Our Tuscany vacations & tours

From Volterra, one of Tuscany’s many hill towns, the landscape rolls away into the distance, sometimes green with vines, sometimes yellow with sun-parched grass, and purpling with mountains at the horizon. Here lies Tuscany’s appeal; it has fantastic landscapes, plus a gorgeous climate ideal for both grape growing and sunbathing, walking and cycling. Can an area live up to its formidably famous reputation? On our Tuscany vacations you won’t be disappointed. We work with suppliers who care about their local area – agriturismi and wine producers who are ensuring that the cultural history of Tuscany remains intact. Support them, and you’ll uncover the ‘true’ Tuscany, and help preserve those views for the next generation of visitors.

Our top Tuscany vacations

Walking vacation in Tuscany

From US $2535 to US $3075
8 days ex flights
A variety of daywalks in the beautiful Tuscan countryside
Small group2026: 5 Sep, 19 Sep, 26 Sep, 10 Oct, 2027: 17 Apr, 24 Apr, 1 May, 8 May, 15 May, 22 May, 29 May, 5 Jun, 28 Aug, 4 Sep, 11 Sep, 18 Sep, 25 Sep, 2 Oct, 9 Oct, 16 Oct

Italian cooking vacation, small group

From £1600
7 days ex flights
Immersive local gastronomy & cooking in undiscovered Tuscany
Small group2026: 26 Aug, 14 Sep

Tuscany food, wine and cookery retreat

From £1200
5 days ex flights
Small group food, wine & cooking retreats in Tuscany
Small group2027: 8 May, 22 May

Tuscany self guided cycling vacation in Italy

From £1319 to £1459
8 days ex flights
Experience local Tuscan life on two wheels
Tailor made

Pisa to Florence biking vacation, Italy

From US $1560 to US $1990
8 days ex flights
The highlights of beautiful Tuscany by bike
Small group2026: 29 Aug, 5 Sep, 12 Sep, 19 Sep, 26 Sep, 3 Oct, 10 Oct, 2027: 27 Mar, 3 Apr, 10 Apr, 17 Apr, 24 Apr, 1 May, 8 May, 15 May, 22 May, 29 May, 5 Jun, 12 Jun, 19 Jun, 26 Jun, 3 Jul, 10 Jul, 17 Jul, 24 Jul, 31 Jul, 7 Aug, 14 Aug, 21 Aug, 28 Aug, 4 Sep, 11 Sep, 18 Sep, 25 Sep, 2 Oct, 9 Oct

Tuscany tours, walking and wine tasting in Italy

From US $3045 to US $4350
8 days ex flights
Walking and wine tasting in Tuscany
Small group2026: 29 Aug, 12 Sep, 10 Oct, 17 Oct, 2027: 10 Apr, 17 Apr, 1 May, 8 May, 22 May, 29 May, 12 Jun, 28 Aug, 11 Sep, 18 Sep, 25 Sep, 9 Oct, 16 Oct

Tuscany hiking vacation, Italy

From 1290 to1690
8 days ex flights
Discover Tuscany hiking from town to town

Tuscany organic farmstay near Florence, Italy

From 80 to130
per accommodation per night (sleeps 2-4)
Organic farm on the hills of Florence, Tuscany

Short break pasta making & Italian food vacation, Tuscany

From £950
4 days ex flights
Make pasta & feast on amazing food in Tuscany
Small group2026: 1 Oct, 2027: 5 Jun
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Tuscany vacation highlights

Tuscan towns

Tuscany is known for its hill towns – defensively-positioned towns that now command superb views, look fantastic from a distance, and hide restaurant after restaurant – the most famous include San Gimignano, with its many distinctive towers and Montepulciano, with its wonderful wine. Most people can’t come to Tuscany and not visit Florence, it’s beautiful capital. Other cities include Siena and Arezzo. In fact, Tuscany is dotted all over with historic towns and cities containing some of the world’s best art and architecture.

