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Tuscan Highlights & Wine

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3 days

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SEMI INDEPENDENT TOUR (FOR AGES 39+): Immerse yourself in the beauty of Chianti with scenic drives through rolling vineyards, expert-led wine tastings, and visits to renowned wineries. Learn about traditional winemaking, sample world-class wines, and explore the medieval charm of San Gimignano, all while enjoying the rich flavours and culture of Tuscany.

For a detailed itinerary and information about visas, money, weather and more.

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Tour Overview

Duration

3 days

Starts

Tuscany

Ends

Tuscany

Range

Worldwide Touring

Tour Guide

Yes - for included sightseeing

Group Size

Min 2 / Max 8

Minimum age

39

Departs

Fridays

Hotel Rating

3-4 star hotels

Countries

Italy

Physical Rating

Easy

Tour Pace

Medium

Arrival Transfer

No

Departure Transfer

No

Meals included

Breakfast: 2
Adults (39+)
Price Breakdown
Shown in USD
Total
USD

$739.50

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Per Person From
$435.00
USD

$369.75

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Tour Highlights

Scenic drives through Chianti vineyards
Expert-led wine tastings, including Chianti Classico and Brunello
Tasting of balsamic vinegar and truffle olive oil
Visit to medieval San Gimignano and world-champion gelato

Included

2 breakfasts
2 nights 3-4 star hotels
Services of a local tour leader for included sightseeing
All relevant transfers and transportation (airport transfers are not included)
Half day Tuscany wine tour to 2 local wineries with wine and olive oil tastings (shared group excursion)
Visit to the medieval town of San Gimignano (shared group excursion)
Discounted optional activities (please speak to your tour leader on arrival)
Note: This tour is operated in conjunction with our trusted partner and you will join travellers from different operators, not solely On The Go.

Not Included

International flights & visas
Meals not mentioned in the itinerary
Airport transfers
Optional activities (must be booked in advance, please contact us no less than 1 week prior to your arrival)
City taxes

Itinerary

Day 1 - Welcome to Tuscany!

Arrive at your accommodation in the heart of Tuscany. The exact hotel varies by tour and will be communicated to you before departure - but wherever you stay, you'll be surrounded by rolling green hills and within easy reach of San Gimignano, Siena, Volterra, and Certaldo.

Check in and enjoy a leisure day - relax by the hotel pool before preparing for dinner. The on-site restaurant serves delicious dishes crafted from traditional regional recipes.

We suggest arriving in the morning on Day 1 to make the most of your time exploring the area. Check-in typically begins at 2:00 PM, but you are welcome to leave your luggage at reception if you arrive earlier.

Overnight: Tuscany

Day 2 - Wine, Scenery & Medieval Charm

Today join our shared group wine tour - an opportunity to connect with fellow Tuscany enthusiasts while sampling exceptional wines and regional specialties. Travel along scenic, quiet roads through Chianti’s rolling hills, where our tour leader will share fascinating insights about the area.

Our first stop is a renowned vineyard, where we’ll meet the winemakers and taste four distinct wines, including Chianti Classico, Brunello di Montalcino, and Super Tuscan. We can also sample a 30-year-old balsamic vinegar and exquisite truffle-infused extra virgin olive oil. A passionate producer will guide usu in refining your palate and recognising unique flavours - learning and enjoyment guaranteed!

Next, visit another esteemed winery for a fresh perspective on winemaking and a deeper appreciation of the craft.

To end the day, explore the medieval town of San Gimignano at leisure, admiring its iconic tower-filled skyline while indulging in gelato from a world-champion gelateria - a perfect finale.

Overnight: Tuscany
Meals: Breakfast

Day 3 - Farewell

Wake up feeling refreshed in Chianti, ready for another memorable day. Check out in the morning, but don’t worry - the experience doesn’t have to end! We can arrange additional activities to make your weekend feel endless (must be booked in advance, please contact us no less than 1 week prior to your arrival).

Choose from a variety of experiences, including a hands-on cooking class at a Tuscan farm, a scenic 1.5-hour horseback ride through the vineyards, or a relaxing morning at the spa. Unwind in heated indoor and outdoor pools (34°C), a sauna, Turkish bath, Tuscan aromarium, cold mist, summer storm showers, and an herbal tea relaxation corner - perfect for recharging before returning to daily life.

Our tour comes to an end after check out and completion of any optional activities. There is on accommodation included tonight and you are free to make your way to your next destination or the airport.

Meals: Breakfast

Hotels

The hotels listed below are ones which we frequently use on this tour. We reserve the right to substitute these hotels to ones of a similar standard.
Hotel Sovestro
Tuscany

Set in the Tuscan countryside, this relaxed hotel is 2 km from the Piazza della Cisterna in the town of San Gimignano. The country-style rooms come with free Wi-Fi, flat-screen TVs and minibars, plus balconies or terraces. Room service is available. Complimentary continental breakfast is served in a warm dining room, or on a shaded terrace. There's a restaurant/bar with exposed wood beams and stone walls, plus 2 outdoor pools and a fitness room.

Our Rating
Standard
Local Rating
3 Star Hotel
Podero II Pino
Tuscany

Set high in the Chianti Hills, Podere Il Pino is surrounded by olive groves and Tuscan vineyards. Offering panoramic views of nearby San Gimignano, it features an outdoor pool and small spa. Il Pino Podere is 3 km from Colle di Val d'Elsa and 10 minutes' drive from Poggibonsi-San Gimignano Train Station. Rooms come with a private patio overlooking the large garden. Each has a kitchen equipped with an oven, microwave and fridge. There is a shared laundry room, and you have free use of the BBQ in the garden. Surrounded by fragrant pine trees, the 18-metre pool features hydromassage and a furnished sun terrace. Bikes can be hired at reception, parking is free and the area is full of cycling and hiking trails.

Our Rating
Superior
Local Rating
Guesthouse

Prices & Dates

Departure dates are guaranteed with a minimum of 2 persons. 'Double/Twin' prices are per person when there are 2 people on the same booking sharing a room. Single rooms are not available on this tour.

2025
Double/Twin
2 May - 4 May
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$435$370
9 May - 11 May
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$435$370
16 May - 18 May
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$625$532
23 May - 25 May
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$625$532
30 May - 1 Jun
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$625$532
6 Jun - 8 Jun
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$625$532
13 Jun - 15 Jun
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$625$532
20 Jun - 22 Jun
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$625$532

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