Join us for our Italian Countryside with The Sisterhood 2027 tour, a thoughtfully curated small-group journey for women who crave meaningful connection, culinary indulgence, cultural discovery, and the freedom to explore at a gentler pace – we call it the joy of slow travel. This 14-day adventure takes you beyond the crowded tourist paths into the heart of Italy – from the ancient ruins of Rome to the serene landscapes of Umbria, the rolling vineyards of Tuscany, and the delicious traditions of Emilia-Romagna.
Unlike whirlwind tours that rush from site to site, this experience invites you to truly soak in each destination. Walk historic streets with expert guides, taste wine and olive oil straight from the source, learn how Parmigiano-Reggiano and balsamic vinegar are crafted, and enjoy intimate meals that nourish both body and soul. Along the way, you’ll forge genuine friendships with like-minded women, sharing laughter, stories, and moments that become memories.
Whether you’re gazing across a hilltop in Pienza, enjoying a truffle hunt in the Umbrian woods, or clinking glasses at a Tuscan villa, this is Italy done differently—slow, immersive, and unforgettable.
Welcome to Italy, Bella! After passing through customs, your private driver will be waiting in the Arrivals Hall to whisk you away to our beautifully situated hotel in Rome. Take some time to unpack, freshen up, and let the magic of Italy sink in. The air smells a little like espresso and fresh-baked focaccia, and you’re officially on Italian time now. This evening, we’ll gather for a casual welcome gathering, a relaxed chance to meet your Group Leader and new Sisters. (No meals are included today)
Hotel: Kolbe Hotel Rome
This morning, we’ll dive into the heart of ancient Rome with a guided walking tour of the Colosseum and Roman Forum, where history comes alive with every step. Enjoy a free afternoon to explore the Eternal City your way with your Sisters. Tonight, we’ll taste our way through the Monti district, known for its cool vibe and incredible eats. Think authentic Roman pizza, local favorites, and a delicious intro to Italy’s food scene. (Breakfast and Dinner included)
Hotel: Kolbe Hotel Rome
We’ll start our morning with a guided stroll through Rome’s Renaissance and Baroque treasures, from the Spanish Steps to the Trevi Fountain and the lively Piazza Navona. Enjoy the afternoon at leisure with your Sisters to shop, explore, or indulge in your next gelato. This is your time to soak in the city’s magic. Tonight, we’ll gather for a Welcome Dinner to toast the next part of our journey through Tuscany and Umbria where the countryside awaits! (Breakfast and Dinner included)
Hotel: Kolbe Hotel Rome
Today we head into the Umbrian hills to Spoleto, where olive trees and ancient stone streets whisper stories of the past. We’ll explore this enchanting town with a local guide, visit the Duomo of Santa Maria Assunta, and take in sweeping views from the Rocca Albornoz fortress. Later, we’ll visit a family-run frantoio (olive mill) for an insider look at traditional oil-making, followed by a delicious EVOO (Extra Virgin Olive Oil) tasting. Welcome to the countryside, our home for the next three nights. (Breakfast and Dinner included)
Hotel: Hotel Dei Duchi Spoleto
Step into the spiritual heart of Umbria with our guided walk through Assisi, the birthplace of St. Francis. We’ll wander cobbled streets, take in sweeping views, and explore the magnificent Basilica of St. Francis, rich with centuries of art and devotion. Then, prepare for one of the most meaningful moments of our trip: a home-cooked lunch hosted by a local family in the Umbrian countryside. We’ll gather around their table, share stories, and experience the kind of warm, personal connection that turns a meal into new memories and friendships. (Breakfast and Lunch included)
Hotel: Hotel Dei Duchi Spoleto
Today, we head into the Umbrian countryside, where the scent of adventure (and truffles!) awaits. With a local truffle hunter and his expert dogs leading the way, we’ll search the forest floors beneath the Apennine foothills for these prized delicacies. After the hunt, we’ll sit down to a rustic, home-cooked lunch featuring the very truffles we helped uncover, a true taste of Umbria’s culinary soul. We’ll return to our hotel in the late afternoon, full of good food, great stories, and a deeper appreciation for the land we’ve walked together. (Breakfast and Lunch included)
Hotel: Hotel Dei Duchi Spoleto
This morning, we say arrivederci to Umbria and make our way into the dreamy hills of Tuscany’s Val d’Orcia, a UNESCO-listed landscape of rolling vineyards, golden fields, and cypress-lined roads. We’ll stop at a local pecorino cheese farm, where we’ll meet the makers, sample their savory creations, and soak up the views of the Tuscan countryside. Then we’re off to Pienza, a Renaissance jewel (UNESCO) known for its charm, blooms, and breathtaking panoramas. This evening is all yours to wander, wine, and dine at your own pace with your Sisters as Tuscany welcomes us with open arms. (Breakfast and Lunch included)
Hotel: Hotel Corsignano, Orcia Valley
Today, we’ll journey deeper into the Orcia Valley, where every curve in the road reveals another postcard-perfect view. Our first stop is the tiny hamlet of Bagno Vignoni, famous for its ancient thermal springs right in the main square and once a healing stop for pilgrims on their way to Rome. Next, we head to Montalcino, the hilltop town renowned for its bold and beautiful Brunello wines. We’ll tour a local estate, explore the cellars, and savor a tasting of these world-class reds. This afternoon, we return to Pienza where the rest of the day is free for you and your new besties to wander the town, relax at a café, or stroll one of the iconic white roads through the rolling farmland. (Breakfast included)
Hotel: Hotel Corsignano, Orcia Valley
This morning, we make our way to Siena, where a guided walking tour brings its rich history to life, especially the thrilling tradition of the Palio Horse Race that defines this medieval city’s spirit. Afterward, enjoy free time to explore at your own pace, perhaps with a visit to the stunning cathedral, admiring Renaissance frescoes, or simply soaking up the views from a quiet piazza. In the afternoon, we’ll drive through the scenic Chianti countryside to our next home: a beautifully restored Tuscan villa, where rolling vineyards and timeless beauty surround us. (Breakfast included)
Hotel: Villa San Lucchese, Tuscany
Today we set out for Florence, the breathtaking Cradle of the Renaissance. With a local expert, we’ll walk the city’s storied streets, crossing the Ponte Vecchio, strolling through Signoria Square, and standing in awe before the grand Piazza del Duomo and Palazzo Vecchio, once the seat of Medici power. After the tour, enjoy free time with your Sisters to explore Florence your way: visit a museum, shop for leather goods, or sip wine and enjoy a delicious meal in a quiet piazza. In the evening, we’ll return to our Tuscan villa to unwind and savor the beauty of our countryside escape. (Breakfast included)
Hotel: Villa San Lucchese, Tuscany
This morning, we visit the iconic hill town of San Gimignano, where medieval towers rise above the vineyards like stone skyscrapers, earning it the nickname “Manhattan of the Middle Ages.” Wander the cobbled streets at your own pace, and don’t miss a scoop (or two!) from an award-winning gelateria, one of the best in all of Italy. We’ll return to our villa mid-afternoon to relax and refresh. Then, as the sun dips over the Tuscan hills, we’ll come together for a Farewell Dinner to Tuscany, to share stories, raise a glass, and celebrate our unforgettable journey thus far. (Breakfast and Dinner included)
Hotel: Villa San Lucchese, Tuscany
Today, we journey north through the Apennine Mountains, crossing into Emilia-Romagna, Italy’s beloved “Food Valley” and home to some of its most iconic culinary and automotive treasures. We’ll stop in Modena, hometown of Enzo Ferrari, where you’ll enjoy free time for lunch (think balsamic drizzles, Parma ham, and aged Parmigiano), followed by a visit to the Ferrari Museum, where vintage cars and legendary engines bring Italy’s racing heritage to life. Later, we’ll arrive in Correggio, our home for the next two nights. After checking in, we’ll take a relaxed orientation walk with our guide before enjoying a free evening with our Sisters to explore and dine at our own pace. (Breakfast included)
Hotel: Phi Hotel Dei Medaglioni Correggio
We start our final day with a visit to a traditional Parmigiano-Reggiano dairy, where this iconic cheese has been crafted the same way since the 1300s. Watch the process, meet the makers, and sample the rich, aged results. Next, we’re off to a family-run agriturismo, where generations have aged balsamic vinegar in wooden barrels tucked away in the attic. We’ll enjoy a tasting and light farm lunch, surrounded by the flavors and traditions of Emilia. This afternoon, we’ll return to Correggio where the rest of the day and evening is your last chance to soak it all in, shop for souvenirs, and enjoy independent dining and a final toast with your Sisters. (Breakfast and Lunch included)
Hotel: Phi Hotel Dei Medaglioni Correggio
This morning, we say arrivederci to the Emilia region and the unforgettable memories we’ve made across Italy’s countryside. Today, we’ll transfer to the Bologna airport for our flights home, carrying with us full hearts, new friendships, and a deep love for the flavors, landscapes, and stories of la bella Italia. (Breakfast included)
PLEASE READ THIS INFORMATION CAREFULLY
This thoughtfully curated journey through Rome, Umbria, Tuscany, and Emilia-Romagna is designed for women who appreciate the joy of slow travel, savoring moments, meals, and meaningful connections without the rush of constant packing and unpacking. With multi-night stays in beautifully situated hotels and villas, the pace is more relaxed than typical Italy itineraries, balancing guided sightseeing with free time to linger, wander, and discover.
Walking & Standing: Expect light to moderate walking most days, especially in historic centers such as Rome, Spoleto, Assisi, Siena, Florence, and San Gimignano. These towns often require walking over cobblestones, narrow sidewalks, and occasional inclines. The Florence walking tour covers approximately 2.7 miles, but at a slower pace. Guided tours and city walks may include periods of standing while listening to commentary, but afternoons often provide free time to explore or rest as you choose.
Terrain, Transport & Activities: Because many historic areas restrict motor coach access, travelers should be comfortable walking from drop-off points into town centers. Terrain ranges from smooth city streets to uneven countryside paths. The truffle hunt includes walking in wooded areas and on unpaved ground, which may be muddy so sturdy, waterproof footwear is recommended. Other activities, such as visiting family farms, vineyards, olive mills, and dairies, involve short walks and periods of standing but are paced to allow for comfort.
Pacing & Accommodations: This itinerary emphasizes immersion over speed. With two to three nights in each location, there is less packing and unpacking and more time to relax into the rhythm of each region. Several meals are included at local farms, homes, and traditional restaurants, offering both cultural connection and a chance to sit, savor, and share. Accommodations are boutique-style hotels and countryside villas, chosen for their atmosphere and proximity to the experiences planned.
