Experience the Romance of Rome & Florence Tour

What to expect on this itinerary
Bask in the romantic experience of a lifetime as you and your partner are treated to the most magical views, tastes, and sounds of Rome and Florence. Far from the reliance on simple candlelit dinners or horse-drawn carriages, this luxury tour leads you and your partner through the streets of Rome on a vintage Vespa to sample the best of Italian cuisine in addition to strolling the streets of Italy’s most charming cities. If you are looking for magic, romance, and utter luxury, this 8-day adventure in two of the world’s most romantic cities is the vacation for you.
Customizable Itinerary
Rome – Ascend the Aventine Hill for a View of Rome Like None Other
Today, you and your partner will embark on the couples tour of a lifetime. Your driver will pick the two of you up from the airport and transport you to your hotel, which will be located at the heart of the Eternal City. You can today slow and allow yourselves to adjust to the bustle of Rome.
Your first day together in Italy will be all about luxurious refreshment. Once you have settled into your suite, your driver will transfer you to what is often referred to as the “keyhole to Rome,” which is the Garden of the Oranges. Perched above the Tiber River, this park opens up to sweepingly stunning views of the city of Rome and are ingrained with the sweet fragrance of the oranges. These orange groves are said to have been planted by Saint Dominic who transported the first sapling from ancient Spain. Legend tells us that Catherine of Siena picked oranges from this grove to create candied fruit for Pope Urban VI. You can climb the Aventine Hill for the best view of the city. You can take your time strolling together through the grounds of an ancient fortress that was constructed in the late 1200s. You can also soak in the symmetrical, 8,000 square-meter setting of a garden that was designed purely for pleasure. You will not want to miss the chance to peek through an inconspicuous keyhole on the iron gate that guards the Priory of the Knights of Malta. This experience will offer a striking view of Saint Peter’s Basilica that is framed by the hedges of the garden.
You will end your first day in Rome with a three-star Michelin dinner in one of Rome’s most prestigious eateries. Your host will guide you through choosing the perfect wine from the 60,000 bottle collection that this restaurant keeps on hand. This restaurant offers not only 3,000 years of history with touches that stem from all throughout ancient and modern Roman history but also a candlelit terrace from which to take in an incredible view of the heart of the city itself.
What's Included:
Rome - Traverse through the Streets on a Vespa to Quartiere Coppede
Rome - Trace the Paths of the Villa and Galleria Borghese
Rome - Discover the Delights of the Testaccio Market
Florence - An In-Depth Tour Through Two of Tuscany's Top Wineries
Florence - Witness the Craft of Ancient Leather-working
Florence - Journey to a City Tucked into the Etruscan Hills
Rome - Indulge in an Ancient Florentine Tradition
Trip Highlights
- Peek through the Keyhole to Rome in the Lush Garden of the Oranges
- Fly through the ancient streets of Rome on a classic Vespa to the fairy tale streets of the city’s smallest district
- Delve into the art and grounds of Rome’s pleasure palace, the Galleria and Villa Borghese
- Immerse yourself into Italy’s top cuisine and products at the Testaccio Market
- Marvel at a rich al fresco opera performance at the Teatro dell’Opera
- Delight in the offerings of two of Florence’s top wineries following private tours of their inner workings
- Descend into the halls of an ancient Franciscan monastery to follow the process of leather crafting from start to finish
- Float down the Arno River on a private, romantic cruise that is complete with wildlife sightings and a gourmet picnic
- Wander the aromatic streets of Fiesole and discover one panoramic view after another with Florence in the distance
- Engage in an ancient Florentine tradition by sharing a sunrise kiss on the steps of the Piazzale Michelangelo
Detailed Description
Discover the magic of Italy during an excursion of Rome and Florence, which has every experience steeped in a romance that cannot be matched. From the streets of the Eternal City to the vineyards of Tuscany, Italy is imbued with an intimate atmosphere like no other country in the world. Your journey will begin in Rome with a stroll through the Garden of Oranges, which is perched high above the city streets, after your private driver transfers you from the Leonardo da Vinci-Fiumicino Airport to your luxurious accommodation in the heart of the city. This romantic garden stroll will be followed by a three-star Michelin meal at a gourmet eatery, which boasts a 60,000 bottle collection of the finest wine that Italy has to offer. Your accommodation’s central location puts all of the scenic and culinary delights of ancient and modern Rome at your fingerprints, allowing you to traverse this iconic city with ease and without missing out on any of the magical experiences that it has to offer.
