The other side of Tuscany starts here. This tour keeps the trip simple for you, with pickup in Florence, a farmhouse base, and a tight small group (max 8) as you move through Val d’Orcia, Chianti, Casentino Valley, and Maremma. I love the local meals and wine tastings built into the days, and I love that you spend time in lesser-frequented towns like Poppi and Montepulciano; the only real catch is you’ll have driving time each day and one day has more hiking-style walking in the Pratomagno area.

What makes this feel different from a big, bus-style Tuscany day is the rhythm. You’re not doing random stops on your own—you’re getting guided visits, planned meals, and time to wander, plus a choice on Day 4 to either rest at the farmhouse or hop the train to Florence. Based on feedback, the guiding style also seems to matter: guides such as Matteo (and driver Paolo) show up often in people’s stories, and the farmhouse hospitality of Francesca and Carlo at Dimora Casa Eugenia in Loro Ciuffenna gets a special shout-out.

Logistically, it’s structured in a way that protects your holiday hours. Start is set for 2:00 pm at Piazza dell’Unità Italiana, 25/6, and pickup is offered if you’re staying in Florence, then you head out by air-conditioned minivan. If you have dietary needs, you can request vegetarian options in advance, and the physical requirement is described as moderate—so it’s best for people who enjoy walking but don’t want to train for a mountain marathon.

Key takeaways

• Farmhouse base instead of changing hotels every night, which saves time and mental effort
• Max 8 people so the guide can tailor the pace and answer questions without rushing you
• Wine is built in: tastings plus multiple winery/castle/cellar visits, not just one stop
• You hit multiple Tuscany regions in one trip, including quieter areas beyond the usual Florence-to-skyline routine
• A real “food day” feel with farm-to-table style meals and local produce stops
• A Pratomagno mountain day that’s shorter (5 hours) but more active than the average sightseeing day

Price and what you’re really paying for

The listed price is $3,810.99 per person, and the value story here is about what’s already handled. You’re getting 7 nights of accommodation, most meals (breakfast 7, dinners 7, and lunches 2), wine tasting, a driver/guide, and transport by air-conditioned minivan.

This matters because Tuscany costs add up fast when you DIY. One car rental becomes two problems—drivers and parking—and lodging outside Florence can be its own planning puzzle. At this price point, you’re paying for route planning, logistics, and a small group experience where you’re not guessing where to go next.

That said, it’s not a “everything is included forever” deal. Alcoholic drinks are not included, airfares are not included, travel insurance is mandatory, and museum or gallery entry fees where applicable are not included. If you’re the type who wants every ticket price covered in advance, plan for a bit of extra spending.

Your farmhouse base in Tuscany (and why it changes the trip)

Most Tuscany tours are a parade of check-ins and check-outs. This one keeps you anchored at a Tuscan farmhouse resort apartment for the full stay, so your evenings feel more like living there than sprinting through it.

Feedback repeatedly praises the farmhouse side, including the hospitality of Francesca and Carlo at Dimora Casa Eugenia in Loro Ciuffenna. That’s a clue to what you’ll likely remember most at the end of the day: a calm base, dinners included, and enough time to decompress before tomorrow’s roads.

If you’re hoping for constant city energy, this is something to consider. Your “home” is countryside first, and Florence is optional on Day 4. The trade-off is that you’ll wake up near villages and move into regions like Chianti and Maremma without starting each day from scratch.

Day 1 in Florence: pickup and your Tuscan home away from home

Day 1 starts with pickup in Florence (offered if you’re staying there), then transport to your Tuscan farmhouse resort apartment. The start time is set for 2:00 pm, and you’ll meet at Piazza dell’Unità Italiana if you’re not being picked up.

This is a good setup if you want your first day to feel organized instead of frantic. You’ll shift out of “arriving” mode and into “settling” mode quickly, which makes the rest of the week feel easier.

One note for your planning: because the tour begins mid-afternoon, you’ll want to keep Day 1 flexible for travel and dinner arrangements before pickup time.

