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How To Spend 3 Weeks In Italy Itinerary
Welcome to our 3-week tour of Italy, where you will have the opportunity to experience the best of what this beautiful country has to offer from the Mountains of the North to the Amalfi Coast and the glittering Mediterranean Sea.
You will discover the rich culture, history, art, architecture, and natural beauty of Italy, taste the delicious cuisine and immerse yourself in the local way of life.
Get ready to embark on a journey of a lifetime and discover the magic of Italy in 21 adventure-filled days.
Watch Our 3-Week Tour Video Overview Here
Day 1: Milan Walking Tour
A guided walking tour of Milan’s city center is a great way to explore one of Italy’s most vibrant and cosmopolitan cities. This tour will take you through some of Milan’s lesser-known gems, giving you a chance to discover the city’s unique character and hidden treasures.
The tour will start in the trendy Navigli district, known for its picturesque canals, charming boutiques, and trendy restaurants. Your guide will take you on a stroll along the charming canals, providing you with interesting information about the district’s history and culture.
Next, you will head to the Brera neighborhood, a charming and bohemian area filled with art galleries, antique shops, and trendy cafes. This neighborhood is known for its lively atmosphere and is considered one of Milan’s most artistic and cultural neighborhoods.
You’ll also pass by the famous Sforza Castle, a beautiful 15th-century castle that houses several museums, including the Museum of Ancient Art and the Museum of Applied Arts. Your guide will provide you with interesting information about the castle’s history and architectural significance.
The tour will also take you through the bustling streets of Milan’s fashion district, where you will see some of the world’s most famous designer boutiques. You will also pass by the famous La Scala Opera House, one of the most famous opera houses in the world.
See The “Last Supper” by Da Vinci
Visiting the Last Supper painting in Milan with a private guide is a unique and unforgettable experience. The painting, located in the Church of Santa Maria delle Grazie, is considered one of the most famous works of art in the world, painted by Leonardo da Vinci. Your private guide will escort you to the church and provide you with an in-depth explanation of the painting’s history and significance.
They will also give you a detailed tour of the church, highlighting its architectural and artistic features, and providing insights into the symbolism and meaning behind the painting. The Last Supper is a fresco painting and is considered a masterpiece of Renaissance art. The painting depicts the final meal shared by Jesus Christ and his disciples before his arrest and crucifixion.
Your guide will also provide information on the conservation and restoration process of the painting, which has undergone several restorations over the centuries. The painting is a must-see attraction for art enthusiasts, history buffs, and anyone who is interested in the religious and cultural significance of the painting.
Day 2: Guided Tour of Milan Cathedral With Rooftops
The Duomo Cathedral is one of the most iconic landmarks in Milan, and this special tour offers visitors the opportunity to experience the cathedral in a unique way. The tour starts at the top of the cathedral, where you will have access to the marble rooftop via an elevator. Here, you’ll be able to take in stunning views of the city while being surrounded by the cathedral’s Gothic spires and magnificent statues.
Once on the rooftop, you’ll be able to take pictures and admire the intricate details of the cathedral’s architecture. The rooftop is also home to several statues and sculptures that adorn the cathedral, including the famous Madonnina, a golden statue of the Virgin Mary that sits atop the highest spire of the cathedral.
After taking in the views from the rooftop, you’ll descend to the interior of the cathedral where you’ll be able to admire the grandeur and beauty of the cathedral’s interior. The Cathedral’s interior is adorned with frescoes, statues, and intricate stone carvings that tell the story of the city and its history. You’ll also see the famous golden altar, a magnificent piece of art that is considered one of the most beautiful in the world.
The tour also includes skip-the-line access, so you can enjoy the unique views of the city from one of the highest points without waiting in line.
Transfer To Como
Your private driver will deliver you and your luggage to Como in the evening. The journey will take approx 45 minutes.
Day 3: A Boat Tour of Lake Como
A full-day boat tour on Lake Como is a perfect way to explore the stunning beauty of one of Italy’s most famous lakes. The tour will take you on a leisurely cruise around the lake, giving you the opportunity to admire the stunning views of the surrounding mountains, picturesque villages, and grand villas.