Together, you will speed through the back streets of the city on a fully personalized Vespa tour, bypassing the tour groups and traffic as you visit the highlights of Rome. During this magnificent tour, you will witness sites that are both well-known and less-traveled, including Rome’s “fairy tale neighborhood,” which is otherwise known as the streets of Quartiere Coppede. The following day, you will meet your guide for an in-depth tour of the pleasure palace of Rome, the Villa, and Galleria Borghese. Here, you will witness the rare art that was collected by 16th century Cardinal Borghese. You will also be provided with a private rowboat for a sunset visit to the Temple of Asclepius.
While in Rome, your private guide will walk you through the ancient art, architecture, and greenery of the city. You will enjoy top tier seats at an al fresco opera performance and indulge in the best products that local creators have to offer in the city’s Testaccio Market, which is a market that includes a food stall that serves Michelin-starred piccoli morsi or small bites. Following your first-class train transfer to the city of Florence, you and your partner will be provided with the opportunity to savor the best that Tuscan wine has to offer at two of the world’s most elite wineries. You will wake up on your first morning in Tuscany to enjoy the breathtaking view of the city from your luxurious hotel before meeting your guide for a walk through an ancient Franciscan monastery to discover the makings of one of Florence’s top creations: leather.
You will touch the most supple, sumptuous leather that has been crafted by leatherworkers in an ancient tradition and carefully preserved through centuries. You will even be able to purchase one of the fine creations if you choose. After the cool darkness of the halls of the monastery, you will float together in the cool breezes of the Arno on an evening river cruise that will be complete with light snacks and a paired local wine. The following day will lead the two of you on a private ride out of the city to a village that is tucked deep within the Etruscan Hills and set high enough so that you can enjoy a panoramic view of the rooftops of Florence. Your driver will return you to your hotel in the evening, so you will be ready to tackle a truly Florentine experience at dawn on your final morning. Day eight will find the two of you climbing the steps of Piazzale Michelangelo, where lovers for generations have shared a traditional kiss at sunrise among the rose garden and Michelangelo replica sculptures that are set against the hills of Tuscany. Afterward, your driver will transfer you directly to your terminal at the Roman airport. Each detail of this luxurious, 8-day trip is optimized so that every moment of your time in Italy is idyllic from your sunset cruise down the Arno River to the early morning view of the streets of Florence. On your adventure, you will see and taste the best that Rome and Florence have to offer, igniting a passion that will follow you for a lifetime.
Italy is a region unlike any other; learn more by seeing how our partner Italy trip operators can personalize the experience for you.Starting Price
$2,900 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
Verified Traveler Reviews
Based on 997 reviews
Zicasso’s tour operator planned the most amazing trip to Italy for us! My requirements were culture, romance, and relaxation. She delivered on every aspect. Although we missed our tour of the Vatican due to the Pope's funeral, my husband and I actually attended his funeral!! Our hotel, though planned many months before, was next to the basilica where Pope Francis was laid to rest. Talk about being a part of history!
We stayed in a beautiful converted villa to boutique hotel in Florence; got whisked away through the Tuscan countryside in a vintage Fiat 500; took cooking classes; sipped lovely wine, accompanied by excellent lunches on our winery tours; soaked in Italy's rich culture and museum scene; and even ticked the relaxation box by spending time by the pool, in the spa, and resting on our large deck overlooking the Amalfi coastline.
Every tour guide was extremely knowledgeable and personable, and it was evident they loved their jobs. Between memories of the boat ride along the Amalfi Coast, tips from the cooking classes I have already started using at home, and the cases of wine we are eagerly awaiting delivery of, my husband and I will forever hold Italy in our hearts and la dolce vita it provided us.