Day 2 Casentino Valley: Poppi, Castello di Poppi, and a Saint Francis monastery

Casentino Valley is where the tour earns its promise of quieter Tuscany. You spend about 9 hours in the region, with lunch in Poppi—an overlooked medieval village that most people skip in favor of the more famous stops.

The day also includes Castello di Poppi dei Conti Guidi and a visit to the ancient monastery of Saint Francis of Assisi before dinner. Even if you’re not a “monastery person,” this kind of stop is usually where you get that real sense of how Tuscany lived before it became a postcard.

The likely drawback is pacing. You’re not just strolling one town for a few hours—you’re doing a themed day with multiple stops plus a scheduled dinner. If you prefer slow travel with no structure at all, you may wish the days were a bit more open.

Day 3 Val d’Orcia: Montalcino for Brunello lessons, then Montepulciano

Day 3 is built around famous wine towns, but it’s guided in a way that turns “pretty” into “understandable.” You visit Montalcino to learn about Brunello di Montalcino, then move on to Montepulciano, a medieval village steeped in history.

You’ll also enjoy dinner at a local trattoria at the farmhouse. That’s a smart pairing: you get the town experience by day, and you get the food side without having to hunt for a reservation after travel.

The big consideration here is that this day may feel heavier on wine and learning than on pure sightseeing. If you’re traveling with someone who isn’t into wine, this is still doable, but you’ll want to set expectations that the day has a more “culture + cellars” structure.

Day 4 Florence on your terms: rest at the farmhouse or take the train in

This is the most flexible day, and it’s a big reason I like the design. You choose between relaxing at the farmhouse or taking the train to Florence to explore freely.

If you’re a Florence person, you get time without being forced into a scripted walking tour every hour. If you’re not in the mood for museums and crowds, you still get a meaningful day at base with downtime that helps you enjoy the countryside parts later.

The only possible downside is decision fatigue. After two active days, you might feel torn between going into the city and conserving energy. My practical suggestion: if you want Florence “later,” use this day for recovery so you don’t burn out before Chianti and Maremma.

Day 5 Chianti: castles, wineries, and cellars along Strada Statale 222

Day 5 is your dedicated wine day, centered on the Chianti Region along Strada Statale 222 Chiantigiana. It’s structured around visiting several castles, wineries, and cellars, and you’ll learn the story of Chianti’s famous wine along the way.

Dinner is at the farmhouse, so the day ends with you not having to find your own table somewhere after tastings and driving. This is the kind of “done-for-you” planning that makes a premium tour price feel less painful.

The main consideration: a wine-focused day can move fast if you’re not into tasting. Since alcohol drinks aren’t included, you can control how much you spend during tastings—but the day is still built for wineries and castle stops. If you’d rather swap a winery for a long village lunch, this tour may feel more structured than you want.

Day 6 La Maremma Toscana: Cantina Antinori, Castiglione della Pescaia, and Etruscan options

Maremma is where your Tuscany week gets a different flavor—more coastline and broader variety in scenery and food. Day 6 lasts about 9 hours and includes Cantina Antinori, lunch at a local fish restaurant in Castiglione della Pescaia, and a medieval castle known for views and entertainment.

After that, you can choose how to spend the afternoon: relax at the beach or explore Etruscan sites. It’s a great “choose your own pace” moment inside an otherwise planned day.

Two practical points to keep in mind. One: lunch is fish-focused here, so if you don’t eat seafood (or hate fish-heavy meals), tell the operator in advance. Two: this is a day with multiple anchors (winery, lunch town, castle, then afternoon option), so you’ll want comfortable shoes and a light, flexible attitude toward timing.

Day 7 Pratomagno mountain day: Loro Ciuffenna, Croce del Pratomagno, and local produce stops

Day 7 is shorter on paper—about 5 hours—but it’s the most active-feeling day. You start with a trip to Loro Ciuffenna and then stop in small medieval villages scattered in the mountainous landscape, with opportunities to sample local produce.

