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.

During our stay, we’ll call B&B La Fontanina home — a charming B&B perfectly located in the town of Siena. From there, we’ll take relaxing day trips through scenic wine country, historic hill towns, local markets, and hidden corners of Tuscany that make this part of Italy so unforgettable.

This is not a rushed sightseeing tour. It’s about sharing wine overlooking the vineyards, wandering quiet Tuscan streets, enjoying long meals together, and experiencing Italy at a relaxed pace alongside fellow travelers who appreciate meaningful experiences.

At Ole Crow Tours, hospitality has always been at the heart of what we do. With more than 100 five-star reviews, our guests know us for creating welcoming, memorable experiences where the details are handled and people feel genuinely cared for. We’re bringing that same approach to Italy.

From the moment the journey begins, we’ll take care of the planning, coordination, and day-to-day logistics so you can simply relax and enjoy the experience. Our goal is to make you feel less like a tourist passing through and more like a welcomed guest experiencing Tuscany alongside friends.

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

• 3-Star B&B in the heart of downtown Siena

• Comfortable, air-conditioned transportation

• 7 breakfasts

• 4 lunches with wine

• 4 dinners with wine

• 6 wine tastings

• 4 food classes/guided tours