Wine and Golf Tour of Italy: An Escape to Vineyards & Fairways

Vineyards surrounding Montalcino in Tuscany, Italy

What to expect on this itinerary

Only in the Italian countryside can the game of golf and exquisite wine tasting go hand-in-hand as you indulge in both throughout your vacation. Your custom tailored tour will combine the pleasures of the serene fairways with the flavors of celebrated wineries in the heart of Italy. See the treasures of Rome and sip a beautiful glass of wine in view of the famous Tuscan hills. Relax in a private villa and practice your swing on a driving range that overlooks the Tyrrhenian Sea. From the historical cellars to the championship courses, you will find the perfect combination of luxury and activity in the beautiful towns, the ancient monuments, and the secluded greens.

Countries Visited

Italy

Places Visited

Rome, Argentario, Murlo, Castiglion del Bosco

Suggested Duration

8 Days

Customizable Itinerary

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Day 1

Rome – Arrive in the Marvelous Eternal City with an Introductory Tour

The splendor of Rome transcends time as the contemporary city maintains an ambiance of classic elegance, accentuated by the ruins and the Baroque and Renaissance embellishments. Your private transfer will meet you at Fiumicino Airport and escort you into the historical center of Rome. The city bustles with excitement around the cobblestones as students and couples linger on the marble staircase known as the Spanish Steps which connect Piazza de Espana to the upper level of the Trinita dei Monti Church.

You will find the comforts of your luxurious hotel that border the open public square of Piazza Repubblica truly refreshing in the midst of the city. Via Nazionale, one of the main streets of Rome, begins in the Piazza adorned by the Fountain of the Naiads was erected in the 19th century under the commission of Pope Pius IX. The fountain and it’s characters depict the Nymphs of the lakes, rivers, and oceans, as shown through the animals, such as the swan, horse, and dragon. Your guide will meet you in the hotel lobby eager to lead you on an intimate introductory tour of Rome, and take you along the iconic monuments connected to the Eternal City, ending in the charming Piazza Navona.

Along the way, you will stop at the Pantheon, a gorgeous structure built in the 2nd century AD after the original temple was damaged in a fire. A magnificent dome rests atop the masonry walls erected in a cylindrical shape as the entrance features 16 granite columns topped with Corinthian capitals to create a dramatic and unforgettable welcome to the Pantheon and the city of Rome. At the end of your tour, you will have a delicious dinner in a local, celebrated restaurant with a glass of wine accompanying each dish to accentuate the flavors of the meal.

What's Included:

Accommodation
Transfer
Tour
Day 2

Argentario – Visit Ancient Cerveteri and Tarquinia en route to Argentario

Day 3

Argentario – Enjoy a Round of Golf and Visit the Settlement of Orbetello

Day 4

Castiglion del Bosco – Bask in the Tuscan Scenery with a Wine Tour and a Half-Round of Afternoon Golf

Day 5

Murlo – Relish Wine Tasting and a Private Lunch before Venturing to Murlo

Day 6

Murlo – Enjoy a Round of Golf in Umbria and Explore the Town of Assisi

Day 7

Murlo – Play a Local Umbrian Club before Visiting Wine Cellars of Torgiano

Day 8

Murlo – Depart for Home

Trip Highlights

  • Enjoy a full round of golf with views of the serene Orbetello Peninsula in the region of Tuscany
  • Relish a challenging course with a championship layout at Antognolla Golf Club in Umbria
  • Indulge in the unique and luxurious characteristics of the wines of Montalcino during a wine tour of the Tuscan province
  • Delight in the flavors of Vino Nobile during a wine tour of the province of Montepulciano including a delectable gourmet lunch
  • Relax in the comforts of a private villa in the countryside of Umbria
  • Wander through Rome on a guided tour of the Eternal City’s famous icons, including the Trevi Fountain and Piazza Navona
  • Witness the impressive architecture and artwork of the Basilica of St. Francis of Assisi, the saint’s birthplace
  • Explore an ancient Etruscan city of the dead on a guided tour of preserved, decorated catacombs
  • Visit private wine cellars in the province of Torgiano to sample the rewarding, flavorful wines of Umbria 

Detailed Description

Greenery surrounds the manicured fairway that guides your eye to the green. Red wine swirls in the opulent glass, reflecting the layers of ruby hues produced on a private vineyard. Your 8-day tour will encompass golf and grapes, fabulous cuisine and delicate history as you are led from Rome to Tuscany, and into the Umbrian countryside. Your tour will begin with your arrival in Rome, often referred to as the Eternal City. Your private transfer will escort you into the heart of the historical city where you will settle in at your luxurious hotel. Your guide will lead you through the streets of Rome on an engaging introductory tour of the iconic monuments ranging from the Spanish Steps to the Colosseum.

You will wake the next day, and your private transfer will meet you at your hotel and take you into the Lazio countryside as you head north to the edge of Tuscany. En route to the Argentario Peninsula, you will stop at the ancient sites of Cerveteri and Tarquinia, both remnants of the Etruscan-Italic tribe. The next day, you will step onto the golf course that edges up to the nature reserve of Laguna di Orbetello. Enjoy a full round of golf before you visit the small, historical town of Orbetello. Continue to travel deeper into the heart of Tuscany as you visit the vineyards around Montalcino, home to the celebrated Brunello wines. After a chance to sample all of the remarkable wines, you can play nine holes at a club who just offer rounds to guests staying at the resort.

