21 Days in Italy: Rome, Naples, Amalfi Coast & Sicily

21 Days / Nights

21 Days in Italy: Rome, Naples, Amalfi Coast & Sicily

21 Days in Italy: Rome, Naples, Amalfi Coast & Sicily

21 Days / 20 Nights


Suggested itinerary

Day one: Arrival in Rome, Evening Food Tour in Trastevere

Welcome to Italy! What could be better than to start your time here with a tour delving into the history and culture of its famous food? Learn how Italian cuisine originated and evolved on this specialized tour throughout Rome, leaving you with a stomach full of delicious dishes and a head full of new insights.

This Trastevere Food Tour will take you to several locally loved venues for over 20 delicious tastings while admiring the beautiful architecture, cobblestone streets, and ivy-coated buildings. Tastings include, among others, 30-year-old balsamic vinegar, truffles, cheese, hams, D.O.C.G wine, pizza, homemade pasta, gelato, and more.

During your next stop, you will indulge in homemade fresh pasta and pizza from the oldest wood-fired pizza oven in Trastevere, and fine wine.

The tour ends at an artisanal gelateria. Become an expert in gelato, by learning how to spot the real from fake gelato. Favorite flavors include ricotta with caramelized figs and salted caramel.

Day two: Exclusive Private Guided Visit of Rome Highlights, Guided Visit of Vatican & Sistine Chapel

Enjoy the Italian «passeggiata», a walk in the heart of Rome to see the highlights during this privately guided visit of the eternal city. Throw a coin into the Trevi Fountain & learn the legend behind this iconic fountain; See why Bernini was one of the most prominent architects of Rome; Enjoy an Italian gelato and find out what makes gelato different from ice cream.

Visit the Vatican City Museums and the Sistine Chapel on a 3-hour guided visit. The Vatican is not only rich in history but also in art, housing some of the most important Renaissance masterpieces in the world–over 2000 years of history under just one roof! You’ll visit the Vatican highlights: Pio Clementio Museum, plus the Gallery of the Candelabra, the Gallery of Tapestries, and the Gallery of the Geographical Maps.

Continue through the museums to the Raphael Rooms, where you can admire the frescoes before entering the incredible Sistine Chapel and St. Peter’s Basilica. Your guide will help you experience the allure of Renaissance art by divulging secret details and untold stories throughout the tour.

The Vatican tour cannot be complete without immersing yourself in Michelangelo’s dramatic statue of the Pietà in St. Peter’s Basilica, a depiction of the Virgin Mary holding her dying child in her arms.Your guide will leave you inside St. Peter’s Basilica, allowing you ample time to continue your exploration. If you so desire, you can see the Papal Tombs and even climb to the top of the cathedral’s dome for amazing views.

Day three: Guided Visit of the Colosseum, Palatine Hill & Roman Forum, Sunset Frascati Wine Experience

Today you’ll visit the world’s largest amphitheater: the Colosseum. Your private guide will bring the Colosseum back to life by explaining how the gladiators entertained the crowds with spectacular fights and show you the engineering applied by the Romans to build such an imposing structure ahead of its time.

After the Colosseum, you will proceed to the archaeological site of the Roman Forum which represented the commercial, legal, and administrative center of ancient Rome. You will feel as if you were brought back in time during the Imperial age of Rome.

In the afternoon, you will visit the town of Frascati, which has been famous for its wines since the era of ancient Rome. Your guide, who is a Frascati local, will meet you at the train station to take you to a 16th-century Farmhouse. Here, accompanied by the winemaker, you will learn about how the artisanal winemaking tradition has been kept alive by a devotion to traditional winemaking techniques, incorporated into the production of our modern DOCG wines.

Day four: Excursion to Visit Roman Castles and Medieval Hilltop Villages

Visit some of the most beautiful hill towns near Rome following the road of the Castelli Romani, south of Rome. In picturesque Monte Porzio Catone, renowned as the city of wine, enjoy a wine tasting of the local wines, while in the lovely and magical town of Ariccia, filled with architectural gems, taste the mouth-watering Porchetta. In Castel Gandolfo, set in a beautiful setting you’ll admire the numerous villas built through the centuries by wealthy Roman families. In all the cities, you’ll enjoy free time to wander around these lovely hilltop villages

Today you will discover the Castelli Romani (Roman Castles) – a group of small villages located just a one hour drive from the busy city. Monte Porzio Catone is the first village you’ll visit. It is nestled between hills covered by olive groves and vineyards. Growing on this unique volcanic territory the grapes have a very distinctive flavor that can’t be found in any other place on the planet. Stop at a local traditional winery for a full wine tasting with some typical homemade delicatessen snacks.