Metropolises these are not. These are historic, museum and monument-strewn places. Whilst they can get very busy with adoring tourists, our vacations strive to take you off the busy trail most travelled. Instead, see the cities as part of a wider tour that also supports rural areas and producers.

Tuscan landscapes

Much of Tuscany has been farmed since the Etruscans, who preceded the more famous Romans in the area. Most of what we think of as quintessentially ‘Tuscan’ is agricultural land – like the Chianti hills. The rolling hills offer ideal grape growing conditions. Between them you’ll find a network of ‘white roads’ – traffic free trails once used by farmers and labourers that now make great cycling routes. Tuscany also contains wilder landscapes, too, like the more mountainous Garfagnana area to the north. Head west to the coast – fronted by the Tyrrhenian Sea, or head east and find yourself in quieter, landlocked Umbria, where the landscape is even quieter and greener. Combine Umbria and Tuscany together on one of our cycling vacations and you’ll reach even further into rural Italy.

Tuscany food & wine

The rolling farmlands of Tuscany deliver in scenery, but also, of course, in produce. There’s the famous Tuscan bean stew, of course, but this isn’t the be-all and end-all. There’s wine: in the famous chianti classico, then pecorino cheese, prosciutto crudo, biscotti, panzanella, and lovely Florentine steak.

On our vacations you don’t just taste – but try for yourself. Learn the art of pasta making and meet the producers behind the produce, from winemakers to beekeepers, and farmers at Tuscany’s network of ‘Mercatali’ – food markets showcasing seasonal food. Plus, by staying in an agriturismo that is part of the Agriturismo Association you ensure that you are staying somewhere which guarantees that it employs local people and uses local produce.

Family vacations

From the outside, Italian family culture is enviable: children are welcomed in many aspects of daily life, and many restaurants are family friendly. There are sunny climes, fun times and endless menus of pasta, pizza and gelato to be had. In Tuscany, you can have a fantastic family vacation that steers clear of busy cities and enjoys more room to roam.

Book one of our family villas or homestays in the region. These come with on-site olive groves, a map of nearby walking routes, and centuries of history etched into the walls. You can pick vegetables in the garden, feed the chickens and make pizzas in the wood-fired oven. Our properties with renewable energy in Tuscany come with solar panels and operate so as to be as responsible possible, whether they’re served by spring water, or use all-local produce.

Walking vacations

Tuscany’s network of villages and towns are close together enough that you can spend satisfying days walking between them on point-to-point trips with luggage transfers, or you can enjoy center-based walking and explore one area in more detail. Expect rolling hills – which means great views, but some strenuous sections – and, if you go in summer, prepare to walk under a very warm Tuscan sun.

On our walking vacations you could find yourself walking a section of the Via Francigena, an old pilgrimage route which ultimately leads to Rome (though it’s worth dragging your heels and dawdling over its beautiful Tuscan sections). Alternatively, head north to Garfagnana, a more mountainous area of Tuscany that contains the Orechiella National Park, deeper woodland and steeper hills. Tuscany’s cities and towns also encourage ‘urban trekking’ – walking routes to discover their streets, car free and at a slower pace.

Our Tuscany vacations reviews

4.7

60Tuscany vacations reviews

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Clare de Castella Mackay01 Jun 2026
Excellentread more
Jane Harris-Matthews01 Jun 2026
Beautiful countryside to walk through and excellent hotels made for a very enjoyable walking vacation.read more
Helen Watson26 Jul 2025
Seeing the different towns and villages en route was fabulous.read more
Heidi Hayes22 Nov 2024
Be prepared to enjoy delicious food and wine! Now is not the time to watch your weight. Enjoy, enjoy, enjoy!read more
Written by Eloise Barker
Photo credits: [Page banner: Luca Micheli] [Tuscan towns: Joshua Kettle] [Tuscan landscapes: Luca Micheli] [Tuscany food & wine: Aleksandrs Karevs]