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.

2018 DATES & PRICES: 7 Days/6 Nights

  • October 7-13, 2018

SUMMER SALE through September 1, 2018:  Regular Trip Price: $4,195, SALE PRICE: $3,795! Save $400!!! Price is per person, based on double occupancy.

Single Supplement $695 USD solo traveler, single occupancy


2019 DATES & PRICES: 7 Days/6 Nights

  • April 28 – May 4, 2019
  • September 29 – October 5, 2019

SUMMER SALE through September 1, 2018:  Regular Trip Price: $4,195, SALE PRICE: $3,795! Save $400!!! Price is per person, based on double occupancy.

Single Supplement $695 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 Arrival Florence Airport, Levanto

  • 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 your seaside accommodations, in the coastal village of Levanto, you’ll meet up with your Strada Toscana expert trip leader for a friendly trip orientation and village/seaside walk. As you get to know charming Levanto – a town that sits on the north end of le Cinque Terre – you’ll notice how it’s maintained its authenticity as a simple, colorful, fishing village. And now you know why we’ve chosen this location for exploring le Cinque Terre. 

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

ACCOMMODATIONS Hotel Palazzo Vannoni (3 nights)

Hotel Palazzo Vannoni is located in the charming, historic center of the seaside village of Levanto, tucked away from the hustle and bustle of le Cinque Terre and just a short stroll from the azure, Ligurian Sea. Built in the early seventeenth century, the hotel boasts rooms with fresh, white linens and painted ceilings. The ideal, beautiful location for easy-access to le Cinque Terre. See gallery.

DAY 2 Cinque Terre

  • Vernazza to Corniglia on the Azure Trail, Manarola panoramic vineyard walk (optional), picnic lunch, limoncello tasting, Riomaggiore ring walk (optional)
  • Breakfast, picnic lunch

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. You must see it with your own eyes – and it’s about to get even better as your expert walking guide leads you along the breathtaking Azure Trail from Vernazza to Corniglia – a stunning pathway that meanders alongside the Ligurian Sea. After exploring the village of Corniglia, we’re off by train to colorful Manarola to enjoy a seaside picnic lunch.

LUNCH: Picnic lunch in Manarola


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 Levanto, followed by dinner on your own. No worries on selecting a place, as we offer plenty of suggestions.

DAY 3 Cinque Terre

  • Levanto to Monterosso al Mare seaside walk, Convento di San Francesco, Portovenere Doria Castle walk (optional)
  • Breakfast, dinner

MORNING: After a generous buffet breakfast, you’ll get an early start on the seaside trail that leads from Levanto to Monterosso al Mare, the northernmost of the Cinque Terre villages – and the only one with an actual beach. Here, in Monterosso, you’ll enjoy some time free time to explore, shop and grab lunch on your own. Looking for extra steps? Climb the winding staircase to the Convento di San Francesco, then reward yourself with a gelato (Monterosso has one of the best gelateria around!).  

LUNCH: On your own in Monterosso al Mare


OPTION 1: Along with your awesome trip leader, take the local ferry to the village of Portovenere – just south side of the Cinque Terre. This picturesque village offers an easy, panoramic walk to the impressive, 12th century Castello Doria. Along the way you’ll make a stop at the Church of St. Peter that hugs the cliffside along the Gulf of Poets. Gorgeous! You’ll return by ferry to Monterosso, and then by train to Levanto. 

OPTION 2: Take the ferry to Portovenere and explore on your own. Return by ferry to Monterosso and then take the train back to Levanto

OPTION 3: Remain in Monterosso al Mare to explore, shop and meander on your own. Take the inter-village train back to Levanto at your leisure. 

EVENING: After returning by train to our “home” village of Levanto, you can kick your feet up and enjoy some time on your own relaxing, sipping a glass of Prosecco, or perhaps simply watching the sun set over the spectacular Ligurian Sea. Dinner is served this evening at our friend’s award-winning restaurant in Monterosso al Mare.

DAY 4 Tuscany, Val d’Orcia

  • Village/seaside walk (optional), transfer by private service to Tuscany, welcome to the Val d’Orcia, countryside walk
  • 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 inviting, 4-star accommodations, Relais Osteria dell”Orcia, 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 at our boutique hotel accommodations, you’ll have time settle in before enjoying a special welcome tour and an invigorating countryside walk through the picturesque, classic Tuscan landscape. You’re in for a treat, as this part of Tuscany – the Val d’Orcia – is one of the most photographed areas of the region with its gentle, rolling hills, medieval hill towns and winding, cypress-lined lanes. Plus you’re just steps away from the charming town of Bagno Vignoni.

