Spend two weeks living "la dolce vita" on this relaxing getaway trip. Spend four days exploring rocky beaches and sprawling summer villas on the Amalfi Coast, then head to Sorrento for beautiful architecture and a cooking class. Go shopping in Naples' glass-roofed Galleria Umberto, then head to Rome to discover Roman ruins, cozy streetside cafés, and serene city parks.


  • Visit the old-time cliffside villages of Positano and Amalfi
  • View world-famous art in the Galleria Borghese
  • Go back in time to Ancient Rome with a tour of the Colosseum
  • Make—and eat!—the perfect Italian meal
  • Take a day trip to the island of Capri to see how Ancient Romans spent the summers

Brief Itinerary

Day Highlights Overnight
Day 1 Arrive in Rome, Transfer to Amalfi Coast, Positano Sunset Cruise Amalfi Coast
Day 2 Day Trip to Capri & Anacapri Amalfi Coast
Day 3 Wine Tasting & Vineyard Tour Amalfi Coast
Day 4 Free Day on the Amalfi Coast Amalfi Coast
Day 5 Transfer to Sorrento, Afternoon Cooking Class Sorrento
Day 6 Day Trip to Pompeii & Herculaneum Sorrento
Day 7 Transfer to Naples, City Tour Naples
Day 8 Free Day in Naples Naples
Day 9 Return to Rome, Afternoon Colosseum & Forum Tour Rome
Day 10 Vatican Tour: Sistine Chapel & St. Peter's Basilica, Rome Walking Tour Rome
Day 11 Galleria Borghese Tour Rome
Day 12 Food Tour of Monti Rome
Day 13 Free Day in Rome or Ostia Rome
Day 14 Depart Rome  

Detailed Itinerary

Day 1: Arrive in Rome, Transfer to Amalfi Coast, Positano Sunset Cruise

View of Positano from the water
View of Positano from the water

Welcome to Italy! Arrive in Rome, then take a high-speed train to Naples on the coast before making your way to your hotel in Amalfi. This stretch of coastline south of Naples is renowned for its exceptional beauty and iconic medieval cliffside fishing villages. Lemon groves and sprawling summer villas cling to the steep cliffs that lead to sparkling blue water. 

In the afternoon, head onto the water with a sunset boat tour to Positano from Amalfi. With its steep houses tumbling down to the sea, old-timey hotels draped in flowering vines, and restaurant terraces, Positano is an obvious favorite with travelers looking for a getaway. Soak in the views of the coast and the Tyrrhenian Sea from the boat as you enjoy a glass of Prosecco and some light aperitifs. Swim or snorkel in the clear blue waters, or simply enjoy the view. 

Disembark in Positano for a romantic dinner with ocean views. Enjoy a pasta dinner with fresh seafood paired with a glass of fruity falcanghina. Return to Amalfi for the night.

Day 2: Day Trip to Capri & Anacapri

Views from the Via Krupp
Views from the Via Krupp

Spend the day enjoying the sunshine, summer villas, and clear blue waters of Capri Island, known locally as the "pearl of the Mediterranean. Capri sits on the south side of the Gulf of Naples and is a popular destination. Ancient Romans used the island for summer villas for the Empire's rich and famous, while the Greeks called Capri the "Isle of Sirens."

In the morning, head out for a scenic drive along the Sorrentine coast to the Sorrento port, where you'll catch a hydrofoil to Capri. From here, go for a guided walking tour of the island's main attractions. See the main harbors (Marina Grande and Marina Piccola), walk along the Belvedere of Tragara (a villa-lined promenade with panoramic views), and explore the ruins of ancient Roman villas. Head up the hill to see Anacapri, the Piazzetta, and Augustus' Garden, as well as the best views of the Faraglioni Rocks. 

In the afternoon, return to the water to explore the Grotta Azzurra, a naturally hollowed sea cave, and soak in the sunshine on the beach.

Day 3: Wine Tasting & Vineyard Tour

Vineyards overlooking the Mediterranean
Vineyards overlooking the Mediterranean

Enjoy a full-day tour of the Marisa Cuomo Winery and experience the magic of the Amalfi Coast vineyards. The steep slopes, sunny weather, and warm breeze that blows from the Gulf of Salerno make the region perfect for growing wine grapes. Tour the vineyard, one of Italy's most renowned, and learn about the traditional techniques and dedication to excellence, which has earned Marisa Cuomo Winery both national and international recognition. Visit the estate's cellars and vineyards, taste the various wines, and enjoy the views.

