Romantic Italian Escapade: Intimacy & Seclusion

View of St. Peter's Basilica in Rome, Italy

What to expect on this itinerary

The passion of history and culture will enchant you during your custom-tailored romantic tour of Italy. Your affection for each other and for Italy will grow in the charismatic towns and villages that preserve tradition within elegant, medieval, Renaissance, and Baroque architecture. Beautiful artwork celebrates the virtues of love and private rendezvous. Grand castles and sophisticated palaces will provide a fairytale ambiance while countryside scenery will embody the idyllic charms for which Italy is known. You will indulge in a couple’s visit to a natural thermal spring, bask in the rich flavor of local wine, and enjoy crafting delicious traditional meals as you share a dreamy Italian romance.

Countries Visited

Italy, Vatican City

Places Visited

Rome, Perugia, Florence, Bologna, orvieto, Assisi, Gubbio, Pisa, Lucca, Montepulciano, Siena, San Gimignano, Parma, Modena, Ravenna, Ferrara, Bobbio, Bardi, Gradara, Tivoli, Vatican City, Viterbo, Bagnoregio

Suggested Duration

21 Days

Customizable Itinerary

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Day 1

Rome – Arrive in the Capital of Italy with Romantic Tiber River Cruise

The Eternal City of Rome will sweep you into the romantic past with a charismatic ambiance that emanates from the combination of grand Baroque palaces and narrow medieval lanes. Monuments decorate the city center, reflecting over 3,000 years of history and a particular golden age when the piazzas, palaces, and churches acted as the capital of the Christian World. Your private transfer will meet you at Fiumicino Airport upon your arrival and will escort you to the comfort of your accommodation.

The great pleasures of Rome will provide a spirited welcome that highlights the passion of Italian culture with traditions dedicated to art, architecture, fashion, and cuisine. The Colosseum soars above the remains of the Roman Forum, and the fountains in Piazza Navona trickle with water in pools as elaborate marble sculptures cradle them. In the evening, you will board a boat from the banks of the Tiber River and set sail on a charming evening cruise complete with a perfect view of the golden light that reflects against the stone of the antique buildings above.

Live music will play inside the dining area as it fills with the aroma of traditional Roman cuisine, such as artichokes bathed in olive oil and white wine with fresh herbs. From the deck, you will have a fabulous view of the Castel Sant’Angelo that towers over the riverbanks. The structure was erected in the second century AD as the tomb for Emperor Hadrian before successive popes transformed the edifice into an elegant fortress. The angelic figures that decorate the bridge were designed by Bernini in the seventeenth century and add an air of grace beneath the mighty walls of the castle.

What's Included:

Transfer
Accommodation
Tour
Day 2 - 3

Perugia – Delight in the Scenery and Medieval Towns of Umbria

Day 4 - 6

Perugia – Discover Bountiful History in Assisi and Orvieto

Day 7 - 8

Florence – Indulge in Famous Art and Culture of Florence

Day 9 - 11

Florence - Embrace the Celebrated Charms of Tuscany

Day 12 - 13

Bologna – Uncover Eclectic History and Flavor in Emilia-Romagna

Day 14 - 16

Bologna - The Byzantine Empire to Dante Alighieri

Day 17 - 18

Rome – Revel in the Romantic Ambiance of Rome

Day 19 - 20

Rome - The Marks of Michael Angelo and the Towns of Lazio

Day 21

Rome – Depart for Home

Trip Highlights

  • Stand beneath the staggering frescoes crafted by Michelangelo in the Sistine Chapel
  • Indulge in the delicacies of Perugia with a private food tour that will introduce you to the complex and mesmerizing flavors of locally made chocolate
  • Discover the majesty of the Renaissance in Florence on a private guided tour through the Uffizi Gallery, which is home to works like Botticelli’s Birth of Venus
  • Enjoy the artful methods for mastering traditional Italian cuisine during a private couple’s cooking class in Bologna
  • Relish the beauty and sophistication of Rome on an elegant evening cruise along the Tiber River
  • Sample the delicious, layered flavors of some of Tuscany’s most prized wines during a wine tasting at Montepulciano
  • Embrace the love story of star-crossed Paolo and Francesca whose famous passion continues to attract couples to dramatic Gradara Castle
  • Relax in the soothing geothermal waters of the historical hot springs in Viterbo that are surrounded by remarkable medieval and Renaissance architecture
  • Explore the charming streets of Assisi with a guide for introductions to the remaining ancient ruins and gorgeous art that decorate the fascinating basilica
  • Wander beneath the former arena floor of the Colosseum for a private view of the Hypogeum, offering a new perspective on Rome’s ancient history

Starting Price

$9,600 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 718 reviews

Italy Trip Review: Rome, Florence, Tuscany, Cinque Terre, Venice, Pizza-Making Class, 2 Weeks

We had an absolute dream trip to Italy with the help of Zicasso's travel specialist! Traveling as a family of five, we visited Rome, Florence, San Gimignano, Greve, Siena, Cinque Terre, and Venice, along with many beautiful towns and smaller areas throughout the country.