The next day, you will give your body and mind a rest with a luxury wine tasting tour of Montepulciano, home to the Vino Nobile. Enjoy a gourmet lunch paired with the flavors of the wine before you stroll through the historical town of Cortona en route to your private Umbrian villa. Continue the next day with a tremendous opportunity to play the championship layout course at Antognolla Golf Club for a complete round. In the afternoon, you will visit the charming hilltop town of Assisi to enjoy the Basilica, the frescoes, and the beautiful medieval architecture.

Next, you will play the uniquely designed course of Perugia Golf Club before you enjoy a wine cellar tour around the famous vineyards of Torgiano. Conclude the next morning as your private transfer will meet you at your private villa. If you have time, you can explore the marvelous city of Perugia before you continue to Umbria’s International Airport for your flight home. You can also opt to return to Rome and delight in more time to discover the layers of a city redesigned throughout the millennia. 

Starting Price

$3,600 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 681 reviews

Switzerland, Italy, Germany Tour Review: Bologna, Florence, Zermatt, Wengen, Lake Como, Matterhorn, Tuscany, Winery Visit, Truffle Hunt, 9 Nights

This travel company was incredibly difficult to work with, and I would not recommend them. The travel agent seemed very annoyed when we asked basic questions about our itinerary. For example, the itinerary he sent us did not have the correct number of rooms booked for our party. When I asked him about it, he rudely told me, "Of course I have booked the right rooms". Later, we found out he was working off the wrong itinerary - our final invoice was based on this wrong itinerary and had a much higher amount than we actually owed. When we pointed that out, he went from being annoyed to flat out rude.

We also identified many gaps in transportation and logistics, with the travel agent continuing to be rude when we asked for clarification or support in fixing the gaps. For example, he had us driving a rental car to the Bologna airport at around 3 AM from rural Italy to make an 8 AM flight. We would be driving right through Florence on the way to Bologna. When I asked why we didn't simply take a later flight out of Florence, I was told there were no options to do this. A simple Google search identified several flights out of Florence at a more reasonable time.

We finally had Zicasso step in, and they were incredibly helpful in cleaning up our itinerary. Unfortunately, we still experienced several logistical issues during our trip despite Zicasso's support. For example, we were dropped off by drivers at train stations and were then on our own to figure out how to get to our hotels - all required lengthy walks up hills to access, and my 81-year old father was not able to do that. So we had to find our own transportation or have my dad attempt to walk (not good at all). As another example, my father really wanted to see the Matterhorn. The travel agent said it was an easy "day trip" from our hotel to the Matterhorn. It turned out to be a 3.5 hour drive each way. The driver left us at a train station below Zermatt (town below the mountain) to figure out on our own how to navigate the city of Zermatt. We had no guidance from the travel agency on how to best see the Matterhorn, and Zermatt was another town with steep hills that my dad had to walk through (with a cane) as we tried to figure out how to best see the mountain. Due to the length of the drive to Zermatt from our hotel, we had less than two hours in Zermatt because the travel company had booked us on a 6:15 AM train the next morning to leave Switzerland. It was a wasted day instead of being the wonderful experience my father had hoped for.

The best part of the trip was the hotels, and the travel company gets credit for selecting hotels with wonderful views and great breakfast options. They were not easily accessible from the local towns, so we had to figure out taxis and shuttles to get to nearby sites.

Most of the time, we were left on our own to find our way around. But we did have a guided tour in Florence and a knowledgeable driver that took us to a winery in Tuscany. Both of these guides were amazing, and it would have been nice to have more guided support throughout this trip (especially in Zermatt).

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Italy Vacation Review: Venice, Florence, Tuscan Hills, Pompeii, Rome, Amalfi Coast, Sorrento, Capri, Cooking Class, Lemon Farm, Wine Tasting, Olive Oil Tasting, 2 Weeks

We had the pleasure of working with Zicasso’s travel agents to create the perfect Italian adventure. I had quite a few specific requests, from travel logistics to hotel preferences, and they were incredibly patient and collaborative, offering multiple variations of the itinerary until it matched exactly what we envisioned.

Our journey began in Venice, where we were seamlessly picked up by a private driver, transferred to a water taxi, and dropped directly at our hotel. After a wonderful stay, we were taken by private driver to the train station for our ride from Venice to Florence, our one and only train trip, as we opted (based on their smart recommendation) for private transportation for the rest of our travels to avoid potential delays and enjoy added convenience.

From Florence, we were driven into the Tuscan hills, where we experienced magical wine tastings, vineyard tours, olive oil tastings, and unforgettable meals with wine pairings. 

Next, our private driver brought us to Pompeii, where we enjoyed a fascinating tour with our private guide, and then continued on to Rome. In Rome, we loved the private golf cart tour of the city’s major landmarks, as well as a delightful cooking class that was arranged for us; it was a real highlight!