Croce del Pratomagno is part of the day’s focus, so you’re going for that mountain viewpoint payoff rather than another stop-and-photo schedule. The tour notes moderate physical fitness, and this is the day that most strongly fits that label.

Possible drawback: this won’t be a “sit in a café all day” experience. If you’re the type who wants minimal walking, you might feel a bit tired by the end. On the flip side, if you enjoy viewpoints and smaller villages, this is likely the day you’ll talk about later.

How the small group of eight changes everything

A max of 8 people can sound like marketing, but it’s actually a quality-of-life thing. With fewer people, you get a better chance to ask questions without the guide having to rush to keep everyone together.

It also affects the vibe at stops. Instead of fighting for a single photo angle, you can spread out a little and actually enjoy the town texture—walls, little churches, shopfronts, and side streets—without feeling like your day is a conveyor belt.

The guide-driven structure also shows up in feedback tied to names like Matteo, who gets praised for local knowledge, flexibility, and planning that includes medieval towns that are not overrun. That kind of “know where to take people” skill matters most when you’re going off the standard route.

Food and wine: what “included” means in real life

This tour includes breakfast 7 times and dinners 7 times, plus lunch 2 times and wine tasting. It’s not just one formal tasting event; you’ll have wine built into the week through visits to castles, wineries, and cellars—especially on Day 5—and through winery time in Maremma on Day 6.

Vegetarian options are available if you request them when booking, which is a big deal on countryside tours where menus can be meat-heavy. If you have allergies or specific dietary needs, make sure you communicate them up front since the tour specifically asks for requests at booking.

Alcoholic drinks are available to purchase separately, so you should treat included tastings and meals as your baseline and plan for extra spending if you want to buy more wine than the standard tasting.

Pace, transportation, and what to expect on the road

You’ll travel by air-conditioned minivan with a driver/guide, and transfer times are approximate depending on traffic. That means you should expect real-world delays in cities like Florence, especially around peak hours.

The itinerary also balances full touring days with at least one reset day (Day 4). That’s important. Without that option, a week of castles and villages can start to feel repetitive.

My practical travel advice: keep your mornings light, pack layers (country evenings can feel cooler), and bring a small day bag. If you’re sensitive to long drives, plan to hydrate and snack between stops since lunch timing is fixed and not always flexible.

Who this tour suits best (and who should look elsewhere)

This works especially well if you want countryside Tuscany with structure, not a DIY scramble. It’s a good fit for couples and small groups of adults (minimum age is 21), wine lovers who want more than one winery stop, and travelers who value local villages over big-city checklists.

It’s probably not ideal if you want nonstop Florence time, want every museum entrance included automatically, or don’t like any hiking/walking beyond short strolls. The Pratomagno day in particular will feel more active than a typical valley day.

Should you book Tuscany Untouched’s farmhouse tour?

Book it if you want a smooth logistics package, a small group vibe, and real regional variety—Casentino, Val d’Orcia, Chianti, Maremma, and Pratomagno—without the stress of arranging cars, lodging, and driving between towns. The included dinners and farmhouse base are also a strong reason to say yes, because they protect your evenings from decision-making.

Skip it if you’re mainly after museum-heavy Florence days, or if you only want laid-back sightseeing with no hiking-style walking. Also consider your comfort with a wine-centered structure: it’s a core theme on Day 3 and especially Day 5.

FAQ

How many people are in the group?

The group size is limited to a maximum of 8 people.

Is pickup from hotels in Florence included?

Yes, hotel pickup and drop-off in Florence are offered, and the tour also lists a meeting point in Florence at Piazza dell’Unità Italiana, 25/6 with a 2:00 pm start time.

What meals are included during the tour?

Breakfast is included for 7 days, dinners are included for 7 days, and lunch is included for 2 days.

Is wine included?

Wine tasting is included. Alcoholic drinks are available to purchase separately.

Do I need travel insurance?

Yes, travel insurance is mandatory.

Is vegetarian food available?

Yes, a vegetarian option is available. You should advise the operator of dietary requirements at booking.