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Italy: Tuscany & Umbria
Guided Walking
Experience a cornucopia of hidden gems on this insider’s walking tour of Tuscany and Umbria. Discover the Basilica of Assisi’s extraordinary frescoes, fresh local cuisine at neighborhood farms and agriturismi, renowned regional wines, wild horses on the slopes of Mount Subasio, and a host of congenial Italian friends.
Italy: The Dolomites
Guided Walking
To dive deep into Italy’s majestic Dolomites, there’s no substitute for the local insight from Country Walkers leaders. As you hike among the soaring massifs of northern Italy, you’ll appreciate their expert mountaineering skills as they bring you an insider’s view of the lofty mountains and their rich alpine culture.
Italy: Pompeii, Capri & the Amalfi Coast
Guided Walking
You won’t find anyone who can bring this iconic region to life like Country Walkers. Our certified local leaders hail from Naples, Positano, Ravello, and Capri—so they know how to avoid the crowds to bring you authentic insights you won’t find on your own.
Italy: Sicily
Guided Walking
While most walking tours of Sicily omit the island’s southern half, this unique Sicilian adventure brings you south of Syracuse to explore the ancient city of Ragusa and the stunning coastal Oasi Nature Reserve.
Italy: Matera, Otranto & the Puglia Coast
Guided Walking
While many walking tours of Puglia miss out on the beauty of Basilicata, on this Country Walkers adventure we’ll guide you through the charming streets of historic Matera. Explore the ancient Sassi district, discover Alberobello’s iconic trulli, and walk along the turquoise coast of the Adriatic Sea.
Italy: Piedmont, Langhe & the Italian Riviera
Guided Biking
If you can’t decide between a trip to the seaside and a visit to Barolo wine country, this innovative cycling vacation has it all! Pairing the opulence of Langhe with the beauty of Liguria creates unparalleled experiences in wine, cycling, and gastronomy.
Italy: The Dolomites, Bolzano to Lake Garda
Guided Biking
This VBT tour was the first to combine easy Dolomite bike paths with the stunning scenery of Lake Garda. It’s our local connections that make this tour a standout—as your local trip leaders introduce you to the people who call this incredible region home.
Italy: Puglia’s Undiscovered Coast
Guided Biking
Cycle along ancient walled cities, explore charming seaside villages, and enjoy farm-fresh food prepared by local hosts on VBT’s Puglia bike tour.
Italy: Sicily, the Noto Valley & Syracuse
Guided Biking
This road cycling tour of Sicily provides scenery, history, hearty cuisine, and a robust welcome from the people who call it home.
Italy: Southern Tuscany & Giglio Island
Guided Biking
With 20 years of experience cycling the Tuscan coast, we know the best seaside routes, award-winning vineyards, and agriturismos that reflect the Maremma’s unique character. Pedal the shores of the Orbetello lagoon, learn to make traditional Tuscan gnocchi during a hands-on cooking class, and enjoy a tasting of Tuscany’s “liquid gold” at a local olive oil mill.
Italy: Lake Como & the Italian Lake District
Guided Biking
Take a cycling tour of Italy’s Lake Como and its surrounds, where flat bike paths weave through a rich tapestry of soaring hills, glittering waters, and scenic vineyards.
Italy: Valleys of the Dolomites
Guided Biking
Road cycling the Dolomites was never more rewarding than this journey, blending spectacular scenic vistas with insights into unique pockets of culture.
Slovenia, Austria & Italy: Alpine Valleys
Guided Biking
Explore three lakes in three countries, experiencing authentic local culture as only VBT can reveal. Your local trip leaders will invite you to learn the secrets of preparing rateški krapi (filled dumplings)—and perhaps try out some traditional Slovenian dance steps during a festive barn party.
Italy: Puglia, Alberobello & Lecce
Self-Guided Biking
Your Pugliese Local Host makes you feel like family on this self-guided tour—sharing deep cultural insights that add dimension to your independent exploration. Explore the UNESCO village of Alberobello, stay in the white-washed city of Ostuni, pedal cobalt-blue shores to Gallipoli, and experience the magical confluence of the Ionian and Adriatic seas in Santa Maria di Leuca.
Italy: The Dolomites, Bolzano to Ora
Self-Guided Biking
If you’ve ever dreamed of cycling the Pordoi Pass, this is your chance to coast down the switchbacks that have thrilled Giro d’Italia fans for years. Spin along quiet bike paths through the Val di Fassa and Val di Fiemme—suffused with South Tyrol’s famous culture, cuisine, and cycling.