Talk with our tour operator; you will be glad you did!
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I apologize for the delay in writing this review, but was very busy the last few months and wanted to dedicate the time it deserved. This review will address my wife and my trip to Italy from September 26, 2025, to October 6, 2025. Please feel free to share all or any portion of this review.
Trip Planning:
As a bucket-list event, I spent a great deal of time doing research, but would not have been able to put together the ideal vacation without the support of Zicasso and the travel company. Upon hearing my general interests, Zicasso provided two groups whom they thought would be able to plan and implement my trip. Both groups interviewed me and my wife about interests and price range, and then prepared an initial itinerary. Both groups would have done a fantastic job by their presentation, but it seemed I was slightly more in tune with the travel company and selected them. This proved to be a very wise choice, as the entire team at the travel company, particularly the travel specialists, were the absolute best and I would recommend their service without reservation. Fully responsive to my many questions before the trip, addressing all potential itinerary changes, and providing invaluable guidance throughout the entire process. Their response to inquiries while in the country was unbelievably prompt and thorough. At our request, the travel specialists made restaurant recommendations and reservations that were spot-on. I can’t say enough good things about these ladies.
Transportation and travel between locations:
Although not involved in the flights, the travel specialists provided great guidance concerning flights, trip insurance, and other logistics.
One key point that I fully expressed was that I did not want to flounder at the various transportation points and did not want to lug luggage in foreign areas on the way to and from lodging. The team took this to heart and provided me with either an escort or driver to and from every terminal. Everyone providing this task was friendly and provided information that made the travel much easier. Particularly valuable were our escorts, who adeptly negotiated our entrance and exit from Venice, and provided great insights into this historic city.
Venice:
Our hotel in Venice seemed to be right in the middle of everything, which allowed us to explore, and we have never had so much fun getting lost. At night, we opened our windows and fell off to sleep listening to nearby music; it was idyllic. The staff was professional and friendly. Breakfast was the best of all the hotels we stayed at in Italy.
The first full day in Venice, the travel company leveraged “skip the line” so we could make the very most of our time and is essential to any planning. Both guides were great and really good company. One guide’s knowledge of the Doge Palace really brought it to life for us. Another guide had a real insider’s view of Burano, as this was her family’s island. As private tours, we could go at our own pace, which we really liked. Probably the least enjoyable tour was the glass factory in Murano. We got the impression most of the tour beyond the initial exhibition was an attempt to sell their products. My wife succumbed and purchased a pair of earrings that broke the first time she wore them. Really disappointing, and I would advise you to spend more time in Burano.
Florence:
As with all the trains, the travel was very comfortable and we enjoyed watching the scenery. Our lodging in Florence was right on the Santa Maria square, superb for people watching. The staff was fine, nothing more. The hotel was near the world’s oldest pharmacy, famous as the world's oldest perfumery. Although there is a line to enter, it goes quickly and is historical, to say nothing of buying a scent more than 400 years old. I strongly recommend you go.
While knowledgeable, our tour guide for the Accademia and Uffizi Galleries was a little too technical for us, leaving us with the feeling that we were taking an art history class.
Dinner was based on the travel specialist's recommendation and it was delicious. A strong recommendation.
Day trip to Pisa:
The travel arrangements were perfect. The purpose of the trip was to take the obligatory picture holding up the tower—hokey, but we loved it.
The private cooking class with our instructor was a lot of fun. The view of the city from her window at sunset was beautiful. My wife and our instructor fell into a real rhythm cooking, and she was kind enough not to scoff at my ham-handed attempts. Her directions were simple enough for me to follow, theoretically. She followed up her lesson with an email containing detailed recipes. We have purchased all necessary utensils and are planning a pasta-making party soon. This was a fun change of pace.
Rome:
Our bed-and-breakfast in Rome was our least favorite lodging. Entry into the building was confusing and, as a B&B, the desk was not manned all the time, which made it difficult to secure a taxi early in the morning (we had to walk to a nearby hotel) or get assistance after 8pm or before 6am. When we came in, we attempted to coordinate laundry service with the person working the front desk, followed his instructions, but when we returned the next day, our dirty clothes were still where we were told to leave them. The initial response from the on-duty staff, who I believe was the owner, was that the individual was no longer an employee. Ultimately, the hotel comped and completed our laundry, which was nice. We would have preferred different lodging.
