Tuscany Walking and Wine

BM-17303

5.0Based on

8 days

“

The entire experience was terrific ... the itinerary was well-paced and exciting, Tuscany is beautiful and the food was awesome, and best of all our guide AJ was the "star of the show" who made the trip really educational and memorable.

John | Traveled in July

5 - Excellent

Carbon neutral

8 daysDuration

Small Group TourUsually 8-12 participants

16 peopleMaximum group size

16 - 99 yearsAge range for participants

EnglishGuide language

Easy

Light physical activity suitable for most people with average fitness levels.

Starts

Ends

Pisa, Italy

Florence, Italy

Select Date

Best price guaranteedNo credit card or booking fees.Carbon neutral tours.

1 other person is considering this tour right now.

Highlights

Tuscan wine tastings – Visit family-run wineries in Chianti and Montalcino, tasting Chianti Classico, Vernaccia and Brunello wines. Medieval hilltop towns – Discover San Gimignano’s famous towers, explore UNESCO-listed Pienza and hike through the beautiful Val d’Orcia to Montalcino. Siena & Florence – Wander Siena’s traffic-free medieval centre and Piazza del Campo, then enjoy free time in Florence to discover its famous sights.

Itinerary

Experience the rolling hills and vineyard-dotted landscapes of Tuscany on the Tuscany Walking and Wine tour, an easy-paced 8-day journey created for travelers who appreciate the finer things in life. Starting in Pisa and ending in Florence, this walking tour blends scenic rambles with rich cultural encounters.

Meander through Chianti’s renowned vineyards, explore the sun-drenched medieval towns of San Gimignano, Pienza, and Montalcino, and sample some of Italy’s most celebrated wines—Brunello and Chianti among them. Along ancient pilgrimage paths, you’ll savor local cuisine and fresh produce, refueling your spirit as well as your palate.

The trip includes accommodations in carefully selected hotels, transport, and delicious meals, ensuring a seamless Italian experience. The unique selling point of this tour package is the harmonious combination of gentle hiking and gastronomic pleasure, offering access to Tuscany’s scenic beauty and culinary treasures. For those seeking an indulgent yet active escape, Tuscany Walking and Wine is the perfect getaway.

day 1Trip starts today in Pisa

Our tour starts today in Pisa. Famous for its leaning tower and Campo del Miracoli, the Tuscan city is awash with sites that remain a testament to a time when Pisa was one of the Mediterranean's major maritime powers. Our tour leader plans to meet everyone at the hotel for a welcome meeting today at 6.30pm and for those that wish, there is the chance to go out for dinner afterwards. If you miss the meeting, our tour leader will inform you of any essential information as soon as you catch up. Airport transfers are not included on this tour but Pisa Airport is close to the centre of town, so getting to our hotel is easy. We recommend using the Pisa Mover - an automated shuttle train that departs from the airport to Pisa Central Station approximately every 10 minutes and takes just five minutes. Tickets cost €5. It's a 10-minute walk from Pisa Central Station to our hotel. If you'd prefer to take a taxi, there's a rank outside the terminal building. From the airport to our hotel, it should cost around €15-20. We won't be climbing Pisa's leaning tower on our tour so if it's on your bucket list, or you'd like to explore Pisa in more depth, we recommend arriving earlier in the day or booking an additional night in the city pre-tour. Pisa is a compact city and is easy to navigate on foot.

Accommodation

Hotel Bologna

day 2Walk to the hilltop town of San Gimignano; enjoy a wine tasting before driving to Castellina in Chianti

day 3Hike along white gravel tracks typical of Tuscany; visit a winery for lunch and a tasting of Chianti wines

day 4Visit medieval Siena on market day; drive to Pienza in southern Tuscany

day 5Take a panoramic walk from Pienza; optional cheese tasting

day 6Drive to hilltop Montalcino Hike through the Val d'Orcia to San Quirico d'Orcia

day 7Drive to Florence; orientation walk and free time to explore this fabulous city

day 8Trip ends in Florence

What's Included

Accommodation

Hotel Bologna (1 night)Hotel Colle Etrusco Salivolpi (2 nights)Relais II Chiostro di Pienza Hotel (3 nights)Hotel San Giorgio (1 night)

Meals

7 Breakfasts, 2 Lunches

Transport

Train

Guide

Explore Tour Leader

Others

Minibus

What's Excluded

Customer Reviews

4.8

based on 12 reviews

Availability

Loading availability...

Good to Know

Travel Insurance

Visa

Other Practical Information

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25,000+ trip reviews, with an average rating of 4.8 out of 5.

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4.67/5

Excellent based on 850 customer reviews from

Karen

Problem-free booking and service right through the process

1 week ago

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