Italy: Tuscany, Chianti & Marina di Castagneto
Guided Biking
On this unique cycling tour, we’ve paired the sun-soaked Tuscan seacoast with the lush vineyards of Chianti. Along the way, you’ll discover a 13th-century castle, learn about the importance of bee preservation at organic hives, visit a family-run olive oil mill, and master the art of Italian cooking in the kitchen of a quintessential Tuscan farmhouse.
Italy: Umbria, Spello, Montefalco & Assisi
Guided Biking
With VBT’s deep Italian roots, we’ve found the most scenic, low-traffic cycling routes in Umbria and Le Marche. Join us on an epic spin through the “green heart” of Italy—including the stunning hilltop city of Assisi, the medieval walled village of Montefalco, and three nights in the enchanting hillside town of Spello.
Italy: Sardinia, Carloforte, Sulcis & Chia
Self-Guided Biking
If you’re looking for an off-the-beaten-path Sardinia cycling vacation with flexibility and support, you’ve found it! While most travel companies focus on Sardinia’s heavily-trafficked northeast seaboard, this VBT adventure avoids the tourist traps to bring you the island’s unsullied west coast.
Discover Italy
Italy has been romancing visitors throughout its history—one that helped to alter the course of the entire world. Hearty, farm-grown Italian cuisine and nectarous red wine lie at the center of a cultural fabric that intertwines with some of the most stunning landscapes on earth, making for one of the most fulfilling and enduring hiking experiences in all of Europe.
Throughout your walking tour of Italy, you’ll be immersed in landscapes that evoke the heady days of Etruscan ingenuity, Roman genius, and Old World splendor. At its center, fabled Tuscany is a fertile patchwork of rolling green hills, where you can explore renowned vineyards and quaint local restaurants in country’s famed hill towns.
In the far north, the snow-capped peaks of the Apennines and Dolomites stand guard atop the nation like majestic sentries. Here, you’ll explore charming Alpine villages, lakeside resort towns and stunning vistas that have welcomed travelers for centuries, all a part of Italy’s remarkable kaleidoscope of natural beauty.
Country Highlights
- Walk the cliffside, pastel-colored villages of Cinque Terre.
- Follow scenic pathways through the forests and vineyards of Italy’s Lakes Region.
- Explore Tuscany’s medieval hill towns, and sample their full-bodied wines.
- Enjoy a feast of fresh Italian cuisine while taking in sweeping views of the legendary Amalfi Coast.
- Sample the pungent truffles and sweet Barolo wine of Piedmont.
Good, Clean and Fair
Explore the alpine foothills of Piedmont, home to the world’s “Slow Food” movement, Italy’s farm-to-table culinary revolution that promotes local artisan chefs, organic farmers, and traditional flavors. Pursue ingredients for your evening meal as the sun rises on an early morning truffle hunt across secret locales.
Don an Apron and Roll Up Your Sleeves
Prepare a meal in an authentic Italian kitchen, where age-old pasta recipes vary in preparation, appearance and flavor from one village to the next, offering you a fascinating insight into how regional identity is interlaced with the country’s cuisine.
An Everlasting Wonder
Only in Italy can one glimpse an entire century of artistic masterpieces under one roof. You can do so in a stroll through the Uffizi Gallery, adjacent to Tuscany’s Piazza della Signoria, where works from Botticelli, Giotto, Cimabue, Michelangelo, Leonardo da Vinci, Raffaello—a spellbinding collection of treasures dating from antiquity to the 20th century.
Featured Walking & Hiking Tours in Italy
View All Italy Tours
Italy: Matera, Otranto & the Puglia Coast
Guided Walking Easy to Moderate
Days 7 From $ 4,645 Tour Only
While many walking tours of Puglia miss out on the beauty of Basilicata, on this Country Walkers adventure we’ll guide you through the charming streets of historic Matera. Explore the ancient Sassi district, discover Alberobello’s iconic trulli, and walk along the turquoise coast of the Adriatic Sea.
Italy: Tuscany & Umbria
Guided Walking Easy to Moderate
Days 7 From $ 6,545 Tour Only
Experience a cornucopia of hidden gems on this insider’s walking tour of Tuscany and Umbria. Discover the Basilica of Assisi’s extraordinary frescoes, fresh local cuisine at neighborhood farms and agriturismi, renowned regional wines, wild horses on the slopes of Mount Subasio, and a host of congenial Italian friends.
Italy: Pompeii, Capri & the Amalfi Coast
Guided Walking Moderate to Challenging
Days 7 From $ 6,795 Tour Only
You won’t find anyone who can bring this iconic region to life like Country Walkers. Our certified local leaders hail from Naples, Positano, Ravello, and Capri—so they know how to avoid the crowds to bring you authentic insights you won’t find on your own.
