Review: San Gimignano, Siena & Chianti Wine Tasting with Lunch

Five things to know before you book

A few things we wish someone had told us before we clicked reserve. Three of the five come straight out of the tour's own lower-star reviews.

• Understand what you're booking. This is a large coach tour — ours was a double-decker carrying somewhere north of sixty people. It is very well run for what it is, but "I thought it would be a smaller group" is far and away the most common complaint in its reviews. If a big bus will spoil your day, book a small-group tour instead and skip the towns.
• Wear real shoes and carry water. The coach cannot park near the historic centres of Siena or San Gimignano. Expect a 15–20 minute walk, uphill, at each stop. Our step counter read just under eight miles for the day. The operator states the tour is not suitable for wheelchair users or travellers with impaired mobility, and in July and August that walk in 35°C is no joke.
• Decide about the Siena upgrades in advance. The base ticket gives you free time in Siena. The guided walking tour is a small upgrade, and skip-the-line entry to the Duomo and the Piccolomini Library is about $25 more. Our advice after doing both: pay for the Cathedral, think hard about the walking tour.
• Ask the shipping cost before you buy wine. Standard wine-country advice — pack a padded wine sleeve and a corkscrew — but here it comes with a warning. More than one traveller was billed hefty import charges on delivery that nobody mentioned at the table, with no receipt to dispute it.
• Get to Piazzale Montelungo early. The meeting point sits behind Santa Maria Novella station and it is chaos at 8am — a dozen operators, hundreds of people, everyone hunting for their guide. Yours wears blue with a CAF Tour & Travel / Gray Line logo, at the end of the ramp from the station. Arrive late and you do not travel, and there is no refund or reschedule.

What the day actually looks like

Departure is around 8am from Piazzale Montelungo, and you are back in Florence around 7pm. Between those two points: roughly 70 minutes to San Gimignano, two hours free there, a short hop to Monteriggioni, about 40 minutes to a winery in the Chianti hills for lunch and a tasting, then Siena for a little over two hours, then an hour and a half home.

Two structural things to know going in, because neither is obvious from the listing.

The order of visits changes, and Monteriggioni drops out of the itinerary entirely from November to March, when the coach also returns to Florence about half an hour earlier. Ours ran San Gimignano → Monteriggioni → lunch → Siena, which seems to be the most common sequence. Several reviewers who got a different order — Siena late in the day, after the wine — found the last stop hard going.

Commentary is delivered in English and Spanish on the same coach. Our guide, Aaron, switched between them seamlessly and was genuinely excellent: funny, unhurried, clearly in love with the region. But you get roughly half the information you would on a single-language tour, and everything takes twice as long to say. This comes up constantly in the reviews and it is the most legitimate structural complaint about the tour. If you booked "English" expecting English only, adjust your expectations now.

San Gimignano — the reason to book

We arrived just after 9.30am, and this was the high point of the day for both of us. San Gimignano is the town with the towers — fourteen still standing out of a medieval seventy-something — and getting there before the coaches and the crowds is a genuine privilege. The main square was almost empty. We had coffee and a pastry on the steps and watched the light come over the stone.

Two hours is a good allocation, though it is front-loaded in an odd way: arrive that early and most of the shops and every museum are still shut, so it is a walking-and-looking stop rather than a doing stop. A few reviewers argue Monteriggioni should come first for exactly that reason. We did not mind — we would rather have the empty square than the open gift shops. If museums are what you came for, this is the wrong tour for San Gimignano and you should give the town its own day.

One note passed along by a fellow traveller and independently confirmed by us at some personal cost: the gelato place your guide points you toward is fine, but Gelateria dell'Olmo is better. We tested both. This is a rigorous publication.

Monteriggioni — thirty minutes, and that's it

Monteriggioni is a perfectly circular walled hamlet that Dante name-checked in the Inferno, and it is genuinely lovely. You climb up to it, photograph the walls, buy nothing, and get back on the coach.

Plenty of reviewers ask why it is included at all, and honestly we understand the question — if the choice were thirty minutes here or thirty more in San Gimignano, we would take San Gimignano. It is a free bonus stop rather than a destination. Treat it that way and it is a pleasant surprise. Remember it disappears from the itinerary between November and March.

The Chianti winery lunch — where the tour and its marketing part company

Here we have to be straight with you, because this is the stop that accounts for the overwhelming majority of this tour's 2- and 3-star reviews.

The listing promises a winery in the Chianti hills, a vineyard and cellar experience, a guided tasting of three wines and a three-course zero-kilometre lunch. What we got was a large modern dining hall built for coach groups, communal tables of ten, three small pours of Chianti poured at the table, a short and quite hard-sell presentation about the estate's wines, and lunch: cured meats and pecorino with bruschetta, penne with ragù, and a slice of jam tart roughly the size of a thumb.

