Small group tours from Florence

Three days out of Florence in our own minibuses, never more than 25 guests, with our own guides and lunch at a family winery. Departures every week, booking confirmed instantly.

You came to Tuscany for a reason, and it probably was not to follow a numbered flag through a car park.

These are the days we would book ourselves. A small group. One of our own drivers, who knows which road to take when the light is right. A family who opens their cellar because they want to, not because a coach is due. You taste the wine where it is made, sit down to a lunch someone cooked that morning, and have time to stand still in a square without being counted.

Twenty-six years of doing this, and the part we are proudest of is not the itinerary. It is that people come back, and bring their friends.

Small group among Tuscan wineries, their olive oil and a proper Tuscan lunch

Small group among Tuscan wineries, their olive oil and a proper Tuscan lunch

8 hours4.91,924 reviews on GetYourGuide

A full day in Chianti: three family estates, olive oil tastings and a Tuscan lunch with the wines. Small group from Florence, free cancellation up to 24h.

  • Small Group Intimacy
  • “Big Three” Wineries
  • Wine & Olive Oil Tastings
from149≈ $173 · £128
Wine Experience in Tuscany

Wine Experience in Tuscany

5 hours4.98,250 reviews on Viator

A small, intimate tour exploring 2 old wineries in Chianti! Live a memorable wine experience in Tuscany with charming views over the countryside.

  • Half-Day Escape
  • Intimate “Small Group
  • Dual Winery Experience
from89≈ $103 · £76
Siena, San Gimignano & the Tuscan countryside

Siena, San Gimignano & the Tuscan countryside

9 hours4.91,811 reviews on Viator

Join our small-group tour for the perfect day trip to Siena & San Gimignano. Visit 2 Tuscan gems and an old winery for a wine tasting and lunch!

  • Guided Walking Tour in Siena
  • Siena, San Gimignano
  • Gems of Tuscany
from149≈ $173 · £128
Viator Experience Award Winner 2025 and 2023 — rated 4.9 out of 5 on Viator and TripadvisorTripadvisor Travelers' Choice Awards 2025

Still not sure?

Ask us anything

A date that is not there, a pickup somewhere else, six people and a pushchair — if something does not fit, tell us and we will work it out. A person answers, usually within a few hours.

The Prestige Rent team in Italy — real people ready to help you

Have questions? Let’s chat!

Meet our native English-speaking experts, Violeta and Carrie. A different pick-up time, a second vehicle for a larger family, a licensed guide, a winery to add, a wheelchair to fit in the boot, a drop-off at the airport on your last day — tell them what your day needs to look like and they will build it.

Not sure yet?

Tell us what your day should look like

Private tours are built, not booked from a calendar. Send us the details and a real person answers — usually within a few hours.

We use your name and contact details to answer this request and prepare your quote. They are stored in our systems and in the CRM our team replies from, and they are not sold or passed to anyone else. Full details, retention times and your rights are in our Privacy Policy.