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
$5,695 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 guide and Tuscan native who will lead you on an insightful visit of Pienza, a remarkable Renaissance gem. Head out on your bikes for a wonderful loop ride and enjoy dinner tonight at the hotel's vibrant restaurant.
Activity:
32 km (20 mi.) warm-up ride from Pienza | Elevation gain: 600 m (2,000 ft.)
Day 2
The highlight of today's loop ride is the majestic Montepulciano, a medieval and Renaissance hill town where wine shops line the cobblestone laneways. Stop at one of the lively cafes and trattorie for lunch before continuing your ride through the enchanting hilltop town of Monticchiello.
Activity:
38 km (24 mi.) of biking loop from Pienza passing by Montepulciano and Monticchiello | Elevation gain: 704 m (2,300 ft.)
Optional ride | 54 km (33 mi.) | Elevation gain: 841 m (2,760 ft.)
Day 3
Embark on a magnificent ride to Siena through the beautifully stark Crete hills on one of the most iconic stretches of road in Tuscany. Take some time to settle into your hotel in the heart of the city before heading out for a stroll through town for dinner.
Activity:
53 km (32 mi.) or 65 km (40 mi.) of moderate to challenging biking from Pienza through the crete senesi | Elevation gain: 833 m (2,730 ft.)
Optional ride | 3 km (2 mi.)
Day 4
Join your guide around Siena to illuminate its medieval wonders, stopping for a glimpse inside its 13 c. cathedral. Stay in town for lunch or grab a picnic to go before returning to your bikes for a ride through the beautiful vineyards and rugged forests of Chianti.
Activity:
24 km (15 mi.) ride from Montaperti to Spaltenna | Elevation gain: 451 m (1,479 ft.)
38 km (24 mi.) long option from Montaperti to Spaltenna passing by San Gusmé | Elevation gain: 853 m (2,831 ft.)
Day 5
Enjoy a loop ride through the rolling hills, passing through the picturesque villages of Gaiole and Radda. 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:
33 km (20 mi.) Spaltenna loop passing through Radda and Gaiole | Elevation gain: 704 m (2,309 ft.)
Optional ride | 38 km (24 mi.) | Elevation gain: 860 m (2,821 ft.)
Day 6
Enjoy one final breakfast before your private car takes you to Florence city centre or airport.
* Itineraries are subject to change. Please confirm exact Trip Start and Trip End locations upon booking.
Featured stays
La Bandita Townhouse
Location: Pienza, Italy
Grand Hotel Continental
Location: Siena, Italy
Castello di Spaltenna
Location: Gaiole In 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.
