Tuscany Harvest Bike Tour

Olives, Truffles, Porcini, Chestnuts... And a Nice Chianti

6 days / 5 nights Level: 3Price From: $6,195Collection: Classic, Specialty

Tour Highlights

  • Experience Tuscany when its culinary treasures are ripe for the picking; take part in a dog-led truffle hunt, cook with our friend Lina in her 15th-century home, and harvest olives to be pressed into oil at a local mill
  • Weave through buzzing vineyards to a scenic family-run estate, where a private tasting lunch featuring award-winning Chianti wines awaits
  • Pedal deep into the forests of Mount Amiata, filled with porcini mushrooms and chestnuts, to a seasonal lunch with a Michelin-starred chef
  • End the tour with a bang; ride across Chianti and finish in Florence’s stunning Piazzale Michelangelo


Hand-rolled pici pasta, pecorino cheese, olio nuovo (fresh-pressed olive oil), truffles, fava beans, artichokes, chestnuts, porcini mushrooms, Chianina beef, and cinghiale (wild boar)


World-famous wines made from native Sangiovese grapes including Brunello, Chianti Classico, and Vino Nobile; international blends known as Super Tuscans; and—in classic Italian fashion—espresso and cappuccino

As featured in:
Print Itinerary
  • Day 1

    Raccolta: The Olive Harvest

    Your journey begins with a transfer to La Chiusa, a former olive oil mill that is now a charming country inn. Enjoy lunch featuring ingredients from the surrounding countryside. Harvest time means there is work to do, and we will jump right into the action, picking olives from La Chiusa’s grove before hopping on our bikes and riding to our friend Paolo’s olive oil mill to get our olives pressed. Taste the alien green olio nuovo (new oil) on warm bruschetta before pedaling on to our first hotel in Pienza; a jewel of Renaissance urban planning. This evening, head to a local farmhouse for dinner featuring cheeses, vegetables, grains, and meats all produced onsite.

    Meals: Lunch / Dinner
    Destinations: Pienza, Petroio
    Accomplished: 19 miles / 29 km, elevation gain: 1,919 feet / 585 meters
    Shorter Option: 14 miles / 22 km, elevation guide: 1,332 feet / 406 meters
    Accommodations: Bandita Townhouse

  • Day 2


    Set off riding through pastures and forests to join the village of San Giovanni. Here we’ll meet up with our friend, a local truffle dog, and her human companion. They’ll lead us into the oak forests that make this area famous for both its black and white tartufi (truffles). Back in San Giovanni we’ll have a truffle-infused lunch at Donatella’s cozy Osteria. After lunch we’ll keep pedaling into the Brunello wine-growing region. It’s a big climb up to Montalcino, the medieval hilltown at the heart of the Brunello zone, but the effort is well-rewarded when we check into our five-star castle hotel.

    Meals: Breakfast / Lunch / Dinner
    Destinations: San Giovanni, Torrenieri, Montalcino
    Accomplished: 35 miles / 57 km, elevation gain: 2,486 feet / 758 meters
    Shorter Option: 23 miles / 37 km, elevation gain: 1,184 feet / 361 meters
    Accommodations: Castello di Velona

  • Day 3

    Chestnuts + Mushrooms

    Today we will ride along the slopes of Monte Amiata, famous for the deep chestnut forests hiding a bounty of porcini mushrooms. Mushroom season in Tuscany means lines of cars parked along the sides of country roads as Tuscans head en-masse into the woods to search for these delicious prizes. We’ll join in the fun, going on our own hunt before a Michelin lunch at a mountain restaurant. After lunch, pedal back to our hotel to relax at the spa. This evening we’ll head back into Montalcino for a cooking class and dinner featuring porcini and chestnuts, of course, in the 15th-century home of our friend Lina.

    Meals: Breakfast / Lunch / Dinner
    Destinations: Vivo d’Orcia, Pescina, Seggiano
    Accomplished: 28 miles / 45 km, elevation gain: 3,818 feet / 1,164 meters
    Longer Option: 43 miles / 69 km, elevation gain: 7,118 feet / 2,170 meters
    Accommodations: Castello di Velona

  • Day 4

    Pane dei Santi: An Autumn Treat

    Ride to a local bakery for another seasonal treat, pane dei santi, a hearty bread with nuts and raisins made only around All Saints’ Day. Spend the rest of the day making your way across stunning Crete Senesi, stopping to visit the Renaissance frescoes at the Abbey of Monte Oliveto. Continue riding along the open ridges of this scenic landscape to meet up with Davide, our host at a small family-run Chianti winery. Taste their selection of wines, from full-bodied Chianti Classico to Super Tuscans and sparkling whites during a private tasting lunch. Tonight you are free to explore the medieval city of Siena or dine at the hotel.

