Where Tuscany wine tours from Florence start
Every Chianti trip we compare starts in central Florence, at one of two addresses. Three leave from beside the main train station and two from an office near Santa Croce. None of them collects you from your hotel, so the walk or taxi ride to the start is yours to plan.
Two meeting points for five tours
The five Chianti trips we compare gather at one of two places in Florence. Three leave from Piazzale Montelungo, the bus terminal area beside Santa Maria Novella station, and two start at the Towns of Italy office on Via dei Vagellai, on the Santa Croce side of the center.
| Tour | Meeting point | Luggage | From |
|---|---|---|---|
| Prestige Rent small group | Piazzale Montelungo | Can stay on the bus | ~$101 |
| Towns of Italy wine and olive oil trail | Via dei Vagellai 22 R (check your voucher) | Not stated | ~$99 |
| Towns of Italy Vespa tour | Via dei Vagellai 22 R, or a second point by option | Not stated | ~$119 per vehicle |
| Ciao Florence | Piazzale Montelungo bus stop | No luggage or large bags | ~$55 |
| Gray Line Florence | Piazzale Montelungo | Not stated | ~$79 |
None of the five listings includes hotel pickup. You make your own way to the start, so where you sleep can tip the choice between two similar tours. What else each fare leaves out sits in our price guide.
Piazzale Montelungo, beside Santa Maria Novella station
Piazzale Montelungo is where many coach and minibus trips out of Florence load their passengers. It sits next to Santa Maria Novella, the main train station, so anyone staying near the station or arriving by train that morning has the shortest walk.
Prestige Rent, our pick, meets its small groups here and brings them back to the same spot after the tasting. Its small-group tour from ~$101 lasts about 4.5 hours. One reviewer mentions a 9 am start, but your booking shows the time that applies to you.
Ciao Florence uses the Piazzale Montelungo bus stop, which its listing puts a 5–10 minute walk from the station. Look for the staff rather than for a sign, since several companies load coaches in the same area at once.
Gray Line Florence starts its long hill-town day from Piazzale Montelungo too. With so many operators sharing one square, read the name on the vehicle before you climb aboard. That full day has its own page, our Siena and San Gimignano guide.
Our pick leaves from beside the station
Prestige Rent takes a minibus of up to 25 people (or 8 on the semi-private option) to two Chianti Classico estates and returns to Piazzale Montelungo. It scores 4.9 from 8,500+ reviews on Viator.
Via dei Vagellai 22 R, near Santa Croce
Towns of Italy runs both its wine and olive oil trail and its Vespa tour from its own base at Via dei Vagellai 22 R. The street meets Piazza Mentana close to the Arno, on the Santa Croce side of the historic center and well away from the station.
The R after the number marks a business door. Florence numbers shops and offices separately from homes on the same street, so typing the number alone into a map app can land you at the wrong door.
The wine and olive oil trail from ~$99 names a different meeting point for later dates on its listing. Whatever this page or the listing page says, the address printed on your voucher is the one to follow.
The Vespa tour shows two meeting points by option on GetYourGuide, so a scooter booking and an e-car booking may not start at the same door. The ride itself, with its license rules, is covered in our Vespa guide.

Bags, suitcases and the day you leave Florence
Some visitors fit a wine tour into the morning they check out. Prestige Rent lets luggage stay on the bus during the tour, which makes that plan workable if your train or flight leaves later in the day.
Ciao Florence allows no luggage or large bags on its coach. With a suitcase on that tour, you need left-luggage storage or a hotel that keeps bags after checkout. The other three listings we read say nothing either way, so ask before you book.
A small daypack is fine on any of them and handy for water and a light layer. On the Vespa tour the weight limit per scooter counts bags as well, one more reason to travel light that day.
Arriving from a cruise ship
Cruise passengers usually come ashore at Livorno or La Spezia. The Prestige Rent listing puts the trip to Florence at about 2 hours each way and says you arrange that transport yourself, so a tour plus two transfers makes a long shore day.
If you try it, build in a margin at both ends, because a tour will not wait for a late train. A shorter tasting such as our pick leaves more slack than the 11-hour hill-town day, which is hard to fit between docking and sailing.
Reaching either point from your hotel
Florence's center is compact, and many hotels inside it are a walk from both meeting points. Allow more time than a map suggests, since the old streets are narrow and the pavements fill up early with other visitors.
Staying near the station or on the west side of town, Piazzale Montelungo is the easy one. Staying near Santa Croce or across the Arno, Via dei Vagellai is closer. Taxis wait at the station rank, while hailing one in a side street is harder than in many cities.
Hotels outside the center change the sum. From a villa in the hills, a taxi to the start can add a fair amount to a cheap fare, and a half day then costs more of your morning too. Our half-day or full-day guide weighs the hours each tour takes.
Bringing children? Ages differ by tour, from 12 on our pick to 13 for Vespa passengers. Our guide for kids and non-drinkers sets out the rules before you pick a meeting point.
Picking a tour by where it starts
- Near the station or arriving by train, Prestige Rent from ~$101, a small group back by the afternoon
- Near Santa Croce, the Towns of Italy trail from ~$99, with a sit-down lunch
- Keen to ride, the Vespa tour from ~$119 per vehicle, from Via dei Vagellai
- Lowest fare, big coach, Ciao Florence from ~$55, with no suitcases allowed
- Towns as well as wine, Gray Line Florence from ~$79, an 11-hour day
Both points are central, so the difference between them is minutes on foot rather than money. Choose by group size and the kind of day you want, then plan the route. Group sizes are set side by side in our minibus or coach comparison.