Tuscany for Newlyweds, Guests & Friends
Are you looking for some romantic time alone in Tuscany? Here’s a typical itinerary that we could do together with newlyweds and/or their families. Keep in mind that it is only an example of what you could do with us in Tuscany. We will customize your touring to include your interests in certain cities, wines, museums, restaurants, etc.
Tuscany is a land where romance lingers in the golden light of the afternoon, where cypress-lined roads lead to ancient vineyards, and where love is celebrated with the finest wines, world-class cuisine, and breathtaking landscapes. Whether you envision intimate vineyard dinners under the stars, private tours through Renaissance cities, or luxurious countryside retreats, our tailor-made itineraries transform your honeymoon—or any romantic getaway—into an experience as timeless as Tuscany itself.
Unlike standard travel packages, our journeys are fully customized to your desires, ensuring every moment is personal, immersive, and unforgettable. From private cooking classes in a Tuscan villa to indulging in the healing waters of ancient spas, every detail is designed to deepen your connection—to each other, to the land, and to the extraordinary beauty of Italy.
An Itinerary Crafted for Romance
Day 1: Arrival in Florence – A Romantic Welcome
Your journey begins in Florence, the cradle of the Renaissance and a city where art, history, and romance intertwine. Upon arrival, your personal driver and luxury vehicle await to escort you to your boutique hotel, a haven of elegance in the heart of the city. After time to relax, celebrate your first evening in Tuscany with a welcome dinner in an intimate Florentine restaurant, where candlelight flickers against ancient stone walls, and every bite is a love letter to Italian cuisine.
Day 2: The Art of Love – Florence & Fiesole
Begin your morning exploring Florence at your own pace—perhaps a private viewing of Michelangelo’s David or a sunrise stroll across the Ponte Vecchio. Later, meet your driver-guide for a scenic journey to Fiesole, a charming hillside village overlooking Florence. Here, in a private villa, an expert chef will guide you through a hands-on cooking class, where you’ll craft a meal together and savor the region’s finest wines. In the afternoon, return to Florence for a guided walking tour, revealing its hidden corners and grand landmarks.
Day 3: Chianti Countryside – Vineyards & Castles
Leave the city behind and immerse yourselves in the rolling landscapes of Chianti, where vineyards stretch as far as the eye can see. Visit an exclusive castle winery, where you’ll stroll through centuries-old cellars and savor a private wine tasting. Lunch unfolds in the courtyard of the estate, surrounded by olive groves and cypress trees. The afternoon continues with a drive through the heart of Chianti, stopping at a family-run vineyard known for its exquisite olive oil and aged balsamic vinegar. As the sun begins to set, arrive at a medieval hamlet-turned-luxury retreat, your home for the next two nights.
Day 4: Siena, Monteriggioni & San Gimignano – Medieval Romance
Explore Siena, one of Italy’s most enchanting cities, on a guided tour through its labyrinthine streets, historic piazzas, and awe-inspiring Duomo. After some free time to wander, enjoy a leisurely lunch in the walled village of Monteriggioni, a storybook setting frozen in time. In the afternoon, visit San Gimignano, famous for its medieval towers that rise like ancient sentinels over the Tuscan countryside. Here, indulge in the world’s most award-winning gelato, a sweet note to end the day before returning to your countryside retreat.
Day 5: Montalcino & the Healing Waters of Tuscany
Travel south to the Brunello wine region, where rolling hills and centuries-old estates define the landscape. In Montalcino, meet a renowned winemaker who will personally introduce you to the art of Brunello production. After a rustic farmhouse lunch amid vineyards, continue to one of Tuscany’s most exclusive thermal spas, where you can soak in mineral-rich waters that have been cherished since the Renaissance. The warm embrace of these healing pools, with the sky stretching endlessly above, is the perfect way to unwind before your next destination.
Day 6: The Elegance of Umbria – Perugia & Deruta
Cross into Umbria, Tuscany’s lesser-known but equally captivating neighbor. Begin in Perugia, where a private guide will lead you through its historic streets, revealing Renaissance masterpieces and hidden artisanal chocolate shops. A tasting of the legendary Baci Perugina chocolates is a must. After lunch, visit the ceramic town of Deruta, where centuries-old workshops craft exquisite hand-painted majolica. Return to your countryside retreat for a romantic candlelit dinner, celebrating the beauty of slow, intimate travel.
Day 7: Assisi & the Spirit of Timeless Italy
Spend your final full day in Assisi, a town that radiates serenity and history. Walk in the footsteps of St. Francis, explore the magnificent Basilica adorned with Giotto’s frescoes, and soak in the peaceful atmosphere of this medieval gem. Later, enjoy an alfresco lunch in the countryside before a final visit to Bevagna, one of Umbria’s most charming villages, where you’ll step back in time to witness traditional paper-making techniques that date back to the Middle Ages.
Day 8: A Farewell in Florence
On your last morning, make one final stop in Cortona, the town that inspired Under the Tuscan Sun. Here, amidst breathtaking landscapes and golden-hued buildings, savor a private farewell lunch in a secluded restaurant, where every detail is designed for romance. As you return to Florence for your departure, Tuscany bids you farewell—not as a place you visited, but as a love story you lived.
