Wonderful Walking Tours of Italy

In a country where wineries form your pit stops, idyllic landscapes form your backdrop, and ancient roads form your path, walking holidays in Italy are the essence of a fine life. 

From the jagged peaks and blue lakes of the Dolomites and the northern region to the cliff-top villages of the Cinque Terre and the Mediterranean bliss of Sicily; Italy’s diverse landscapes provide the perfect setting for a guided walking holiday. 

Not only is the scenery incredible but walking in Italy presents an assorted array of options through its distinct regions: crossing Tuscany one picturesque village at a time; stopping to marvel at ancient architecture on a Rome walking tour, or admiring the fairytale trulli swellings in Puglia as you stroll through the region. The possibilities are endless, and each one brings with it a plethora of hidden gems. 

Italy is a country known for its passion; Italians pour it into every activity from creating incredible food to creating walking tours of Italy that perfectly showcase the Italian culture. Walks of Italy tours mean moving at a slower pace through a particular region of the country; fully immersing in the customs, traditions and culture of each place and appreciating the substantial regional variations as you go. 

An abundance of options present themselves with walking tours of Italy; we’ve gathered together the most wonderful walks of Italy and the best tips to bear in mind when planning your trip!

Best Times for a Walking Tour of Italy

Italy is beautiful year-round. However, different times of the year bring different climates, crowds and options for walking tours. Overall, the best time to go to Italy for optimal weather and crowd control is the shoulder seasons, either side of the hottest summer months. 

During these months, from April to June and September to November, the weather is cool and more comfortable than the stuffy summer months, there are fewer crowds, and the scenery is spectacular with these being the spring and autumn months respectively. 

The Best Seasons for Italy Hiking Tours & Tips on Seasons to Avoid

As a long and narrow country, Italy can experience some different weather depending on where you are in the country. To best plan your walking tour of Italy, you can pick the regions you plan on visiting then check when is the best time to go. 

As a quick guide, these are the months you should avoid and tips you should bear in mind for the main walking regions;

Cinque Terre and Amalfi Coast:

• Walking tour or not, it’s best to avoid the summer months (July and August) in these regions of Italy as they are very crowded. However, one advantage you have with hiking is that you can avoid the busy beaches and towns, taking the opportunity to seek out the more remote areas.

Closures in Winter:

• Many hotels and restaurants in the main tourist areas close up from November until March (the winter months), so make sure you don’t get caught out. Book ahead if you plan to go during these months. 

The Summer Heat:

• July and August can reach stifling temperatures of up to 40°C with high humidity in some parts of Italy. These temperatures can make hiking extremely strenuous and dangerous, so make sure to bear this in mind. 

A Soggy Winter:

• As well as many places being closed, the winter months can also bring a lot of rain. These cold and the wet can make hiking from November to March pretty miserable. However, skiing, cross-country hiking and snowshoeing in the north during these times make for an exciting adventure if you don’t mind the cold. 

Avoid Lake Regions in May:

• The northern lake region, especially Lake Como, experiences the highest level of rainfall in May. If you plan to visit during these months, bring waterproofs!

Watch Out for the Snow Melt:

• In the spring months, the snow begins to melt in the Mont Blanc mountain region. With this, many boulders and rocks can become loose. It is advisable to walk with a helmet and a qualified guide. Our Local Designers in Italy can arrange this as part of your tailored hiking trip if you wish to go during these months. 

Trips you may like

5-Day Rome, Florence & Venice Getaway

Embark on a getaway to three of Italy’s most-loved cities! Your Italy itinerary is 5 days from Rome to Venice, beginning in the Eternal City, where you’ll learn all about the rich history of the Roman Empire through the city’s beautiful monuments. Moving on, you’ll catch the fast train to Florence where you’ll discover why this city is known as the ‘Cradle of the Renaissance’. Your final stop will be in Venice, a city built entirely on water and spread over 100 islands that captivates each and every visitor! This 5-day Italy itinerary takes you to some of the finest artistic gems in the country while remaining open so that you can enjoy your time in Italy in your own way.

