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

Vineyards and countryside landscape in Maremma, Tuscany, Italy
A 8 day trip to Italy 
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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. 

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General Information

Detailed Itinerary

Places Visited 

Rome, Argentario, Tarquinia, Cerveteri, Torgiano, Orbetello, Murlo, Orvieto, Castiglion del Bosco, Montalcino  

Departure Dates 

Dates are flexible and customizable for private departures.

Detailed Itinerary 

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, dinner

Day 2: Argentario – Visit Ancient Cerveteri and Tarquinia en route to Argentario

In the morning, the aroma of rich espresso emanates from the corner cafes of Rome. Local businesspeople sip their espresso at the bar before they make their way quickly to work. The cobblestone streets fill with life and activity in front of the elaborate window displays along Via Condotti. Your private transfer will meet you at your hotel and escort you out of Rome and north of the peninsula of Argentario. The hills of Rome continue to roll along the landscape outside of the city as olive orchards, and golden plains reach into the distance. You will arrive at the ancient Etruscan city of the dead known as Cerveteri. The Italic tribe settled across the regions of central Italy before succumbing to the growing power of the Roman state around the 3rd century BC.

The scents of the fresh grass and rich soil emanates from the archeological site. Your guide will lead you along the pathways between the camouflaged mounds that rise out of the earth. The necropolises date back to the 9th century BC and include thousands of Etruscan tombs while resembling a city-like design with streets and neighborhoods. Your guide will lead you down the stairs into the Tomb of the Reliefs, which was built between the 4th and 3rd centuries BC. Stucco reliefs decorate the walls and depict household utensils and pets, along with images of a Cerberus-like creature. You will return to the fresh air and continue to the heritage site of Tarquinia before you reach the relaxing luxuries of your resort situated near the Orbetello lagoon. 

What’s Included: accommodation, transfer, tour, breakfast

Day 3: Argentario – Enjoy a Round of Golf and Visit the Settlement of Orbetello

Wake up among the charming Tuscan hills as they roll against the shimmering turquoise waters of the Tyrrhenian Sea. Vineyards and cypress trees roll along the mountain with the sound of splashing water echoing across the quiet expanse as the soft grains of the white Tuscan beach reach beyond the hills. After breakfast, you will step onto the golf course for an early round of 18-holes. The picturesque course totals 6,840 yards, averaging a par of 71. Various holes offer stunning views of the Orbetello lagoon and the hills of Maremma. Hole six is a par five that reaches 493 yards from the pin to the green as the refreshing breeze brings the aroma of herbaceous grass and the ocean across the course.

You will have a view of the lagoon in the distance, and the two water hazards cause a narrow isthmus at the center of the fairway. You may lay-up to your left and miss the water, allowing you easy access to the pin, bordered in the back by a sand trap. After your time on the course, you will enjoy the facilities on the property before you make your way to the town of Orbetello, whose roots date back to the 3rd century BC as an Etruscan settlement. The polygonal ancient city walls remain a symbol of the city’s history, which predates the creation of Rome. On the outskirts of town, the sails of a single mill continue to spin above the water as they have since the Spanish built the mill in the 16th century. 

What’s Included: accommodation, tour, breakfast

Day 4: Castiglion del Bosco – Bask in the Tuscan Scenery with a Wine Tour and a Half-Round of Afternoon Golf

You will listen to the sound of the waves as they lap against the white sand beaches of Tuscany each morning. At breakfast, the aroma of rich cappuccino accompanies the buttery scent of freshly baked brioche as you eat leisurely. Your private transfer will meet you in the hotel lobby and escort you to the edges of the central Tuscany. The landscape is lush with cypress trees, vineyards, and chestnut trees as olive orchards sprout along the hillsides. With your first stop the historical town of Montalcino, you will explore the historical wines produced around the province.

Montalcino has maintained its streets and structures from the 16th century to create a unique Late Renaissance ambiance. Red and yellow flowers blossom in the narrow valleys outside of town alongside the ancient oak trees. You can see country roads in the distance that lead to elaborate vineyards and the nearby hilltop towns. The medieval, 14th-century walls of Rocca strike an imposing, and impressive, posture at the edge of town as the clock tower adorns Palazzo dei Priori and casts a shadow over the main square of Piazza del Popolo.

Your guide will sweep you away from the cobblestone streets of Montalcino for your first taste of the celebrated wines that produced around the province, beginning with a small, organic winery within walking distance of the Montalcino’s town center. The steep street leads you down to a fairytale winery, with vines that reach across the terraced hill. Your guide will explain the importance of the climate and the soil before offering you a sample of the wine, which emits layers of complex flavors. You will sip to find concentrated aromas of spices and dried fruits with a lingering cedar finish.

What’s Included: accommodation, transfer, tour, breakfast

Day 5: Murlo – Relish Wine Tasting and a Private Lunch before Venturing to Murlo

Today you will give your body a rest from the golf courses along the Tuscan hills. At breakfast, you will have a marvelous view of the lush landscape and the vineyards on the property of your resort, situated inside a refurbished 800-year-old estate. After your meal, your private transfer will lead you to the province of Montepulciano, which surrounds the eponymous medieval town. Renaissance palaces and historic churches line the piazzas and cobblestone streets and the province is also known for its production of Vino Nobile, the “Noble Wine.”

You will stop next at a local vineyard for a tour of the opulent and tranquil setting and then have a chance to taste some of the ripening Sangiovese grapes before you sample a number of wines produced on the property, including a glass of Vino Nobile. The ruby hue gives way to an aroma of cherry and tobacco, and you may notice a hint of balsamic and white pepper on your palate. Your guide will bring out a selection of local cheeses, including a creamy pecorino to accompany your wine selection.

Continue your day of relaxation and exploration in Cortona, a charming town enclosed by stone walls and standing nearly 1,970 feet above sea level. The open views around the walls take in the remarkable verdant landscape that leads to the shores of Lake Trasimeno. The Girifalco Fortress adorns the hilltop and was erected in the 16th century under the commission of the Medici. The Renaissance Cathedral in the heart of town was erected in the 11th century over a former Etruscan temple, and the interior includes great 16th and 17th centuries frescoes.

What’s Included: accommodation, transfer, tour, breakfast

Day 6: Murlo – Enjoy a Round of Golf in Umbria and Explore the Town of Assisi

The beauty of Umbria surrounds you in the morning at your private villa that overlooks the limestone cliffs, the rugged hills, and the verdant oak trees. The estate was established in the 11th century, of which only the square tower remains. The stone retains heat in the winter and cool air in the summer, making it a comfortable accommodation, along with a unique way to experience rich history. You will have an early start to get back onto the golf course, but you will feel rested and refreshed, especially after the rich espresso you will enjoy before you take your practice swings at the driving range. 

Embark on the challenging 18-hole Championship Antognolla Golf Course, designed by the celebrated architect Robert Trent Jones Jr. The aroma of olive orchards and chestnut trees drifts along the fairway. The masterwork of the course comes from its shifting appearance, at first seeming unconquerable, but revealing its accessibility as you play. The course encompasses 2,983 yards of play, featuring a par five as the longest hole.

The manicured patches of greenery are sporadic within the first 50 yards. A pond separates the 18th hole from the first hole, and a sand trap stands in the foreground of the green which curves suddenly to the left. You will enjoy a good challenge on the green and swing eagerly and then await your ball as it lands in the distance. In the afternoon, you will enjoy a guided tour of Assisi, the birthplace of St. Francis and home to a breathtaking hillside Basilica that overlooks the valley floor.   

What’s Included: accommodation, tour, breakfast

Day 7: Murlo – Play a Local Umbrian Club before Visiting Wine Cellars of Torgiano

In the morning, you will venture south to the Perugia Golf Club, located within 15 miles of your private villa. On the edge of the course, you will see the vineyards shimmering with emerald leave. The local club has a par 72 and encompasses a total of 5,824 yards. Rich vegetation borders the fairways and acts as natural boundaries to each hole. When you step up to the tee, you will realize that the course is a test of control and touch, requiring elegance of play to succeed along the small, and sometimes narrow greens.

After you play the full 18-holes, your guide will meet you in the lobby of the club before you continue to the town of Torgiano. The medieval architecture rests inside old walls with an imposing tower, and the town is known for its wine as it produces celebrated reds and whites with respect to provincial tradition. Follow your guide along the cobbled paths, set between antique buildings as the aroma of fresh pasta and simmering tomato sauces escape from hidden trattorie. You will then visit your first of five wine cellars along the Strade del Vino.

Seasoned roads connect to wineries that house historical, and even legendary, bottles of wine produced in Umbria for centuries. The grapes change with the season and offer an abundance of fragrances absorbed through the soil and the vines. At your first cellar, you will feel the cool air on your skin as it differs from the warm sunlight outside the natural cavern. Your guide will pour you a sample of a Lungarotti wine known as Torgiano Rosso Riserva Vigna Monticchio to enjoy as the vineyard encompasses nearly 80 acres of the Umbrian countryside.

What’s Included: accommodation, tour, breakfast

Day 8: Murlo – Depart for Home

In the morning, you will have breakfast as you overlook the undulating hills of Umbria. The rich aroma of your espresso blends with the surrounding oak trees as they rustle in the breeze. When you are ready, your private transfer will meet you at the villa and escort you to the town of Perugia, the capital of Umbria. If you have time, you can wander through the hillside city, which was first settled by the Etruscans. The settlement walls continue to surround the ancient center and reach a length of more than 9,000 feet.

The historical streets have a youthful atmosphere deriving from the University., which opened its doors in September of 1308. Wandering along the elegant cobblestone streets and straw colored buildings offers a hint of chocolate emanating from the local confectionaries. The former Dominican monastery now houses the Archeological Museum, which contains artifacts dating as far back as the 16th century BC, including an Etruscan inscription from the 2nd century. After one last morning of exploration, your private transfer will take you to the International Airport of Umbria with plenty of time to check-in for your flight home.

What’s Included: breakfast, transfer


Starting Price 

This trip is customizable for your private travel.

What's Included 

  • Accommodations
  • In-country transportation
  • Some or all guided tours and activities (dependent on season)
  • Expert trip planning
  • 24x7 support during your trip
The starting price is based on travel during the low season for a minimum of two travelers staying in shared 3-star accommodations. Please inquire for a custom trip quote based on your travel preferences and travel dates.