Florence & Tuscany Explorer - 5 Days



Trip Snapshot
Age range
18 - 100Start / End
- Florence
- Florence
Physical rating
Guide style
Self GuidedMeals included
4Highlights
- Florence - Admire the Duomo, Ponte Vecchio and Piazza della Signoria on a guided walk through the heart of the Renaissance city
- Chianti - Sample regional wines and Tuscan specialities at boutique wineries surrounded by vineyard-covered hills and cypress-lined roads
- San Gimignano - Wander cobbled medieval streets beneath soaring historic towers in this beautifully preserved UNESCO-listed hill town
- Montepulciano - Experience the rich wine heritage of this Renaissance hilltop town renowned for its celebrated Vino Nobile wines

Everything you need to picture the adventure and pack with confidence — in one free PDF.
What's inside the PDF
Day-by-day itinerary
Every day mapped out, covering activities, travel times, meals and where you'll stay.Packing & kit list
Exactly what to bring, from clothing and essentials to luggage guidelines and what's available to hire locally.What's included
Accommodation, transport, guides and meals, so you can see exactly what your price covers.
Summary
Uncover the charm of Tuscany on this scenic 5-day journey through Florence, Chianti and Italy’s most beautiful hilltop towns. Wander Florence’s Renaissance streets before heading into the countryside for Chianti wine tastings, vineyard visits and stunning rural landscapes. Medieval destinations including San Gimignano, Siena, Cortona and Montepulciano blend history, culture and authentic Italian atmosphere, while a hands-on Tuscan cooking experience adds the perfect finishing touch before returning to Florence.
Itinerary
Day 1
Arrival in Florence & City Tour
Once you have arrived in Florence, make your way to your accommodation for check-in from 2 PM. Settle in and then join your guide for a welcome walk through the historic centre of the city and discover some of Florence’s most iconic landmarks. During our walk, we will admire the impressive Duomo, the lively Piazza della Signoria, and the famous Ponte Vecchio spanning the Arno River.
In the evening, you will have free time to experience Florence at your own pace. You may choose to enjoy dinner in a traditional trattoria, relax with a glass of Tuscan wine in a local café, or continue wandering through the city’s charming streets. For those wanting a more local experience, you can also join an optional Florentine aperitivo with spritz and regional specialities.
Meeting point: Check-in available from 2:00 pm. Tour will officially start in the afternoon (6:00pm approx).
Day 2
Florence at Leisure
Today, you will have a full day to experience Florence at your own pace. From Renaissance landmarks and world-famous galleries to lively piazzas and hidden side streets, the city offers countless opportunities to explore its rich history, art, and atmosphere.
You may choose to visit some of Florence’s iconic sights, relax in a local café, browse artisan boutiques, or simply wander through the historic centre and soak up the city’s unique character. If you are interested in joining any optional activities during the day, we can assist you.
Day 3
Siena, Cortona & Montepulciano
Florence - Siena - Cortona - Montepulciano - San Gimignano. After breakfast, we will leave Florence behind and journey through the rolling countryside of Tuscany, passing vineyard-covered hills, cypress-lined roads, and traditional hilltop villages along the way. Our first is Siena, where we take a stroll through the medieval streets to the breathtaking Piazza del Campo and admire its magnificent Gothic cathedral,
We travel on to Cortona, a hilltop town perched above the Val di Chiana with views stretching as far as Lake Trasimeno on a clear day. Here you can admire the sweeping views and browse the artisan shops before we enjoy a food tasting at a local farm, where the cooking draws on whatever is in season.
This afternoon we visit Montepulciano, home of Vino Nobile, one of Tuscany's most respected reds. Explore the town at a leisurely pace, taking in the views over the Val d’Orcia while learning about its rich history and wine culture.
By evening, we arrive in San Gimignano to spend the night inside the historic centre. The medieval towers are best seen once the day visitors have left, when the streets quieten and the town takes on a different character entirely.
Day 4
Chianti Wine Country & San Gimignano
This morning we drive through the rolling hills of Tuscany, to a boutique Chianti winery, set amid postcard-perfect scenery. Here, we meet passionate local winemakers, learn about the region’s viticulture, and enjoy a guided tasting of Chianti wines paired with delicious regional specialties. Then we travel on family-run estate in the heart of Chianti, where we sample award-winning wines and learn about the traditions that have made this area world-renowned.
In the afternoon return to San Gimignano and enjoy the rest of the day at leisure, soaking up the serene beauty of the Tuscan countryside.
Day 5
Tuscan Cooking Class & return to Florence
San Gimignano - Florence. Today, we will take part in a hands-on Tuscan cooking class led by a local chef, where we will learn how to prepare traditional regional dishes using authentic ingredients and recipes. After the class, we will sit down together to enjoy the meal we have prepared, accompanied by a glass of local wine.
Later in the afternoon, we will return to Florence, arriving back in the city by approximately 5 PM.
What's Included
Meals
Breakfasts: 4, Lunches: 0, Dinners: 0
Vegetarian options are available on all meals throughout the adventure.
Vegetarian options availableLocal Guide
Self GuidedWifi
Wifi is available during the adventure. In some areas and / or accommodation / transport Wifi may be free.
Dates & Prices
Oct 2026
from £1,880Nov 2026
from £1,880Mar 2027
from £2,022Apr 2027
from £2,022May 2027
from £2,224Jun 2027
from £2,491Jul 2027
from £2,022Aug 2027
from £2,022Sep 2027
from £2,491Oct 2027
from £2,224Nov 2027
from £1,880Dec 2027
from £1,880
- Friday 2 Oct 2026to Tuesday 6 Oct 20264 spaces of 8 left£1,880Best offer
- Tuesday 6 Oct 2026to Saturday 10 Oct 20264 spaces of 8 left£1,880Best offer
- Friday 9 Oct 2026to Tuesday 13 Oct 20264 spaces of 8 left£1,880Best offer
- Tuesday 13 Oct 2026to Saturday 17 Oct 20264 spaces of 8 left£1,880Best offer
- Friday 16 Oct 2026to Tuesday 20 Oct 20264 spaces of 8 left£1,880Best offer
- Tuesday 20 Oct 2026to Saturday 24 Oct 20264 spaces of 8 left£1,880Best offer
- Friday 23 Oct 2026to Tuesday 27 Oct 20264 spaces of 8 left£1,880Best offer
- Tuesday 27 Oct 2026to Saturday 31 Oct 20264 spaces of 8 left£1,880Best offer
- Friday 30 Oct 2026to Tuesday 3 Nov 20264 spaces of 8 left£1,880Best offer

Make this tour private
Every departure on this trip can be booked just for your own group — your dates, your people, the same expert local guides.
What changes when you go private
Travel with just your own group
No other travellers on the trip — just the people you choose to bringTravel on your schedule
Pick your exact start date—no fixed group departures or rigid timetables.Exclusively for your party
Enjoy this handcrafted itinerary with a dedicated private guide just for you.
Essential trip information
Our Important Notes and Packing List cover all essentials, from necessary equipment to inclusions, ensuring you're fully equipped and informed for this extraordinary adventure and more.
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