Italy: The Dolomites
Guided Walking Moderate to Challenging
Days 7 From $ 6,745 Tour Only
To dive deep into Italy’s majestic Dolomites, there’s no substitute for the local insight from Country Walkers leaders. As you hike among the soaring massifs of northern Italy, you’ll appreciate their expert mountaineering skills as they bring you an insider’s view of the lofty mountains and their rich alpine culture.
Italy: Sicily
Guided Walking Easy to Moderate
Days 7 From $ 6,095 Tour Only
While most walking tours of Sicily omit the island’s southern half, this unique Sicilian adventure brings you south of Syracuse to explore the ancient city of Ragusa and the stunning coastal Oasi Nature Reserve.
Italy: Sardinia, Carloforte, Sulcis & Chia
Self-Guided Biking Moderate to Challenging
Days 6 From $ 2,895 Tour Only
If you’re looking for an off-the-beaten-path Sardinia cycling vacation with flexibility and support, you’ve found it! While most travel companies focus on Sardinia’s heavily-trafficked northeast seaboard, this VBT adventure avoids the tourist traps to bring you the island’s unsullied west coast.
Slovenia, Austria & Italy: Alpine Valleys
Guided Biking Easy
Days 7 From $ 4,745 Tour Only
Explore three lakes in three countries, experiencing authentic local culture as only VBT can reveal. Your local trip leaders will invite you to learn the secrets of preparing rateški krapi (filled dumplings)—and perhaps try out some traditional Slovenian dance steps during a festive barn party.
Italy: Sicily, the Noto Valley & Syracuse
Guided Biking Easy to Moderate
Days 7 From $ 4,395 Tour Only
This road cycling tour of Sicily provides scenery, history, hearty cuisine, and a robust welcome from the people who call it home.
Italy: The Dolomites, Bolzano to Lake Garda
Guided Biking Easy
Days 7 From $ 5,495 Tour Only
This VBT tour was the first to combine easy Dolomite bike paths with the stunning scenery of Lake Garda. It’s our local connections that make this tour a standout—as your local trip leaders introduce you to the people who call this incredible region home.
Italy: Puglia, Alberobello & Lecce
Self-Guided Biking Easy to Moderate
Days 7 From $ 2,795 Tour Only
Your Pugliese Local Host makes you feel like family on this self-guided tour—sharing deep cultural insights that add dimension to your independent exploration. Explore the UNESCO village of Alberobello, stay in the white-washed city of Ostuni, pedal cobalt-blue shores to Gallipoli, and experience the magical confluence of the Ionian and Adriatic seas in Santa Maria di Leuca.
Expert Local Leaders
Experience your destination like an insider with people who call it home.
Alessandro Gullo
Alessandro Gullo has Sicilian ancestry and was educated in the US as well as Italy. He is a certified guide of historic monuments who effortlessly combines his charming personality with a vast knowledge of the culture, art, history, food, and wine of Italy.
Keegan Alagna
With his American mother and Sicilian father, Keegan Alagna grew up in a bilingual home in the Umbrian countryside near Assisi. From his childhood on a working farm to post-graduate work in geology, he has always pursued his passion and curiosity for the outdoors, through teaching, guiding, and exploring. He brings his depth of knowledge of geology, nature, Italian history and culture to his walking tours and to his position as a key member on Italy’s premier outdoor group—the CAI, the Club Alpino Italiano.
Claudia Piombi-Barnabe
Claudia Piombi-Barnabé infuses all guests with her passion for mountains and professional expertise in geology. A formal mountaineering guide of the Italian Alpine Club (CAI), Claudia brings a high level of precision and safety to all her tours. Her knowledge and love of the mountains is matched only by her appreciation of the Italy’s food.
Stories from Italy
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Paths Less Traveled: Exploring Italy’s Hidden Gems on Foot
Walking with our experienced Italian Trip Leaders frees you to immerse yourself in the moment, uncovering hidden gems and timeless landscapes at a pace that lets you savor every detail....
Read Story
Vibrant and Diverse: Italy is a Kaleidoscope of Adventure
Whether you’re perusing shops of colorful ceramics along the Amalfi Coast, plunging into a refreshing aquamarine grotto off the coast of Puglia, or strolling a stately cypress-lined footpath in Tuscany,...
Read Story
Oh, the People You’ll Meet on Italy’s Amalfi Coast!
The village of Ravello is a tumult of pastel-colored homes cascading gracefully towards a sunlit Mediterranean Sea. It’s also the home of Country Walkers trip leader Vincenzo Falcone—and, apparently, he...
Read Story
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