Italy Retreat & Pilgrimage 2027

Your Italian adventure will begin at the spectacular La Torre Resort, a stunning organic farm and vineyard surrounded by the rolling hills of Tuscany. After settling into your rooms, we'll get together for our welcome session, where you'll meet the wonderful group of people who will be sharing the journey with you.

In the evening, we'll gather poolside to celebrate the beginning of an unforgettable week with a five-star wood-fired pizza dinner along with other incredible Tuscan dishes, beer, mocktails, and wines produced right on the estate. It will be the perfect introduction to the beauty, hospitality, and flavors of Tuscany.

Start your day with a delicious Tuscan breakfast, then join us for teaching, discussion, and a workout designed to accommodate every fitness level.

The afternoon is all yours. Take a walk through the vineyards, relax by the pool, curl up with a good book, or simply enjoy some downtime. There's no wrong way to spend it.

On our final evening at La Torre, we'll gather around the table for a wonderful Tuscan dinner as we celebrate our time together before lacing up our hiking shoes and beginning our pilgrimage the next morning.

After breakfast, we'll begin our pilgrimage along the ancient Via Francigena. As we make our way through rolling hills, vineyards, olive groves, and the peaceful Tuscan countryside, it's easy to see why travelers have been drawn to this path for centuries.

By afternoon, we'll arrive in the beautiful hill town of San Gimignano, known for its medieval towers, charming streets, and incredible views. You'll have time to wander the shops, grab a gelato, or simply soak in the atmosphere before we gather for dinner, swap stories from our first day on the trail, and settle in for the night inside the historic city walls at Hotel L'Antico Pozzo.

Following breakfast and a short devotional, we'll continue our walk toward the beautiful walled town of Colle di Val d'Elsa. This stretch of the Via Francigena is one of my favorites, winding through vineyards, cypress trees, rolling hills, and the kind of countryside you've probably seen in postcards.

After we arrive, you'll have time to explore the town before we gather for a fun olive oil and balsamic vinegar tasting. That evening, we'll head to a local restaurant for dinner, which will be a perfect way to end another incredible day on the trail.

We'll enjoy breakfast on the hotel's terrace before setting out on a shorter, more relaxed walk. It may be one of our easier days, but it's an extra special one as we follow a peaceful river through the beautiful Tuscan countryside.

Later that afternoon, we'll arrive at Monte Castelli Organic Farm, where you'll have plenty of time to relax by the pool, wander the beautiful property, or simply enjoy a quiet afternoon. Before dinner, we'll gather for a stretching session and some practical teaching on exercise and nutrition.

One of the highlights of our stay is the food, and trust me, it's every bit as delicious as you'd hope. Nearly everything we eat is grown or produced right on the farm or sourced from nearby local farms. It's not unusual for vegetables to be picked from the garden that very day, making every meal incredibly fresh, flavorful, and a true taste of Tuscany.

If you're anything like me, you don't often give yourself permission to do...well...not much at all. That's what makes today so special. Sleep in, enjoy a leisurely breakfast, relax by the pool, read a book, spend some quiet time with God, or simply sit outside and enjoy the beauty of Tuscany. Sometimes the most refreshing days are the ones with the fewest plans.

If you're looking for a little pampering, you can schedule an optional massage. Or, if you'd rather be a little more hands-on, join us for an optional cooking class and olive oil tasting—a fun way to experience the flavors and traditions of Tuscany.

Throughout the day, we'll get together for teaching, discussion, and inspiration before ending the evening gathered around the table for another delicious farm-to-table dinner.

Today is our biggest hiking day, but don't let that intimidate you. We'll take our time, enjoy plenty of breaks, and soak in some of the most beautiful scenery of the entire trip. Along the way, we'll stop in the medieval village of Monteriggioni, where you'll have time to wander the tiny streets, grab a coffee or lunch, and enjoy one of Tuscany's true hidden gems.

By late afternoon, we'll arrive at Relais La Costa, our home for the next two nights. After a day on the trail, there's nothing quite like slipping into the pool, looking out over the rolling Tuscan hills, and realizing this is your backyard for the evening.

We'll wrap up the day with another wonderful Tuscan dinner, celebrating all we've accomplished together before settling in for a well-earned night's rest.

Today we complete our pilgrimage as we walk into the beautiful city of Siena. There’s something incredibly rewarding about reaching the end together. We’ll celebrate with pizza, fresh salad, and time to explore one of Italy’s most iconic cities before heading to our hotel.

Tonight we’ll stay at Il Chiostro del Carmine, a beautifully restored 14th-century monastery just a short walk from Piazza del Campo. With its historic character, peaceful courtyard, and views over the Tuscan countryside, it’s a pretty special place to spend our final night.

Our final dinner is always one of my favorite evenings of the trip. We’ll reflect on the week, laugh about the unexpected moments, and celebrate everything we’ve experienced together. It’s hard to believe how much can happen in just a few days, and I have a feeling you’ll leave Tuscany grateful you said yes to the adventure.

After one last breakfast together, it'll be time for hugs, goodbyes, and the journey home. My hope is that this week becomes more than a wonderful memory. I hope it serves as a reminder that even back home, we can choose to slow down, spend time with God, enjoy the people around us, and savor the life He's given us.