walking vacations in Italy

Experience Italy’s less visited gems on one of our art walks or walking vacations in Italy!

Find an authentic Italy of today steeped in rich beauty and a colorful past. Our Italy walking vacation on the Italian Riviera and Lake Como is an idyllic vacation for those who have seen the big cities of Italy or want to do something unique and very special. Together we will walk between Mediterranean towns and lakeside villages. We will travel coastal paths and ancient Roman trails. Beautiful views and generous hospitality will welcome our small group of travelers. Of course wonderful tastes of the region will sustain us along the way.

Read on for our favorite highlights of the Italian Riviera and Lake Como regions of Italy.

Milan and the Italian Riviera

The cosmopolitan city of Milan offers all the advantages of a large city, but it’s relatively small, making it easy to get to most of the city’s attractions and museums on foot.  Some of Milan’s most beautiful attractions include the Duomo di Milano, an impressive Opera House, a striking castle, ancient churches, and a great variety of museums and art galleries. 

Piazza del Duomo is the main square of Milan.  In fact, it has been the true commercial center of Milan for the last seven centuries!  The Piazza is bordered by the Cathedral of Milan, Galleria Vittorio Emanuele II – an elegant 19th century shopping arcade housing some of the most luxurious boutiques, including Prada and Gucci, Carminati Palace, and the Royal Palace of Milan. 

One of our favorite Italian rituals is that of the aperitivo.  It’s a lovely way to cap a day of walking the Italian countryside. Similar to the American happy hour, the aperitivo is a cocktail and light meal that takes place at the end of the workday, sort of warm up to dinner, which is typically not eaten until 8 or 9 p.m. 


After visiting Milan, travel by rail to Rapallo on the lovely Italian Riviera. Rapallo is a charming harbor town with a sunny promenade, sea views, and historic city center.  From just about anywhere you can access the Vittoria Veneto promenade, the seaside walkway in the shade of stately palm trees.  Along the way you’ll find bars, ice cream parlors, and terrace cafes where you can stop for a quick bite and watch the people go by.  For amazing views, take a panoramic funivia ride. 

walking vacation Italian Riviera and Lake Como

Rapallo is the perfect base to explore the five coastal villages Cinque Terre – Monterosso, Vernazza, Corniglia, Manarola, and Riomaggiore – each with its own history and hidden treasures.  Listed as a UNESCO World Heritage site, Cinque Terre’s picturesque villages full of colorful houses are perched atop rock cliffs overlooking the sea.  

In the direction opposite of Cinque Terre lies Portofino, one of the most iconic spots on the Italian Riviera.  Here, the clear water reflects the pastel colors of the building facades, the sky, and lush green hillsides.  All of this lovely scenery is arranged around the famous Piazzetta di Portofino, overlooking the harbor.

From Portofino, indulge in a walking tour that follows the spectacular coastline to Santa Margherita Ligure, a vibrant seaside resort brimming with heritage, culture, and incredible scenery. The picturesque Chiesa di Santa Margherita towers over the plaza where daily markets are held. At the end of your visit, it’s an easy return to Rapallo by a scenic ferry ride.

Lake Como

Lakeside walks allow you to discover quiet paths and unique views. If you’d prefer to raise your elevation, professional mountain guides may be hired to lead the way. The ferries that crisscross the lake make hopping between villages a breeze. 

The entire perimeter of Lake Como is dotted with charming villages and towns. The most popular destinations are certainly Bellagio, Varenna, and the city that gives the lake its name, Como. In each of these locations, as well as in the others, there is no shortage of opportunities for shopping, walking in nature, visiting beautiful villas and botanical gardens, or having unforgettable experiences.

The Villages of Lake Como

The posh village of Bellagio, referred to as the “Pearl of the Lake”, is a small jewel located on the promontory that separates the two southern branches of Lake Como.  It is home to a colorful historic center, beautiful gardens like the parks of Villa Serbelloni and Villa Melzi, as well as charming neighborhoods such as Pescallo or San Giovanni.  The narrow streets of Bellagio are so beautiful that a simple walk is worth the visit. 

Another short ferry ride carries you across the lake to Varenna, a picturesque and traditional village. This small village is home to elegant villas with botanical gardens (such as Villa Monastery and Villa Cipressi) and beautiful walks between history and nature (Castello de Vezio and Sentiero del Viandante).

Join us for a fun, relaxing, and delicious tour in beautiful Italy!  Click here for more information and for details about our other walking vacations in Italy.