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8-Day Luxury Italy from Milan to Rome

Embark on an unforgettable road trip from Milan to Rome, exploring Italy’s rich tapestry of cities and landscapes. Over eight beautiful days, you’ll visit, explore and get to know four iconic cities in Italy as you travel from Milan to Rome. This journey offers a delightful mix of stunning views and charming stops, from the vibrant streets of Milan to the historic allure of Rome. Your journey begins in Milan, the bustling metropolis of northern Italy. Known for its fashion, design, and vibrant urban life, Milan beautifully merges the old with the new. Before embarking on your long drive south, take some time to explore the city of Milan on a guided walking tour. These iconic sites include the magnificent Milan Cathedral, the Sforzesco Castle, the Vittorio Emanuele II Gallery, and the world-renowned Uffizi Gallery. Experience the panoramic views and beautiful architecture that define northern Lazio. Leaving Milan, you will catch a high-speed train to Venice through the fertile plains of Emilia Romagna. With its intricate network of canals, stunning architecture, and rich history, it is unlike any other city in the world. Start your Venetian adventure by visiting St. Mark’s Square, home to the impressive St. Mark’s Basilica and the Doge’s Palace. Don’t miss a gondola ride along the Grand Canal, where you can enjoy panoramic views of Venice’s beautiful palaces and churches. Continuing south, you’ll enter the picturesque region of Tuscany. This stretch of your journey offers stunning views of rolling hills, vineyards, and olive groves. Florence, the capital of Tuscany, is a must-visit. Spend some time walking through its charming streets, visiting its museums, and enjoying the panoramic views from Piazzale Michelangelo. Immerse yourself in the vibrant local market of San Lorenzo and savour a delightful wine-tasting experience paired with regional cold cuts. Let our experienced local designer lead you on a journey through the rich history of Italian culinary traditions. If you have time, take a short detour to the medieval town of San Gimignano. On the day after, you will take a car ride to the Florence Train Station and head to Rome, the capital of Italy. Rome needs no introduction. It is a place where history comes alive, with every street and building telling a story of the past. From the grandeur of the Colosseum to the artistic wonders of the Vatican Museums, Rome does justice to its reputation. Pocket tips for you: Plan Your Route: While the main highway from Milan to Rome is straightforward, consider taking alternative routes to explore more of Italy’s countryside. Book Hotels in Advance: It’s advisable to book your hotels in advance to save time and ensure a place to stay, especially in peak seasons. Visiting in October or later in the fall can offer a more relaxed experience, with fewer tourists and cooler weather. Stay Flexible: While having a plan is helpful, allow yourself the flexibility to take detours and discover unexpected places along the way. Watch for Speed Limits: Italy’s highways are well-maintained, but speed limits are strictly enforced. Keep an eye on the signs to avoid fines. Sample Local Cuisine: Each region has its own culinary specialities. Don’t miss the opportunity to enjoy local food at each stop along your route. A luxury trip from Milan to Rome is more than just a journey from one city to another; it’s an exploration of Italy’s rich cultural and natural diversity. From the bustling streets of Milan to the historic charm of Rome, with scenic detours through Tuscany and beyond, this trip offers a comprehensive look at what makes Italy so special. Along the way, immerse yourself in the art, history, and culinary delights that define luxury travel. For the discerning traveller, this is not just a road trip—it’s an unforgettable Italian odyssey. Scroll down to check out the detailed 8-Day Luxury Italy from Milan to Rome below.

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8-Day Venice and Rome Tour

Looking for a holiday means you want to escape for a short while to take it easy, so sit back, kick those feet up on a gondola down the elegant Venetian canals and over a glass of wine and lunch in the Castelli Romani. You will also make the most of guided tours around Venice and the nearby islands of Murano, Burano and Torcello in the Venetian lagoon, as well around Rome and Vatican City, still leaving you one day to spend however you wish in the ‘Eternal City’.

