Book Early and Save $200 Per Person ![](/sites/default/files/2025-03/1%20Meals%20%28red%29_19.png) 31 Meals ![](/sites/default/files/2025-03/2%20Small%20Group%20%28red%29_7.png) Small Group Max 25 Travellers ![](/sites/default/files/2025-03/3%20CT%20Ratings%20%28red%29_20.png) CT Rating 4/5 - Very Challenging ![](/sites/default/files/2025-03/3%20CT%20Ratings%20%28red%29_19.png) Led by Karen Scott Caplice **From Renaissance cities to authentic Tuscan experiences** Experience Tuscany on foot, from the rolling vineyards of Chianti Classico to the scenic shores of the Tyrrhenian Sea. Walk through olive groves, wooded hills and picturesque countryside, discovering Florence, San Gimignano, Lucca and Pisa along the way. Savour regional wines, enjoy traditional Tuscan lunches at local farms and wineries, and visit Leonardo da Vinci’s birthplace. Follow ancient Etruscan paths between Sovana and Pitigliano, explore Maremma Natural Park and take a ferry to the beautiful island of Elba. With our Journey Leader and local guides, enjoy a memorable blend of scenic walks, cultural discoveries and authentic Tuscan flavours. .button { display: inline-block; padding: 10px 20px; margin: 5px; font-size: 16px; font-weight: bold; text-decoration: none; border-radius: 6px; background-color: gray; /* default color */ color: white; } .button:hover { opacity: 0.9; } [Book Now](https://enrollment.craigtravel.com/booking?departurecode=TEU141027:20271014) [Download Brochure](https://lp.constantcontactpages.com/sl/Qr9P9aM/TuscanyOct2027) [![Tuscany on Foot Map](/sites/default/files/2026-10/Map_Tuscany_2023.jpg)](https://www.craigtravel.com/sites/default/files/2026-10/Map_Tuscany_2023.jpg) ### Tour Highlights - SCENIC TUSCAN WALKS - Walk from Fiesole into Florence, through Chianti Classico vineyards from Greve, along Etruscan paths between Sovana and Pitigliano and around the Orbetello Lagoon to Monte Argentario and Porto Ercole. - UNESCO GEMS - Explore the UNESCO-listed historic centres of Florence and San Gimignano, admire Pisa’s iconic Leaning Tower and stay in Montecatini Terme, part of the UNESCO-listed Great Spa Towns of Europe. - UNIQUE CULINARY EXPERIENCES - Savour a wine-grower’s lunch at a Chianti Classico winery, lunch at an olive oil farm near Vinci with regional wine tastings led by a sommelier, wild boar stew in the Maremma and fresh fish in Porto Ercole. - TUSCAN LIFE & COAST - Visit Leonardo da Vinci’s birthplace, share wine and appetizers at the home of local hosts Christian and Caren, take the ferry to Elba and enjoy six nights in the seaside town of Castiglione della Pescaia. ### Inclusive Features - International and domestic flights, plus airport transfers, with air-inclusive packages - Carefully selected accommodation as listed, or similar - All sightseeing and entrance fees as described - Meals as indicated in the itinerary - B: Breakfast (12) L: Lunch (7) D: Dinner (12) - Dedicated journey leader, national guides, and local specialists where applicable - All gratuities, surcharges, fees, and taxes - International eSIM to keep you connected - Free insurance quote (contact us for details) ### Itinerary Overview Full View DEPART CANADA October 14, 2027 We gather in Toronto for our overnight flight to Rome, Italy. MONTECATINI TERME October 15, 2027 Upon arrival in Rome, we are welcomed by our national guide. We travel north along the Apennine mountain range toward the renowned spa centre and hill town of Montecatini Terme. Tonight, we gather for our welcome reception and dinner. ***Hotel Columbia Wellness & Spa - 6 nights*** Dinner FLORENCE October 16, 2027 Our private coach transports us to the Florence area, setting the stage for an unforgettable walking adventure as we trek across the scenic hills of Fiesole along the Arno Valley down into Florence. Next, we enjoy the afternoon at leisure in Florence, the cradle of the Renaissance, before returning to Montecatini for dinner. ***Walking time: 2 hrs*** Breakfast, Dinner ELSA RIVER VALLEY / SAN GIMIGNANO September 4, 2027 Today, our walk begins at Colle di Val d’Elsa, taking us through scenic vineyards and woods to a charming garden restaurant. Here, we enjoy a rustic meal featuring crostini, various types of pasta and wine. Afterwards, we travel by coach to San Gimignano, where striking medieval towers built by rival merchant families still stand today, earning the town its famous nickname, “Town of Fine Towers”. During our free time, we can visit one of the most renowned ice cream parlours in Tuscany before returning to Montecatini. ***Walking time: 3 hrs*** Breakfast, Lunch, Dinner CHIANTI CLASSICO October 18, 2027 This morning, we drive to the world-famous Chianti Classico wine region, where our walking journey takes us from the picturesque wine village of Greve through lush forests and past rolling vineyards to one of the area’s historic world-class wineries. Following an exclusive tour of the centuries-old wine cellars, we gather for a traditional wine-grower’s lunch featuring homemade sausages and other savoury ham specialties, accompanied by our choice of excellent regional wines before we return to Montecatini for dinner.  ***Walking time: 3 hrs*** Breakfast, Lunch, Dinner VINCI October 19, 2027 Setting out across the rolling hills of Montalbano, we make our way past scenic olive groves and vineyards toward Vinci, the hometown of history’s most renowned genius, Leonardo da Vinci. Our path leads us to his picturesque birthplace and on to a local vineyard and olive oil farm, where we enjoy lunch accompanied by regional wine tastings led by a sommelier. In the afternoon, we take a short stroll from the village of San Baronto to our host Christian’s home for wine and appetizers before returning to Montecatini.  ***Walking time: 1.5 hrs*** Breakfast, Lunch, Dinner MONTECARLO / LUCCA October 20, 2027 Venturing across the rolling hills surrounding the historic village of Montecarlo, we pause for a delightful lunch served in an old farmhouse featuring exceptional local cuisine and fine wines. elegant boutiques or sip a warm cappuccino at a cozy street café before returning to Montecatini.  ***Walking time: 1.5 hrs*** Breakfast, Lunch, Dinner PISA / CASTIGLIONE DELLA PESCAIA October 21, 2027 Saying goodbye to Montecatini Terme, we travel west toward Pisa for a quintessential Tuscan experience at the legendary Piazza dei Miracoli, home to the iconic Leaning Tower. After a brief visit, we continue down the scenic Tyrrhenian coast, heading south to Castiglione della Pescaia, widely regarded as the most beautiful seaside resort in the region.  ***Hotel L’Approdo - 6 nights*** Breakfast, Dinner MAREMMA NATURAL PARK October 22, 2027 Stepping into Maremma Regional Park, we explore a protected natural landscape rich in flora and fauna. Afterwards, we transfer to a quaint medieval town to enjoy a traditional lunch featuring authentic local specialties like homemade pasta and savoury wild boar stew. We then return to Castiglione with the rest of the day at leisure to explore the beautiful seaside town. ***Walking time: 3 hrs*** Breakfast, Lunch, Dinner SOVANA / PITIGLIANO October 23, 2027 We set out along ancient pathways between the historic towns of Sovana and Pitigliano, communities that once flourished during Etruscan times and later evolved into powerful medieval republics. Enjoy a packed lunch along the way, followed by free time in the afternoon to wander the area before returning to Castiglione.  ***Walking time: 2.5 hrs*** Breakfast, Lunch, Dinner ELBA ISLAND October 24, 2027 A short coach ride brings us to the lively port of Piombino, where we board a ferry bound for Elba Island, the jewel of the Tuscan Archipelago. On arrival, we explore the island on a guided coach tour, pausing at spectacular lookouts and storied historic sites. Later in the afternoon, we sail back across the shimmering sea and return to Castiglione. Breakfast, Dinner CASTIGLIONE DELLA PESCAIA October 25, 2027 This day is entirely ours to relax and unwind. We might take advantage of our hotel’s wonderful amenities, stroll along the nearby beach, or venture out independently to discover the area’s charming corners. Breakfast, Dinner PORTO ERCOLE / PORTO SAN STEFANO October 26, 2027 For our last hiking day, we set out on our most ambitious route yet, saving one of the region’s most breathtaking landscapes for the finale. Our trail traces the edge of the tranquil Orbetello Lagoon toward Monte Argentario, a dramatic rocky promontory that once stood alone in the Tuscan Archipelago and is now connected to the mainland by two narrow strips of dune. We make our way to the picturesque fishing port of Porto Ercole, guarded by three fortresses, to explore briefly before we head to a seaside restaurant for a feast of fresh local fish. Later, we continue to the stylish harbour town of Porto Santo Stefano to stroll at leisure. In the evening, we return to Castiglione to celebrate the close of our Tuscan walking journey with a festive farewell dinner. ***Walking time: 3.5 hrs*** Breakfast, Lunch, Dinner CASTIGLIONE DELLA PESCAIA October 27, 2027 We transfer to the airport this morning for our return flights to Canada, bidding farewell to Tuscany. Breakfast [Download Brochure](https://www.craigtravel.com/sites/default/files/2026-10/Tuscany%20on%20Foot%20TEU141027%20%2822OCT26%29.pdf) [![Leaning Tower of Pisa](/sites/default/files/styles/gallery/public/2026-10/Leaning-Tower-of-Pisa-AdobeStock_288114243.jpeg.webp?h=790be497&itok=I69uf9D8 "Leaning Tower of Pisa")](https://www.craigtravel.com/sites/default/files/2026-10/Leaning-Tower-of-Pisa-AdobeStock_288114243.jpeg) [![Craig Travellers walking through the Tuscan landscapes](/sites/default/files/styles/gallery/public/2026-10/IMG_1312.jpg.webp?h=ebed0208&itok=OMTLwDIG "Craig Travellers walking through the Tuscan landscapes. Credit: Detlef Dransch.")](https://www.craigtravel.com/sites/default/files/2026-10/IMG_1312.jpg) [![Aerial views of San Gimignano](/sites/default/files/styles/gallery/public/2026-10/AdobeStock_382472791.jpeg.webp?h=8f348b8a&itok=1A44O6-N "San Gimignano")](https://www.craigtravel.com/sites/default/files/2026-10/AdobeStock_382472791.jpeg) [![The coastline of Elba Island](/sites/default/files/styles/gallery/public/2026-10/Tuscany_Elba_Island.jpg.webp?h=faad150e&itok=VPQuFeGF "Elba Island")](https://www.craigtravel.com/sites/default/files/2026-10/Tuscany_Elba_Island.jpg) [![Porto Ecole](/sites/default/files/styles/gallery/public/2026-10/Porto-Ecole-AdobeStock_375109355.jpeg.webp?h=853a43b2&itok=B5eghm60 "Porto Ecole")](https://www.craigtravel.com/sites/default/files/2026-10/Porto-Ecole-AdobeStock_375109355.jpeg) [![Wine in Tuscany](/sites/default/files/styles/gallery/public/2026-10/iStock-505951623.jpg.webp?h=9f5479df&itok=f4cJlQZP "Savour Tuscan wines in the Chianti region")](https://www.craigtravel.com/sites/default/files/2026-10/iStock-505951623.jpg) [![San Gimignano Gelato](/sites/default/files/styles/gallery/public/2026-10/Gelato_San_Gimignano_AdobeStock_547766587.jpeg.webp?h=4b88e375&itok=12bkhLFs "San Gimignano Gelato")](https://www.craigtravel.com/sites/default/files/2026-10/Gelato_San_Gimignano_AdobeStock_547766587.jpeg) ### Have any questions? Contact Lisa Guiotto at lguiotto \[at\] craigtravel.com or call [1-800-387-8890](tel:1-800-387-8890) ### Tour Cost in Canadian Dollars Per Person Land-Only $8,145 Toronto $9,325 Ottawa / Montreal $9,495 Winnipeg / Halifax $9,595 Calgary / Edmonton / Vancouver $9,645 St. John's / Saskatoon / Regina $9,725 Victoria $9,725 Single Supplement $1,495 [Book Now](https://enrollment.craigtravel.com/booking?departurecode=TEU141027:20271014) ### **Payment and Booking Terms** Deposit is **$900 per person** Final payment is due **July 7, 2027** Prices are in Canadian dollars per person. Land only members join at the hotel in Montecatini Terme and leave at the hotel in Castiglione della Pescaia. Airfares from other gateways are available on request. Tour price is based on sharing a twin-bedded room. Prices are based on a minimum of 20 members and on rates, taxes and fees effective October 2026 and are subject to change due to factors beyond our control. Group to be escorted with a minimum of 20 members. Refer to the [terms and conditions](https://www.craigtravel.com/terms-conditions) webpage for more details. Canadian passport holders may require an ETIAS travel authorization prior to departure. Comprehensive travel insurance is strongly recommended. #### CT Rating **4/5 - VERY CHALLENGING** This journey involves a number of walks on hilly, uneven surfaces for up to 4 hours per day, based on the group’s pace. Walk times listed are estimated and refer to the total time spent on the trail throughout a full day. Travellers must be in excellent physical condition and be able to maintain the group pace. Alternate activities may be available for those unable to complete some of the hikes. Depending on weather and location conditions, daily activities may have to be altered or adjusted. Accommodations will be in comfortable traditional European hotels with atmosphere and character. Trail conditions may vary and are subject to change. Do you have any questions about this journey? [Email Us](mailto:sales@craigtravel.com?cc=lguiotto@craigtravel.com&subject=Tuscany%20on%20Foot%20OCT%202027) #### Journey Leader ![Profile picture for user KarenScottCaplice](/sites/default/files/styles/user/public/pictures/2026-10/WhatsApp%20Image%202025-12-14%20at%208.32.18%20PM%20%281%29.jpg.webp?h=8930adc6&itok=pqaO5eVe) Karen Scott Caplice - brings over 35 years of travel industry experience, spanning retail travel, sales, leadership, and the cruise sector. Having explored more than 40 countries and taken over 70 cruises, she brings a wealth of firsthand knowledge to every journey. She has hosted groups ranging from intimate gatherings to several hundred travellers. Outside of travel, Karen is an avid hiker who enjoys water sports and spending time outdoors. Warm, outgoing and always up for an adventure, she loves bringing people together, sharing plenty of laughs and creating lasting travel memories and friendships along the way. ![](/sites/default/files/2024-07/1%20CT%20Loyalty%20Points_9.png) [Craig Travel Loyalty Points ](/loyalty-club) ![](/sites/default/files/2024-07/3%20Pay%20By%20Cheque_9.png) [Pay by Cheque Discount](/pay-cheque-discount) ![](/sites/default/files/2024-07/2%20Refer%20a%20Friend_9.png) [Refer a Friend](/refer-friend) ![](/sites/default/files/2024-07/5%20CT%20Rating_9.png) [About CT Ratings](/craig-travel-ratings) ![](/sites/default/files/2024-07/4%20Travel%20Insurance_9.png) [Travel Insurance](/travel-insurance)