Iconic Italy: Fast-Paced Exploration from Venice to Sicily

Mount Etna in Sicily, Italy.

What to expect on this itinerary

Discover Italy's diverse history, pristine nature, and contemporary culture on this 14-day journey. From hiking Mount Etna to zooming around Rome on a Segway, witness this magnificent country from many different vantage points. Be immersed in Italy's renowned cuisine, discover the wines of Chianti and Sicily, and attend a cooking class in Florence.

Countries Visited

Italy

Places Visited

Venice, Milan, Sorrento, Chianti, Amalfi Coast, Rome, Sicily, Taormina, Florence

Suggested Duration

14 Days

Customizable Itinerary

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Day 1

Milan - A Chic Arrival

Upon your arrival, you will be met and transferred by your driver to your accommodation in the heart of Milan. Depending on your time of arrival, you may wish to rest at your hotel or set out for an independent exploration of the city. Milan has emerged as a fashion capital, which is on full display throughout the city, especially in the Galleria Vittorio Emanuele II. You may also wish to visit some of Milan’s architectural gems, such as the Duomo, La Scala Theatre, or Sforza Castle.

What's Included:

Transfer
Accommodation
Day 2

Venice - Discover "La Serenissima"

Day 3

Venice - Wander the Canals

Day 4

Florence - Discover Florence's Magic

Day 5

Florence - Lean in at Pisa

Day 6

Florence - ATV Tour of the City

Day 7

Sorrento - On the Amalfi Coast

Day 8

Sorrento - Day-Trip to Capri

Day 9

Rome - Scoot through Rome

Day 10

Rome - Secrets at Vatican City

Day 11

Taormina - Fly to Sicily

Day 12

Taormina - Mount Etna and Wine Tasting

Day 13

Taormina - Luxuriate in Taormina

Day 14

Taormina - Departure

Trip Highlights

  • Explore the breathtaking Tuscan countryside of Chianti on quad-bike ATVs
  • Skip the line and hunt for secrets at the Vatican Museums
  • Visit Florence’s iconic churches and museums
  • Embark on an exhilarating hike on Mount Etna with a post-hike wine tasting
  • Enjoy a romantic gondola ride through the canals of Venice
  • Luxuriate in the classic beauty of Capri
  • Visit relics from Italy's ancient past
  • Indulge in the diverse cuisines from around the country, from regional dishes to local wine

Starting Price

$6,200 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.

4.9

Verified Traveler Reviews

Based on 909 reviews

Italy Trip Review: Milan, Florence, Lake Como, Venice, 11 Nights

When we started planning our trip to Italy, I knew I wanted to work with a travel agent—specifically, someone who specialized in Italy and was based there. After reaching out to several agencies and reviewing their responses, we chose Zicasso and, more specifically, our travel agent. She is based in Milan and from my very first interaction with her, I knew we had made the right choice.

Our trip could not have been more perfect. Our agent put a lot of thought into every location and planned activity. At the outset, we had a few discussions with her about what we wanted from the trip and, after that, we were happy to leave most of the details in her capable hands. Our goal was to explore mid-to-northern Italy and everything—from the hotels and tours to the free time and transportation—was beautifully organized.

Our 11-night trip started in Milan and ended in Florence, with overnight stays in Milan (one night), Lake Como (three nights), Venice (three nights), and Florence (four nights). Initially, I was hesitant about staying at Lake Como for three nights, but our agent encouraged me to do a little research. I’m so glad she did, as it turned out to be incredible. We had more self-guided time at Lake Como, which was perfect as we adjusted to the time change. In Venice, our itinerary became more structured, but we still had plenty of time for our own explorations. By the time we reached Florence, we had activities and tours planned for every day, which was just what we wanted.

A highlight for my family was a full-day trip into Tuscany, where we visited San Gimignano, an organic vineyard in Chianti, and finished with a tour of Siena. Our day trip to Rome allowed us to see the main attractions and we concluded the journey with a tour of Florence and the Accademia Gallery. Every tour our agent arranged was spot on.

Throughout our trip, she was wonderfully communicative—always available when we had questions, but never intrusive. She even helped us with a couple of last-minute requests: booking a hotel in Milan for one night and arranging train tickets to Verona for an impromptu visit to Juliet’s balcony. Whenever we needed something, she was there.

When we return to explore the mid-to-southern part of Italy, there’s no question that we’ll be asking her to plan our trip again. I highly recommend her to anyone looking for a seamless, thoughtfully curated Italian adventure.

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Italy Tour Review: Rome, Amalfi Coast, Taormina, Sicily, Sorrento, Capri, Mount Etna, Pizza-Making Class, Boat Ride, Wine, Local Cuisine, 9-Night Trip

We were absolutely thrilled with our first trip to Italy! This was a journey we had dreamed about for many years and we decided to make it happen as a special way to celebrate our anniversary this year.

The planning process with Zicasso was seamless, easy, and incredibly efficient. We were amazed by all of the thoughtfully planned activities, tours, and transfers throughout our trip. We visited Rome, the Amalfi Coast, and Taormina, Sicily—each destination offering something unique and unforgettable.