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14-Day Rome, Amalfi Coast & Puglia

Embark on a journey around the most stunning parts of southern Italy on this two-week Rome, Amalfi Coast and Puglia tour! Beginning in Rome, you’ll explore the finest monuments of this historic city before moving on to Naples where you’ll spend a large part of your trip exploring the ancient city of Pompeii, the island of Capri and the stunning Amalfi Coast. After Naples, you’ll move onto your Puglia tour during which you’ll explore the towns of Lecce, Ostuni and Alberobello. After falling in love with the heel of the boot of Italy, you’ll travel to the stunning coastal city of Salerno before returning to Rome!

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10-Day From Rome to Palermo through Southern Italy

From Rome to Palermo this 10-day tour of Italy is about finding the best of the south. In each city you will visit, you will get to see the main sights and learn about their histories and how they differ in feel and style. Whether it is in Rome, Naples, Syracuse, or Palermo, you will admire the Italian architecture and local life. With private guides, you’ll get to know each city on this Rome to Sicily tour.

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6-Day Culture and Wine in Tuscany

Tuscany is one of the most famous and beautiful regions of Italy, home to stunning landscapes of rolling vineyards, traditional houses and quaint medieval hilltop villages and towns. Let yourself be charmed by the rich heritage, delicious food and drink that the region is famous for on this Tuscany wine tour. During this six-day trip, you will visit Pisa, Lucca, San Gimignano and Montalcino whilst learning all about the rich heritage, the countryside and the gastronomy of Tuscany. This tour also includes a guided tour of Siena and walking tour of Florence.

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Optimal Gear for Happy Feet

It’s clear that depending on when you plan to go walking in Italy, you’ll sometimes need some extra gear. However, ultimately the most crucial item in your luggage on any walking tours of Italy, self-guided or not, is your footwear. 

Top Tips & What to Wear on Your Walking Tour of Italy

#1 Bring hiking boots you have broken in: A walking tour, whether multiple days or not, is not the place to try out your brand new shoes. Make sure you bring with you a pair of comfortable walking shoes that you have broken in.

#2 Carry a light waterproof jacket on you: Even if you have arranged your walking tour in the optimal weather months, it is still worth carrying a light waterproof with you as a precaution. Then, if a sudden shower does present itself, you don’t have to let it dampen your plans.

#3 Bring a scarf or sarong: If you are walking in the summer months, you will want to bring with you a light scarf or sarong that can double up as sun protection from intense heat and a cover-up for when entering churches and religious buildings. 

#4 Bring shoes to let your feet breath at night: You’ll want to kick off those boots as soon as you can if you are on a multiple-day hiking trip. Bring a few pairs of shoes including sandals for allowing your feet to breathe after a long day of walking. 

#5 Fashion is an integral part of Italian culture: Just because you are on a walking tour, don’t forget about your dressier outfits for the evenings. Italians will leave you feeling a little dishevelled with their effortless fashion, so make sure to bring a few outfits that add a little sparkle to your evening. 

Walking the Amalfi Coast

While many walks of Italy start in Rome, this seven-day hiking trip of Italy begins in Naples. To introduce you to Italian food, culture and traditions, you’ll embark on a Naples walking tour on your first day, and the following day, you’ll explore the ruins of the ancient city of Pompeii. 

With it being such proximity to Naples and the Amalfi Coast, it would be a crime not to visit the stunning island of Capri while in this region. You’ll spend a day immersed in the gardens bursting with flowers, sumptuous villages and beautiful azure waters of Capri while hiking to and from its various communities. 

The stream of adventurous, challenging and stunning walks will ensue as you tackle the crater walk of Mount Vesuvius, hike the Path of Gods from Agerola to Positano and cross the scenic valley of the mills to Ravello on the Amalfi Coast. 

Highlights of 7 Days Walking the Amalfi Coast

#1 Hiking to the Stunning Viewpoints on the Island of Capri Overlooking the Bay of Naples

#2 Hiking to the Crater of the Mighty Bubbling Mount Vesuvius

#3 Historical Walking Tour of Naples, Italy’s High-Energy Volcanic City

Distance Walked

You’ll be walking and hiking for around four hours each day.

Duration of Trip

This Amalfi Coast walking trip is seven days long. However, you can customise this trip with one of our Local Designers in Italy to make it shorter or longer to include more destinations. 

