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 603 reviews

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: 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 Trip Review: Rome, Venice, Florence, Opera, Walking Tours, 10 Nights

We had a fantastic experience for a first-time trip to Italy. I wasn't sure how this would be, considering I learned about Zicasso while trying to plan the trip myself. Zicasso put me in touch with a travel specialist and the whole team was incredibly responsive to my many, many questions. If they were ever annoyed, it didn’t show.

I really wanted a smooth experience for my family of five, including three teens, one of whom has Celiac. Our agent was great in helping plan out the experience we wanted. As you may know, it is challenging to find rooms for five in Europe, but the travel company found apartments (usually two bedrooms with a pull-out couch) in the heart of town. You can really customize what you do, but we elected to plan our own meals and handle some of our own transport. We did have one issue where the van driver taking us to the train failed to show. I got one with Uber and the travel company quickly (I mean before we got home quickly!) refunded that amount.

Our contact in Italy was amazing and patient. I can’t give her enough credit. Any time I was unsure of something, she was there. The tours were great, especially Florence and Rome. You may be able to find the companies online, but ours seems to have the connections to get the best guides.

As for meals, we didn’t have any issues. We used an app and got a few recommendations from the travel company and local guides. Even our wine-tasting tour out in Tuscany was accommodating.

I would use our travel company and Zicasso again. I think the only downside is we tried to cram a lot in and it was hot. I probably should have asked for one to two fewer or shorter walking tours, especially on days we switched cities. Otherwise, it was excellent.

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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: Rome, Florence, Tuscany, Vatican, Colosseum, Cooking Class, Food Tour, Cheese Sampling, Wine Tasting, 10 Nights

We've taken many family vacations over the years, but we all agreed this was the best one yet!

The team at Zicasso’s travel company did an exceptional job tailoring the perfect trip for our family. Every detail was thoughtfully planned, making the entire experience seamless and truly enjoyable from start to finish.

We had wonderful drives and knowledgeable, engaging tour guides who made each destination come to life. Some of our favorite highlights include a hands-on cooking class in Florence, exploring the beautiful Tuscan countryside, and having effortless access to iconic sites like the Vatican and the Colosseum.

The experiences were unforgettable, from the best food tour in Rome to a fun and unique golf-cart tour through the city. We also loved visiting a Parmigiano-Reggiano factory and a Parma ham producer, along with an extra-special stop at the Ferrari Museum that was such a memorable surprise.

Every moment felt thoughtfully curated and we came home with incredible memories that we will cherish for years to come. We highly recommend the travel company to anyone looking for a truly personalized and exceptional travel experience.

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Italy Trip Review: Rome, Florence, Capri, Sorrento, Cooking Classes, Vineyard Dinner, 13 Nights

We just got back from an amazing two-week vacation with our children and our eight-year-old granddaughter. The travel specialists at Zicasso's tour company were incredibly knowledgeable, responsive, and professional. They took all of my ideas and managed to incorporate them seamlessly into our itinerary. I had quite a few requests and even made some last-minute changes, which they accommodated without any hesitation. One specialist, in particular, was exceptionally kind and helpful!

The organization of the trip was smooth and effortless. The transportation, drivers, and guides were all top-notch! We traveled in clean and well-maintained Mercedes vans, with well-dressed and personable drivers. The local guides were not only knowledgeable, but also spoke English clearly, sharing fascinating insights that allowed us to dive deeper into the history and culture. The hotels we stayed at ranged from good to very good. If I were to plan this again, I might choose a different location in Rome; the area was a bit congested and the hotel could use some upgrades, but it was conveniently situated.

The wine tastings were enjoyable and dinner at the vineyard was truly magical! Our standout activities were the cooking classes in Florence and Rome. The chefs were professional and imparted a lot of knowledge, giving us valuable skills to take home.

The highlight of our trip was definitely the private boat charter in Capri! We had a perfect day on a brand-new yacht, with an experienced captain and crew who took us to hidden caves away from the crowds, allowing us to swim in stunning locations. It was an absolutely fantastic trip!

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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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