View of the city of Assisi and the Sacro Convento monastery, nowadays theological seminary, Italy

Amazing 14-Day Italy Itinerary with Capri

Ratings of Zicasso's Service

Customizable Itinerary

This is a sample itinerary to inspire a personalized trip designed with your travel specialist

Countries Visited

Italy, Vatican City

Places Visited

Rome, Sorrento, Vatican City, Capri...

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Suggested Duration

14 Days

Bask in the authentic charm and the simple wonder of Italy during your custom-tailored tour taking you from Rome to Capri, Lake Maggiore to Assisi. Travel across breathtaking horizons to uncover hidden sagas while gaining cultural insight into more than 3,000 years of history. Engage with the stories of the Medici family and witness the fruits of Michelangelo’s celebrated hands. Wander through lavish galleries showing the wealth of the former aristocracy and sample the treasured flavors of the...

Customizable Itinerary

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Trip Highlights

  • Enjoy the best views over the entire island of Capri by taking the open-air chairlift to the top of Monte Solaro 
  • Uncover the World War II history of Italy in the preserved and restored art found at the Monte Cassino Abbey and the Campo Santo in Pisa 
  • Wander into the hidden chamber of the mysterious Council of Ten who quietly pulled the strings of Venice inside the Doge’s Palace
  • Explore the intricate details of Milan’s Cathedral decorated with thousands of statues, poignant spires, and an equally dramatic Gothic interior 
  • Witness the breathtaking work of Michelangelo with the David in Florence and the captivating Sistine Chapel in the Vatican Museum 
  • Relax in the serene ambiance of Italian Alps when visiting the mixture of medieval and Belle Époque architecture of Bellagio on Lake Como 
  • Sample the remarkable breadth of flavor and aromas captured in the Tuscan wine Brunello di Montepulciano 
  • Discover the vastness of Pompeii with the unearthed art, architecture, and preserved history of infamous port buried under pumice and ash
  • Traverse the magnificent art of Rome captured in the elegant piazzas and famous fountains including Piazza Navona the Trevi Fountain 
  • Bask in the unique splendor of a meal inside the former villa of infamous Florentine philosopher Niccolò Machiavelli, author of The Prince

Detailed Description

Discover the best of Italy during your two-week tour featuring fantastic cities, enchanting towns, and the famous island of Capri. Celebrate the sweet life known as La Dolce Vitafanning the flames of your love affair with the cuisine and wine, history and culture. Pasta is delectable, artwork takes your breath away, and ancient ruins strike imposing figures shaping the heritage on which much of Western Civilization was built. Italy emphasizes its epic place in a contemporary and historical context as you visit the favorite cities of Rome, Florence, and Venice, intermixed with tranquil and charming Verona, Lake Maggiore, Assisi, and Sorrento. 

Your adventure crisscrossing the marvels of Italy begins with your arrival in Rome. Five nights in Southern Italy will bring to light the majesty of mosaics and phenomena of art spanning Etruscan settlements, Roman ruins, medieval frescoes, and the Renaissance evolution. The city of Rome brims with fascinating churches and adornments of the imperial capital. Visit the Pantheon, wander the galleries of Vatican to view Egyptian artifacts, Raphael’s staggering frescoes, and renowned ceiling painted by Michelangelo in the Sistine Chapel. Dive deeper into the history of the Second World War at the Abbey of Monte Cassino which once held 1,400 unique works of art. 

The Ruins of Pompeii reveal the iconic frescos of preserved businesses and sporadic mosaics featuring gods, battles, and allegorical figures. Spending time in the luxurious seaside city of Sorrento brings you near to the Amalfi Coast and an easy ferry ride to the shores of Capri. The island offers a sensational mixture of immaculate views, marvelous histories, and fashionable boutiques. The town of Assisi in Umbria represents the charm of preserved medieval hillside settlements while also accentuating the treasured life of St. Francis of Assisi with magnificent frescos decorating the iconic basilica.

Eight nights in Northern and Central Italy allow the wonders of storytelling, architecture, and artistry to merge and bring the diversity of Italy’s epic history. The city of Verona accentuates romance with the likes of Shakespeare’s Romeo and Julietwhile also basking in gardens, castles, and Roman ruins along the banks of the Adige River. Venice reflects the prestige of the former republic rising above the canals. The well-known and secret spectacles of the city surround St. Mark’s Square decorating the basilica and hiding within the walls of the Doge’s Palace. 

Milan’s graceful demeanor befits Italy’s capital of commerce and fashion embodied in the elaborate Gothic cathedral before you arrive on the shores of gorgeous Lake Maggiore. Spending time in the Italian Alps offers a relaxing ambiance, storybook scenery, and a connection to the endless charisma of the lakeside towns climbing up the mountainsides. The city of Pisa contains more than the Leaning Tower emerging as a place of beauty, thought, and artful talent. San Gimignano features elegant towers and remarkable views of the countryside and a different perspective on the battles between city-states in the past. Tuscany continues to shine with wines, villas, flavorful cuisine, and the splendor of preserved Renaissance architecture and artwork of Florence inside the Accademia, Duomo, and Museo dell’Opera del Duomo.  Read some Zicasso travelers’ Italy travel reviews to gain further inspiration for your own trip.

Starting Price

$3,845 per person (excluding international flights)

Your Zicasso trip is fully customizable, and this sample itinerary is a starting place for your travel plans. Actual costs are dynamic, and your selection of accommodations and activities, your season of travel, and other such variables will bring this budget guideline up or down. Throughout your planning experience with your Zicasso specialist, your itinerary is designed around your budget. You can book your trip when you are satisfied with every detail. Planning your trip with a Zicasso travel specialist is a free service.

What's Included

  • Accommodations
  • In-country transportation
  • Some or all activities and tours
  • Expert trip planning
  • 24x7 support during your trip

Your final trip cost will vary based on your selected accommodations, activities, meals, and other trip elements that you opt to include.

Reviews of Zicasso's Referral Service

4.87 stars based on 104 reviews.

Europe Travel Review: France, Greece, & Italy, Vatican...
"All of the detail and planning that was done worked out...

Reviewed By Garry B.

Family Trip to Italy Travel Review: Bergamo, Assisi, Siena,...
"Exceptional trip for a second time."

Reviewed By Tim C.

Family Trip to Italy Travel Review: Florence, Pompeii, Vatican...
"We really just had to show up and [the tour company] organized...

Reviewed By Jason D.

Luxury Italy Tour Review: Pompeii, Sorrento, Vatican City,...
"Every aspect of the trip was considered and managed for...

Reviewed By Bill B.

Vacation Review: Italy, Florence Walking Food Tour, Rome...
"Our guides...truly gave us a nice taste of these cities...

Reviewed By Josie P.

Italy & Greece Vacation Review: Venice, Santorini, Vatican...
"Our vacation with this travel agency and the travel planner...

Reviewed By Morgan F.

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