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Self-Guided Tours & Trips in Tuscany
Self-Guided Tours & Trips in Tuscany

Self-Guided Tours & Trips in Tuscany

Explore a wide diversity of self-guided tours through Tuscany. We have 52 adventures that vary from 3 days to 9 days. With the greatest number of departures in August, this is also the most popular time of the year.

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2026

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2027

Jan
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2028

Jan
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1 Adult2 Adults, 1 Child2 Children

Who is travelling?

AdultsAges 18 or above

2

ChildrenUnder 18

0
  1. Postcard Southern Tuscany - Cycling Cortona, Montalcino, Siena - Classic Self GuidedMap of Postcard Southern Tuscany - Cycling Cortona, Montalcino, Siena - Classic Self Guided
    Bicycle

    GPS navigation guides cyclists through Tuscany's heart. Daily rides of 22-67km connect Cortona to Siena, with stays at Hotel S. Luca and Hotel dei Capitani. Brunello wineries and UNESCO landscapes unfold at your chosen pace with included luggage transfers.

    Duration 8 days
    DestinationsCortona, Lake Trasimeno Regional Park, Montepulciano, Pienza, Monticchiello, Trequanda, Montalcino, San Quirico D'orcia, Bagno Vignoni, Siena
    Age Range All Ages Welcome
    OperatorBikesPlus Travel

    From

    US$1,723
    View tour
  2. 3-Day Private Florence Spa & Wellness: Classic Heritage & Natural Cave ExperienceMap of 3-Day Private Florence Spa & Wellness: Classic Heritage & Natural Cave Experience
    Health, Spa & Wellness
    Duration 3 days
    DestinationsFlorence, Montecatini
    Age Range All Ages Welcome
    OperatorTUI Italia

    From $1,340

    15% Off
    US$1,139
    You save $201
    View tour
  3. Luxury Italy by High-Speed TrainMap of Luxury Italy by High-Speed Train
    Explorer

    Skip the lines at Siena's UNESCO-listed Piazza del Campo and San Gimignano's medieval towers as you wind through Tuscany's hills. A family vineyard in Castellina in Chianti hosts you for homemade lunch with Chianti tastings, then you'll head to Florence to see the Duomo and walk across Ponte Vecchio.

    Duration 9 days
    DestinationsRome, Florence, Castellina in Chianti, Siena, San Gimignano, Venice
    Age Range Ages 10+
    OperatorFlag Travel Holidays

    From

    15% Off
    US$5,069
    View tour
  4. Tuscany Escape: 7 days Through Art, Wine & Hills, Self-DriveMap of Tuscany Escape: 7 days Through Art, Wine & Hills, Self-Drive
    Explorer

    The Tuscan countryside unfolds from Florence's Ponte Vecchio to Chianti's wine routes. Self-drive freedom lets you uncover Siena's Piazza del Campo and San Gimignano's medieval towers. Includes 4-star stays at Grand Hotel Adriatico and Hotel Le Pozze di Lecchi.

    Duration 7 days
    DestinationsFlorence, Pisa, Greve in Chianti, Gaiole in Chianti, Siena, San Gimignano
    Age Range All Ages Welcome
    OperatorTUI Italia

    From $1,275

    15% Off
    US$1,084
    You save $191
    View tour
  5. Pearls of TuscanyMap of Pearls of Tuscany

    Your rental car takes you to Siena's UNESCO-listed Piazza del Duomo, San Gimignano's towers, and Florence's Uffizi Gallery with Botticelli and Leonardo works. Walk Lucca's 4km Renaissance walls, climb Torre Guinigi to see its rooftop oaks, and visit Puccini's birthplace museum before standing before David at Galleria dell'Accademia.

    Duration 6 days
    DestinationsPisa, Siena, San Gimignano, Florence, Lucca
    Age Range All Ages Welcome
    OperatorWorldee

    From

    15% Off
    US$551
    View tour
  6. In the Heart of the Renaissance: Pisa & FlorenceMap of In the Heart of the Renaissance: Pisa & Florence

    The Worldee App guides your self-drive route from Pisa's UNESCO-listed Piazza dei Miracoli to Florence's Renaissance treasures. Stay at Le Cascine in Pisa, about 1km from the Leaning Tower, then move to Hotel Balcony in Florence, a 10-minute walk from Uffizi Gallery and Ponte Vecchio.

    Duration 5 days
    DestinationsPisa, Florence
    Age Range All Ages Welcome
    OperatorWorldee

    From

    15% Off
    US$353
    View tour
  7. 5 Day Florence With Car RentalMap of 5 Day Florence With Car Rental
    Explorer

    Create your Tuscan adventure with a rental car and Hotel Luxor Florence base. Freedom to explore the Uffizi Gallery, discover Oltrarno's authentic neighborhoods, and visit local artisan workshops at your own pace.

    Duration 5 days
    DestinationsFlorence
    Age Range All Ages Welcome
    OperatorSTM Tours LLC

    From $1,398

    27% Off
    US$1,020
    You save $377
    View tour
  8. Best of Italy in a Week  (Milan, Florence, Rome)Map of Best of Italy in a Week  (Milan, Florence, Rome)
    Explorer
    Duration 7 days
    DestinationsMilan, Florence, Pisa, Rome, Vatican City
    Age Range All Ages Welcome
    OperatorWiseYatra

    From $1,930

    30% Off
    US$1,351
    You save $579
    View tour
  9. A quick trip to sunny TuscanyMap of A quick trip to sunny Tuscany
    Duration 5 days
    DestinationsPisa, Bologna, Florence
    Age Range All Ages Welcome
    OperatorWorldee

    From

    30% Off
    US$340
    View tour
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Who is travelling?

AdultsAges 18 or above

2

ChildrenUnder 18

0

Select departure month

2026

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

2027

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec

2028

Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec