Looking for the best 2-week Italy itinerary for your next trip? Heading to Italy and wondering what to do on your 14-day stay? You’re in the right place.

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Travelers often find it difficult to plan a trip to Italy, and one can clearly see why. Rome, Venice, Milan, Florence, Amalfi Coast, Dolomites, Sicily…and we could go on and on. There’s just so much to see and do that putting together an itinerary can feel overwhelming. To help you out, in this article we suggest five alternative 2-Week Italy itineraries, each one tailored to fit a certain taste and style.

Are you dreaming of the postcard-perfect Italian summer escape? You simply must include a stop on the Amalfi Coast. 

If you’re interested in history, art, and architecture, then in Rome and Florence you will be in your element.

2-Week Italy Itinerary: Map

Before moving on to the list, take a look at the 2-Week Italy Itinerary Map below to get an overview and a sense of the distances involved.

2-Week Italy Itinerary Map First Timers

Now read on to compare all the itineraries in detail, pick the one that speaks to you the most, and start planning your Italian trip!

A) Best of Northern Italy – Milan, Lake Como, Cinque Terre, Venice

This 2-week itinerary highlights the absolute best Northern Italy has to offer, taking you from Cinque Terre in the West to Venice in the East, and throughout iconic Italian classics, such as Milan and Lake Como.

best 2-week italy itinerary cinque terre

Day 1-3: Milan and Lake Como

Milan is the perfect starting point for this Northern Italy 2-week itinerary. A dynamic, metropolitan city, Milan is famous for international events like Fashion Week and Design week, as well as its many landmarks. To name a few, the iconic Duomo Cathedral, the Cenacolo by Leonardo Da Vinci, Sforza Castle, and Brera district. In addition, Milan is just a 1-hour train ride from the dreamy shores of Lake Como. With a spectacular combination of mountain vistas, charming towns, and opulent villas, Lake Como is truly one of the most beautiful lakes and destinations in the world.

For more details on how to organize your 3 days in Milan and Lake Como, check out this post.

Day 4: Milan to Cinque Terre

Monterosso, one of the five villages of Cinque Terre (literally “five lands”), is just a 3-hour train ride from Milan. You can leave the city at 9 am and get there in time just in time for lunch. Monterosso is the most popular village of Cinque Terre, as it boasts a cute beach and is home to several dining options and hotels. Being also well connected to all the other towns, Monterosso is usually the village we recommend to pick for your stay in Cinque Terre.

Day 5-7: Cinque Terre

The five fishing villages of the Cinque Terre – Monterosso, Manarola, Vernazza, Corniglia and Riomaggiore – are among Italian Riviera’s most iconic destinations. All the villages are spectacularly scenic, each one in its own way, blessed with picturesque harbors, lush hillsides, dramatic cliffs, and colorful architecture. They are also conveniently connected through a local train service which takes you from one town to the next in just a few minutes. Ferries are a bit more expensive, but you’ll want to enjoy this signature experience (and view) at least once.

For more details on how to organize your 3 days in Cinque Terre, check out this post.

Day 8: Portofino Day Trip

North of the Cinque Terre is the stylish town of Portofino, which is a must-see as well. Once a small fishing village, Portofino is nowadays a glamour town full of exclusive hotels, boutiques, and restaurants. On a day trip to Cinque Terre, you have the chance to walk around its iconic narrow streets, have a fancy Italian Aperitivo and then visit Brown Castle.

Day 9: Cinque Terre to Venice

In order to get to Venice from Monterosso, you have to catch a train back to Milan first, and then hop on a direct train to Venice. The entire journey takes about 6 hours, so you may want to get an early start on day 9.

Day 10-14: Venice

At the end of your ultimate 2-week Northern Italy itinerary, you’ll be delighted to learn we have saved the best for last. Among those who’ve been lucky enough to see it in person, the conclusion is unanimous: Venice is the most beautiful city in the world.

During your 5-day stay in Venice, make sure to visit the iconic St. Mark’s Square first thing in the morning, before the big crowds arrive. Walk to the Ponte dei Sospiri (Bridge of Sighs), for that iconic shot. Stop in for a treat at one of the cute old pastry shops in the city, try out some zaleti, or a tiramisu, or (and?) a bigné. Stroll toward Rialto Bridge, the most famous of the four bridges that cross the Venice Grand Canal. Visit the Basilica di Santa Maria Gloriosa dei Frari, a Gothic church whose humble exterior conceals its soaring, beautiful interior. Walk down Campo Santa Margherita for some good old people watching, and then stop for a tramezzino at a local restaurant. Check out the Libreria Acqua Alta, one of the most unique bookshops in the world, where books are piled in bathtubs, bins, and even gondolas.

On your last day, take a Venetian water bus, the vaporetto, to San Giorgio Island and visit the beautiful San Giorgio Maggiore church. Slowly climb up to the campanile, and take in one last, sweeping view of Venice.

B) Italian Mountains and Lakes Milan, Lake Como, Venice, Dolomites

Do you like hiking? Are you looking for some beautiful routes and lakes in Italy? This 14-day Italy itinerary is the perfect one for you. Starting in Milan and moving West for a quick stop in Venice, this 2-week Italy itinerary has you exploring one of the most beautiful mountain ranges of Europe: the Dolomites.

best 2-week italy itinerary dolomites

Day 1-2: Milan and Lake Como

Thanks to the presence of multiple international airports, Milan is usually an ideal starting point for any Northern Italy itinerary. After one full day of exploring the city, hop on a train for a day trip to Lake Como. The ‘Greenway’ in Lake Como is a spectacular walking route of about 6 miles (10 km) which stretches from Colonno to Cadenabbia. This walk is suitable for everyone, both expert hikers and beginners, and offers spectacular views of the lake that you will fall in love with.

Day 3-6: Venice

Venice is just a 3-hour train ride from Milan, and you cannot possibly miss a visit to the most romantic city in the world.

Make your 4 days in Venice one of the best travel experiences of life. Admire the contour of gondolas floating on water, the Byzantine domes of the basilica watching over San Marco Square, and the arches of the Rialto bridge. Take in the incredible, romantic renaissance feeling to the city fueled by the centuries-old, untouched buildings.

Day 7: Venice to the Dolomites

This 2-week Italy itinerary takes you to the best hikes, summits, and lakes of the country. For this exact purpose, the next (and final) stop is to the worldwide famous Dolomites.

The Dolomites is the name of a mountain range located in North-Eastern Italy. It’s shared by the Italian regions of Veneto and Trentino-Alto Adige and given its proximity to the border with Austria, you’ll see many signs in German, too. The best way to discover the Dolomites is by car, which is why we highly recommend renting one at this exact point of your itinerary. Given its scale, there are several villages to choose from as base when traveling to the Dolomites. The glamorous town of Cortina d’Ampezzo is certainly ideal for travelers looking to do some winter sports but is also excellent for summer hiking. From Venice to Cortina d’Ampezzo, it is just a 2-hour ride.

Day 8-14: Dolomites

The entire region provides endless opportunities for outdoor activities and adventure, while still allowing plenty of relaxation among striking panoramas. This place is ideals for those who prefer to be among natural beauties rather than man-made attractions, at least for a portion of their 2-week Italy itinerary. Must-see in this region include Lake Braies, The ‘Tre Cime di Lavaredo’ hike, Lake Carezza and the “Seceda” mountain.

This article highlights the best places you absolutely must see while road tripping in the Dolomites, and the best hikes to do if you’re looking for some adventure. All the mentioned places and activities are listed by proximity to Cortina d’Ampezzo, so it’s easy to arrange a schedule according to your preferences.


C) Italian Classics – Florence, Tuscany countryside, Rome

This 2-week Italy itinerary will take you on a journey from the sunflower fields of Tuscany, through the beauty of Florence, and into the heart of Italy in Rome. The Tuscany countryside offers an incredible diversity of landscape and culture, not to mention some of the finest food and wine in the world.

best 2-week italy itinerary venice tuscany

Day 1-4: Florence

Florence is indisputably the city of Renaissance and Italian art, the city of Michelangelo and Brunelleschi, where beauty is always right on your doorstep. The striking architecture, the Uffizi gallery, and the little cobblestone streets make this famous city one of the most visited in Italy. Florence has incredible energy and a youthful feel that is absolutely unique in the country. Explore the art, shop, dine, go wine tasting or take a walking city tour to take it all in!

Day 4-6: Tuscany countryside & Val d’Orcia

As you may know, Florence is located in the beautiful Italian region of Tuscany. With scenic vineyards, charming villages, and jaw-dropping landscapes, Tuscany’s countryside is a must-visit attraction in itself.

Specifically, the area you absolutely must visit is called Val d’Orcia, located South of Florence and Siena. You may or may not have come across this name, however, you can be sure you have seen pictures of it. You know the quintessential Tuscany landscapes, with cypress trees, sunflower fields, rolling hills, and gorgeous villas? That is Val d’Orcia.

Day 8-14: Rome

From Florence, it is just a 2-hour train ride to Rome, the eternal city.

After more than 2,000 years in existence, there are enough things to see to keep you busy for years – delicious Italian food to indulge in, plenty of archaeological sites, churches, and museums to visit, and enough art to overload your senses. You’ll see, Rome is an open-air museum. From the Colosseum to the Trevi Fountain and St. Peter’s Basilica, get ready to have your mind blown.

D) La Dolce Vita – Rome, Amalfi Coast, Capri

If you are looking for the crème de la crème in romantic Italy itineraries, look no further. Starting in Rome, and ending in the postcard-perfect Amalfi Coast, this 2-week Italy itinerary takes you where la Dolce Vita can actually be lived. If you’re looking for a balance between cultural explorations and a romantic getaway, this is the perfect itinerary for you.

best 2-week italy itinerary amalfi coast

Day 1-7: Rome

Your first stop is Rome and that is something for you to be really excited about. There are just too many reasons to fall in love with Rome: the magnificence of the Colosseum and the Roman Forum; the exquisite Baroque of Piazza Navona; the art galleries and antique shops of Via Margutta; the crowded trattorias of Trastevere; the scooter-driving Romans. Rome is a city like no other in the world, which is why no travel guide will ever come close to accurately describing such a place. All you can do is go and see it for yourself.

Day 8: Rome to Amalfi Coast

The Amalfi Coast is no doubt one of the most beautiful places on the planet.

However, getting there can be a bit of a challenge, as there is no direct transportation from Rome to the Amalfi Coast. The best option if you’re on a budget is to take a high-speed train from Roma Termini to Salerno Station, and from there take a bus directly to the town of Amalfi. Alternatively, you can take a high-speed train from Roma Termini to Naples, and then hire a private driver to take you to the Amalfi Coast.

Day 9-14: Amalfi Coast and Capri

Pastel-colored houses perched on the sides of lush cliffs. Terraced groves where lemons are cultivated to be turned into delicious limoncello. The ever-present sight of the sun-soaked blue sea.

This is the Amalfi Coast.

A small corner of Southern Italy consisting of over 10 towns that vary in size, the Amalfi Coast is one of the most romantic places in Europe. Positano is the first cliffside village. Have your camera ready, because this gorgeous little town is every photographer’s dream. Lying between Positano and Amalfi, Praiano is a tranquil fishing town still unknown to many, but absolutely worth a visit. Immediately after Praiano, along the highway, you can find the only fjord existing in Italy, Furore. Tucked in between green mountains and sea, Amalfi is an elegant town full of artistic monuments, antique shops, and fascinating traditions. A few kilometers away, high up in the mountains, Ravello is a terrace over the sea, with its two Villas – Villa Cimbrone and Villa Rufolo – that will take your breath away. And then there’s Capri. The legendary, glamorous island is just a short ferry ride from the Amalfi Coast and an absolute must-see.

This 2-week Italy itinerary allows plenty of time to explore this incredible region and absorb its unique spoils. For more details on how to organize your 5 days in the Amalfi Coast, check out this post.

E) Sicilian Adventures – Northern Sicily and the Aeolian Islands

Thinking of a scenic Mediterranean island for your next trip? Looking for more interesting, off-the-beaten-path 2-week itineraries for Italy? Head to Sicily for an unforgettable road trip. Sicily is the largest Italian island, and its combination of beautiful beaches, fascinating towns, and wild mountains make this place a perfect destination for adventure lovers. The island is full of history too and crammed with ancient artistic gems and architectural treasures.

Starting in Palermo and ending in the elegant Aeolian Islands, this 14-day itinerary shows off the best Northern Sicily has to offer.

best 2-week italy itinerary sicily

Day 1-3: Palermo

Your own Sicilian love affair starts in Palermo, the island’s capital and biggest center. Once a melting pot of a million different influences, the city is home to numerous architectural styles, and you’ll often find Arab Norman-style buildings right next to Baroque churches. A locals’ favorite, the ancient markets of Ballarò and Capo are the perfect places to discover Sicilian traditions. Wander down the maze of narrow cobbled lanes where kiosks are piled with piles of cherry tomatoes, spicy cheeses, olives, capers, spices, and so much more.

And if you need a bit more relaxing time, you’ll be happy to know the famous Mondello beach is just an easy 20-minute bus ride from the center of Palermo.

Day 4-6: Zingaro Reserve and Scopello

Day four of this Sicily itinerary leads you to a unique place that is very close to Palermo, yet feels a million miles away: the Zingaro Reserve.

The Zingaro Nature Reserve is a scenic national park that follows an 8km stretch of coast and is located precisely one hour west of Palermo. This is the perfect place to organize days of trekking through jaw-dropping cliffs, amazing views, and gorgeous hidden beaches you can stop at for a refreshing swim. Just a couple of miles away, Scopello is a medieval village that recently became Instagram-famous for its picturesque Tonnara, an old fishery operating till a few years ago.

Day 7-9: Cefalù

In Cefalù it’s easy to combine sightseeing with some relaxing time at the beach: once a fishing village, the city boasts a long sandy beach that lies right at the foot of the historic old town. The maze of buildings and streets that suddenly end in the sea is a unique sight to behold, and the entire city is permeated by this incredible vibe that rises from the beach.

Use it as the locals do, for a sunset stroll, a cool place to visit to simply relax on a bench with a granita or gelato in your hand, and watch the sea roll in.

Day 10: from Cefalù to the Aeolian Islands

From Cefalù, it’s a 1.5-hour ride west to reach Milazzo. And off Sicily’s northern coast, at a 2-hour ferry ride from Milazzo, are the volcanic Aeolian Islands. Formed by volcanic eruptions, the Aeolian Islands are seven inhabited islands surrounded by the Tyrrhenian Sea in the north of Sicily: Lipari, Vulcano, Salina, Stromboli, Filicudi, Alicudi, Panarea, and Basiluzzo.

Pick one as your home base, and spend your days exploring the others by boat.

Day 11-14: Aeolian Islands

Lipari is the largest and most popular island among tourists who enjoy hot springs and charming architecture. Another traveler favorite, Panarea is perhaps the most fashionable and expensive of the islands. The islands of Stromboli and Vulcano feature both active volcanoes, and many adventurous visitors take the opportunity to hike up their craters. The island of Salina, my personal favorite, is known for its delicious food, mountain peaks, and laid-back vibe.

Far from the crowds, Filicudi and Alicudi are the oldest islands of the archipelago, the furthest from the coast, and therefore the most authentic and unspoiled.

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