Ole Crow Tours presents our Inaugural Italian Journey

Tuscany: September 18–25, 2026

Imagine waking up in the rolling hills of Tuscany, surrounded by vineyards, medieval villages, and some of the most beautiful countryside in Italy.

Join Ole Crow Tours for our very first hosted Italian journey — an intimate small-group experience designed for travelers who want to experience Italy slowly, personally, and authentically.

With no more than 6 guests, this Tuscan journey is intentionally small, allowing us to travel comfortably, connect naturally, and enjoy the flexibility larger tours simply cannot offer.

Your Tuscan Experience Includes

September 17 – Departure Day
Guests will be transported from the Charlottesville area to Washington Dulles International Airport for our overnight flight to Italy.

September 18 – Arrival in Tuscany
After arriving in Florence and driving to Siena, we'll settle into our accommodations and enjoy a relaxing welcome dinner featuring traditional Tuscan cuisine and local wines.

September 19 – Discover Siena
Our adventure begins with a guided walking tour of Siena's magnificent historic center, including the famous Piazza del Campo and the city's stunning medieval architecture. We'll enjoy a hosted group lunch together before taking time to explore the city at your own pace. In the evening, we'll gather for a hands-on Tuscan cooking class and dinner, creating authentic regional dishes while learning the culinary traditions that make Tuscany famous.

September 20 – San Galgano, Parco dei Mulini & Montalcino
Travel through the scenic Tuscan countryside to visit the remarkable Abbey of San Galgano, one of Italy's most unique historic treasures. We'll continue to the fascinating Parco dei Mulini, where ancient waterways and historic mills tell the story of Tuscany's past. A hosted group lunch will be included before we journey to Montalcino for a winery tour and tasting in the home of the legendary Brunello wine. We'll gather again in the evening for a wonderful hosted group dinner.

September 21 – Val d'Orcia & Montepulciano
Experience the breathtaking landscapes of Val d'Orcia, one of Tuscany's most photographed regions. We'll enjoy scenic drives through rolling vineyards and picturesque villages before exploring Montepulciano with a guided tour of its historic center and renowned wine cellars. A tasting of the area's celebrated Vino Nobile wines completes the day. Dinner this evening is open for guests to enjoy one of Siena's many wonderful restaurants at their leisure.

Inaugural price of $2,799 per person/without airfare

Tour Highlights

• Seven nights in Siena, Tuscany

• Daily breakfast included at our accommodations

• Guided tour of Siena

• Visit to the spectacular Abbey of San Galgano

• Visit to Parco dei Mulini

• Scenic touring through Val d'Orcia

• Guided visits to Montepulciano, Monteriggioni, and San Gimignano

• Full-day Chianti wine country experience

• Multiple winery tours and tastings throughout Tuscany

• Hands-on Tuscan cooking class

• Four hosted group lunches

• Four hosted group dinners

• Comfortable transportation throughout Tuscany

• Small-group experience with Ole Crow Tours

• Round-trip transportation to and from Dulles Airport for guests in or near the Charlottesville area

September 22 – Monteriggioni & San Gimignano
Step back in time as we visit the perfectly preserved walled village of Monteriggioni before continuing to the iconic hill town of San Gimignano, famous for its medieval towers and spectacular views. A hosted group lunch is included, along with guided touring and a tasting of the region's celebrated Vernaccia wines. We'll conclude the day with another hosted group dinner.

September 23 – Chianti Wine Country Experience
Today we'll venture into the heart of the world-famous Chianti region. Spend the day exploring charming vineyard estates, historic wineries, and picturesque Tuscan countryside while enjoying multiple wine tastings featuring Chianti Classico and other regional favorites. A hosted group lunch will be served at one of the area's beautiful wineries, allowing us to fully savor Tuscany's renowned food and wine culture. The evening is yours to explore Siena and enjoy dinner on your own.

September 24 – Flexible Exploration Day
Our final full day in Tuscany is intentionally left open. Guests may choose to relax in Siena or join an optional excursion to another Tuscan destination of interest. Whether it's a charming village, a local market, an additional winery, or a hidden gem recommended by the group, this day allows us the flexibility to create one more memorable Tuscan experience together. In the evening, we'll gather for a special farewell dinner to celebrate an incredible week of friendship, food, wine, and adventure.

September 25 – Departure
After breakfast, we'll depart Siena and transfer to Florence Airport for our return journey home, bringing with us unforgettable memories of Tuscany's history, culture, cuisine, and countryside.