In the afternoon, enjoy the sunny weather with one of these recommended activities:

  • Tour a Mozzarella farm and the Paestum Temples, which date back to 600 to 450 BCE
  • Enjoy nature in the Villa Cimbrone, a beautiful garden in Ravello
  • Soak in the sun at Gavitella Beach (Vettica Maggiore), Lannio Beach (Centra), and Arienzo Beach (Positano)
  • Get an adrenaline rush with a windsurfing adventure in Praiano

Day 4: Free Day on the Amalfi Coast

Lemons, a staple of the Amalfi Coast
Lemons, a staple of the Amalfi Coast

Today is a free day to explore the area and enjoy the pace of life on the coast. Go for a walk on the Lemon Path in Minori or see the illuminated sea cave Grotta dello Smeraldo. See the local ceramics manufacturing process in Vietri, or go for a half-day hike on the Path of the Gods

Other suggestions include:

  • Visit the beautiful Villa Cimbrone and Terrace of Infinity in Ravello 
  • Soak in the sunshine on Gravitella Beach in Vettica Maggiore, Lannio Beach in Centra, or Arienzo Beach in Positano
  • Try your hand at windsurfing in Praiano
  • Check out Praiano's nightlife at the Africana and Music on the Rocks nightclubs 
  • Rent a kayak and explore emerald green grottos, tiny hidden beaches, and impressive sea caves 
  • Enjoy a quiet day in the serene town of Atrani, far away from the hustle and bustle of the larger villages 
  • Explore the Fiordo di Furore, Italy's only fjord
  • Visit the Cloister of San Francesco in Sorrento, an oasis of tranquility that's located steps away from the town's historic Sant'Antonino piazza 
  • Enjoy nature in the Ferriere Valley Nature Reserve, famous for its postcard-perfect fishing villages and striking countryside crisscrossed with hiking trails

For dinner, head to a family-run restaurant for the best Italian pizza paired with a glass of the perfect local wine.

Day 5: Transfer to Sorrento, Afternoon Cooking Class

Cozy street side cafe in Sorrento
Cozy street-side café in Sorrento

After a relaxing breakfast, say goodbye to the Amalfi Coast and head north to Sorrento. Sorrento is a long-time favorite with Italian and international travelers for its beautiful views, tranquil atmosphere, and cascading lemon terraces. The city's focal point is the Piazza Tasso, a central square built over a gorge that splits the city. Other notable attractions include the beautiful nearby Marina Piccola Bay, the Villa Pollio Roman ruins in Capo di Sorrento, the Sorrentine Peninsula Archaeological Museum, the 11th-century Duomo, and the Basilica di Sant'Antonino, which houses the remains of the city's patron saint. 

In the afternoon, learn how to prepare traditional Italian dishes during a four-hour cooking class at the Sorrento Cooking School. The school is the first of its kind in Sorrento and offers daily cooking lessons for amateur cooks and for those looking to enjoy a day of learning about Italian flavors and ingredients from a talented local chef. 

You'll learn about traditional Italian dishes, including pasta, pizza, fish, and local desserts, as well as the techniques for preparing the perfect dough and the perfect garnish for each dish. Finish the course with a delicate pastry, then sit down to enjoy your hard work with a delicious meal. Buon appetito!

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Day 6: Day Trip to Pompeii & Herculaneum

Ancient street in Pompeii
Ancient street in Pompeii

Spend the day exploring two of the area's most notable attractions, Pompeii and Herculaneum, on a full-day guided tour. Start with a tour of the ruins of Pompeii, a bustling seaside city that was buried underneath 13-20 ft (4 to 6 m) of ash and volcanic debris after the 79 CE eruption of Mount Vesuvius. The ash, which killed many of the city's residents, acted as an archaeological time capsule by preserving many of the city's original buildings and features completely intact. 

The city was lost for 1,500 years following Mount Vesuvius' eruption before its accidental rediscovery in 1599. Items from jars to furniture were frozen in time, and even people who were unable to flee the oncoming ash were perfectly preserved. The walking tour of Pompeii's ancient streets will show off preserved villas, shops, public buildings, and plazas, giving you an insider's look into life 2,000 years ago. Afterward, stop in a local workshop to see the production process for various regional handicrafts, such as cameos and coral jewelry. 

