Iconic Italy: Fast-Paced Exploration from Venice to Sicily

View of Capri Island from Mount Solaro in 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 39 reviews

Mary a.
Italy 3-Week Trip Review: Ravello, Positano, Vintage Fiat Ride, Cooking Class, Lemon Tour

We want to thank you and your team for planning an amazing trip for us. We got home late Monday and are still reliving all our fabulous experiences.  Ravello and Positano are just magical.All are transfer drivers were so prompt, on time and friendly. Vehicles were clean and beautiful. Seamless!The hotel in Positano had a wonderful staff. Our room, the Comfort Suite had a lovely water view with spacious terrace. They had a vintage Fiat whose driver would take us to town and our dinners complimentary. A real plus.The Amalfi Lemon tour was at times difficult with a lot of climbing and walking, so be aware of this with your clients who have any walking difficulties even minor.  We did fine but it was a challenge.  Cooking class and lunch there was wonderful. The hotel in Positano was my favorite. Location and staff was fantastic and treated us like family.. Our room in the annex, Punta Caterina was spectacular.  We had our own private Villa. Just be aware a lot of stairs up to room level in Annex. . So again not for clients with any walking issues. We were fine with it..All the other tours you planned were wonderful, especially loved Fattoria Terranova.  So special. 

During our planning process your communication and reply to our questions were always prompt and efficient. Thanks again!!! 

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Kathy R.
Northern Italy Travel Review: Tuscany, Como, Artisan Tour in Venice, Leather Making & Mosaics, Wine Tasting & Local Cooking Class

We interviewed several travel agents before choosing our agent and this travel company.  The other travel agents just seemed to be going through a script and then provided an uninspired itinerary.  Our travel agent took the time to listen to our desires and from that created a bespoke itinerary.  Our agent excelled in both listening and creativity. He understood our desire to have an artisan experience and that we wanted downtime. 

We are a family of both artists and craftsmen, so we weren't looking for the generic tour the typical top 10 things to do.  We wanted a curated experience, a chance to meet artisans at work.  Through numerous phone calls, emails, and tweaks to the itinerary they made sure it was perfect.  Not a single detail was missed from the transportation to the tours to making sure they found a place for us to get Covid tested before flying back to the US.

The tours they provided were amazing, from the artisan tour in Venice, leather making and mosaics in Florence, wine tasting in Chianti, to Italian cooking lessons in Como.  What was unique is we got to meet the artisans, ask questions, and learn about their craft.  It was not just the artisan experience, but the guides they hand picked to provide the tours were experts in their field.  All of them were passionate about their cities and made us feel welcome. They were all so gracious and kind.  The other important factor was we never felt stressed or worried about how to navigate in whatever city we were in.

Our travel agent made sure the transportation was always on time and the drivers would always communicate ahead of time. The agent was also always available to answer any of our texts from how much to tip to where is the best Florentine steak at a local's restaurant.  Our agent was responsive within minutes and when he was not going to be available he let us know ahead of time. No question was ever too small and he never seemed annoyed by what were probably inane questions.

The itinerary provided was very detailed and included all the contact information for the drivers, guides, etc.  We never felt lost or stressed.  I have to say it was the most stress-free vacation we have been on. Our entire family agreed this is the best family vacation we have been on, and we have traveled a lot.  I would rate our agent and the travel company a 10 out of 10!!! I would not hesitate to use them again and have already referred them to my sister.  My only regret is that we couldn't have stayed longer in Italy.

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Arlene O.
Travel Review: Luxury Italy Trip, Sicily, Catania, Siracusa, Taormina

Trip was well organized by the company. They were always very responsive when I had questions. The tour guides were very professional and passionate about Sicily. We had heavy rain one day (Friday) of the trip and all archaeological sites in Sicily were closed by the authorities. The company quickly readjusted the tour and flipped Sunday’s tour (Catania and Siracusa) on the rainy day which worked out beautifully.I strongly recommend this company for those thinking of going to Italy.

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Amy D.
Travel Review: Italy Vacation, Venice, Alba, Bra, Cheese Tasting, Wineries, Peggy Guggenheim Collection, 9-Day Tour

Our trip to Venice and Alba was terrific. The tour guides were friendly and extremely well-informed. Our driver was a fountain of information. He was always on time and was patient with us when we were tardy. I loved the private tours-- so much better than fighting a crowd. Our hotels were interesting and comfortable. A great experience! 

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Shawn H.
Travel Review: Italy 20th Anniversary Trip, Parmigiano-Reggiano, Balsamic, & Prosciutto Tour, 8-Day Tour

All of our hotels were extremely comfortable, in convenient locations, and we always felt safe. The staff in each hotel exceeded our expectations. 

The tours were THE BEST! Our travel specialists arranged both private and small group tours. The guides were informative and very, very friendly. One of our guides was so entertaining and funny that we will be requesting him again!

All of our drivers were on time and familiar with the area. 

The travel company made our vacation so effortless. Thank you for a wonderful 20th Anniversary.

Next time we will book our vacation with you for southern Italy!

Grazie Mille!

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Cat B.
Travel Review: Italy Vacation, Venice, Florence, Rome, Walking Food Tour, Cicchetti Experience, 6-Day Trip

What an amazing trip! We chose to seek help with our first trip to Italy to ensure comfort and ease. That is exactly what we received from the travel company. We used their services of transportation, hotels, and a guided tour for each city we visited. It was so nice to not have to worry about getting to and from the airport and or train station. All of our drivers were friendly and helpful setting each leg of our journey up for success. Our trip included time in Venice, Florence, and Rome. The travel company set us up with a small tour group in each place. Our tour guides were knowledgeable and passionate about their respective cities. Having such small groups (2-6 people) really created a more personal vibe. We encountered one transportation issue, but it was quickly resolved. In fact, our agent reached out personally and made sure all was well. We felt comfortable knowing someone was available should we need anything. I would absolutely use this travel company to plan future Italian adventures.

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Customizable Itinerary

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

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