EVENING: Aperitivo hour followed by a delicious welcome dinner at the outstanding Osteria dell’Orcia.

ACCOMMODATIONS Relais Osteria dell’Orcia (3 nights)

The philosophy of the 4-star Relais Osteria dell’OrciaBagno Vignoni, is to surround oneself with the beauty of Tuscany – its landscapes, nature, history and culture – and to enhance the art of hospitality with excellent products from local farms. With its elegant, yet inviting, rooms and proximity to historic walking trails, Relais Osteria dell’Orcia rates as our favorite accommodation for exploring Tuscany on foot. See gallery

DAY 5 Pienza, San Quirico, Bagno Vignoni

  • Pienza ring walk, Pienza duomo and labyrinth, thermal spa (optional/extra)
  • Breakfast, picnic lunch

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. Join your expert Tuscan walking guide for a walk along the town’s picturesque “ring walk” that features 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. Then you’ll have free time to explore your way along Pienza’s cobbled avenues, with its fine artisan shops, Pope’s palace, and pecorino cheese shops.

LUNCH: Today’s lunch is taken picnic-style along Pienza’s outdoor “balcony”, called simply la passeggiata.


OPTION 1: After lunch, join your trip leader for a jaunt to the medieval village of San Quirico. After a peek inside the 12th century Collegiate church of San Quirico (built on 8th century foundations) you’ll venture onto a well-traversed pathway that leads to back to Bagno Vignoni. Built over thermal springs, Bagno Vignoni’s charming main piazza boasts a centuries-old thermal pool – a picturesque jewel of the village. Take a rest at one of the charming wine bars, or continue on to the hotel at the foot of town. 

OPTION 2: Head from Pienza to Bagno Vignoni by our private van service, and the Centro Benessere le Terme for a long, luxurious soak in the mineral rich thermal waters. (on-your-own, extra) We’re happy to book a wellness treatment or massage on your behalf, as well. Ahhhhh … what a relaxing and rejuvenating way to spend an afternoon. 

OPTION 3: Head from Pienza back to the hotel, via our private van service, to enjoy for an afternoon of free time and relaxation.

EVENING: After a friendly apertivo hour on our hotel’s charming terrace, you’ll have dinner on your own in Bagno Vignoni or in the excellent hotel dining room. The choice is yours, and we’re always on hand to offer suggestions.

DAY 6 Montalcino, Montepulciano

  • Montalcino to Sant’Antimo walk, private winery tour & wine tasting with lunch, Montepulciano exploring and shopping, farewell dinner
  • Breakfast, lunch and dinner

MORNING: After a hearty breakfast at our boutique hotel accommodations, you’ll be off, via our private service, to the hill town of Montalcino with its fortified medieval walls and sweeping views across Tuscany. From here, your fabulous (and fun!) trip leader will escort you on a panoramic countryside walk to the beautifully preserved Abbey of Sant’Antimo, nestled amidst silvery olive groves and expertly-tended brunello vineyards. Then it’s on to Molino di Sant’Atimo, where our friends will give you a fabulous private tour and delicious, Tuscan-style lunch served up with (you guessed it) their excellent brunello. Now, this is the way to have a wine tasting!

LUNCH: Lunch at our friends’ award-winning Molino di Sant’Atimo


OPTION 1: After lunch you’ll travel on to regal, Montepulciano, for a scenic, 1.5 hour afternoon walk from Montepulciano to nearby Montefollonico along a strada bianca that passes directly through sweeping, Vino Nobile vineyards. After exploring the tiny village of Montefollonico, head back to the hotel via our private service. 

OPTION 2: Visit the Reniassance hill town of Montepulciano – home of the famous Vino Nobile di Montepulciano – where you can shop your way from Piazza Grande to Porto di Prato (i.e. from top to bottom) or simply explore the steep, centuries-old avenues. We’ll be sure point out our favorite artisan shops – including copper and leather – and have your camera ready along the way, as the views from Montepulciano’s medieval walls are out of this world!

OPTION 3: After lunch, head back to the hotel for relaxation and free time.

EVENING: Gather together with your fellow travelers for a special aperitivo hour, hosted by our dear friends at the Relais Osteria dell’Orcia, followed by a delectable 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 hand-selected boutique hotels
  • All breakfasts, 2 picnic lunches and 4 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.