We did not see a vine. We did not see a cellar.

To be fair: the antipasto was good, the pasta was fine, we sat with a couple from Melbourne and talked for an hour, and we have had far worse group meals. The wine was pleasant, honest, everyday Chianti — the sort of thing you would happily order a carafe of anywhere in Tuscany for eight euros. Our host was a showman who introduced himself as "Winestein," which half the room found charming and half found exhausting.

But the pattern across the recent reviews is remarkably consistent, and it is worth knowing before you pay: undercooked pasta, small portions, a dessert that does not survive being divided by ten, a tasting that adds up to less than a single full glass across all the pours, and a distinct sales-pitch atmosphere. Some groups have arrived to tables not set for their numbers. Gluten-free and vegetarian menus are available on request — ask when you book, and confirm again at the table, because at least one traveller with an allergy was handed a bowl of plain pasta and then argued with about it.

How to set your expectations: this is lunch with wine included, at a winery. It is not a wine tour. If tasting is the actual reason you are going to Tuscany, this is the wrong booking and you will be annoyed all afternoon — go and read the Chianti wine tours guide instead. If you want a decent meal and a glass or three in the middle of a hill-town day, it does the job.

Siena — which rescued the afternoon

Siena is the best part of the day for a lot of people, and it nearly was for us.

The coach drops you a long walk from the centre. Budget genuinely 15–20 minutes each way and take it out of your free time before you plan anything, because plenty of reviewers did not and lost half of Siena to the walk. Then you come down into the Piazza del Campo — that impossible sloping shell of a square where they run the Palio twice a summer — and it is worth every step.

We had paid for the Cathedral and would do it again in a heartbeat: the striped marble, the inlaid floor, the Piccolomini Library with its frescoes still absurdly bright. Skip-the-line entry earns its keep here.

The guided walking tour is the piece to think twice about. Ours ran about half an hour rather than the hour we had pictured, the radio receivers were crackly, and it is easy to lose a guide in a crowded street when they are not carrying a flag. Several travellers also got the sequence we did — free time first, guided tour second — which means you wander the city alone and then get walked around the same streets again. If you can influence it, take the tour first and keep your free time for afterwards.

One scheduling warning: the Cathedral closes mid-afternoon, and some groups have arrived to find the interior visit no longer possible that day. If it is the reason you are booking, message the operator about your date's timings before you travel.

The things that can go wrong

Gathered from our day and from a careful read of the tour's recent lower-star reviews. The first two are structural; the rest are luck of the draw.

• Air conditioning. This is the recurring one, summer after summer. The coaches are big and some are old, and on genuinely hot days the upper deck becomes punishing — several travellers describe the AC failing outright on an eleven-hour day, and one reported a case of heat exhaustion. If you are travelling in July or August and you have any choice of seat, take the lower deck.
• Toilets. Some coaches have a working WC, some have one that is locked for the day, some have none. Plan around town facilities rather than the bus.
• Breakdowns and delays. More than one review this summer describes the coach breaking down and adding an hour or two to a day that was already eleven hours long. Guides handle it gracefully; it is still a long day made longer.
• Group management. With sixty-plus people, the guides are effectively shepherds — and most are outstanding at it. Aaron, Ricardo, Cristiana, Hilary, Sandro, Marta, Fabiana and Aleksandra are all named repeatedly and warmly in the reviews, and the drivers Nino and Halim have their own fan mail. But a few travellers have been walked away from at a meeting point or found the pace punishing. Save the guide's number in your phone and write down your departure time at every stop.
• The audio guides. Once they are handed to you they are your responsibility, and a lost unit is charged at €80. Worth knowing before you put one down on a café table.

So — would we book it again?

Yes, with our eyes open, and we would tell a friend the same thing.

For roughly $82 we saw three of the most beautiful towns in Tuscany, ate a decent lunch with wine included, drove through the Chianti hills for hours with someone knowledgeable narrating, and never once thought about parking, tickets, or who was staying sober. The 4.58-star average across nearly 3,900 reviews feels about right: a well-organised, genuinely good-value logistics operation with two soft spots — the winery stop and the size of the group.

Book this tour if you have limited days in Florence, you want the greatest hits covered efficiently, and wine is a welcome part of the day rather than the whole point of it.

Book something else if you came to Tuscany specifically to taste wine, you want a cellar tour and a properly guided flight, or the idea of a double-decker coach makes you wince. Spend the difference on a small-group Chianti estate day — you will visit two working wineries, taste properly, and eat better.

We did the small-group version later in the week, for the record. It was the better wine day. This was the better Tuscany day.

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