Break for lunch, then continue to Herculaneum, the nearby city that was also buried by the ash. During ancient times the city was a holiday resort for the Roman nobility and wealthy. Today it is a manufacturing center for leather goods, buttons, glass, and wine known as Lacryma Christi (Tear of Christ). Your guide will show you around the city, pointing out key differences between this site and Pompeii. 

Return to Sorrento in the evening.

Day 7: Transfer to Naples, City Tour

Aerial view of Castel Nuovo and Galleria Umberto
Aerial view of Castel Nuovo and Galleria Umberto

In the morning, transfer to Naples. Naples sits strategically on the Bay of Naples near the still-active Mount Vesuvius and has been continuously settled for millennia. The city is renowned for its art, architecture, food, and religious frescoes. Naples's historic city center holds a UNESCO World Heritage Site denomination, and the city's many historic sights attract visitors worldwide. 

Notable city highlights include the 17th-century Palazzo Reale, which houses a museum and two theaters, the centrally-located Piazza del Plebiscito, the Teatro di San Carlo (one of the Royal Palace's theaters), the beautiful Galleria Umberto, a massive 19th-century glass-roofed shopping mall, and the Basilica di San Francesco, built as a tribute to the emperor. The Castel Nuovo (a fortress protecting the port), Baroque-Gothic 13th-century Duomo, and historic Via Toledo shopping street are also popular destinations.

Enjoy an afternoon guided three-hour tour of Naples by bus to see the above sites, as well as the historic Spaccanapoli Street and other top landmarks.

Day 8: Free Day in Naples

Intricate mosaics in the Toledo metro stop
Intricate mosaics in the Toledo metro stop

Today is a free day to explore the city. Select from the following suggestions to make the most of your time in Naples:

  • Visit the Naples Archaeological Museum to see Roman, Greek, and Renaissance-era ruins, including artifacts from nearby Mount Vesuvius
  • Tour the 6th-century Castel dell' Ovo, a seaside castle located on the former island of Megaride
  • See the 16th-century Museo Cappella Sansevero, which houses thousands of veiled sculptures
  • Go underground to see the network of tunnels and passageways in the San Gennaro Catacombs
  • Get outside in nature and see the dormant Solfatara Volcano, located a half-hour drive west of Naples
  • Head to the Santa Lucia district to experience authentic Naples culture
  • View world-class modern art in the Museo d'Arte Contemporanea, named after the Gothic 14th-century church that sits within its walls 

In the evening, go for a stroll along the Caracciolo e Lungomare di Napoli, a waterfront walking promenade, then head to the Quartieri Spagnoli, a lively commercial hub, for dinner at a small trattoria. On the way, stop to see the Toledo Metro station—Stazione della Metropolitana dell'Arte—to see beautiful mosaic inlays.

Day 9: Return to Rome, Afternoon Colosseum & Forum Tour

The ancient Roman Colosseum
The ancient Roman Colosseum

After a relaxing breakfast, it's time to say goodbye to Naples. Catch a high-speed train back to Rome, then check in to your hotel. The long-time center of the powerful Roman Empire, Rome boasts nearly 3,000 years of architecture, history, and culture. These days, Italy's capital is considered one of Europe's top cities thanks to its ancient monuments, incredible art masterpieces, and cosmopolitan vibe. It's center for fashion with a buzzing food culture and has a growing nightlife scene. Visitors and locals wanting to soak in the sunshine flock to the beautiful Giardino degli Aranci, the city's vibrant orange tree gardens on Aventine Hill, or relax in the lush greenery of the Villa Borghese Gardens.

In the afternoon, dive into the history of the Roman Empire with a walking tour of the Colosseum, the world's largest amphitheater. Walking through the ancient amphitheater is like taking a trip back in time to the days of the Roman Empire. Learn about some of ancient Rome's most famous and illustrious citizens, such as Julius Caesar, Emperors Augustus and Nero, and the Flavian Emperors who built the Colosseum. 

After visiting the Colosseum, continue to the Roman Forum and Palatine Hill. Walk along the ancient Roman street Via Sacra to see the Temples of Vesta, Antonino, and Faustina. See the ancient Basilica Julia and Aemilia and experience the grandeur of the Roman Empire.

