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Tuscany Self-Guided Tours & Trips
Explore a wide diversity of tours through Tuscany tailored to suit your taste and thirst for adventure. We have 19 tours that vary from 4 days to 11 days. With the greatest number of departures in May, this is also the most popular time of the year.
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19 trips through Tuscany
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Self-Guided Cycling in Tuscany: Pisa to Florence
"Enjoyed the tour except first day. Could not follow the instructions. Got lost and..."
- destinations
- Pisa, Lago di Massaciuccoli, Lucca, Collodi, Pescia, Montecatini, Vinci, Pistoia, Florence, Empoli+9 more
- starts/ ends in
- Pisa / Pisa
- age range
- 12 to 80 year olds
- accommodation
- Hotel
- transport
- Bicycle
- Country Region
- Central Italy, Tuscany
- Travel style
- Bicycle
- operator
- Exodus Travels
- Days
- 8
- Our saving
- $55
- From
- US $ 1,310
View MoreGetDownload Brochure- days
- 8
$164 per day23 Mar 2019 6 spaces left 30 Mar 2019 6 spaces left 
Headwater - A Taste of Tuscany Cycling
8 day bicycle tour through Chianciano Terme, Radicofani, Sarteano and 4 other destinations in Italy
- destinations
- Chianciano Terme, Radicofani, Sarteano, Montepulciano, Pienza, Val d'Orcia, Bagno Vignoni+6 more
- starts/ ends in
- Chianciano Terme / Chianciano Terme
- age range
- 12 to 99 year olds
- accommodation
- Hotel
- transport
- Bicycle
- Country Region
- Central Italy, Tuscany
- Travel style
- Food & Culinary, Self-Guided, Wine tasting+2 more
- operator
- Exodus Travels
- Days
- 8
- Our saving
- $83
- From
- US $ 2,002
View MoreGetDownload Brochure- days
- 8
$250 per day4 May 2019 8 spaces left 11 May 2019 8 spaces left 
Classic Tuscany - Self Guided
8 day bicycle tour through Florence, Radda in Chianti, Siena and 4 other destinations in Italy
- destinations
- Florence, Radda in Chianti, Siena, San Gimignano, Vinci, Lucca, Pisa+6 more
- starts/ ends in
- Florence / Pisa
- age range
- 2 to 90 year olds
- transport
- Bicycle
- Country Region
- Central Italy, Tuscany
- Travel style
- Self-Guided
- operator
- Cycle Europe
- Days
- 8
- Our saving
- $60
- From
- US $ 1,452
View MoreGetDownload Brochure- days
- 8
$182 per day4 Apr 2019 10 spaces left 11 Apr 2019 10 spaces left Cycling Southern Tuscany - Self Guided
8 day bicycle tour through Cortona, Lake Trasimeno, Montepulciano and 5 other destinations in Italy
- destinations
- Cortona, Lake Trasimeno, Montepulciano, Pienza, Monticchiello, Montalcino, Bagno Vignoni, Siena+7 more
- starts/ ends in
- Cortona / Siena
- age range
- 2 to 90 year olds
- accommodation
- Hotel
- transport
- Bicycle
- Country Region
- Central Italy, Tuscany
- Travel style
- Self-Guided
- operator
- Cycle Europe
- Days
- 8
- Our saving
- $58
- From
- US $ 1,386
View MoreGetDownload Brochure- days
- 8
$173 per day2 Apr 2019 10 spaces left 9 Apr 2019 10 spaces left Cycle Pisa to Florence
8 day self-guided tour through Pisa, Lucca, Collodi and 4 other destinations in Italy
- destinations
- Pisa, Lucca, Collodi, Montecatini, Vinci, Florence, Empoli+4 more
- starts/ ends in
- Pisa / Pisa
- age range
- 2 to 99 year olds
- accommodation
- Hotel
- Country Region
- Central Italy, Tuscany
- Travel style
- Bicycle, Discovery
- operator
- UTracks
- Days
- 8
- Our saving
- $46
- From
- US $ 1,114
View MoreGetDownload Brochure- days
- 8
$139 per day23 Mar 2019 2 spaces left 30 Mar 2019 2 spaces left Francigena Way: Lucca to Siena
"Excellent week, will definitely go again."