Finally, we traveled by private driver to Sorrento. From there, we had a breathtaking driving tour of the Amalfi Coast, a lemon farm tour, and an amazing day trip to Capri. Every detail was thoughtfully planned and executed.

Summary:

Planning and Itinerary Creation: Zicasso’s consultants made the entire process easy and stress-free. They worked closely with us to perfect the itinerary and were always receptive to changes and feedback.

Hotels: My sister and I requested adjoining rooms and were provided with beautiful family suites throughout the trip. Each hotel was ideally located, comfortable, and well-appointed, with all the amenities we needed.

Transportation: Every transfer was smooth and punctual. The private drivers were professional, friendly, and knowledgeable. (A special shoutout to our driver in Florence/Tuscany – he was the best!)

Communication: Throughout our trip, the travel company’s team was always accessible. Whether we needed to make adjustments or had a question, they handled everything promptly, allowing us to relax and fully enjoy our vacation.

We spent just over two unforgettable weeks in Italy and it was absolutely perfect, all thanks to the hard work, attention to detail, and excellent communication from Zicasso’s travel company! I highly recommend them and would not hesitate to use them again for future adventures.

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Italy Tour Review: Amalfi Coast, Ravello, Positano, Florence, Rome, Siena, Winery Visit, 11 Nights

Overall, the trip was perfect! The hotels were really nice and the itinerary was great.

A few things I would have changed. First, the Amalfi tour day. There was not enough time in Ravello or Positano. We needed more time to relax and shop.

The class of train could have been nicer for the Florence-to-Rome portion of the trip.

We've been to many wineries throughout Europe and the one we went to on our way to Siena was okay, but we have been to much nicer wineries, with better wine and food tastings. It was not a great wine tour experience.

Everything else was wonderful and we really enjoyed the trip with our sons!!!

Thank you!

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Italy Tour Review: Capri Private Boat Cruise, Wine Tasting, 10-Day Vacation

The drivers were timely, professional, and very prompt. The guides were very knowledgeable and generally designed the tours to match our requests. The hotels were exceptional and our only comment is that there was an odd odor in our room in one of the hotels.

Our only true complaint would be about the wine tasting on May 22. The location was not aware of our reservation. The couple running the vineyard seemed confused by our arrival. After a bit, they offered to accommodate us, but we felt like we were imposing on them. Then, at our lunch at a restaurant on Capri, they did not have a record of a reservation and placed us at a table without a view, near the entrance. We made the best of the meal, but for the price we paid, we would have expected confirmed reservations and a table with a view.

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Italy Tour Review: Venice, Florence, Rome, Naples, Pompeii, Tuscany, St. Mark's, Food Tour, Vineyard Visit, 2-Week Trip

The travel professionals at Zicasso’s travel company worked with us for over a year to plan the most amazing 14-day tour of Venice, Florence, and Rome. They were beyond patient and kind, fielding my endless questions and providing assurances for every detail. Every day was jam-packed with guides and travel. Well, one really doesn't know until you get to Italy, right?

Upon our late-evening arrival to Venice, we had our personal escort waiting for us at the airport, with private transport to our hotel in Venice. She did not leave until we had our bags in the lobby. I knew right then and there we had made the right choice with the travel company.

We found that everything was taken care of by the travel company, down to the smallest detail. Every guide, and there were many, came to our hotels to greet us and escorted us back to our hotel upon conclusion of our tour. Every single guide was a treasure. We never had to hail a taxi, which to me was the most amazing thing, as the travel company had private drivers picking us up or waiting for us at hotels and train stations.

Upon leaving Venice for Florence, our personal escort from the airport was waiting for us at the hotel, with a water taxi to the train station. She walked us through the train station and showed us how to find our gate for our train to Florence. Upon arrival in Florence, we had a private driver waiting for us for transport to the hotel. Same from Florence to Rome, Rome to Naples (for Pompeii and back to Rome).

We had multiple food tours and they were all amazing. We spent every day with private guides. Believe me, the travel company knows the very best guides in Italy. They are there 24/7 for you if things don't go as planned. Trust me on this.

In Venice, our tickets for St. Mark's Basilica that were reserved for our guide disappeared. There we were, no access. Our guide tried to secure tickets on her own and access was sold out. She called the travel company, which somehow secured access, even to the second level, where we could visit the four bronze horses.

Did I mention our day in Tuscany? The travel company insisted we were spending too much time with tours and insisted we take a day in Tuscany. We visited a vineyard in Tuscany for what turned out to be a private tour and lunch hosted by the vineyard owner. We had a table set up overlooking the vineyard and indulged in what may have been the best food we experienced in all of Italy. Everything was made on-site and perfectly paired with the vineyard wines. We were entertained by her three wonderful dogs, two of which were lovable and goofy Labrador retrievers. What a perfect day!

Without a doubt, the travel company is the finest travel agency we have ever had the privilege to work with. As I said earlier, everything was taken care of, nothing was missed: drivers, trains (business class), guides, food tours. The best vacation we have ever had.

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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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Customizable Itinerary

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

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