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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 44 adventures that vary from 4 days to 9 days. With the greatest number of departures in May, this is also the most popular time of the year.

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2026

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2027

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2028

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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, Val d'Orcia, Montalcino, San Quirico D'orcia, Bagno Vignoni, Siena
    Age Range All Ages Welcome
    OperatorBikesPlus Travel

    From

    US$1,726
    View tour
  2. Tuscany AbsoluteMap of Tuscany Absolute
    In-depth Cultural

    Florence's Hotel Executive welcomes you to discover Accademia Gallery and Ponte Vecchio independently. Move on to Montepulciano's Villa Cicolina, exploring Siena's medieval streets and Piazza del Campo. Flexible itinerary includes breakfast and private transfers.

    Duration 7 days
    DestinationsFlorence, Siena, San Gimignano, Castellina in Chianti, Montepulciano
    Age Range All Ages Welcome
    OperatorFlag Travel Holidays

    From $3,053

    20% Off
    US$2,442
    You save $611
    View tour
  3. 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, Gaiole in Chianti, Siena, San Gimignano
    Age Range All Ages Welcome
    OperatorTUI Italia

    From $1,278

    15% Off
    US$1,086
    You save $192
    View tour
  4. 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 $1,401

    35% Off
    US$911
    You save $490
    View tour
  5. In the Heart of the Renaissance: Pisa & FlorenceMap of In the Heart of the Renaissance: Pisa & Florence

    Navigate Tuscany at your own pace through the Worldee App Guide, starting at Piazza dei Miracoli in Pisa where you'll photograph the iconic 12th-century Leaning Tower before traveling to Florence. See Renaissance masterpieces by Botticelli at the Uffizi Gallery, admire Michelangelo's David at Galleria dell'Accademia, and wander through Boboli Gardens behind Palazzo Pitti. Stay at Le Cascine in Pisa (rating 8.2/10) and Hotel Balcony in Florence (rating 8.2/10), located just 400 meters from Santa Maria Novella station.

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

    From

    35% Off
    US$378
    View tour
  6. Pearls of TuscanyMap of Pearls of Tuscany
    Duration 6 days
    DestinationsPisa, Massaciuccoli, Tuscany, Siena, San Gimignano, Lucca, Florence
    Age Range All Ages Welcome
    OperatorWorldee

    From

    35% Off
    US$311
    View tour
  7. Luxury Italy by High-Speed TrainMap of Luxury Italy by High-Speed Train
    Explorer
    Duration 9 days
    DestinationsRome, Florence, Castellina in Chianti, Siena, San Gimignano, Venice
    Age Range Ages 10+
    OperatorFlag Travel Holidays

    From $5,081

    20% Off
    US$4,065
    You save $1,016
    View tour
  8. 4 Days in Florence.Map of 4 Days in Florence.
    Explorer

    Spend 3 nights at River Hotel & Spa Firenze with convenient airport transfers from Florence Municipal Airport included. The UNESCO-listed historic center is yours to see at your own pace, with optional skip-the-line access to the Accademia Gallery where you'll find Michelangelo's David plus masterworks by Giotto and Bernardo Daddi. The self-guided package works for groups of 10-90 travelers aged 18+ and includes daily breakfast. You're free to wander Florence's art-filled streets - the Duomo, Ponte Vecchio, and beyond - completely on your own schedule.

    Duration 4 days
    DestinationsFlorence
    Age Range Ages 18+
    OperatorRemaz Tours GmbH

    From

    20% Off
    US$1,580
    View tour
  9. Tuscany based in one hotelMap of Tuscany based in one hotel
    Bicycle
    Duration 8 days
    DestinationsMontecatini, Pisa, Florence, San Gimignano, Vinci, Lucca
    Age Range All Ages Welcome
    Operated in English, German
    OperatorEurobike

    From

    20% Off
    US$1,169
    View tour
  10. A Taste of Tuscany CyclingMap of A Taste of Tuscany Cycling
    Bicycle

    GPS directions guide you through Tuscany from Agriturismo La Pietriccia. Wander Montallese's mountain trails, Radicofani's hilltop views, and Sarteano's medieval center. Features host Stefano's briefings, cooking class, and route planning from Chianciano Terme.

    Duration 8 days
    DestinationsChianciano Terme, Radicofani, Sarteano, Montepulciano, Pienza, Val d'Orcia
    Age Range Ages 13+
    OperatorExodus Adventure Travels

    From

    20% Off
    US$2,180
    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