Excursion Overland experience: a taste of tuscany tour at Livorno

A captivating journey through the heart of Tuscany, where rolling hills, hilltop villages, and unforgettable flavors come together in perfect harmony. In this mid-land program, explore Siena and its deep-rooted Palio traditions, discover charming Cortona of Under the Tuscan Sun fame, and enjoy authentic farm experiences, cheese making, and wine tastings in the idyllic Val D’Orcia. From the Renaissance beauty of Pienza to the prestigious wine estates of Montepulciano and Montalcino, this tour offers the very essence of Tuscany, history, scenery and exceptional cuisine.

02MIDLIV-B Overland Experience: A taste of Tuscany

Duration: 3 Days/2 Nights

Departs from: Livorno, Tuscany  

Re-join ship: Porto Santo Stefano, Tuscany

Reserve: At least 90 days prior to sailing

IMPORTANT NOTE:

This Silver Shore Overland Experience requires advance booking through Silversea Reservations no later than 90 days prior to the sail date. Requests received after this date may be accommodated on a space-available basis. Tickets are available in limited quantities, and participation cannot be guaranteed for those guests not booking well in advance. A minimum number of participants is required to operate this programme. If this minimum number is not met, Silversea reserves the right to offer the programme at a different rate based on private arrangements, or to cancel the specific departure. Cancellation fee, unless otherwise advised, 90 - 0 days prior to the initial sailing date: 100% of the programme fare per person is due.

Payment in full is due at time of final payment.  Bookings made within 120 days of sailing require full payment within seven days of booking or sooner, as specified by Silversea.

All Overland Experience fares are subject to change, and not guaranteed until payment is received in full by Silversea. All Overland Experiences are non-transferable, and non-refundable, within 90 days of sailing. Minors under the age of 18 must be accompanied by someone 18 years of age or older. All Overland Experiences are owned by independent contractors, and Silversea makes no representations and assumes no responsibility for the services provided by these operators. Overland Experiences may be modified by the operators at their sole discretion.

VISA INFORMATION:

Please check with your travel professional for details regarding visa requirements. It is the responsibility of each guest to obtain all appropriate visas before cruising.

LOCAL CURRENCY:

The local currency is Euros; however, US Dollars and British Pounds are well-accepted by most vendors. Local ATMs are available in some locations visited, and credit cards are accepted in most larger shops and hotel.

DAY ONE – Siena’s Palio Spirit, Cortona’s Timeless Charm

Experience the heart of medieval Tuscany and immerse yourself in the living traditions of the Palio.

Your Tuscan adventure begins with a scenic drive of approximately 2 and half hours through the rolling countryside from the port of Livorno to the captivating city of Siena, one of Italy’s best-preserved medieval gems. Upon arrival, meet your expert local guide and stroll through the narrow cobbled lanes of the old city center. As you walk past Gothic churches and Renaissance palaces, your guide shares the fascinating story of how Siena’s proud history is still deeply entwined with its unique neighborhood system “the contrade”.

Your destination is the Museum of the Contrada della Civetta, located in a historic fortified house dating back to the 12^th century. This is no ordinary museum visit: you will step into the private and sacred world of Siena’s Palio. Explore hidden underground tunnels and learn how each contrada functions like a close-knit community with its own traditions, ceremonies, and fierce loyalty. In the company of a former barbaresco (horse handler), gain personal insights into the emotional bond between rider, horse, and contrada in preparation for the world-famous Palio horse race.

After this unforgettable cultural immersion, enjoy an authentic Tuscan lunch at Il Mugolone, a beloved local trattoria in the heart of Siena.

After lunch, continue through the lush hills of southern Tuscany to Cortona, a hilltop town with Etruscan origins and a warm, golden charm. You will enjoy a brief guided walk through Cortona’s atmospheric alleys, stone staircases, and panoramic terraces. This town found worldwide fame through the book and film Under the Tuscan Sun, and its real-life charm lives up to the legend.

Check into the luxurious Monastero di Cortona Hotel & Spa, a beautifully restored monastery blending elegance, history, and tranquility. After some time to relax, savor a welcome dinner at the hotel’s gourmet Osteria del Santo, where local flavors are elevated in an intimate, artful setting.

Overnight accommodations in a Deluxe Room at Monastero di Cortona Hotel & Spa – Cortona

DAY TWO – Farm Life, Renaissance Beauty, and the Wines of Montepulciano

Delight in the flavors of the Val d’Orcia and the harmonious beauty of Pienza.

After breakfast, set out through the scenic Val d’Orcia, a UNESCO-listed landscape that looks like it stepped out of a Renaissance painting. Golden wheat fields, cypress-lined roads, and rolling hills set the stage for your visit to Podere Il Casale, a family-run organic farm that embodies the spirit of sustainable Tuscan living.