The wonderful vacation rental accommodations were thoughtfully chosen and every detail of our trip was carefully planned. The local tour guides were incredibly knowledgeable and gave us a truly authentic experience. Our private transfers, train transfer, and private tours were efficient, informative, and made traveling from place to place seamless and stress-free.

The communication between all tour guides and transportation providers was great, as was that of each vacation rental host, who contacted us in advance to prepare us for our arrival.

One of our favorite parts of the trip was discovering the smaller, less-touristy areas within the larger cities, places we likely never would have found on our own. We enjoyed exploring Tridente for shopping and Trastevere in Rome for a private pizza-making class (highly recommended), artisan shops, excellent restaurants, and a vibrant nightlife.

Florence was wonderful, but we had the opportunity to travel to a few other areas, such as Siena, Greve, and San Gimignano. We even had a private vineyard tour and chef's meal while in Chianti. A must-see is the walk to the Boboli Gardens across Ponte Vecchio and, on the way back to our apartment, a stop at Piazzale Michelangelo.

While staying in Cinque Terre (Monterosso al Mare), be sure to take a private boat to visit all of the other villages and maybe even snorkel. The water is so clear!

Venice had great history, but we also enjoyed our boat tour to Murano to watch the glassmaking process and Burano, filled with gorgeous multicolored homes and artisan shops.

Every experience felt personal, meaningful, and special.

This trip was truly an absolute dream and we are so grateful to him for helping make our family vacation to Italy unforgettable. We highly recommend him to anyone looking to plan an incredible, seamless, and memorable trip!

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Italy Honeymoon Travel Review: Florence, Rome, Amalfi Coast, 8 Nights

Our honeymoon in Italy was absolutely magical and so much of that is thanks to our travel company. From our very first call, they took the time to understand what we wanted and crafted an itinerary through Florence, Rome, and the Amalfi Coast that felt personal rather than cookie-cutter. Every detail was handled: hotels, transfers, and tours all ran seamlessly, so we could simply relax and enjoy being newlyweds.

Florence stole our hearts with its art and charm, Rome was awe-inspiring at every turn, and ending the trip on the Amalfi Coast, with those breathtaking sea views, was the perfect romantic finale. The guides were knowledgeable and genuinely passionate, bringing each city to life in a way we never could have experienced on our own.

Communication before and during the trip was prompt and reassuring, and it was clear the team truly cared about making our honeymoon special.

We came home with memories we'll treasure forever. We can't recommend this travel company and Zicasso highly enough. We're already dreaming about our next trip with them!

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Italy Trip Review: Rome, Siena, Orvieto, Venice, Pienza, Vatican, Colosseum, Roman Forum, Vespa Tour, E-Bike Tour, 10 Nights

Our trip to Italy was amazing! The tours that were organized for us were all excellent and engaging. 

The Vespa sidecar tour was an incredible way to kickstart the trip and our two teenage boys really enjoyed it. Our walking tours of the Vatican museums and the Colosseum and Roman Forum tours with our guide were excellent. We loved her. She was fantastic. Our tour of the crypts and catacombs was very interesting and the guide was very good.

The hotels were very nice and accommodating, especially in Rome and Venice. The car rental in Rome was good and the car was the perfect size for what we needed. It was just big enough to fit our luggage. 

The hotel in Orvieto was a bit spartan and had plumbing issues. Our tour guide in Orvieto was also great. The hotel in Siena was very nice. Our tour guide in Siena was very nice, but we had some difficulty hearing her. She did explain things nicely and took us to some interesting locations around the city, but not being able to hear her was a little challenging. The e-bike tour in Montepulciano was incredible. The scenic landscapes and the visit to Pienza was a nice surprise. 

Returning the car in Florence was very difficult and our only suggestion is that on the travel documents, the return address be included on the page of the event. We did not think to look back at the rental agreement. Driving in Florence is very difficult and can be overwhelming for some people. 

The train station was organized and it was easy to locate the train. The train ride itself was very easy and fast. 

Venice was outstanding. Our hotel was beautiful and comfortable, and the breakfast was incredible. Due to the difficulty we had in returning the car in Florence, our travel company was kind enough to buy us dinner at an wonderful restaurant in Venice, which was one of the highlights of the trip. 