Difficulty

Some days will be more challenging than others, but anyone with a reasonable level of fitness will find this trip very enjoyable.

Cinque Terre Walking Tour

Self-guided walking tours of Cinque Terre, Italy’s fine coastal region, are a great way to travel somewhat slowly through a slice of Italy while absorbing all of its cultural, historical and gastronomical riches. 

Over seven days, you’ll hike to and from the five villages of this incredibly beautiful Italian coastline on some of the most iconic trails. Heading straight into the heart of the action, you’ll be based in the picturesque village of Manarola and each day, you’ll head out to explore a different stretch of this UNESCO World Heritage Site. 

For those that love to get off the beaten track, the quaint villages and pretty trails of the Cinque Terre are perfect. You’ll spend your lunch breaks and evenings refuelling on delicious seafood dishes and washing it down with fine Italian wines. 

Highlights of Walking Tours of Italy – Cinque Terre

#1 Dining on Fresh Seafood in the Marina of Manarola

#2 Hiking the Panoramic Trail from Corniglia via Volastra to Manarola through Vineyards and Terrace Fields

#3 Hiking the Spectacular Trail from Riomaggiore to Portovenere with a Panoramic View of the Cinque Terre Coast

Distance Walked

You’ll be walking and hiking for around five hours each day.

Duration of Trip

This Cinque Terre walking tour is seven days long; however, you can customise this trip with one of our Local Designers to make it shorter or longer to include more destinations. 

Difficulty

As every day of this trip involves a large part of the day spent hiking so you should bear this in mind. This trip will best suit individuals, couples or small groups looking to discover this part of Italy in a unique way. 

Just a Day – Florence Walking Tour & Other City Walking Tours

The beauty of walking tours of Italy is that they can be customised to any distance or duration that suits you and the type of trip you are looking for. 

Setting off on foot is one of the best ways to explore a region, a city or even a small town and walking tours are something our Local Designers in Italy specialise in. 

One-Day Walking Tours to Highlight Italy’s Beauty

A Florence Walking Tour with a Local Guide

• There are many free walking tours of Florence. Still, few compare to the experience of having your expert local guide taking you through the iconic monuments of the city and sharing the anecdotal history of each one. Better yet, this guided Florence food tour on foot invites you to discover the city’s beautiful architecture while sampling the best of its local food markets. 

Embark on a Venice Walking Tour

• On this 10-Day Northern Italy Tour, one of the highlights of the trip is a guided tour of Venice with several opportunities to sample the typical Venice finger food, Cicchetti, and some Venetian drinks.

Rome Walks with a Hefty Dose of Italian History

• On this 12-Day Family Tour of Italy, you’ll spend a day exploring ancient Rome on foot, skipping the long lines and discovering the Colosseum, Roman Forum and Palatine Hill. With a private guide, you’ll learn more about the history, traditions and culture of the city than you would on a self-guided Rome walking tour. 

Walking Tour of Milan

• Milan’s elegance oozes from its streets, on every corner a beautiful building invites you to discover the unique local culture of the city. From elegant shopping galleries to historical churches and everything in between, you’ll fall in love on this guided tour of Milan.

Walking Tour of Siena

• On this 2-week Italy trip from Rome to Venice to Florence and Siena, you’ll have ample time in each city to soak yourself in history, art and architectural excellence. A walking tour of Siena, Italy’s enchanting Tuscan city, home to the thrilling Palio horse race, is the perfect way to get acquainted with all that it offers. 

Customise Your Own Walking Tour of Italy!

Walking tours are galore in Italy. Whatever you’re looking for, whether that be an Italy food tour visiting various cities, exploring them on foot and eating your way through the local delicacies; a Tuscany walking tour or even, one of the many walks of Italy from Venice; the offer is abundant. 

Designer Journeys’s in-destination Local Designers in Italy are carefully vetted by our global team to ensure they deliver nothing but extremely high-quality, tailor-made tours. Whether you want a fully-guided tour, a self-guided tour with a rental car or even a family trip of a lifetime on public transport, our Local Designers can design a trip to suit your interests, travel style and budget.