• What makes Italian cities unique?
    • From the busy cosmopolitan Milan to the tiny villages of Sicily, Italian cities are a sensory delight with layers of history and culture and so much art in everything around you.
  • Which cities in Italy have the most famous museums?
    • You will visit hundreds of museums with the world’s most priceless treasures in Florence, Rome, and Milan, but it is the beauty of the streets, markets, squares, and fountains that will leave the most lasting impression.

This post may include affiliate links. Click here for Affiliate Disclosure.

1. Rome


Explore ancient ruins and see iconic landmarks on a bucket-list retirement trip.

Rome

© Courtesy of Noppasinw - Fotolia.com

Coming to Rome, be prepared for a total sensory overload. The entire city is a living, breathing museum.

Everything around you is thousands of years old, from the cobblestones you walk on to the massive fountains and ancient stone houses that line the narrow streets.

There is so much beauty all around you that it is difficult to take it all in, especially if you are trying to cram all Rome has to offer in a few days: the Vatican, St. Peter's Square, St. Peter’s Basilica and eighteen additional basilicas, the Trevi Fountain, Spanish Steps, Colosseum, Piazza Navona, Roman Forum, Aquaducts, Catacombs, and so much more.

And then there is Via Veneto with all its fabulous shops, small gellaterias, and trattorias with aromas that pull you in from miles away. As you sit in one of the fabulous outdoor cafes on Piazza Navona, you have to wonder how anyone can get any work done with so much beauty all around.

2. Pisa


Visit the Leaning Tower and walk charming streets during a quick photo stop.

Pisa

© Courtesy of ilolab - Fotolia.com

Once a powerful Italian maritime republic and a university city that attracted young minds since 12th century, Pisa is now attracting millions of tourists who come to see its famous leaning church tower – one architectural project that went wrong.

Naturally, you will start your exploring by visiting the magnificent Piazza del Miracoli with its bright white leaning tower surrounded by a field of green grass. It is stunningly beautiful, and the Cathedral and the Baptistry are nearby.

Climb the tower, as the view at the top is spectacular, and then walk through ancient streets of Pisa with its magnificent Romanesque houses, imposing Gothic churches, beautiful Renaissance piazzas, opulent palaces, fountains, and museums. Walk along the River Arne, sit in one of the quintessential outdoor Italian cafes, and enjoy the vibrant, lively atmosphere of this incredibly charming university town that even ancient Romans considered old.

3. Castellina in Chianti


Taste regional wines and stroll vineyard lanes on a romantic countryside escape.

Castellina in Chianti

© Courtesy of sumos - Fotolia.com

Castellina in Chianti is a small municipality in Tuscany about 22 miles from Florence.

It is part of the beautiful Chianti Hills region and stretches between Elsa, Pesa, and Arbia river valleys. Ancient cobblestoned streets lined with old stone houses are perched on the hill, and they are wonderful for exploring and for soaking up the feel of ages past.

The most impressive sight is enormous 14th century Rocca or castle where you can learn about the Etruscan culture in a small museum. Visit beautiful old Church of San Salvatore to see the breathtaking 15th-century fresco Madonna with Child.

Some of the most beautiful palaces in and around the city are Palazzo Ugolini-Squarcialupi and Palazzo Bianciardi. Venture around the city and enjoy the view of the orderly lines of grapes and ancient olive groves and stop at one of many trattorias to try local wine and food.

4. Corniglia


Hike coastal cliffs and explore colorful homes in this quiet fall village.

Corniglia

© Courtesy of Pat on stock - Fotolia.com

Corniglia is one of five incredibly picturesque villages of Cinque Terre in Liguria in Northern Italy.

Its colorful old stone houses are clinging to the steep rock that on one side drops almost vertically to the Mediterranian and on three others is dotted with vineyards and olive groves. Corniglia is ancient, incredibly beautiful and unique, and it is connected to four other villages by the Sentiero Azzurro cliffside hiking trail.

To get to the sea and small picturesque port, you have to climb 382 steps cut in the stone, but there is also a normal road. The views from anywhere in the village are breathtaking, and spending some time roaming its streets and tasting the famous pesto in one of the local trattorias always makes for an special experience.

5. Florence


Admire Renaissance art and walk cobbled streets on a dream weekend getaway.

Florence

© Courtesy of nicomax - Fotolia.com

One of the wealthiest and most powerful European cities from medieval times, Florence is called “the cradle of Renaissance,” and its magnificent architecture, churches, and palaces full of art never stopped attracting artists and art lovers.

Its center is closed to traffic, and walking through ancient cobblestoned streets presents you with surprises on every corner.

