Experience Monteriggioni, Siena and Chianti as you savor Tuscan wines, cook local cuisine and explore medieval towns in Italy’s countryside.
Starting from $1,944 per person.
A Taste of Tuscany Tour | Vacation Packages for 2025 – 2026
4 Days/3 Nights
Starting from
$1944
per person*
Unforgettable Italian Journeys, Designed for You
Curated by passionate Italy experts, this sample itinerary is just the beginning of your Italian adventure. Every journey we design is unique, crafted around your interests, pace, and dreams so you can experience Italy’s beauty and culture like a true insider. Let us transform your vision into a one-of-a-kind travel experience, filled with authentic moments and lasting memories
Day 1
MONTERIGGIONI, SIENA
Tuscan Legends Behind Stone Walls
- Arrival and check-in at your hotel in Monteriggioni, near Siena
- Welcome drink and time to relax in the Tuscan countryside
- Welcome dinner at a traditional restaurant in Siena or the Monteriggioni area
- Overnight stay at your hotel in Monteriggioni
Day 2
CHIANTI REGION, WINE TASTING, SIENA
Rolling Vineyards and Timeless Stone Streets
- Breakfast at the hotel
- Suggested morning excursion through the Chianti Classico wine region
- Visit a renowned Chianti Classico winery with guided cellar tour and wine tasting
- Afternoon in Siena to explore the historic center and Piazza del Campo
- Discover the city of the Palio horse race, medieval streets, and Gothic architecture
- Dinner on your own and overnight stay in Monteriggioni
Day 3
TUSCAN COOKING CLASS IN A LOCAL VILLA , SAN GIMIGNANO
Where Stone Streets Tell Ancient Stories
- Breakfast at the hotel
- Morning Tuscan cooking class in a local villa
- Prepare a full Tuscan menu and enjoy it for lunch, paired with local wines
- Suggested afternoon visit to San Gimignano, famous for its medieval towers and walls
- Free time to stroll the historic center, shops, and panoramic viewpoints
- Dinner on your own and overnight stay in Monteriggioni
Day 4
MONTERIGGIONI, SIENA, MONTALCINO, SAINT’ANTIMO ABBEY
Winding Roads to Walled Wonders
- Breakfast at the hotel and check-out
- Scenic drive through the Val d’Orcia to reach Montalcino
- Guided visit and wine tasting in a historic Brunello di Montalcino cellar
- Suggested visit of Montalcino’s historic center and fortress
- Recommended stop at the nearby Sant’Antimo Abbey
- End of services
MAKE THIS ITINERARY YOURS
Turn this sample itinerary into your dream Italy vacation – tailored to your pace, passions, and budget.
Day 1
MONTERIGGIONI, SIENA
Tuscan Legends Behind Stone Walls
Arrive at your hotel in Monteriggioni, a charming medieval village set in the heart of the Tuscan countryside just a few kilometers from Siena. After check-in, enjoy a welcome drink and some time to unwind, taking in the rolling hills, vineyards, and olive groves that define this iconic region. In the evening, savor a welcome dinner at a traditional restaurant in Siena or nearby Monteriggioni, where you can taste authentic Tuscan dishes paired with local wines. Overnight at your hotel in Monteriggioni.
Day 2
CHIANTI REGION, WINE TASTING, SIENA
Rolling Vineyards and Timeless Stone Streets
After breakfast, we recommend starting your day with an excursion into the famous Chianti region, known worldwide for its vineyards, cypress-lined roads, and hilltop villages. Stop at one of the most renowned Chianti Classico wineries for a guided visit of the cellars and a tasting of their signature wines. In the afternoon, head to Siena to explore its UNESCO-listed historic center. Wander through narrow medieval streets, admire the magnificent Piazza del Campo—home of the Palio horse race—and take in the city’s Gothic architecture and vibrant atmosphere. Enjoy dinner on your own at a local trattoria before returning to your hotel in Monteriggioni for the night.
Day 3
TUSCAN COOKING CLASS IN A LOCAL VILLA , SAN GIMIGNANO
Where Stone Streets Tell Ancient Stories
Begin your day with breakfast, then immerse yourself in Tuscan cuisine with a hands-on cooking class in a local villa. Under the guidance of an expert cook, you’ll prepare a complete Tuscan menu using fresh regional ingredients, then sit down to enjoy your creations for lunch, perfectly paired with local wines. In the afternoon, we suggest visiting San Gimignano, a splendid medieval town renowned for its skyline of ancient towers, well-preserved walls, and cobbled streets. Explore the historic center, browse artisan shops, and enjoy gelato or a glass of Vernaccia di San Gimignano while taking in the views. Return to Monteriggioni in the evening; dinner is on your own and you’ll spend the night at your hotel.
Day 4
MONTERIGGIONI, SIENA, MONTALCINO, SAINT’ANTIMO ABBEY
Winding Roads to Walled Wonders
After breakfast, check out and drive through the iconic Val d’Orcia, a UNESCO World Heritage landscape of rolling hills, vineyards, and cypress trees, to reach Montalcino—home of the world-famous Brunello di Montalcino wine. Enjoy a guided visit and tasting in a historic Brunello cellar, learning about the production and characteristics of this prestigious red wine. Afterwards, we suggest exploring Montalcino’s historic center and fortress, then continuing to the nearby Sant’Antimo Abbey, a peaceful Romanesque church set amid olive groves and vineyards. Your journey through Tuscany concludes here, with the end of our services.
This Package Includes:
– 3 nights accommodation in 4 Star Hotel in Monteriggioni around Siena or similar;
– Daily breakfast;
– Welcome Dinner in a Medieval Restaurant;
– Visit and wine tasting in a Chianti winery;
– Visit and wine tasting in a Montalcino winery;
– 3 Hours Tuscan Cooking class w/ lunch and beverages;
– 4 Days of Car Rental Class B (Fully Inclusive Coverage Included)
– Vat Taxes and service Charges.
This Package Does Not Include:
– All Land & Air prices: Additional U.S. & Foreign Departure Taxes and Surcharges Fee(s) assessed by the Airlines.
– Hospitality city tax which varies by city and hotel category. If applicable it has to be paid locally to the hotel.
– Transportation, Entrance Fees to Monuments or Museums, Tips, Extras.
– Beverages during meals.
– All which is not mentioned under PACKAGE INCLUDES.
Terms and Conditions:
Fly and Drive independent tour package.
Available all year around on request.
Minimum number of participants: 2 people.
(*) Rate based on two adult persons sharing a double or twin bedded room with private bathroom. Single rooms are available at an additional supplement. Childrens, triple room rates and alternative accommodation arrangements are available upon request. (Additional and different charges may apply).