    Meals: Breakfast / Lunch
    Destinations: Buonconvento, Monte Oliveto, Asciano, Siena
    Accomplished: 29 miles / 46 km, elevation gain: 2,083 feet / 635 meters
    Longer Option: 48 miles / 77 km, elevation gain: 3,972 feet / 1,211 meters
    Accommodations: Borgo San Felice or Le Fontanelle

  • Day 5

    Wine + Wild Boar

    Pedal through the olive and cypress trees deep into the hills of Chianti where fortified hamlets and castles are a testament to the area’s unsettled past. Pass countless estates as we weave our way through forests and vineyards, completing the loop in time for a relaxed lunch at the hotel with time to enjoy the spa and grounds. Tonight we’ll convene for a joyous farewell dinner at our dear friend Serena’s Tuscan abode. Here, a bounty of autumn’s Tuscan specialties awaits, including cinghiale (wild boar).

    Meals: Breakfast / Lunch / Dinner
    Destinations: Castelnuovo, Brolio, Castagnoli
    Accomplished: 31 miles / 50 km, elevation gain: 2,673 feet / 815 meters
    Longer Option: 40 miles / 64 km, elevation gain: 3,575 feet / 1,090 meters
    Accommodations: Borgo San Felice or Le Fontanelle

  • Day 6

    Ride to Florence

    On our last day, choose between a late morning at the hotel or ride all the way across Chianti for a triumphant finish in Florence’s Piazzale Michelangelo. Whether you rode here or took a transfer, we say our goodbyes with the stunning Florentine skyline as our backdrop as guides see you off to your next adventure.

    Meals: Breakfast
    Destinations: Panzano, Greve, Florence
    Optional ride: 32 miles / 52 km, elevation gain: 2,470 feet / 753 meters
    Longer Option: 43 miles / 69 km, elevation gain: 3,477 feet / 1,060 meters

DuVine itineraries may be subject to slight route changes, hotel substitutions, and other modifications.

Arrival Details

Airport City: Rome or Florence, Italy Pick-Up Location: Chiusi Train Station Pick-Up Time: 11:00 am
Departure Details

Airport City: Rome or Florence, Italy Drop-Off Location: Florence Piazzale Michelangelo Drop-Off Time: 1:30 pm

Please note that Arrival + Departure Details for 2025 tours could be subject to change.

Any scheduled tour can be made private. Your group, your dates. Go Private

2024Single Supplement From: $2,000
2025Single Supplement From: $2,000

See our cancellation policy

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  • Thoughtfully selected accommodations that reveal the true character of the region
  • Luggage transfers


  • Daily breakfasts, all lunches, nutritious snacks, and après velo cocktails
  • 4 gourmet dinners at our favorite local restaurants and renowned culinary establishments
  • Carefully selected local wine, beer, or spirits with every meal


  • Wine tastings and activities as outlined in the tour itinerary
  • Entrance fees to historic sites, museums, parks, and all other exclusive events
  • Gratuities for baggage, porters, and hotel service


  • Top-of-the-line bicycle selection
  • Bike helmet
  • Complimentary DuVine gear including a custom cycling jersey, DuVine t-shirt, water bottle, and drawstring bag
  • GPS in most destinations


  • Expert bilingual guides with extensive local knowledge
  • Support vehicle that follows the day’s route, distributes refreshments, and offers lifts
  • Pick-up and drop-off before and after your tour from predetermined meeting points
  • Daily bike maintenance to ensure optimal performance

See our FAQs page for answers to common questions.

See FAQs

Synapse 2 RLE

Manufacturer: Cannondale

Type: Road

Included in trip price

Roadmachine AMP TWO

Manufacturer: BMC

Type: Road E-Bike

$400 supplement, subject to availability

Turbo Vado SL 4.0

Manufacturer: Specialized

Type: Hybrid E-Bike

Included in trip price