Our first afternoon, we took a four-hour golf cart tour, which was our favorite tour of the entire trip. Adding an extra hour to the traditional length and having only my wife and me allowed us to do everything we wanted to do. Our driver took us everywhere. He would drop us at the top of the Spanish Steps and meet us at the bottom, and would conveniently bring us closest to all other locations. I can’t believe how much we did in four hours. Our driver brought all these iconic sites to life with his marvelous insight and provided a great insider view of these monuments. This is a must-do for all first-time visitors to Rome. The only thing we were not able to do, due to no fault of our driver, was the Aventine Keyhole. When we got there in the afternoon, the line was 45 minutes and not a wise use of our time. If this is a strong interest, he recommends going early in the morning.
The travel specialists arranged tickets for the Papal general audience on Wednesday. Rising at sunrise was worth it to get the seats as close as we were able to secure. Most online sites suggest getting there an hour and a half before the start time, but I think that is much too late. I recommend you get there three to four hours ahead to get the best seats. The best seats are on the end near where the Pope drives by, ideally near an infant, and His Holiness will stop to personally bless these children. Facing the stage, the right side filled up quicker than the left side, so go directly to the left side of the audience. Being so close to the first American-born Pope was a memory I will never forget. His Holiness blesses all items in the audience's possession, so load up on rosary beads; they will make great Baptism and Communion gifts.
The afternoon was our first group tour at the Vatican Museums. It might be that we were spoiled with the previous private tours, but linking up with the group was chaotic and the quality of the tour was contingent on those in our group. Fortunately, all our groups were good, considerate, and friendly people. The main value was skipping the line for entrance. As with the Doge Palace, our guide was a little too academic and didn't really manage time well, potentially a victim of being in a group, but I would have rather spent more time in the Sistine Chapel and the Basilica. Taxis were extremely hard to get back to the hotel and I would arrange a ride if I were to do it again.
The Thursday tour of the Colosseum and Forum was also a group tour, but led by a guide who brought this ancient land to life. An archaeologist by trade, our guide seemed to know everything and also took a great picture.
The end of a very long but enjoyable day was another group tour of the catacombs and Santa Maria Maggiore. While the catacombs were the main attraction, the after-hours and behind-the-scenes access to Santa Maria Maggiore was an unexpected gem. Going through a second Holy Door, viewing the magnificent nighttime skyline from the roof, seeing the location of a relic from the baby Jesus’ manger, and being struck by the modesty of Bernini’s and Pope Francis’s tombs were all highlights. Unfortunately, taxis were again hard to come by.
Sorrento:
We took a train from Rome to Naples. While there was a national strike, it did not prove more than an inconvenience, no worse than New York City on a regular day. Our driver from Naples told us this simply provided us with a genuine Italian experience. I wish I could remember this driver’s name because he was the best of a very good group of drivers during this trip. En route to Sorrento, we stopped for a tour and meal at a winery and a private skip-the-line tour of Pompeii. We were so impressed with the quality of the winery that we made a large purchase of wines and olive oils that, thankfully, included free shipping.
During our drive to Sorrento, our driver took us through his hometown, which we really enjoyed. Going through the town, he pointed out the birthplace of Bruce Springsteen’s mother. Little did he know, we were from New Jersey and are HUGE Springsteen fans.
Our hotel in Sorrento was a nice place, close to the center of town. I would have preferred a hotel with a view of the coast.
On Saturday, we took a private tour up the coast. This was the most comfortable car I have ever ridden in, with heated and cooled seats, and a convenient icebox. The driver made clear he was at our disposal. The scenery was marvelous and it was a thrill to dip our toes in the Med. Our driver hooked us up with a restaurant on a cliff overlooking the water—beautiful and scrumptious.
