10-Day Epic Italian Holiday

Advisor - Amna Ismail
Curated By

Amna Ismail

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  • Italy

  • Active Travel

  • Adventure Travel

  • Arts & Culture

  • Beaches

  • City Travel

  • Food & Wine

  • Luxury Travel

  • Multi-City

  • History

  • Countryside

a colorful city perched atop the hillside of an island
Curator’s statement

Stunning views, beautiful beaches, delicious cuisines, and magnificent architecture! Italy has everything you might look for in an incredible travel experience. Italy is known for glamour, leisure, and a zest for life. If you are a history buff, you will love the immersive experience of luxury, culture, authenticity, and heritage. Travel to Italy for a dose of history, adventure, shopping & fun. Making everlasting memories with your loved ones with this 10 days in Italy travel guide. Make sure you read till the end, I have some bonus tips for you!

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Where to stay

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Palazzo Manfredi

Housed in a 17th century residence just a stone's throw from the Colosseum, this small luxury hotel is in the very heart of Imperial Rome.

Fora Perks
  • $100 food / beverage credit.

  • Breakfast daily.

  • Upgrade & extended check-in/out whenever possible.

Le Sirenuse

Positano's most iconic hotel remains family-owned, full of character and always in demand.

Fora Perks
  • $100 hotel / resort credit.

  • Breakfast daily.

  • Upgrade & extended check-in/out whenever possible.

Aman Venice

Luxury property set in a 16th-century palace with elegant rooms near the Grand Canal.

Fora Perks
  • $100 food / beverage credit.

  • Breakfast daily.

  • Upgrade & extended check-in/out whenever possible.

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Advisor - Amna Ismail

Unlock perks by contacting Amna to book your trip.

Day 1: Arrive in Rome

view from the tops of a shallow set of stairs that lead to a bustling old city

Notable attractions, Spectacular Ancient Architecture, & Delicious Italian Cuisine

Upon arrival a car awaits you to transfer to your hotel to relax for a few hours before you start exploring this historic city.

The first stop is Piazza Navona, a famous square enclosed by beautiful Baroque buildings and features three magnificent fountains. There is something for everyone. Stroll through to explore numerous street performers, artists, cafes, and restaurants. You will love the diversity of Piazza Navona which brings a lot of energy with its vibrant and lively atmosphere.

Walk along to check out the Pantheon and witness the beautiful Fontana di Trevi also known as Trevi Fountain, and throw a coin into the fountain with your right hand over your left shoulder which ensures that you will return to Rome someday.

Next we head to the Spanish Steps, or Scalinata di Trinità dei Monti, a famous staircase located in Rome's historic centre. At the bottom of the Spanish Steps, you will find the Barcaccia Fountain, another beautiful example of Baroque architecture. Take some time to unwind at a corner cafe or go shopping at some of the best luxury retailers.

Day 2: Visit the historical center of Rome

birds eye view of a ancient city with a central Colosseum

Historical Center, Masterpiece of Renaissance and Baroque Art

With a private guide you will take a step back in time to the historic centre of Rome by visiting the Colosseum and Forum where spectacular ancient architecture, stunning fountains, and historical tombstones are sure to take your breath away. Rome has a maze of narrow streets and alleys, and strolling through the winding cobblestone streets is a truly memorable experience.

Appreciate the art beautifying every street, square, and sidewalk…so magical, so unique.

Day 3: Vatican Museums and Sistine Chapel

hall of a museum with ornate tile and sculptures lining the walls

Paintings, Sculptures, and Tapestries

Witness a vast collection of paintings, sculptures, tapestries, and other works of art from around the world at the Vatican Museums and learn everything about the Vatican’s history. An expert guide will walk you through the Vatican Museum and Sistine Chapel. Inside the museum you will find art from masters like Raphael, De VInci, Michelangelo, Romano, Laureti, Reni and more.

Bring your walking shoes as you will get your steps in today! Take in all in and then unwind with a quick bite at Pinecone Courtyard Cafe and tickle your taste buds with Italian specialties as you explore the Vatican Museums and Sistine Chapel. However, if you want to eat in a more casual environment, you can visit the nearby L'Isola della Pizza, which serves up tasty pizzas.

Day 4: Train to Naples and drive to Positano

a coastal city on the side of the mountain with colorful buildings and a busy harbor

Breathtaking Views, Calmness, Serenity

Positano is breathtaking and the energy you feel there is unlike any place else. Take the train from Rome to Naples and then head to Positano to experience the magnificence of Southern Italy.

The train ride to Naples offers breathtaking views of the Italian countryside along the way. Once you exit the train your driver awaits to take you through the breathtaking and beautiful journey to Positano.

The 1/1.5 hour drive to Positano is truly unforgettable as you get to experience the stunning views of the Mediterranean Sea and the rugged cliffs that define the coastline.

Settle into your hotel and enjoy the views and walk around town. One of the most famous landmarks of Positano is the Church of Santa Maria Assunta, which is located at the top of a flight of steps and features a colourful dome that can be seen from afar. You can also explore the many boutique shops, cafes, and restaurants that line the streets of the town.

End your day in the utmost calmness and serenity that is Positano, unwind at your hotel, relax, and recharge for the next day.