Day 10: Vatican Tour: Sistine Chapel & St. Peter's Basilica, Rome Walking Tour

St. Peter's Square and the Vatican
St. Peter's Square and the Vatican

Today you'll visit the Vatican City museums and Sistine Chapel, as well as other top sights, for an exclusive six-hour tour of the city's incredible art and history. Start at the Vatican, where you'll visit the Pio Clementio Museum, Gallery of the Candelabra, Gallery of Tapestries, and Gallery of the Geographical Maps. Continue to see the magnificent Raphael Rooms, ending in the breathtaking Sistine Chapel and St. Peter's Basilica. Experience the magic of Renaissance art as you learn about the secret details and untold stories of the masterpieces.

Afterward, continue into a city for a tour of the city's most notable landmarks. Cross Piazza della Repubblica to see the Fountain of the Nyands, then continue to see the Trevi Fountain, La Colonna di Marco Aurelio, and the Palazzo di Montecitorio, which Bernini designed. Admire the exterior of the Pantheon and head inside for a look at the ancient Roman temple, then head to Palazzo Madama—the Senate seat—ending at Piazza Navona.

End your evening with a stroll to the neighborhood piazza for gelato and some people-watching.

Day 11: Galleria Borghese Tour

Exhibition of Gian Lorenzo Bernini
Exhibition of Gian Lorenzo Bernini

In the morning, stroll through the tangle of narrow streets in Centro Storico, one of Rome's most iconic historic districts, to see classical Roman and Baroque architecture and style.

In the afternoon, join a guided tour of Galleria Borghese, one of the world's premier art museums, to see works by extraordinary artists Bernini, Caravaggio, Canova, and Rafaello. The gallery's highlights include sculptures and paintings from Cardinal Scipione Borghese's collection (1579 - 1633). Admire Caravaggio's most important paintings, including "Boy with Basket of Fruit," and see Bernini and Canova's sculpture collection, boasting works such as "Apollo and Daphne" and "David." Rafaello's "Entombment of Christ" is also a must-see.

Walk through the ornate rooms of the Galleria Borghese and explore the splendid frescoes, stories, and masterful techniques behind the world's most beautiful art museums. End the tour with a peaceful stroll around the Villa Borghese gardens, enjoying its beauty and calm, far from the chaos of the city.

Day 12: Food Tour of Monti

Small cafe in the city center
Small café in the city center

In the morning, head to the Colle Aventino, one of Rome's famous seven hills. Stroll through the Roseto Comunale, the rose garden on the site of a former Jewish cemetery, and the Orange Tree Park overlook (Parco Savello), then find the famous keyhole, which gives visitors a direct view of the Vatican. Grab a cappuccino and lunch from one of the adjacent cafés. 

In the afternoon, go on a food tour to explore the eclectic (and less crowded) Monti neighborhood in the historical city center. Together with your guide, stroll through the cobblestone streets, making stops at small cafés to sample a variety of wood-fired pizzas, small plates, and alcoholic drinks. This tour is a great way to learn about Rome's history and local stories as you eat and drink your way through the neighborhood.

Day 13: Free Day in Rome or Ostia

Sun-filled street in Trastevere
Sun-filled street in Trastevere

Today is a free day to explore the city. Suggested activities include:

  • Visit the Museo Nazionale di Castel Sant'Angelo history museum 
  • Tour the Renaissance Villa Farnesina in the Trastevere district
  • Visit the historic and fascinating neighborhood of Testaccio to see the giant Monte Testaccio, an ancient pile of discarded olive oil jars from the second century 
  • Spend an afternoon at the Musei Capitolini, the oldest and one of the best museums in Italy

Or, head out of the city for a day at the Ostia beach for miles of sand and warm sea. In the evening, head back to the Trastevere neighborhood for dinner at an osteria or a trattoria, followed by drinks at a trendy wine bar.

Day 14: Depart Rome

Little details of life in Rome
Little details of life in Rome

Time to say goodbye to the country of love! After one last cappuccino over breakfast, head to the airport for your connecting flight home. Safe travels!

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Map of Relaxed Amalfi Coast, Naples & Rome - 14 Days
Map of Relaxed Amalfi Coast, Naples & Rome - 14 Days