Self-Guided
Tuscany Self-Guided Biking
Explore Italy's pleasures
6 Days, 5 Nights
Activity Level:
B&R Activity Levels
Best Time To Go
April – June, September – October
Priced per person from
$6,395 USD
Prices May Vary For Groups Larger Than Two
Carbon Neutral Trip
Tuscany’s calling—and this self-guided spin lets you answer at your own pace. Cycle past cypress-lined hills to storybook towns like Pienza and Montepulciano, sip from sun-soaked vineyards, and feast at trattorie that know their way around a wild boar ragu. With local tips for living la dolce vita, Tuscany never felt so personal.
Explore every corner of Tuscany’s stunning scenery by bike, from its charming medieval towns to its Renaissance hilltop villages.
Meet our trusted local friends and guides, who will welcome you with open arms and offer exclusive access to the heart of the region.
Savour authentic flavors at our favourite local restaurants and stop for tastings from the region’s finest winemakers, all at your own pace.
Preview the itinerary
No two trips are ever the same, but this will give you a taste of what your journey will be like.
Day 1
Meet Carlo, your local host and Tuscan native, for a short introduction to Pienza, a Renaissance gem.
Set out on a warm-up ride through the Val d’Orcia countryside, passing the charming hamlets of Montefollonico, Petroio and Castelmuzio before returning to Pienza.
Activity:
Morning ride | 32 km (20 mi.) | Elevation gain 600 m (2,000 ft)
Guided walk through Pienza with your guide Carlo
Day 2
Today’s loop leads to Montepulciano, a storied hill town known for its Vino Nobile and lively wine bars. Wander cobbled streets lined with cafés and boutiques—an ideal stop for lunch.
On your way back, pause in the hilltop village of Monticchiello, where stone lanes, medieval walls and sweeping views over the Orcia Valley capture the quiet beauty of Tuscany.
Activity:
Morning ride | 38 km (23.6 mi.) | Elevation gain: 704 m (2,300 ft)
Optional ride | 53.6 km (33 mi.) | Elevation gain: 841 m (2,760 ft)
Day 3
Ride through the striking Crete Senesi, one of Tuscany’s most iconic landscapes, en route to Siena. Pause in Monteaperti before a short taxi transfer into the city.
Take some time to settle into your hotel in the heart of the city before heading out for a stroll through town with a gelato in hand for dinner.
Activity:
Morning ride | 53 km (32 mi.) or 65 km (40 mi.) | Elevation gain: 833 m (2,730 ft)
Optional ride | 3 km (1.8 mi.)
Day 4
This morning, Carlo returns to guide you through Siena, including the magnificent 13th-century cathedral and the storied Piazza del Campo, home of the famed Palio horse race.
After lunch in town or a picnic to go, transfer back to your bikes for a ride through the vineyards and forests of Chianti.
Activity:
Morning ride | 26.8 km (16.6 mi.) | Elevation gain: 577 m (1,893 ft)
Optional ride | 9 km (5.5 mi.)
Day 5
On your final day, ride through Chianti’s rolling hills, passing the postcard-perfect villages of Gaiole and Radda, both ideal for a relaxed lunch.
In the early evening, enjoy an aperitivo on the hotel’s terrace overlooking vine-covered hills in every direction. Savour one final dinner in Tuscany and raise your glass to an incredible adventure.
Activity:
Morning ride | 50 km (31 mi.) | Elevation gain: 986 m (3,241 ft)
Optional ride | 61 km (37.9 mi.) | Elevation gain: 1,281 m (4,202 ft)
Day 6
Enjoy one final breakfast before your private car takes you to Florence city centre or airport.
Get in touch
We always love to chat travel. Let’s see what trip is right for you.
Featured stays
La Bandita Townhouse
Location: Pienza, Italy
Grand Hotel Continental
Location: Siena, Italy
Borgo San Felice
Location: Chianti, Italy
What's included
Accommodation & dining
All accommodation as indicated on the itinerary.
All breakfasts, lunches and dinners as indicated on the itinerary.
Restaurant suggestions along the way.
Active essentials
Choice of bike as appropriate for terrain (see below), equipped with handlebar bag and helmet.
A biodegradable B&R water bottle.
Use of a smartphone with downloaded GPS routes provided via RideWithGPS.
Guided services
Private guided tour of Pienza.
Private guided tour of Siena.
Transportation & logistics
Drop off in Florence.
Baggage transportation.
What's Not Included: International flights, travel protection, gratuity for your guides, pick up in Pienza
This trip is carbon neutral. Learn more about our Sustainability commitment.
Experience Designer
Good to know
Rides
Your daily routes include plenty of challenging up and downhills. For non-avid cyclists, consider an e-bike for extra support.
Pre and Post trip
If you have extra time, consider extending your trip with a visit to Florence or Rome.
Packing
Tuscany can have variable weather throughout the day in October. We recommend packing a Gore-Tex raincoat to stay comfortable and dry.
Why choose a Self-Guided trip?
Total Freedom, Tailored to You
With a self-guided trip, you are the master of your own adventure. Every route, hotel, and dining experience is meticulously planned by our expert team, leaving you free to explore at your own pace. Follow our guidance or take that unmarked path that catches your eye—it's your call.
Set Your Own Pace
Whether you're an early bird who loves watching the sunrise or a traveller who prefers leisurely mornings, self-guided trips let you design each day to your rhythm. No strict schedules or group timetables—just the perfect balance of adventure and relaxation, as you like it.
Support Behind the Scenes
Though you're on your own, you're never truly alone. Our local experts are just a call away, ready to offer support if needed. From roadside assistance to restaurant recommendations, we're there to ensure your journey is seamless and stress-free.
A Private Escape
Craving a solo adventure or a getaway with your closest companions? A self-guided trip offers the privacy to create lasting memories with your travel partner(s), free from distractions. The world is yours to explore, with no group to keep up with or slow you down.
Discover further
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6 Days, 5 Nights | April – June, September – October
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