The tour will begin in the charming town of Bellagio, known as the “pearl of Lake Como.” Bellagio is a popular destination and is renowned for its beautiful villas, charming cobblestone streets, and picturesque gardens. You’ll have the opportunity to explore the town and take in the views of the lake before embarking on the boat tour.
As you cruise around the lake, you’ll pass by the grand villas that line the shores. Some of the famous villas you will see include Villa Balbianello, Villa Carlotta, and Villa Melzi d’Eril. These villas are known for their beautiful gardens and fascinating history.
Your tour will also take you to the town of Varenna, a charming village that is known for its picturesque streets and views of the lake. You’ll have time to explore the village and take in the views of the surrounding mountains.
You’ll also visit the town of Menaggio, a charming town that is known for its beautiful villas and gardens. You’ll have time to explore the town and take in the views of the lake before returning to Bellagio.
This tour is an ideal way to experience the beauty of Lake Como and its charming towns while enjoying the beautiful views of the lake and its surrounding mountains.
Day 4: Wines & Cuisine of The Canton Ticino, In The Mendrisio Area
The Wines and cuisine tour of the Canton Ticino, in the Mendrisio area tour, is a unique and exciting experience that offers visitors the opportunity to explore the most beautiful and picturesque locations in the area, while sampling the region’s finest wines and traditional cuisine.
The tour begins at 9:00 am with departure by private car or van, with an English-speaking driver, who will take you to the first stop of the tour, the Azienda Agricola Fumagalli in Balerna. This is a family-run winery that produces some of the finest wines in the region. During the guided visit, you will have the opportunity to taste the wines and learn about the winemaking process.
After the wine tasting, you will enjoy a delicious lunch at Osteria Ul Furmighin, where you will be able to sample some of the local menus and taste the wines that are paired with the meal.
Following lunch, you will have a short visit to the Gole del Breggia Park, a natural reserve that offers beautiful views of the Breggia River and its surroundings.
After the park, you will continue to the Azienda Vitivinicola Avra in Castel San Pietro, another family-run winery where you will have the opportunity to taste more of the region’s wines and learn about the winemaking process.
Finally, at 18:00, the tour will be back to your accommodation in Como.
Day 5: Fast Train From Milan To Florence
Your chauffeur will deliver you to Milan station as you take your seats on the first class carriage as you prepare to make the 1 hour and 55-minute journey to Florence.
Upon arrival, your private driver will deliver you to your accommodation.
Day 6: Florence Museums Tour: Uffizi & Accademia
Your first stop of the day, The Uffizi Gallery is one of the most famous art museums in the world, and a guided tour is an excellent way to explore its vast collection. Your guide will take you through the galleries, highlighting some of the most famous works of art on display.
You will have the opportunity to see masterpieces such as Botticelli’s “The Birth of Venus,” “Primavera,” and “Adoration of the Magi.” The Uffizi Gallery also houses works by Raphael, Michelangelo, and Caravaggio, among many other famous artists.
Your guide will provide you with information about the historical and cultural context of the works on display, as well as the artists and their techniques. The tour also includes skip-the-line access, so you can avoid the long waiting times and make the most of your time inside the gallery.
Your guide will then take you to the Galleria dell’Accademia di Firenze, also known as the Galleria dell’Accademia.
A guided tour of the museum is an excellent way to explore its vast collection and learn about the history of Italian art.
The highlight of the museum is Michelangelo’s David sculpture, a masterpiece of Renaissance art and one of the most famous sculptures in the world. The tour guide will provide you with in-depth information about the sculpture and its significance in the art world.
The gallery also houses other works by Michelangelo such as the unfinished Slaves, and a collection of plaster casts of the artist’s works, as well as works by other prominent Italian Renaissance artists such as Botticelli, Ghirlandaio, and Rosselli.
Day 7: Florence Walking Tour
A full-day walking tour in the city of Florence is a wonderful way to explore one of Italy’s most beautiful and historic cities. The tour will take you through the charming streets of Florence, giving you the opportunity to experience the city’s rich cultural heritage and unique character.
