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Discover Tuscany over 5 days with wine tastings, a cooking class, and visits to San Gimignano, Siena, Cortona, and Val d'Orcia on this small-group tour from Florence.

The Florence & Tuscany: 5-Day Ultimate Combo Tour offers a balanced mix of guided exploration and free time, perfect for those looking to experience Tuscany’s landscapes, towns, and flavors. Priced with the flexibility to reserve and pay later, this 4.7-star rated experience is ideal for couples, friends, and first-time visitors eager to enjoy wine tastings, a hands-on cooking class, and visits to iconic hilltop towns.
The tour spans five days, starting in Florence, where you can check in at your preferred accommodation from 3:00 pm, and features small-group sizes limited to 8 participants. It combines guided walking tours with leisure time, offering a relaxed pace that allows for immersive exploration without feeling rushed. While the tour includes many highlights, it offers flexibility for additional activities like a trip to Pisa or Cinque Terre, making it adaptable to personal interests.
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Planning more time in Florence? We've covered other experiences worth considering.

The tour begins in Florence, where arrival is flexible. You can check in from 3:00 pm and begin exploring the city on your own or join a welcome walk with your guide through the historic center. Landmarks like the Duomo, Piazza della Signoria, and Ponte Vecchio are highlights seen during this initial introduction.
Evening hours in Florence are yours to enjoy. You might dine at a traditional trattoria, sit with a glass of local wine in a cozy café, or wander through lesser-known streets. This part of the tour offers a balance of guided insights and personal discovery, setting the tone for the days ahead.

The second day provides even more freedom to explore Florence independently. Optional activities include a day trip to Pisa and Cinque Terre or visiting the Accademia and Uffizi museums with a walking tour. This approach caters to different interests, whether art, history, or local neighborhoods, allowing travelers to customize their experience.
This flexibility helps accommodate varied energy levels and preferences, ensuring that each participant enjoys Florence in their own way, whether through culture or relaxed sightseeing.
On day three, the journey departs Florence mid-morning, heading into the scenic Tuscany countryside. The first stop is at a boutique Chianti winery for a guided wine tasting, where you’ll sample Chianti wines paired with regional specialties. Later, a visit to a family-run estate deepens your appreciation for Tuscan viticulture.
By mid-afternoon, the tour arrives in San Gimignano, a UNESCO World Heritage site famous for its medieval towers and sweeping views. The town’s winding streets and historic architecture make it a captivating stop, perfect for wandering at your own pace. The guide recommends booking two nights in San Gimignano to fully enjoy its charm.
More Great Tours NearbyDay four begins with a visit to Siena, known for its medieval architecture and the stunning Piazza del Campo. The city’s atmospheric streets lead visitors to explore its historic sites and enjoy the lively square, considered one of Italy’s most beautiful.
From Siena, the tour continues to Cortona, made famous by the film “Under the Tuscan Sun.” Cortona offers breathtaking views of the surrounding valleys, artisan shops, and a timeless Tuscan vibe. A local food tasting at a countryside farm adds a culinary element to this stop.
The afternoon features a visit to Montepulciano, celebrated for its medieval streets and the renowned Vino Nobile di Montepulciano. The town’s relaxed environment and panoramic vistas over Val d’Orcia make for memorable exploration. The day concludes back in Chianti, where you can reflect on the day’s discoveries.
The last day centers on a hands-on Tuscan cooking class. Led by a local chef, you learn authentic recipes, which you then enjoy during a shared meal accompanied by local wines. This culinary experience highlights Tuscany’s traditions and flavors.
The tour wraps up with a return to Florence by 5:00 pm, offering a final opportunity for last-minute sightseeing or shopping. The combination of guided activities and free time ensures a well-rounded experience with flexibility to suit individual interests.
Participants can arrive in Florence at their convenience, with check-in available from 3:00 pm. The tour features a live English-speaking guide and maintains a small group size limited to 8 people, fostering personalized interactions and minimized crowds.
Transportation between towns is arranged in advance, ensuring smooth transfers through Tuscany’s scenic landscapes. The tour’s structure balances organized visits with free exploration, ideal for travelers who appreciate both guided insights and independent wandering.

The reservation process allows for free cancellation up to 24 hours in advance and the option to reserve now and pay later, adding convenience and peace of mind. The inclusion of a cooking class, wine tastings, and visits to multiple historic towns makes this package a compelling value.
The experience is designed for those seeking a curated blend of guided tours and personal discovery, with an emphasis on local food, wine, and architecture. It’s especially suitable for couples, friends, first-time visitors, and anyone wanting a relaxed, authentic taste of Tuscany.
This 5-day Tuscany experience suits travelers looking for a slow-paced, small-group journey with opportunities to enjoy wine, food, and iconic towns. The tour’s flexibility means it appeals to foodies, culture enthusiasts, and those wanting a genuine Tuscan experience without heavy logistical stress.
While the tour offers a lot of guided content, it also allows for personal exploration, making it a good fit for adventurous and independent-minded visitors.
The Florence & Tuscany: 5-Day Ultimate Combo Tour offers a practical yet immersive introduction to Tuscany’s landscapes, towns, and traditions. Its small-group format, authentic food and wine experiences, and flexible itinerary make it attractive for many types of travelers.
While it provides a solid overview of key sights and flavors, travelers should note the potential for additional optional activities and the need to arrange their own accommodations. This tour provides a genuine slice of Tuscan life, highlighting its scenic beauty, historic towns, and culinary delights.
What is included in the tour price?
The tour includes guided visits, wine tastings, a cooking class, and transportation between towns. Accommodation is arranged independently.
Can I join the tour on any day?
Availability depends on the schedule; check current dates to confirm starting days.
Is the tour suitable for children?
The tour caters to adults and small groups; specific suitability for children depends on individual age and interest.
How much free time is there each day?
Most days combine guided activities with free periods, particularly in Florence, San Gimignano, Siena, and Cortona.
What should I bring?
Bring a camera, comfortable walking shoes, and weather-appropriate clothing.
Are meals included?
The cooking class meal is included; additional meals are at your discretion during free time.
How flexible is the itinerary?
The tour offers a good balance of guided activities and free exploration, with optional add-ons available.
What makes this tour different from other Tuscany trips?
Its small-group size, combination of guided and free time, and inclusion of a hands-on cooking experience distinguish it.
Is transportation provided between towns?
Yes, all major transfers are arranged in advance, ensuring smooth travel through Tuscany’s scenic areas.
What type of accommodation should I expect?
Travelers select their own lodging, with recommendations to stay in San Gimignano for two nights.