Back on the road, drive along the famous Via Appia, ancient Rome’s gateway to the east, in order to reach Castel Gandolfo. This Apostolic Palace is still in use today, specifically by the Popes who have their summer residence here to enjoy the cooler climate. The next town is a short drive away. Ariccia was once the main residence of the powerful Chigi family, but today it is famous for roasted pork, known in Italian as porchetta. In the center wander the charming streets and check out Bernini’s Baroque Square, Palazzo Savelli-Chigi, and the Santa Maria Assunta church.

Day five: Rome to Amalfi Coast, Amalfi Coast Sunset Cruise

Experience the Amalfi Coast on a cruise. Sailing at sunset, you will depart from Positano or Sorrento, following the coastline, stopping at picturesque islands, and enjoying aperitifs while taking in the view. Along the coast, you will be able to see some local gems: Queen Giovannas Bath surrounded by the ruins of the oldest Roman villa of Sorrento, Marina di Puolo, Marina della Lobra, Mitigliano Bay, and Punta Campanella.

Day six: Private Full Day Amalfi Driving Experience

Your Private Full Day Amalfi Driving Tour begins with your private Chauffeur picking you up from your hotel in the Naples or Amalfi area.

The Amalfi Coast is a UNESCO World Heritage Site that features 13 stunning seaside towns, breathtaking blue sea views, and steep cliffs with beautiful houses defiantly arranged together on terraced landscapes. The steep, narrow, winding roads along this coastline offer memorable views and photo opportunities. But they can also pose a great challenge to drivers that are unfamiliar with the area. Your Private Driving Tour with us eliminates the stress of trying to navigate on your own and allows you to sit back, relax, and enjoy the ride!

Explore the historic center of Sorrento and admire its famous marquetry, ornate inlaid wooden boxes, furniture, and other items. Visit the historic town of Amalfi, once the important Maritime Republic, and famous for its historic white buildings and its Emerald Grotto. Climb the steep staircases of the vertiginous and posh town of Positano, admiring the pastel houses that seem to defy gravity. Travel back in time to Ravello, a charming town known for beautiful coral jewelry and features a collage of ancient, medieval, and modern architecture.

After a full day of immersing yourself in the rich local culture and unbeatable scenery, your tour will conclude with your private chauffeur returning you to your hotel. This luxurious adventure is a once-in-a-lifetime opportunity for making beautiful memories!

Day seven: Day Excursion to Capri Island and Anacapri

Texto day seven: 

Spend the day enjoying the sunshine and clear blue waters of Capri Island. Known locally as the «Pearl of the Mediterranean,» the ancient Greeks called it the «Isle of Sirens.» Capri sits on the south side of the Gulf of Naples and has been a popular vacation destination for millennia. The ancient Romans, in fact, built summer villas here for the Empire’s VIPs.

In the morning, you’ll head out to catch a hydrofoil to Capri. Visit the Marina Grande and Marina Piccola harbors, walk along the Belvedere of Tragara (a villa-lined promenade with panoramic views), and explore the ruins of ancient Roman villas.

Then head up the hill to Anacapri to see the Piazzetta and Augustus’ Garden, and enjoy the best views of the Faraglioni Rocks. Should you choose, you can later return to the water and explore the Grotta Azzurra, the famous «Blue Grotto,» which is located inside a hollowed sea cave. Afterward, we recommend spending the remainder of the afternoon soaking in the sunshine on the beach, before taking the ferry back in the evening.

Day eight: Amalfi Coast to Naples, Neapolitan Street Food Experience

Take a delicious journey of taste and flavors through the traditions of Neapolitan street food. Enjoy fresh buffalo mozzarella and let the pizza fritta (fried pizza) tickle your tastebuds. Learn the history behind one of the oldest cities in Italy, and hear stories and anecdotes, all while you enjoy a slice of pizza margherita and a shot of limoncello.

Listen to the story of the Greek polis via dei Tribunali and see one of the most ancient bell towers in Europe before being delighted by the unique taste of fresh buffalo mozzarella. Stop for some pizza fritta and listen to the story of Pulcinella d’Acerra, a funny Neapolitan theatre character from the 16th century.

You’ll discover the flavor of the frittatina, a mini omelet made with leftover pasta before heading to the small limoncello factory in the heart of the city. Smell the lemon zest as you enter and enjoy a sip of the citrus-flavored liqueur. Continue to San Gregorio Armeno, the road known around the world for its small shops and artisans dedicated to Christmas nativity traditions before heading to Spaccanapoli. Are you ready for dessert? Sfogliatella, baba’, or a gelato is waiting for you here! Just remember to come hungry and you won’t regret a single bite!

Day nine: Volcano Hiking Experience: Vesuvius, Free Afternoon in Naples

Today you will enter the Vesuvius National Park, where you can observe the vegetation and the beautiful views. You will hear explanations from a park guide about the numerous transformations of the mountain due to its volcanic nature, learning how this force of nature was able to destroy the cities of Pompeii and Herculaneum. Afterwards, you’ll have free time to walk around the crater and take photos before returning to Naples.