The tour will start in the Piazza del Duomo, where you will be able to admire the stunning Cathedral of Santa Maria del Fiore, one of the most famous landmarks in Florence. The cathedral is a masterpiece of Gothic architecture and is known for its beautiful dome, which was designed by Filippo Brunelleschi.
You will then walk through the charming streets of the city center, where you will pass by some of Florence’s most famous landmarks, such as the Piazza della Signoria, a beautiful square that is home to several important statues and sculptures.
Next, you will head to the Ponte Vecchio, one of the most famous bridges in the world. This medieval bridge is lined with jewelry shops and offers beautiful views of the river.
The tour will also take you through the charming neighborhoods of Florence, where you will have the opportunity to experience the city’s unique character and charm. You will pass by charming squares, picturesque streets, and traditional markets that offer a glimpse into the local culture.
Day 8: Leaning Tower of Pisa, Lucca, & Wine
The tour starts at 9:00 am with your private chauffeur collecting you from your accommodation and making your way to the first stop of the tour, the winery Villa Maionchi. This winery is located on the hills and offers visitors the opportunity to taste some of the finest wines in the area and learn about the winemaking process.
After the wine tasting, you will continue to the town of Lucca, where you will have a guided visit along the old walls. These walls, which date back to the 16th century, are now a popular spot for walking and offer beautiful views of the town and the surrounding hills.
You’ll then have lunch at Osteria Baralla in Lucca, where you will be able to sample some of the local menus and taste the wines that are paired with the meal.
After lunch, you will continue to the Piazza dei Miracoli in Pisa, where you will have a guided visit to the Cathedral and Cemetery. The Piazza dei Miracoli is a UNESCO World Heritage site and is home to the famous Leaning Tower of Pisa, a beautiful marble bell tower that is known for its distinctive tilt.
Your chauffeur will return you to Florence in the evening.
Day 9: Transfer To Siena
This private chauffeured transfer will take approx 1 hour.
Siena Walking Tour
Siena, the treasure of Tuscany, is celebrated not only for its renowned annual Palio horse race but also for its well-preserved medieval heritage. The city center, a UNESCO World Heritage Site, showcases Siena’s rich history through its architecture and urban design, which rivaled that of neighboring Florence during its prime.
During this walking tour, history buffs will have the opportunity to step back in time as they stroll through Siena’s cobblestone streets and discover the Gothic details that have been preserved since the 12th to 15th centuries. This tour will transport you to a different era and immerse you in the charming atmosphere of this ancient Tuscan city.
Your tour will take you to the renowned 13th-century Duomo, featuring remarkable works by renowned artists such as Donatello, Bernini, and a young Michelangelo. You will stroll through picturesque side streets, surrounded by centuries-old terracotta buildings and rich history. Your guide will share fascinating anecdotes and trivia about the city as you explore.
When you need a break, take a seat in the bustling Piazza del Campo and soak in the local atmosphere like a true local.
Return to Florence in the evening.
Day 10: San Gimignano & The Chianti Classico
This tour offers a unique and exciting opportunity to explore the world of Gallo Nero, the famous black rooster, and the heart of Tuscany’s wine country. The tour will take you to the beautiful town of San Gimignano, a UNESCO World Heritage Site, where you will have a pleasant walking tour, and then to the charming towns of Badia a Passignano, and Greve in Chianti, renowned for their wine production.
The tour starts at 9:00 am with a departure from your location by a private Mercedes van and English-speaking driver, who will take you to the first stop of the tour, the town of San Gimignano. This medieval town is known for its beautiful towers and charming streets, and you will have the opportunity to take a guided walking tour and learn about the history and culture of the town.
After the walking tour, you will enjoy a delicious lunch at Restaurant Osteria delle Catene, where you will be able to sample some of the local menus and taste the wines that are paired with the meal.
After lunch, you will continue to visit the cellars of Setriolo and wine tasting, where you will have the opportunity to taste some of the finest wines in the area and learn about the winemaking process.
You will then visit the winery Buondonno, another opportunity to taste more wines and learn about the winemaking process. The tour will end at 18:30 when you will be back at your location in Florence. This tour is perfect for wine lovers and anyone who wants to explore the heart of Tuscany’s wine country.
Return to Florence in the evening.
Day 11: Montalcino & Montepulciano
This itinerary offers a unique and exciting opportunity to explore the famous wine region of Tuscany and discover the rich culture and history of the area. The tour will take you to some of the most famous and renowned wineries in Tuscany, where you will have the opportunity to taste some of the finest wines in the area and learn about the winemaking process.
The tour starts at 9:00 am with a departure with your English-speaking guide-driver, who will take you to the first stop of the tour, the Poggio di Sotto winery. This winery is known for its production of Brunello, one of the most famous wines in the world, and you will have the opportunity to taste the wine and learn about the winemaking process.
After the wine tasting, you will make a short stop at the San Antimo Abbey, a beautiful and historic abbey that is known for its stunning architecture and rich history.
After the visit, you will enjoy a delicious lunch at Restaurant Locanda Sant’Antimo, where you will be able to sample some of the local menus and taste the wines that are paired with the meal.
After lunch, you will continue to visit the winery Poliziano, where you will have the opportunity to taste Nobile wine and learn about the winemaking process. Then you will have a short stop in Piazza Grande in Montepulciano, where you will visit the ancient cellars of Palazzo Contucci, another opportunity to taste more wines and learn about the winemaking process. The Palazzo Contucci is an ancient palace that has been converted into a wine cellar, and it offers visitors the chance to explore the history and culture of the area.
In the evening you will make your way back to your accommodation in Florence with your chauffeur.
Day 12: Saturnia, Pitigliano, & Wine Tasting, Ending In Rome
Your private driver will pick you up from your accommodation and take you on an exciting journey to discover the beauty of Tuscany.
The first stop on the tour is the stunning Saturnia waterfalls, also known as “Cascate del Mulino” or “Cascate del Gorello”. These waterfalls have fascinated people from around the world for years. The water, which begins as raindrops falling on Mount Amiata, filters through the rocks, traveling for 40 years underground, and emerges as a miraculous gift of well-being in the center of the Terme di Saturnia Resort. The waterfalls are completely wild and can be visited at any time of the day.
Next, you will visit the charming town of Pitigliano, which is carved out of “Tufaceous” rock (volcanic rock) and sits on one of the suggestive tuff spurs. The town’s unique beauty is part of an area called “borghi del tufo” – towns carved of tuff stone – located quite close to the border of Tuscany and Lazio. You will spend approximately 2 hours here and have some time to eat before moving on to the next stop.
To finish the day, you will stop at a local winery to taste the delicious wines of the region. There’s no better way to end the day than with a glass of wine and memories of the beautiful sights and experiences you had on the tour.
End the day with your driver delivering you to your Rome accommodation.
Day 13: Rome Walking Tour
Experience the beauty of Rome on this guided walking tour that combines ancient history with modern life.
Your expert guide will take you on a leisurely stroll through the city’s historic streets and piazzas, visiting famous landmarks such as the Trevi Fountain, Spanish Steps, Pantheon, and Piazza Navona, as well as hidden gems along the way.
Get a deeper understanding of the city’s political, historical, and artistic significance, as well as the local legends and traditions that make Rome so captivating.
This is the perfect tour for first-time visitors to the Eternal City.
Skip The Line Colosseum, Roman Forum, & Palatine Hill
Embark on a journey through ancient Rome and discover the scandals, intrigues, and passions that shaped the city’s history.
This guided tour will take you through some of Rome’s most iconic archaeological sites, including the Roman Forum, Palatine Hill, and the Colosseum. Along the way, you’ll learn about the powerful figures who transformed Rome from a hilltop village to a global superpower.
You’ll explore the Colosseum’s history, including its construction on an artificial lake and the origins of its name, and you’ll be able to envision the bustling heart of ancient Rome – the imperial Roman Forum – while also taking in breathtaking views of the city both ancient and modern from the same hill where, according to legend, Rome was founded by Romulus.
Day 14: Skip The Line Vatican Tour: Museums & Sistine Chapel
Explore the riches of the Vatican on this guided tour, where you will witness some of the most incredible art and artifacts housed in the Vatican Museums.
Your expert guide will take you through the museum’s network of corridors and galleries, showcasing ancient sculptures, Renaissance masterpieces, and Michelangelo’s breathtaking frescoes on the Sistine Chapel ceiling.
Your guide will provide context and insights into the stories and scandals behind these famous works of art, and also introduce you to some hidden gems that are often overlooked by other visitors.
Get ready to be amazed and entertained by this feast for the eyes and mind.
Wine Tasting In Rome
Experience the rich and diverse flavors of Italian wine on a wine-tasting tour in Rome.
Led by a knowledgeable and passionate guide, you will taste a variety of wines from different regions of Italy, including the famous wines of Tuscany, Piedmont, and Veneto.
The tour will take you through the historic wine cellars and vineyards of Rome, where you will learn about the history and process of winemaking.
You will also discover the different grape varieties, how to properly taste wine, and how to pair it with food. Enjoy a guided wine tasting of some of the best wines, accompanied by delicious local cheeses, meats, and bread.
Day 15: Bike Tour On The Appian Way
Experience the history and beauty of Rome on a bike tour of the Appian Way. The Appian Way is an ancient Roman road that was built in 312 BCE and is considered one of the oldest and most important roads of the Roman Republic. The tour starts at the Appian Way’s starting point, the Porta San Sebastiano, and takes you through the ancient Roman countryside, passing by the remains of tombs, aqueducts, and catacombs.
Your knowledgeable guide will share with you the history and significance of the Appian Way, as you pedal past landmarks such as the Circus of Maxentius and the Baths of Caracalla. The tour will also take you through the Parco degli Acquedotti, an important archaeological site that is home to the remains of ancient Roman aqueducts.
One of the highlights of the tour is a stop at the Catacombs of San Callisto, an ancient underground cemetery where early Christians buried their dead.
Trastevere Food Tour
On this food and wine walking tour, take a culinary journey through the charming streets of Trastevere, one of Rome’s most picturesque medieval neighborhoods.
Led by a private guide, you’ll explore the area’s vibrant food and drink scene, sampling some of the best dishes and beverages Rome has to offer.
Your guide will help you tailor the tour to your tastes, whether you’re in the mood for traditional Roman street food, delicious cured meats, and cheeses, authentic Italian pasta dishes, or locally produced wine.
Discover hidden gems and family-owned businesses that have been serving the community for generations and get a taste of the local way of life.
From artisan cafes to lively wine bars and craft beer spots, this tour is a delicious way to experience the best of Trastevere.
Day 16: Fast Train From Rome To Naples
The journey time is just 1 hour and 15 minutes. Your chauffeur will be there to meet you at the station, collect your luggage and drive you to your accommodation in Naples.
Naples Street Food Tour
Take a culinary and cultural tour of Naples with a local guide who will guide you through the city’s historic streets and introduce you to the rich traditions of Neapolitan street food.
As you explore one of the oldest cities in Italy, your guide will share stories and anecdotes about the history and culture of Naples. Along the way, savor fresh buffalo mozzarella, and taste pizza fritta (fried pizza) and other local delicacies. A slice of pizza Margherita and a shot of limoncello, are two of the city’s most famous culinary specialties.
Day 17: Pick Up St Naples & Transfer To Pompeii
Just 20 minutes away from your Naples accommodation, your private driver will deliver you to the ruins of the ancient city of Pompeii where you will meet your private guide.
Pompeii Tour
Discover the rich history and fascinating ruins of Pompeii on this guided tour.
Led by expert guides, you’ll navigate the ancient city’s extraordinary relics and learn about its history in an engaging and interesting way.
Step back in time as you explore the Roman Forum, baths, theater, brothel, and ancient shops, and get a glimpse into the lives of the city’s former inhabitants through their houses and the streets they walked on daily.
One of the highlights of the tour is the opportunity to see the famous plaster-cast bodies of Pompeii’s citizens, frozen in their final moments as Vesuvius erupted. Learn about how and where the ancient Romans lived, the food they ate, and their daily activities.
Transfer From Pompeii To Sorrento
Your chauffeur will collect you at the end of your Pompeii tour to deliver you to Sorrento, just 30 minutes away.
Day 18: The Best of the Amalfi Coast Tour
Experience the beauty and charm of the Amalfi Coast on a one-day tour with a private driver guide. Your guide will take you on a scenic journey along the winding roads of the coast, passing by picturesque towns and villages such as Positano, Ravello, and Amalfi.
Begin your tour in Positano, known for its colorful houses that cascade down to the sea and its beautiful beaches. Take in the stunning views of the coast and the Mediterranean sea, and if you wish, you may take a stroll along the beach or take a boat tour to see the coastline from the sea.
Next, your guide will take you to Ravello, a small town perched high on a hilltop, known for its beautiful gardens, elegant villas, and the famous Ravello Music Festival. Take a stroll around the town, admire the views and visit the beautiful Villa Rufolo.
Finally, you’ll visit the town of Amalfi, which was once an important maritime republic, and is known for its beautiful cathedral, narrow streets, and picturesque piazzas. You’ll have some free time to explore the town on your own, maybe do some shopping and taste some local cuisine.
Throughout the tour, your guide will share with you the history, culture, and anecdotes of the Amalfi Coast and will be happy to make suggestions and recommendations according to your interests.
Day 19: Capri Boat Tour
Join our private boat tour of Capri and take in the island’s natural beauty and crystal-clear waters with a local sailor as your guide.
The tour includes stops at some of the island’s famous grottos such as the Blue Grotto, White Grotto, or Green Grotto. You will also have the opportunity to take a dip in the sea and explore the hidden grottos that surround the island.
To finish off the tour, you’ll be served a chilled glass of sweet limoncello, homemade by the boatman’s family. This tour offers a unique and relaxed way to explore the island, with stunning views and local insights that can only be provided by a true local.
Day 20: The Amalfi Coast Wine Tour
Experience the rich flavors and traditions of the Amalfi Coast on a full-day wine tour, starting and ending in Sorrento. The tour begins with a scenic drive along the winding roads of the coast, passing by picturesque towns and villages such as Positano, Ravello, and Amalfi.
Your first stop will be at a local winery, where you’ll learn about the history and production of the wines of the region and have the opportunity to sample a variety of wines, paired with local cheeses and meats.
Next, you’ll visit a family-run lemon farm, where you’ll learn about the cultivation of lemons and the production of limoncello, a traditional Italian liqueur. You’ll have the chance to sample different varieties of limoncello and purchase bottles to take home as souvenirs.
The tour continues with a visit to a traditional pasta-making factory, where you’ll learn about the process of making handmade pasta and get to taste some of the fresh pasta.
After a delicious lunch, the tour will take you to a scenic point where you can admire the beautiful view of the Amalfi Coast and the Mediterranean Sea.
The tour ends with a drive back to Sorrento in the evening, where you’ll have the opportunity to reflect on the day’s experiences and the delicious flavors of the region.
Day 21: Transfer to Airport
Your 3-week tour of Italy draws to a close as your private driver drops you off at the airport for your return flight home.
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Contact Our Itinerary Planning Specialists
Our 3-week from the Mountains to the Sea tour of Italy itinerary is a once-in-a-lifetime opportunity to experience the rich culture, history, and beauty of one of the most fascinating countries in the world.
From the ancient ruins of Rome to the charming streets of Florence and the stunning views of the Amalfi Coast, this tour offers an unforgettable experience. You will taste the delicious cuisine, and enjoy the art, architecture, and natural beauty that make Italy so unique.
If you are interested in a customized version of this tour, please do not hesitate to contact our tour planning specialists. We will be more than happy to help you plan an itinerary that meets your specific needs and interests.
Email us
Let us know your questions!
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