Our last day was supposed to be the Gozzo tour of Capri, but was canceled due to weather. We refunded the canceled boat tour, but ate the driver and ferry fees. In hindsight, knowing this day was largely contingent on weather, I would have liked to have a contingency plan and would advise the travel company to plan this in the future.
Based on how smoothly things went, we will be contacting Zicasso to arrange a trip to Iceland and Ireland next fall, and hope they can refer a team as talented as this travel company.
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Kudos to Zicasso’s tour operator! This is our second time using them, and they didn’t disappoint us. They had to deal with two families, seven in all, all adults, with two separate trips. One trip for all seven to Rome and Florence. Two for Naples and Ischia.
The apartment in Rome was in a good location for us, as we usually stay near there. The only problem I found in this apartment was the smaller unit had a step down into the living room. The floors are dark, and the step needs to be highlighted so one remembers to step down. Several of us kept missing it, and luckily no one fell. Other than that, it was a nice apartment.
In Florence, our apartment was perfect. My husband and I would stay there again; however, it has four bedrooms, four baths, a nice kitchen, and a large living room, so it would be a little big for two people. It was perfect for families. It is on the third floor.
Since my husband and I have been to Rome and Florence many times, we did not have too many requests for tours. My cousin and her family were first-time visitors. I suggested a tour of the Vatican Museums, Ancient Rome, the Accademia Gallery, the Duomo Skywalk, a private tour of the Uffizi Gallery, the Vasari Corridor, and the Boboli Gardens. In Rome, all seven of us did a golf cart ride at night, which seemed to be a big hit. We also had a wine tasting and olive oil sampling in Chianti, which was very nice.
At one point, we thought we were going to have a wedding proposal. A place was planned for the proposal at one of the wineries. Unfortunately, the groom-to-be decided not to do it there since the future bride’s parents would not be there. I felt bad with all the work the travel company did to make this day special for the couple.
Since we were two families, all adults, sharing vacation rentals, the tour operator found two apartments to meet our needs. All of our drivers and guides were on time and very knowledgeable.
We made some last-minute changes on our trip from Florence to Ischia. Changes to the train tickets were made, but we were asked to check with the ferry service to see if they could take us earlier. Our driver went with us to the ticket office and was able to exchange our ferry tickets. Then we notified our travel agent, so they could call the hotel to send our driver earlier than planned.
We have used this tour operator before and would highly recommend them. The hotels they selected were excellent. We stayed at our hotel in Naples last year and asked for the same hotel again. The views were fantastic from our room, and the rooftop bar had views of Mount Vesuvius and the Bay of Naples. The staff were superb, and there was a wonderful breakfast.
We also asked for the same hotel in Ischia, but that hotel closed earlier this year. Another property was selected, our resort in Ischia. Unfortunately, we did not get a chance to use the spa this time, but the hotel had beautiful views from the restaurant, terrace, and our room. Both hotels were beautiful, and the staff were very attentive. Our resort in Ischia was not far from Ischia Porto. A bus stop was a short walk away, and the return stop was right in front of the hotel. The food and drinks were great, and we even walked into town one night, which took about 15 minutes.
I can’t wait to use the travel company again next year.
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We enjoyed all of the planned tours in Italy and Greece. Favorites included the Vatican, Colosseum, Roman walking food tour, and a day exploring the Tuscany wine region.
We loved all of our hotels (favorites being our hotel on Via Emilia in Rome and then our hotel on Nikodimou Street in Athens). All of our drivers at our various locales were always on time, even early, and were friendly and engaging.
We did have various questions come up and any time of day/night, Zicasso's travel professional and the tour company were responsive and so helpful.
Our long-awaited 45th anniversary trip came off seamlessly. I appreciate all of the time and planning that went into planning our venture. I will happily recommend you to our friends and family.
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Zicasso's tour company did a wonderful job of planning our dream honeymoon! Our travel agent took into consideration our wants and wishes, and created half- and full-day activities for us throughout the trip. We were able to visit four locations (Rome, Sorrento, Florence, and Venice) while in Italy. The trip was a perfect mix of relaxation and exploration. The tour company took away the stress of traveling and allowed us to enjoy the days without worries.
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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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