Our family had a wonderful experience and the trip was so well planned and organized. I will be using our travel company for future trips and, on behalf of my family, I would like to thank you for the time of our lives!

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Italy Tour Review: Milan, Lake Como, Bologna, Ferrari Museums, Winery Visit, Food Tour, Cooking Class, Boat Ride, 12-Day Trip

Zicasso's travel specialist organized an amazing 12-day series of private tours, taking us from Milan to the lake regions (Como, Maggiore, and Garda) and down to Bologna. Our days were filled with visiting churches, museums (including the Ferrari and Enzo Ferrari museums), a winery, parmigiano, prosciutto, and traditional balsamic manufacturing, a cooking class, boat tours, and food tours.

Along the way, we saw testing at the Ferrari track and a small portion of the women’s Giro d’Italia. With all that, we still had sufficient downtime to search the streets to find our own gems.

Our trip coordinator checked in with us daily to confirm the daily itinerary and transportation. When we had questions or needed to make a change due to the weather, she was thorough, attentive, and responsive in a way that was reassuring and comforting. She was simply amazing.

I would highly recommend using this travel specialist and team for any of your Italian travel needs.

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Italy Anniversary Trip Review: Rome, Florence, Bologna, Venice, Capri, Grand Canal, 11 Days

Zicasso's travel specialists did a magnificent job planning our itinerary to Rome, Florence, Bologna, and Venice. Our hotels were all beautiful and perfectly located. We really loved having luxury vehicles to bring us everywhere instead of having to get a taxi. It made a huge difference in ease and comfort, plus all the drivers were so nice and knowledgeable. The tours we went on were all enjoyable.

They also provided restaurant lists for each location. Of course, the best part was that we got married in Capri 20 years ago and this was our anniversary trip to bring our daughters with us and renew our vows together. They planned a lovely ceremony in a palace located on the Grand Canal, with a gorgeous private garden. It exceeded our expectations and ended our trip with a memory that will last forever!

We were sad to leave and can’t wait to go back, and will absolutely use this travel specialist and his crew again.

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Italy Tour Review: Venice, Florence, San Gimignano, Siena, Rome, Vatican, Amalfi Coast, Capri, Sorrento, Positano, Doge's Palace, Colosseum, Palatine Hill, Boat Ride, 12 Days

This was possibly the best trip of my life!

Once I arrived in Venice and put myself in the hands of Zicasso’s tour company, I was supremely well taken care of.

I left my passport on the plane, so I was held up in the airport for probably two hours. This was the first time I used the emergency number (or the chat app). The communication was answered immediately and we were able to let my first guide know I was being held up. I thought the first person who helped me was just someone to get me to the hotel, but she was also a guide in the sense that she described many of the things we saw on the way to the hotel. A very pleasant and gracious guide who made sure also that I was prepared for where to be the next day. It was a very great first experience of the tour company’s service.

Throughout this adventure, the guides were outstanding, the hotels were located practically on top of the interesting sites (especially in Rome) and very pleasant to be in.

Also, I continued to use the emergency number or the chat app multiple times. They were very responsive, very pleasant, and perfectly helpful each time. I don't know if I was high-maintenance compared to other clients the tour company has had, but though I felt like it in my mind, I was treated completely graciously each time.

I loved every destination and I loved having a structured tour, combined with a good portion of free time to explore on my own. Perfect.

I was very well guided on each travel day, being met by drivers to drop me off and to pick me up, and the train travel was very fun.

I think there was only one guide who I thought was just going through the motions, but all the other guides were the height of professionalism. I loved being met by our guides at Doge's Palace, which was absolutely outstanding. Walking around old Florence was great fun! The drive out to San Gimignano and Siena was well-planned and well-guided! In Rome, the guide who took us to the Colosseum and Palatine Hill was outstanding, and it was a great outing. (I had also already pretty much visited all the sights since my hotel was practically in the middle of it all.)

The trip to the Vatican was a whole other story. Unfortunately, I forget that guide's name. This guide was also excellent—entertaining, informative, approachable, and professional. The trip to the Amalfi Coast was a long train ride, followed by a very long car ride, but it was worth it. What a beautiful setting! My trip to Capri was absolutely fulfilling and I was a little sad to say goodbye to the guide—we connected with him so well. The next day was our boat tour from Sorrento to Amalfi and Positano. I absolutely enjoyed being guided by our guides! On the way back after that beautiful excursion, we were just cruising along the water, 1970s music playing, wind rushing by and I had a peak moment of happiness. Truly.

This trip was as if the tour company had read my mind and provided even more than I had imagined. I come away deeply grateful.

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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