Upon arrival, you will be welcomed by the farmers themselves for a guided exploration of the farm, including the stables, olive groves, gardens, and cheese production facilities. Watch a live cheese-making demonstration, learning how Pecorino and Ricotta are still crafted using traditional methods. This is not just a visit, it’s an invitation into a way of life. Afterwards, enjoy a farm-to-table lunch featuring homemade pastas, fresh cheeses, and estate-produced wines, all served against a spectacular backdrop overlooking the valley.

In the afternoon, drive to Pienza, a jewel of Renaissance urban planning, lovingly rebuilt by Pope Pius II as the ideal city. Wander through its cobblestone lanes, browse artisan shops specializing in Pecorino cheese, and admire the harmony of its architecture. Pienza isn’t just a beautiful town, it’s a living embodiment of the humanist ideals of the Renaissance.

From here, continue to a nearby Montepulciano wine estate for a relaxed yet refined tasting of Vino Nobile di Montepulciano, one of Tuscany’s most historic and elegant red wines. Sip and savor four different wines, accompanied by small Tuscan bites, while learning about the winemaking philosophy of the estate.

Return to Cortona for a leisurely evening. Dinner is served at Gli Affreschi, your hotel’s charming restaurant, where vaulted ceilings and candlelight set the tone for a serene end to a rich day.

Overnight accommodations in a Deluxe Room at Monastero di Cortona Hotel & Spa – Cortona

DAY THREE – Montalcino’s Medieval Splendor and the Bold Brunello

Discover one of Italy’s most prestigious wines in a town rooted in tradition and elegance.

After breakfast and check-out, your final day begins with a journey into the heart of the Brunello di Montalcino region, arguably Tuscany’s most prestigious wine-producing area.

Arrive in Montalcino, a picture-perfect medieval town perched above the surrounding vineyards of the Val d’Orcia. With its massive stone fortress, scenic towers, and quiet streets, Montalcino offers a sense of timeless serenity. Explore the town with your guide and enjoy time to browse small shops or take in sweeping views from its historic walls.

For lunch, dine at a traditional Osteria in the heart of town, such as Il Giardino or Osteria Porta al Cassero, where regional dishes are served with heart and heritage.

The highlight of the day comes in the afternoon with a visit to the renowned Ciacci Piccolomini d’Aragona estate (or a comparable winery). The experience includes a private tour of the historic Molinello cellar, followed by a guided tasting of four exceptional wines: Rosso di Montalcino, Sant’Antimo, and two vintages of Brunello di Montalcino DOCG. You will also sample the estate’s own organic olive oil, paired with Tuscan-style snacks.

Finally, continue your journey to Porto Santo Stefano, where your cruise ship awaits, and reflect on three days filled with immersive culture, unforgettable food, fine wine, and the ever-enchanting landscapes of Tuscany.

Please note: This lOverland Experience involves a moderate amount of walking, including over uneven, cobbled surfaces and occasional inclines, particularly in Siena, Cortona, Pienza, and Montalcino. Guests should be in good physical condition and able to walk unassisted for up to 1.5 kilometers at a time. This tour is not recommended for guests with limited mobility or those who require wheelchairs or walking aids. Comfortable walking shoes with non-slip soles are strongly recommended. Weather in Tuscany can vary; guests should dress in layers and bring sun protection, a hat, and a light rain jacket. Modest attire is required for visits to religious or sacred sites. Shoulders and knees must be covered.Tastings include wine and dairy products. Guests with allergies or dietary restrictions are advised to inform the Shore Concierge in advance. The tour includes several countryside drives ranging from 30 minutes to 1.5 hours; rest stops are included where possible. Local conditions may require adjustments to the order of visits or substitution of similar venues. Participants must be at least 18 years of age to consume alcohol during tastings and meals. Luggage allowance is limited to one medium-sized bag and one small carry-on per guest. Please carry a valid ID at all times. We advise leaving valuables and excess cash securely on board the ship. All services, accommodations, and logistics are of the highest quality available in the region, though standards may differ slightly from those found in major urban centers. Your understanding and flexibility are appreciated.

Programme Includes:

• Two-night stay at Monastero di Cortona Hotel & Spa (Deluxe Room)
• Two breakfasts, three lunches, and two dinners (wine included)
• Guided visits and tastings as described
• All transportation and luggage handling during the program
• English-speaking local guides and tour escort

Not Included:

• Meals or drinks not specified above
• Gratuities for guides and drivers
• Personal expenses such as souvenirs, laundry, or phone calls