Day 5: Explore Positano and Sorrento

view of an island coast on a clear day

Local Culture, Beach and Sights

Positano is home to several beautiful beaches, including Spiaggia Grande and Fornillo Beach, where you can soak up the sun and enjoy the crystal-clear waters of the Mediterranean. There are also several hiking trails in the area, including the famous Path of the Gods, which offers breathtaking views of the coastline.

In Sorrento, you can visit the 14th-century cathedral and the ancient Roman ruins at the Villa Pollio.

If you're feeling active, both Positano and Sorrento have some great hiking trails that offer stunning views of the coast. The Path of the Gods is a popular trail in Positano, while the Valle delle Ferriere is a beautiful hike in Sorrento.

Day 6: Boat to Capri

yellow boat in rock formation emerging from the ocean water

Magnificent Rock Formations, Fishing Villages, Hidden Coves, and Rugged Cliffs

Today you’ll explore Capri and its surroundings. Set sail on your private charter and head to the famous Blue Grotto, located on the northern side of the island. The Blue Grotto is a natural sea cave that glows with an otherworldly blue light, thanks to the sunlight reflecting off the water. You can take a small boat to enter the cave and admire its beauty.

Take a boat tour around the island to see its rugged coastline and hidden coves. Once you arrive at the Marina Grande, take the funicular to reach the town of Capri, located on the top of the hill. The funicular ride takes about 3 minutes. Lunch at one of the cafes in the town square, Piazza Umberto I.

From there, you can enjoy stunning views of the sea and the island. Alternatively, you can spend the midday exploring the town of Anacapri, located on the western side of the island. Anacapri offers a more relaxed and less crowded atmosphere than Capri town, and you can visit attractions such as the Villa San Michele, a museum and garden that offers stunning views of the sea. Head back to Capri town in the late afternoon and take a stroll along the pedestrianised Via Camerelle, where you can find high-end boutiques and designer stores.

Enjoy an aperitivo at one of the bars in Piazza Umberto I, where you can sip a refreshing cocktail and people-watch. For dinner, try some of the local seafood dishes at one of the restaurants in town, such as Ristorante Michel'angelo or La Capannina. Finish off your meal with a Limoncello, a sweet lemon liqueur that is a specialty of the region.

Don't forget to bring sunscreen and a hat to avoid sunburn.

Day 7: Positano to Naples and then fly to Venice

bridge over a canal

Luxury & Stunning Views

Car to Naples and flight to arrive in Venice, take a water taxi to your hotel. When in Venice, strolling around the squares will give you an absolute immersion in the Venetian atmosphere!

Plan to explore the main tourist spots, landmarks, and attractions. Some must-see sights include St. Mark's Basilica, the Doge's Palace, Rialto Bridge and the Bridge of Sighs. Venice has a rich culinary tradition, and you have many options to indulge in some of the finest restaurants, offering gourmet cuisine and exceptional wine lists.

Day 8: Explore Venice

canals of venice

City of Canals, The Floating City, and Serenissima

Apart from the architecture, Venice is also famous for its art and culture. You can visit the Peggy Guggenheim Collection, the Accademia Gallery, and the Palazzo Grassi to indulge in the artistic heritage of Venice. Venice has a long tradition of opera, and several historic theatres offer performances throughout the year.

Perhaps the most enjoyable thing about exploring Venice is simply getting lost in the maze of narrow streets and alleys. The city is full of hidden gems, such as local shops, cafes, and markets. Take a stroll through the backstreets to discover some of Venice's hidden treasures.

Day 9: Train to Milan and explore the city center and shop

colorful street on a canal

Extraordinary Fashion & Ultimate Shopping Experience

Sit back, relax, and immerse in the beautiful Italian countryside as you travel from Venice to Milan.

Once you arrive in Milan, there are plenty of hotels to choose from from luxurious and modern design, to a more traditional and charming experience.

The city centre of Milan is a must-visit destination, you should take some time to explore the city centre and indulge in some retail therapy. Don't miss the opportunity to visit the iconic Duomo, which is one of the largest Gothic cathedrals in the world.

You can’t resist shopping in Milan. For high-end designer brands, head to the Quadrilatero della Moda, also known as the "fashion quadrilateral". For a more local shopping experience, check out the Navigli district, where you'll find independent boutiques and vintage shops. Buy souvenirs to take some beautiful memories home.

Day 10: Late Checkout and Fly Back Home

historic city at golden hour

Take your time and enjoy your last day in Italy to the fullest. Late check-out will give you flexibility and a chance to enjoy your last few hours before heading back home.

Get a massage before you leave and reflect on the beautiful journey you have had. It’s time to cherish the moments and bring back home beautiful memories that you will cherish forever.

Pro Tips for a Hassle Free 10 Days in Italy

  • Italy has a Mediterranean climate, so it's essential to pack layers to accommodate temperature changes throughout the day.

  • Comfortable shoes are a must, especially when exploring the cities by foot.

  • Keep your camera with you to capture beautiful memories that you can cherish for life.

  • Always keep a mix of payment methods, cash, credit cards, or traveller's checks.

Advisor - Amna Ismail

Travel Advisor

Amna Ismail

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This guide is part of our ongoing series on travel to Italy.