- destinations
- Lucca, Gambassi Terme, San Gimignano, Gracciano, Monteriggioni, Siena+5 more
- starts/ ends in
- Lucca / Siena
- age range
- 2 to 99 year olds
- accommodation
- Hotel
- transport
- Train & Rail
- Country Region
- Central Italy, Tuscany, Via Francigena+1 more
- Travel style
- Discovery
- operator
- UTracks
- Days
- 8
- Our saving
- $46
- From
- US $ 1,113
View MoreGetDownload Brochure- days
- 8
$139 per day1 Apr 2019 2 spaces left 2 Apr 2019 2 spaces left Tuscany Self-Guided Walking
6 day self-guided tour through Tuoro Sul Trasimeno, Pienza, Montepulciano, Chiusi in Italy
- destinations
- Tuoro Sul Trasimeno, Pienza, Montepulciano, Chiusi+3 more
- starts/ ends in
- Tuoro Sul Trasimeno / Chiusi
- Country Region
- Central Italy, Tuscany
- Travel style
- Self Guided Walking Holidays, Hiking & Trekking, Christmas & New Year+2 more
- operator
- Butterfield & Robinson
- Days
- 6
- From
- US $ 2,995
View MoreGetDownload Brochure- days
- 6
$499 per day16 Dec 2018 2 spaces left 17 Dec 2018 2 spaces left Headwater - Chianti Classic Walk
11 day self-guided tour through Volterra, Casole d'Elsa, Colle Val d'Elsa, San Gimignano in Italy
- destinations
- Volterra, Casole d'Elsa, Colle Val d'Elsa, San Gimignano+3 more
- starts/ ends in
- Volterra / Volterra
- age range
- 8 to 99 year olds
- Country Region
- Central Italy, Tuscany
- operator
- Exodus Travels
- Days
- 11
- Our saving
- $99
- From
- US $ 2,366
View MoreGetDownload Brochure- days
- 11
$215 per day13 Apr 2019 8 spaces left 15 Apr 2019 8 spaces left Headwater - Classic Chianti Cycling
11 day bicycle tour through Volterra, Certaldo, Poggibonsi and 5 other destinations in Italy
- destinations
- Volterra, Certaldo, Poggibonsi, Colle Val d'Elsa, Siena, Florence, Colle di Val D'elsa, San Gimignano+6 more
- starts/ ends in
- Volterra / Volterra
- age range
- 8 to 99 year olds
- Country Region
- Central Italy, Tuscany
- Travel style
- Self-Guided, Discovery
- operator
- Exodus Travels
- Days
- 11
- Our saving
- $113
- From
- US $ 2,722
View MoreGetDownload Brochure- days
- 11
$247 per day13 Apr 2019 8 spaces left 15 Apr 2019 8 spaces left Headwater - Volterra to San Gimignano Walk
9 day self-guided tour through Volterra, Casole d'Elsa, Colle di Val D'elsa, San Gimignano in Italy
- destinations
- Volterra, Casole d'Elsa, Colle di Val D'elsa, San Gimignano+3 more
- starts/ ends in
- Volterra / Volterra
- age range
- 8 to 99 year olds
- Country Region
- Central Italy, Tuscany
- operator
- Exodus Travels
- Days
- 9
- Our saving
- $89
- From
- US $ 2,126
View MoreGetDownload Brochure- days
- 9
$236 per day13 Apr 2019 8 spaces left 15 Apr 2019 8 spaces left Walking in the Apuane Alps
8 day self-guided tour through Fornaci di Barga, Cardoso, Verni and 4 other destinations in Italy
- destinations
- Fornaci di Barga, Cardoso, Verni, Fornovolasco, Monte Forato, Grotto del Vento, Pania della Croce+6 more
- starts/ ends in
- Fornaci di Barga / Fornaci di Barga
