Tuscany vacations
Don't discount Tuscany vacations – nor the Chianti produced from Tuscany’s soft vine-swathed hills. Florence’s artistic treasures are complemented by Siena’s Gothic splendour (and its almond biscuits!), San Gimignano’s startling medieval high rises, Renaissance Lucca – and a rather wonky tower in Pisa.... And don’t forget Elba – the rugged Tuscan island that once held Napoleon (briefly) captive but which now captivates hikers and bikers.
25 Tuscany vacations found
Tuscany tours, walking and wine tasting in Italy
Walking and wine tasting in Tuscany
From US $2,617US $2,545 to US $2,925 8 days ex flights
Small group travel:
2024: 6 Apr, 13 Apr, 20 Apr, 4 May, 11 May, 25 May, 1 Jun, 15 Jun, 24 Aug, 31 Aug, 14 Sep, 21 Sep, 28 Sep, 12 Oct, 19 Oct
2025: 5 Apr, 12 Apr, 19 Apr, 3 May, 10 May, 24 May, 31 May, 14 Jun, 23 Aug, 30 Aug, 13 Sep, 20 Sep, 27 Sep, 11 Oct, 18 Oct
2025: 5 Apr, 12 Apr, 19 Apr, 3 May, 10 May, 24 May, 31 May, 14 Jun, 23 Aug, 30 Aug, 13 Sep, 20 Sep, 27 Sep, 11 Oct, 18 Oct
Up to US $70 off selected dates.
Late availability on these dates: 06 Apr, 13 Apr, 20 Apr, 04 May, 11 May
Late availability on these dates: 06 Apr, 13 Apr, 20 Apr, 04 May, 11 May
Short break pasta making & Italian food vacation, Tuscany
A Tuscan food adventure, learn to make pasta
From £900 to £1,025 4 days ex flights
Small group travel:
2024: 21 Apr, 9 Jun, 6 Oct
Walking vacation in Tuscany
A variety of daywalks in the beautiful Tuscan countryside
From US $2,098US $1,890 to US $2,400 8 days ex flights
Small group travel:
2024: 30 Mar, 20 Apr, 4 May, 11 May, 18 May, 25 May, 1 Jun, 31 Aug, 7 Sep, 14 Sep, 21 Sep, 28 Sep, 5 Oct, 12 Oct, 19 Oct
2025: 29 Mar, 12 Apr, 19 Apr, 26 Apr, 3 May, 10 May, 17 May, 24 May, 31 May, 30 Aug, 6 Sep, 13 Sep, 20 Sep, 27 Sep, 4 Oct, 11 Oct, 18 Oct
2025: 29 Mar, 12 Apr, 19 Apr, 26 Apr, 3 May, 10 May, 17 May, 24 May, 31 May, 30 Aug, 6 Sep, 13 Sep, 20 Sep, 27 Sep, 4 Oct, 11 Oct, 18 Oct
Up to US $200 off selected dates.
Late availability on these dates: 30 Mar, 20 Apr, 04 May, 11 May
Late availability on these dates: 30 Mar, 20 Apr, 04 May, 11 May
Chianti self guided cycling vacation in Italy
Pedal through the archetypal Tuscan countryside
From £2,519 to £2,539 11 days inc UK flights
Tailor made:
This trip has departures every two days throughout April - Oct, please enquire for further details.
Contact Us
Call us for a chat about our vacations. We are happy to discuss your vacation and help in any way we can. No bots, queues or awful hold music.
1-866-821-6866
Call toll free
Calling from outside the USA
rosy@responsibletravel.com
Florence to Pisa cycling vacation,
Fall in love with provincial Italy on this cycling adventure
From US $2,750US $2,612 to US $3,030 8 days ex flights
Small group travel:
2024: 27 Apr, 11 May, 25 May, 15 Jun, 29 Jun, 13 Jul, 27 Jul, 3 Aug, 17 Aug, 7 Sep, 14 Sep, 21 Sep, 28 Sep, 5 Oct
Up to US $130 off selected dates.
