Self-Guided Tuscan Hilltowns and the Roads of Val d’Orcia Bike Tour

Arrival Information

Your cycling journey begins in Cortona, a historic hill town in Tuscany. The recommended arrival airports are Florence Airport (FLR) and Rome Fiumicino Airport (FCO).

From Florence Airport, take a shuttle or taxi to Firenze Santa Maria Novella railway station, approximately 30 minutes by shuttle, then continue by train to Cortona. The train journey usually takes around 1 hour and 30 minutes, depending on the connection.

If you arrive at Rome Fiumicino Airport, travel to Roma Termini by train, shuttle or taxi, then take a train towards Cortona. Check current schedules and connections before departure.

Once in Cortona, make your way to your hotel and settle in before meeting the local team for your bike fitting and tour briefing. The meeting is typically scheduled between 2:00 pm and 4:00 pm, so plan your arrival accordingly.

We recommend arriving with enough time to reach Cortona, check in and prepare for your journey through the Tuscan countryside.

Departure Information

Your cycling holiday concludes in Siena after breakfast on Day 8. From here, you can travel onwards to Florence or Rome for your return flight, or extend your stay to explore more of Tuscany.

For Florence Airport (FLR), trains from Siena to Florence generally take around 1 hour and 30 minutes to 2 hours, sometimes with a connection in Empoli. Bus services are another option, with a journey of approximately 1 hour and 30 minutes, depending on the service and traffic. Allow additional time to reach the airport.

For Rome Fiumicino Airport (FCO), travel from Siena to Roma Termini, a journey estimated at around 3.5–5 hours, and continue to the airport by train, shuttle or taxi.

Tuscany offers excellent cycling conditions from March through October. Spring (March-May) brings mild temperatures (15-22°C/59-72°F) with vibrant green landscapes and wildflowers, though occasional rain showers are possible. Summer (June-August) is warm to hot (25-35°C/77-95°F) with long daylight hours, though July and August can be quite hot for cycling. Early fall (September-October) is ideal with comfortable temperatures (18-25°C/64-77°F), grape harvest season, and stunning autumn colors transforming the vineyards and hills. The high season (May-June 15 and September-October 15) offers the best combination of pleasant weather and beautiful landscapes for cycling.

Packing smart is essential for a safe and enjoyable cycling adventure. From essential biking gear to clothing and travel necessities, this guide ensures you're prepared for any terrain or climate.

Recommended Bicycling Clothes & Gear

• Bicycling shoes or stiff-soled sneakers.
• Padded cycling shorts.
• Short-fingered cycling gloves.
• Brightly colored cycling jerseys or synthetic T-shirts for visibility.
• Synthetic cycling socks.
• Sunglasses with UV protection.
• Personal helmet, if preferred.
• Personal saddle, if you ride one at home.
• Rain jacket or windbreaker.
• Cycling water bottle.

Note: Helmets, gloves, and water bottles are personal items, so bringing your own is recommended for maximum comfort and hygiene.

Clothing

• Light, breathable fabrics like cotton or linen.
• Full-sleeved clothing for sun protection.
• Warm layers for chilly mornings and evenings when needed.
• Comfortable footwear for non-cycling time.
• Bring a compact rain jacket in case of sudden weather changes.
• Modest clothing for exploring towns, villages, and temples.

Other Necessities

• Basic toiletries, including insect repellent and sunscreen.
• Hand sanitizer and wet wipes.
• Plug socket adaptor.
• Binoculars if you enjoy spotting wildlife or distant landscapes.

Pro Tips

• Pack light but plan for varying temperatures, winds, and road conditions.
• Use bright clothing for visibility on the road.
• Leave some room for route-side shopping and souvenirs.

Luggage

Please limit your luggage to one medium-sized suitcase and one carry-on bag. Mark your luggage with your name, address, and phone number.

Italy is part of the Schengen Area. US, Canadian, Australian, and UK citizens can visit Italy for up to 90 days within a 180-day period without a visa for tourism purposes. Ensure your passport is valid for at least three months beyond your planned departure date from the Schengen Area. Always check current visa requirements with your country's foreign affairs department or the Italian embassy before travel.

Medical insurance that covers medical costs in case of an accident during the trip is mandatory to participate in our tours.

We recommend purchasing adequate travel insurance to protect yourself from unforeseen events. Our experience shows that guests who purchase travel insurance, including coverage for all activities on the itinerary, trip cancellation, interruption, delay, baggage damage, loss or theft, personal accident, death and repatriation costs, medical and emergency expenses, and personal liability, travel with greater peace of mind.

Is proof of medical insurance required?

Yes. You must provide your insurer's name, policy number, and emergency contact through our reservation form. If you cannot provide proof, you'll need to purchase insurance before traveling with us.

Can I use my credit card insurance?

Yes, as long as it meets our requirements and provides adequate coverage. Keep your emergency contact number and policy number accessible while traveling.

When should I buy travel insurance?

Purchase travel insurance as soon as you've paid in full or booked your flights.

Does Art of Bicycle Trips sell travel insurance?

We do not sell travel insurance directly. We recommend comparing policies and choosing the one that best fits your needs. A useful place to start is Insured Nomads.