re uniquely you, and we think that’s fabulous! That’s why we provide you options and flexibility each and every day. Prefer a bit of time on your own? Choose an explore-on-your-own option. Wanting more steps? Choose an optional, extra walk. Tailor each and every day to suit your unique desires.
  • Memorable accommodations for 6 nights in a hand-selected boutique hotel and private Tuscan villa
  • All breakfasts, 3 lunches and 5 dinners with wine
  • Full-time experienced trip leader/walking guide, local guides and experts, behind-the-scenes support staff and support vehicle(s)
  • Tours, visits and hands-on experiences with local residents and artisans
  • Private land transportation throughout the trip
  • Daily guided walks, plus non-walking options: WALKING RATING: Easy to moderate, with durations on average of 1.5 – 3 hours and distances on average 5-10 kilometers (3-5 miles) – ideal for active travelers with or without hiking experience. You can expect hard cobblestones, uneven pavement, steps and steep hills. In addition, elevators are not available at our boutique hotel accommodations. Although non-walking options are provided throughout the tour, we caution that this trip is not the right fit for those who have difficulty walking or have a health-related condition that would limit participation and/or impede or inconvenience others.
  • Gratuities for hotels and meals

Not included: Airfare, ground or water transportation outside of that listed in the trip itinerary, alcoholic drinks, wines or meals ordered “on your own”, gratuities for drivers

The Unexpected is Part of the Journey: At Strada Toscana we weave amazing, authentic experiences into every trip, but sometimes unexpected things come up. If Mario calls to tell us they’re pressing olives at just this moment, off we go (I mean, we wouldn’t let you miss his newly pressed olive oil!), and if a site has an unscheduled closing, we improvise to include something equally as wonderful and interesting. On that note, if our usual boutique hotels or B&Bs can’t accommodate us (which rarely happens), you can rest assured you’ll stay somewhere of an equal or higher level. The quality of our tours is never at risk, as our team is committed to excellence, along with our vast, local, Italian connections.



WHY CHOOSE a Strada Toscana Tour?

  • YOU’RE NOT JUST A NUMBER. We care deeply about our guests. In fact, we think of our small groups as a kind of family of like-minded travelers.
  • SMALL GROUP – BIG BENEFITS. Our maximum small-group size is 14, which means we’re able to stay in centrally located, boutique hotels (that often have limited rooms), eat in tucked away, family-run restaurants (that are always the best!) and use twin Mercedes Benz vans to reach restricted areas in historic villages.
  • WE’VE GOT YOUR BACK. Our support staff is always at hand to help you with everything from translating a menu to finding that special leather purse.
  • GORGEOUS & COMFY. You stay in upscale, boutique hotels with beautiful sleeping rooms, ensuite bathrooms and lovely touches that reflect the character of the region.
  • BEST VALUE. Because we’re destination experts and operate only in Italy, we know how to get the BEST quality for the very best price – that we then pass along to you. Our tours are an extraordinary value. Period.
  • YOU GET RIGHT TO IT. Spend less time transferring around in vans and more time experiencing. Your accommodations are in ideal locations for stepping outside to walk and explore.
  • PRIVATE DRIVERS. Strada Toscana teams up with exceptional drivers who own their own vans and their own businesses – and are really more like family. No conglomerates and no outside services.
  • AUTHENTICITY. Our trip leaders and guides are locals who are from the areas in which we tour. They know the region, the sites and the people like the back of their hand.
  • EXCEPTIONAL MEALS. The owner-run, top-notch restaurants on our tours are extraordinary, which means you enjoy delectable dinners in a welcoming, friendly atmosphere.

Learn more about our unique approach to traveling in Italy.