Late availability on these dates: 27 Apr, 11 May
Late availability on these dates: 27 Apr, 11 May
Tuscany hiking vacation, Italy
Discover Tuscany hiking from town to town
From €1,290 to €1,690 8 days ex flights
Tailor made:
This trip can be tailor made throughout the year to suit your requirements
Italian cooking vacation, small group
Immersive gastronomy & cooking trips in undiscovered Tuscany
From £1,550 to £1,800 7 days ex flights
Small group travel:
2024: 5 May, 24 May, 23 Jun, 1 Sep, 20 Sep
Pisa to Florence biking vacation, Italy
The highlights of beautiful Tuscany by bike
From US $1,390 to US $1,670 8 days ex flights
Small group travel:
2024: 30 Mar, 6 Apr, 13 Apr, 20 Apr, 27 Apr, 4 May, 11 May, 18 May, 25 May, 1 Jun, 15 Jun, 29 Jun, 6 Jul, 13 Jul, 20 Jul, 27 Jul, 3 Aug, 10 Aug, 17 Aug, 24 Aug, 31 Aug, 7 Sep, 14 Sep, 21 Sep, 28 Sep, 5 Oct, 12 Oct
Late availability on these dates: 30 Mar, 06 Apr, 13 Apr, 20 Apr, 27 Apr, 04 May, 11 May
Tuscany small group tour
Explore the charms of laid-back Umbria
From US $6,110 to US $6,925 8 days ex flights
Small group travel:
2024: 16 May, 25 May, 15 Jun, 20 Jun, 13 Jul, 8 Aug, 10 Aug, 31 Aug, 5 Sep, 7 Sep, 14 Sep, 21 Sep, 26 Sep, 3 Oct, 12 Oct
2025: 10 Apr, 24 Apr, 1 May, 8 May, 15 May, 22 May, 29 May, 5 Jun, 12 Jun, 19 Jun, 21 Jun, 26 Jun, 3 Jul, 17 Jul, 31 Jul, 2 Aug, 16 Aug, 21 Aug, 23 Aug, 30 Aug, 4 Sep, 6 Sep, 11 Sep, 13 Sep, 18 Sep, 20 Sep, 25 Sep, 27 Sep, 2 Oct, 9 Oct, 16 Oct, 30 Oct
2025: 10 Apr, 24 Apr, 1 May, 8 May, 15 May, 22 May, 29 May, 5 Jun, 12 Jun, 19 Jun, 21 Jun, 26 Jun, 3 Jul, 17 Jul, 31 Jul, 2 Aug, 16 Aug, 21 Aug, 23 Aug, 30 Aug, 4 Sep, 6 Sep, 11 Sep, 13 Sep, 18 Sep, 20 Sep, 25 Sep, 27 Sep, 2 Oct, 9 Oct, 16 Oct, 30 Oct
Southern Tuscany walking and wine vacation
A walking holiday in southern Tuscany
From US $2,410 to US $2,560 8 days ex flights
Small group travel:
2024: 21 Apr, 28 Apr, 12 May, 26 May, 9 Jun, 16 Jun, 8 Sep, 15 Sep, 6 Oct, 13 Oct
Late availability on these dates: 21 Apr, 28 Apr, 12 May
Italy food vacation, tailor made
Discover the gastronomic delights of Italy
From US $7,100 12 days ex flights
Tailor made:
This trip can be tailor made throughout the year to suit your requirements
Tuscany self guided cycling vacation in Italy
Experience local Tuscan life on two wheels
From £1,959 to £1,984 8 days inc UK flights
Tailor made:
This trip can depart on Saturdays throughout April - Oct, please enquire about your tailor made trip.
Tuscany self guided walking vacation in Italy
A full immersion into local Tuscan life
From £1,909 to £1,934 8 days inc UK flights
Tailor made:
This trip can depart on Saturdays throughout April-Oct, please enquire for details.
Umbria to Tuscany walking and cooking vacation
Come to discover Umbria, cook and walk just like a local
From €1,590 5 days ex flights
Small group travel:
2024: 28 Apr, 20 Sep
Contact Us
Call us for a chat about our vacations. We are happy to discuss your vacation and help in any way we can. No bots, queues or awful hold music.
1-866-821-6866
Call toll free
Calling from outside the USA
rosy@responsibletravel.com
Umbria to Tuscany cycling & cooking vacation
Cycling and cooking holiday between Umbria and Tuscany
From €1,690 5 days ex flights
Small group travel:
2024: 28 Apr, 20 Sep
Tuscany family vacation, Italy
Active and cultural family adventure in Italy
From US $1,830 to US $2,190 8 days ex flights
Small group travel:
2024: 26 May, 14 Jul, 4 Aug, 18 Aug
Francigena Way walking vacation Lucca to Siena
Walking vacation through the Tuscan countryside
From US $1,190 to US $1,220 8 days ex flights
Tailor made:
This trip can be tailor made throughout the year to suit your requirements
Tuscany villa vacation, 10 days
Experience small-town Italy like a local
From US $3,500 11 days ex flights
Small group travel:
2024: 14 Sep, 25 Sep
Italy wine tour in Umbria & Tuscany
-taste best umbrian and tuscan wines, great culinay holiday
From €1,980 6 days ex flights
Small group travel:
2024: 4 May, 27 Sep
Tuscany culture vacation, tailor-made
Capture the true spirit of Tuscany
From €1,220 to €1,380 5 days ex flights
Tailor made
Rome to Venice cultural tour in Italy
Discover Italy on the classic route Rome to Venice
From €1,970 to €2,120 10 days ex flights
Tailor made:
This trip can be tailor made throughout the year to suit your requirements
Tuscany biking vacation through Siena & Chianti
Cycle the most evocative and romantic landscapes
From US $3,000 to US $3,300 8 days ex flights
Small group travel:
2024: 11 May, 18 May, 8 Jun, 7 Sep, 5 Oct
Late availability on these dates: 11 May
Cycling vacation in Umbria, Italy
The peace of Tuscany & Umbria by bicycle
From US $1,750 8 days ex flights
Tailor made:
This trip can be tailor made throughout the year to suit your requirements
Rural villas in Tuscany, Italy
Traditional apartments in the heart Tuscany
From €390 to €1,550 per accommodation per week
Accommodation
Tuscany organic farmstay near Florence, Italy
Organic farm on the hills of Florence, Tuscany
From €70 to €130 per accommodation per night (sleeps 2-4)
Accommodation