- age range
- 2 to 99 year olds
- accommodation
- Hotel, Guesthouse
- Country Region
- Central Italy, Tuscany
- Travel style
- Discovery
- operator
- UTracks
- Days
- 8
- Our saving
- $44
- From
- US $ 1,050
View MoreGetDownload Brochure- days
- 8
$131 per day1 Apr 2019 2 spaces left 2 Apr 2019 2 spaces left Walking South of Siena
8 day self-guided tour through Siena, Asciano, SI, Buonconvento and 5 other destinations in Italy
- destinations
- Siena, Asciano, SI, Buonconvento, Montalcino, Bagno Vignoni, San Quirico D'orcia, Pienza, Montepulciano+6 more
- starts/ ends in
- Siena / Montepulciano
- age range
- 2 to 99 year olds
- accommodation
- Hotel
- Country Region
- Central Italy, Tuscany
- Travel style
- Discovery
- operator
- UTracks
- Days
- 8
- Our saving
- $60
- From
- US $ 1,437
View MoreGetDownload Brochure- days
- 8
$180 per day1 Apr 2019 2 spaces left 2 Apr 2019 2 spaces left Cycle San Gimignano to Siena
5 day self-guided tour through San Gimignano, Volterra, Monteriggioni, Siena in Italy
- destinations
- San Gimignano, Volterra, Monteriggioni, Siena+3 more
- starts/ ends in
- San Gimignano / Siena
- age range
- 2 to 99 year olds
- accommodation
- Hotel
- Country Region
- Central Italy, Tuscany
- Travel style
- Bicycle, Discovery
- operator
- UTracks
- Days
- 5
- Our saving
- $42
- From
- US $ 1,012
View MoreGetDownload Brochure- days
- 5
$202 per day1 Mar 2019 2 spaces left 2 Mar 2019 2 spaces left Tuscany Cycle Explorer
8 day self-guided tour through San Gimignano, Volterra, Monteriggioni, Castellina in Chianti, Siena in Italy
- destinations
- San Gimignano, Volterra, Monteriggioni, Castellina in Chianti, Siena+4 more
- starts/ ends in
- San Gimignano / Siena
- age range
- 2 to 99 year olds
- accommodation
- Hotel, Guesthouse
- Country Region
- Central Italy, Tuscany
- Travel style
- Bicycle, Discovery
- operator
- UTracks
- Days
- 8
- Our saving
- $56
- From
- US $ 1,341
View MoreGetDownload Brochure- days
- 8
$168 per day1 Apr 2019 2 spaces left 2 Apr 2019 2 spaces left Tuscany Cycle for Families
8 day self-guided tour through San Giuliano Terme, Pisa, Lucca and 3 other destinations in Italy
- destinations
- San Giuliano Terme, Pisa, Lucca, Altopascio, Vinci, Florence+5 more
- starts/ ends in
- San Giuliano Terme / Florence
- age range
- 2 to 99 year olds
- accommodation
- Hotel
- transport
- Train & Rail, Bicycle
- Country Region
- Central Italy, Tuscany
- Travel style
- Bicycle, Discovery
- operator
- UTracks
- Days
- 8
- Our saving
- $52
- From
- US $ 1,247
View MoreGetDownload Brochure- days
- 8
$156 per day1 Mar 2019 2 spaces left 2 Mar 2019 2 spaces left
Tuscany Self-Guided Tour Reviews
"Enjoyed the tour except first day. Could not follow the instructions. Got lost and..."
Self-Guided Cycling in Tuscany: Pisa to Florence"Excellent week, will definitely go again."
Francigena Way: Lucca to Siena
Other Regions in Italy
- Central Italy290
- South Italy273
- Northern Italy129
- Campania100