For this trip, we wanted a balance of adventure and relaxation, along with a few specific requests, and the team went above and beyond to make it happen. They truly bent over backwards to incorporate everything we envisioned and exceeded our expectations in every way.

We highly recommend traveling with Zicasso! They connected us with outstanding partners who truly elevated our experience and made our trip unforgettable. We honestly wouldn’t have changed a thing.

From the bottom of our hearts, Grazie mille!

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Italy Honeymoon Trip Review: Tuscany, Venice, Sorrento, Rome, Amalfi Coast, Pasta Cooking Class, Wine Tasting, Limoncello Tour, Local Cuisine, 10 Nights

My wife and I consulted with a handful of travel agencies in order to pick the right one for us to curate our dream honeymoon, and I could not be happier with our final decision to trust Zicasso’s tour company with this task.

Our travel agent was amazing throughout the process of building our itinerary, choosing experiences that fit exactly what we were looking for in an Italy honeymoon.

Start to finish, our overall experience was seamless. We decided to pack a lot into 10 nights, visiting Tuscany, Venice, Sorrento, and finishing the trip with one night in Rome. The tour company perfectly constructed our itinerary in a way that did not make our experience feel rushed in any of these locations. We had ample time to relax and explore these beautiful places on our own, while also fitting in world-class experiences specific to the region in which we were staying, all hand-selected by the tour company and their local expertise.

Every experience we had was incredible. From a private pasta cooking class and wine tasting in Tuscany to a limoncello tour in a quiet, picturesque village along the Amalfi Coast, each will be an experience my wife and I will never forget.

I would recommend this travel company to anyone visiting Italy for the first time or even those who have been to Italy, but want to experience breathtaking excursions curated by a local team of experts.

Our honeymoon was all we dreamed of and more, and I look forward to having the opportunity to use them for our next adventure.

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Italy Trip Review: Sorrento, Positano, Amalfi, Ravello, Pompeii, Herculaneum, Naples, 5 Days

Zicasso’s travel company helped us plan and execute a vacation to the Amalfi Coast. The travel specialists suggested sites and arranged hotels, ground transport, and guides. It was all accomplished flawlessly; we had a perfectly paced itinerary.

Not only were the drivers well experienced with the incredible labyrinth of roads along the coast and in Sorrento and Positano, where we stayed, but they were also great sources of local colorhighly experienced with the incredible labyrinth of roads along the coast and in Sorrento and Positano, where we stayed, but they were also great sources of local color and conversation, and, above all, they conversation, and, above all, showed their love for the country and region.

We had several guides who were spot-on, including an archaeology graduate for Pompeii and Herculaneum, and an incredible historian on a walking tour of Naples.

The hotels were wonderful, with experience and professionalism throughout.

The drive along the coast to Amalfi and Ravello was spectacular!

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Italy Tour Review: Venice, Tuscany, Rome, Amalfi Coast, Capri, Cooking Class, Ferrari Experience, 2-Week Vacation

We had the best time during our wonder trip to Italy. We explored Venice, Tuscany, Rome, and the Amalfi Coast. Zicasso's travel agency arranged the most beautiful hotels, with exceptional service, and fun and exciting tours in each location.

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Italy Family Tour Review: Rome, Amalfi Coast, Moliterno, Matera, Bari, Mount Vesuvius, 9-Night Trip

Our family of six just returned from the trip of a lifetime and we owe it all to our incredible Zicasso travel specialist. Every detail was thoughtfully planned, allowing us to simply relax, explore, and make unforgettable memories together.

Our journey began in Rome, where we stayed in beautiful hotels and were greeted by professional, reliable drivers who made every transfer seamless. From there, we traveled south by train to experience Mount Vesuvius, a truly breathtaking day that combined history, adventure, and spectacular views. Next came the Amalfi Coast, where we stayed in a stunning waterfront hotel. Waking up to the beauty of the Mediterranean each morning felt like something out of a dream. Every recommendation was perfect, from the accommodations to the transportation and, of course, the local restaurants.

One of the most meaningful parts of our journey was traveling to Moliterno, the hometown of my wife's family. Visiting the place where her family story began was an emotional and unforgettable experience. Our private driver made the journey comfortable and enjoyable, allowing us to fully appreciate the beautiful Italian countryside. From there, we continued to the ancient city of Matera, where we spent several incredible days exploring one of the most fascinating and beautiful places we've ever visited. Finally, we departed through Bari, enjoying one last glimpse of Italy's stunning Adriatic coast before heading home.

Throughout the entire trip, every hotel was exceptional, every driver was punctual and courteous, and every transition was effortless. The itinerary struck the perfect balance between iconic destinations, hidden gems, relaxation, and meaningful family experiences.

This wasn't just a vacation. It was a journey our family will treasure for the rest of our lives. We cannot thank our travel specialist enough for creating such a seamless, personalized, and unforgettable experience. If you're looking for someone who truly listens, plans with care, and delivers beyond expectations, look no further. We give our highest recommendation and are already dreaming about our next adventure together.

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Customizable Itinerary

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

32,000+ Verified Traveler Reviews