Afterwards, you’ll have a free afternoon in Naples, the third largest city in Italy, is one of the oldest, most artistic and most beautiful. A rich and intense mix of bustling street life, exquisite palaces, archaeological treasures and inspiring sights. Its historic center is also a UNESCO World Heritage Site. Welcome to Italy’s most unconventional masterpiece!

Day ten: Half-Day Trip to Pompeii

Today you head to Pompeii. Once a thriving city, all that changed in 79AD when the fearsome Vesuvius (which is still active) erupted. An earthquake destroyed what hadn’t already been decimated in the initial volcanic eruption. The town was covered in 4 to 6 meters of ash, perfectly preserving some bodies and animals which you can see on your tour! You will see the most important sights of Pompeii, including the Forum, and the Baths, as well as more humble establishments like the bakery and the brothel.

Day eleven: Naples to Palermo, Evening Guided Tour

At the designated time, a driver picks you up at your hotel for transfer to the airport for your flight to Palermo.

In the afternoon head out for a 3-hour guided tour of the city’s historical sites. Tour stops include the Piazzas Bellini and Pretoria to see their Arab, Norman, Byzantine, and Spanish art and architecture. Centuries of seafaring travel and influences from different cultures have resulted in eclectic and diverse architectural styles. You’ll see a lot of these influences during your stay in the city.

The tour continues across Palermo’s oldest street, the Cassaro, whose name comes from the Arabic word for «fortress». The street is also known as Via Vittorio Emanuele II. On the opposite side are the 13th century San Francesco Church (Chiesa di San Francesco d’Assisi) and the Piazza Marina. Take a walk around the plaza and the adjoining Garibaldi Garden to see ancient palaces used by the Spanish Inquisition. Tour the nearby Santa Maria dello Spasimo Church, a roofless 16th-century building with a quiet and contemplative atmosphere. You’ll also see Palermo’s massive Ficus tree, which stands in the Piazza Marina.


Day twelve: Palermo Street Food Experience

One great way to experience Palermo is on a street food tour. You’ll snack your way through the city’s historic streets while visiting back-alley markets, modest bakeries, old bars, and various food stalls while on the hunt for sweet and savory eats.

You’ll meet your guide in the morning and meander over to the Vucciria and Capo markets. These two open-air markets are so abuzz with activity that they’re reminiscent of Arab souks. You’ll discover how Sicily’s unique culinary history informs its street food scene as vendors of local produce and seafood proffer their goods.

Day thirteen: Free Day in Cefalù

Start your morning with a scenic one-hour train ride along the coast to Cefalù, a historic port town. You can start a self-guided tour in the city center at the Lavatoio Medievale, a 16th-century washhouse that utilizes running water from the River Cefalino in its stone basins. Nearby is the Porta Pescara, a gate to Cefalù Beach featuring great views of the coast. Perhaps take a walk to the old harbor and stroll the seaside promenade; the city’s Lungomare Beach is also a popular destination.

You should definitely visit the 17th-century Bastione di Capo Marchiafava, one of many old defensive fortresses located along the coast. In the evening, stop at a beachside bar for an aperitivo.

Day fourteen: Self-Drive Palermo to Trapani via Scopello and Zingaro Nature Reserve

Today you’ll venture west along the Tyrrhenian coastline to the port city of Trapani. En route, you can stop to visit one of Sicily’s popular parks, Zingaro Nature Reserve, Sicily’s first. Stunning at any time of the year, this national park stretches along the northwestern coastline of the Gulf of Castellammare between San Vito Lo Capo and Scopello and offers the perfect sea-nature destination. You may wish to bring a packed lunch with you to enjoy a picnic, after which you’ll continue further west to Trapani where the rest of the afternoon is yours to explore the historic city and its wonderful coast at your own pace.

Shaped like a sickle, Trapani sits at the foot of Mount Erice, along the western tip of Sicily and acts as a gateway to the Aegadi Islands. Settled in the 13th century BCE by the Elymians, its Old Town and port is easily walkable by foot and includes a number of notable monuments and churches, most of which date back to the late medieval period or 17th and 18th centuries.

Day fifteen: Trapani to Agrigento, Guided Tour of Valley of the Temples

You’ll have the whole day to explore Agrigento and its popular UNESCO World Heritage archaeological site, the Valley of the Temples. Meet with your licensed guide to walk through the well-preserved Greek temples and the ancient city of Akragas with the option to spend time at the popular archaeological museum.

Along the way, you’ll stop to marvel at the temples of Hera, Concordia, and Herakles as your expert guide reveals historical insight that brings the ruins to life. You’ll also learn how these ridge-top temples once served as beacons for homecoming sailors. After the tour, you’ll have the rest of the day to spend as you like.