Walk from the magnificent Duomo cathedral, the Uffizi gallery, and Pitti Palace to the Baptistry, the Bargello, and the Accademia and churches such as Santa Maria Novella and Santa Maria della Croce. You can also admire the priceless art treasures left behind by Leonardo da Vinci, Botticelli, Giotto, and Michelangelo. Cross the Ponte Vecchio Bridge over River Arne packed with artists and visit modern Florence in Oltrarno, spend some time in the majesty of Boboli Gardens, and go up the hill to the San Miniato al Monte church to take in the view of the timeless beauty of Florence.

6. Lucca


Bike the old walls and explore cozy alleys with the whole family.

Lucca

© Courtesy of daliu - Fotolia.com

Just a short drive from Florence, Lucca is one of the most beautiful cities in Tuscany.

Surrounded by wonderfully preserved 16th and 17th-century Renaissance walls, it is an ancient city perfect for walking and discovering the layers of its history in its cobbled streets, shady promenades, and glorious piazzas. The massive old walls are now topped by a large park wonderful for strolling and biking.

Stop by Casa di Puccini, a museum dedicated to the famous composer born within its walls. Visit the old Roman amphitheater at the Piazza dell'Anfiteatro, check out the Church of San Michele in Foro at the Piazza of San Michele, and climb the fascinating Guinigi Tower with holm oaks growing on its top. Don’t forget to find time to sit in one of many outdoor restaurants on the Lucca’s spacious piazzas to try the local goodies.

7. Manarola


See pastel buildings and walk cliffside trails on a breathtaking summer adventure.

Manarola

© Courtesy of orpheus 26 - Fotolia.com

One of the five incredibly beautiful villages of Cinque Terre on the rugged coast of Ligurian Sea, Manarola’s colorful houses look like they are piled on top of each other, dug into the side of the vertical cliff that drops into the sea.

Established in 12th century by inhabitants of the nearby village of Volastra, Manarola is the oldest of the five villages and has a unique fishing port – fishermen have to lift their boats by crane and park them on one of the terraces like cars.

You can explore the village through narrow steep streets and even jump into the clear blue sea and watch the incredible feat of engineering and human ingenuity while swimming on your back in the warm Ligurian waters.

8. Milan


Shop luxury boutiques and visit grand architecture on a stylish trip.

Milan

© Courtesy of Boris Stroujko - Fotolia.com

Once a capital of imperial Rome, the Milan of today is a modern metropolis in northern Italy; it is a European economic powerhouse and a fashion and design capital that is elegant, sophisticated, and incredibly beautiful.

Walking through downtown Milan means peeling back the layers of history, architecture, and art. With the Gothic majesty of Duomo cathedral, Leonardo da Vinci’s mural “The Last Supper” at the Santa Maria delle Grazie convent, Sforza castle, La Scala opera house, upscale shops at La Galleria, magnificent fountains, parks, passages, and squares, there is so much to see and enjoy in Milan.

And when you get tired, sit in one of the outdoor restaurants and enjoy superb Lombardian cuisine and good Italian wines and watch fashionable Milan residents go about their business.

9. Monterosso


Relax on sandy beaches and explore seaside cafes perfect for couples.

Monterosso

© Courtesy of pabrady63 - Fotolia.com

The only Cinque Terre village with a large beach and a waterfront promenade, Monterosso is the most popular with tourists and gets more crowded than its sister villages high up on the cliff.

The city traces its roots to 62 ancient hilltop residents of Monterosso who moved down to the coast in order to escape barbarian invaders.

There is a ruin of an old fortress up on the hill that houses the town cemetery, the spectacular Aurora tower, the San Francesco church with a magnificent Van Dyck painting, and narrow cobblestoned streets lined with old stone houses so Italian and so ancient you can almost imagine people passing through the area centuries ago.

Monterosso has a large modern hotel and a new contemporary part of the village on the other side of the Aurora tower.

10. Riomaggiore


Walk along colorful alleys and see fishing boats docked during a peaceful spring afternoon.

Riomaggiore

© Courtesy of Noppasinw - Fotolia.com

If you watch Riomaggiore from the sea, it looks like colorful kids’ blocks piled up on top of each other.

Snuggled in a small valley, the houses are built vertically into the steep cliff that drops down to the sea, where one can find a tiny wharf and even smaller beach. Riomaggiore is the first of five Cinque Terre villages as you travel from La Spezia and is their unofficial headquarters.

Its main and only street Via Colombo is where everything touristy goes on with a number of restaurants, shops, and cafes. Everywhere else you have to climb endless number of stairs, or take the scenic path of Via dell’Amore, which goes to the neighboring Manarola. The village is ancient and very charming, and it is a pure delight just being surrounded with so much history.

Map:


Plan Your Trip


Table of Contents: