Taste & Travel Tuscany: Your Complete Guide to Florence, Food & Culinary Adventures

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Advisor - Michelle Tuzzolino
Curated By

Michelle Tuzzolino

  • Tuscany

  • Arts & Culture

  • City Travel

  • Food & Wine

  • Local culture

Advisor - Taste & Travel Tuscany: Your Complete Guide to Florence, Food & Culinary Adventures
Curator’s statement

Tuscany is special to me because it feels like stepping into a living masterpiece—where history and art come alive in every street and landscape. The rolling hills and golden light create a sense of peace that slows life to its most beautiful rhythm. I love the warmth of the people who open their homes and kitchens, sharing not just meals but genuine connection. Whether running through the quiet countryside or savoring a homemade dish, Tuscany always feels like belonging.

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Day 1: Arrive in Florence

Arrive in Florence early in the morning, ready to begin your Tuscan adventure. After checking into your hotel, take a moment to refresh before heading out for a leisurely lunch and a rich Italian coffee at a cozy local café—perfect for easing into the city’s rhythm.

Spend the afternoon strolling through Florence’s charming streets, browsing small boutiques, artisan shops, and open-air markets while soaking in the beauty of Renaissance architecture and the vibrant atmosphere. As evening approaches, enjoy a delicious first dinner at Trattoria San Lorenzo, where authentic Florentine flavors set the tone for your journey ahead. Afterward, return to your hotel for a good night’s rest in preparation for an early start tomorrow.

Day 2: Art & everyday Florence

Begin your morning with a local guide who will lead you through the Galleria dell’Accademia before the crowds arrive, giving you an intimate view of Michelangelo’s David and other Renaissance masterpieces. After soaking in the art and history, step back outside to wander Florence’s lively streets, camera in hand. Capture glimpses of daily life—the shopkeepers arranging colorful displays, locals chatting over espresso, and sunlight dancing across centuries-old facades. Let your guide share hidden corners and stories that bring the city’s spirit to life, as you experience Florence not just as a visitor, but as a part of its rhythm.

Spend a relaxing afternoon at your own pace—perhaps with a gelato in a quiet piazza or some time to unwind at your hotel. As evening falls, dress for a memorable rooftop dinner at B-Roof, where you can savor Tuscan flavors paired with breathtaking views of Florence’s skyline and the iconic Duomo glowing in the sunset.

Day 3: Siena’s timeless charm

After breakfast in Florence, journey south through the rolling Tuscan countryside to the enchanting city of Siena, where medieval streets and warm hospitality await. Check into the elegant Grand Hotel Continental Siena, a historic gem in the heart of the city.

Meet your local guide for a leisurely walk through Siena’s narrow lanes, discovering its rich history, stunning architecture, and hidden corners. In the late afternoon, unwind in the Piazza del Campo, savoring creamy gelato as music drifts through the square and the golden light softens the city’s stone walls.

As evening settles in, experience true Sienese warmth by joining a local family in their home for a private cooking class—sharing stories, laughter, and a heartfelt homemade meal that captures the soul of Tuscany.

Day 4: A day in Cortona

Set out after breakfast for a scenic day trip to Cortona, a hilltop town that perfectly captures the quiet beauty of the Tuscan countryside. Stroll through its charming cobblestone streets, where every turn reveals stunning views over the Val di Chiana and terracotta rooftops glowing in the sun. Browse the local boutiques and artisan shops, discovering handmade ceramics, leather goods, and regional delicacies.

Pause at a café for a light lunch or espresso, soaking in the town’s relaxed pace and timeless atmosphere. As the afternoon winds down, take one last look at Cortona’s sweeping vistas before returning to Siena, your heart full from another day steeped in Tuscany’s beauty and simple pleasures.

Day 5: Explore Montepulciano

Today’s adventure takes you to the hilltop town of Montepulciano, a quintessential Tuscan gem known for its charm and breathtaking views. You can take the local trolley to the top and enjoy a leisurely walk down through the town, or embrace the climb on foot, winding your way up through narrow alleyways that open to unexpected vistas of vineyards and rolling hills.

As you explore, browse inviting shops filled with local crafts, ceramics, and delicacies, and pause often for delicious bites of regional cuisine or a perfectly made espresso. Every corner of Montepulciano offers a glimpse of authentic Tuscan life—beautiful, welcoming, and full of quiet wonder.

Day 6: Return to Florence

On your final day, make your way back to Florence for one last evening in the heart of Tuscany. Settle into your hotel and take a relaxed stroll through the familiar streets, revisiting your favorite spots or discovering a few you may have missed. Enjoy a leisurely dinner at a cozy trattoria, reflecting on the flavors, friendships, and unforgettable moments that have filled your journey. As the city lights glow against the Arno and the Duomo stands gracefully in the distance, savor your last night in Florence—a perfect ending to your Tuscan adventure.

Advisor - Michelle Tuzzolino

Travel Advisor

Michelle Tuzzolino

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For more inspiration and insider recommendations, visit our Tuscany page.