Day sixteen: Agrigento to Syracuse, Guided Visit of Syracuse

Take the day to immerse yourself in historic Syracuse, a UNESCO World Heritage Site. Renowned for its rich Greek history, culture, architecture, as well as the birthplace of engineer and mathematician Archimedes, Syracuse was long regarded as one of the major powers in the Mediterranean.

Dedicate the tour to explore the ancient ruins of the Ionian coast on a guided tour of Syracuse (about three hours). Venture to the Neapolis Archaeological Park for a stroll among the ruins and ancient relics together with your expert guide. Learn about the region’s Greek and Roman history as you explore the architecture and then continue the walking tour through Ortygia—Syracuse’s beautiful old town, located on a spit of land which extends into the Mediterranean.

Day seventeen: Self-Guided Day Trip to Ragusa Ibla, Modica, & Scicli

Make the most of your proximity to the incredible UNESCO-listed cities of Ragusa Ibla, Modica, and Scicli. In 1693 a devastating earthquake almost erased every town and city in southeastern Sicily after which they were rebuilt in the Sicilian Baroque style.

First, drive 1.5 hours west to the hilltop town of Ragusa Ibla. You can meander the narrow lanes of its historic center, stopping to relax in a café or gelateria. If you’re up for it, climb the 250 steps to the 18th century Duomo di San Giorgio, a great example of baroque style.

About 30 minutes south of Ragusa Ibla is Modica. Built on the sides of a canyon, this city is known for its artisanal chocolate. Wander its labyrinthine streets through Modica Bassa (Lower Modica), where you’ll find many restaurants amid elegant 18th/19th-century buildings.

If there’s time, travel south (20 minutes) to the ancient town of Scicli. You can stroll its pedestrianized Via Penna for nice views of nearby baroque palaces and churches, or visit one of its most beautiful baroque buildings, the Palazzo Beneventano, located on nearby Via Duce d’Aosta. If there’s time, take the zigzagging path up to the 19th-century San Matteo Church. Perched on a cliff, it affords sweeping vistas of the town below. You can also visit an old cave settlement in the Chiafura district. After a full day, when you’re ready, make the 1.5-hour drive back to Syracuse.

Day eighteen: Syracuse to Catania, Catania Private Walking Tour

Enjoy a stroll in Catania city center with a private tour guide and see this stunning city through the eyes of a local. Let your knowledgeable guide show you many of the city’s main landmarks and listen to fascinating historical stories.

Stroll the city center with your professional guide who will fascinate you with the city’s history. Your guide will point out monuments built centuries ago that are still standing to this day. Many of the structures you will witness date back to the Greek colonization of the city back in the 8th century BCE.

Your tour will last about two hours and will include the following landmarks: the Piazza Duomo, Pescheria,Castello Ursino, Piazza San Francesco, Via Teatro Greco, Piazza Dante, Via Gesuiti, Scalinata Alessi, Piazza Università, Piazza Vincenzo Bellini, and the Piazza San Placido. If you are in Catania, this tour is simply a must-do!

Day nineteen: Mount Etna Half-Day Tour & Wine Experience

After breakfast, your guide will pick you up from your hotel to start today’s adventure to Mount Etna! Start with a hike accompanied by an expert naturalist guide. Along the route, you’ll discover craters, ancient lava flows, and breathtaking landscapes, and have the chance to explore a lava cave with helmets and torches.

After scaling Mount Etna, discover the famous wine of the region, notable for its distinct characteristics given by the fertile, mineral-rich soil surrounding the volcano. Taste a selection of local wines, and enjoy a typical Sicilian lunch made with local products.

Day twenty : Day Excursion to Taormina and Castelmola

Today you are greeted at your accommodation and drive to Castelmola: warm friendly people and spectacular panoramas characterize this village. Castelmola offers a balcony over Taormina and the bay of Giardini Naxos and is framed by the mysterious and beautiful active volcano, Mount Etna. Its narrow winding streets and Olde world charm make Castelmola a destination for anyone wishing to experience the enchanting beauty of Sicily from one of its most spectacular villages.

Then a short drive takes you to Taormina, the world-famous resort of Sicily. You will have the opportunity to visit the Greek-Roman Theatre. There are also several minor sites to be discovered around Taormina. The attractive principal thoroughfare, Corso Umberto is pedestrian and ideal for strolling and window-shopping. Picturesque lanes above and below the Corso are interesting to explore, while if you want to stretch your legs further there are attractive walks up into the hills, or down to the sea. Given its compact size, Taormina has a huge range of bars, cafes, and restaurants where you can spend pleasant hours while admiring the views.

Day twenty one: Depart Catania

Your trip finishes here! At the designated time, a driver picks you up at your hotel for transfer to the airport. Today you catch your flight home full of memories of Italy and wishing your stay had been longer.

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