7 days
From US $1,395
Self-guided Extremadura Bike Tour
Discover the rugged charm and quiet grandeur of Spain’s Extremadura region on this self-guided cycling adventure from Oropesa to Cáceres. This immersive journey blends rich history, unspoiled landscapes, and cultural depth, offering a unique view of one of Spain’s most authentic and underexplored regions. You’ll pedal through Mediterranean woodlands, fertile valleys, and gently rolling dehesa—pastoral land dotted with cork oaks and grazing Iberian pigs.
The route leads you to some of the region’s most striking towns, each steeped in history and architectural splendor. Explore Jarandilla de la Vera’s medieval castle, stay in elegant Parador hotels, and ride into the walled city of Plasencia with its Gothic and Renaissance treasures. Glide through Monfragüe National Park, a birdwatcher’s paradise and haven of natural beauty, before arriving in the magnificent hilltop town of Trujillo, known for its conquistador legacy.
The journey ends in Cáceres, a UNESCO World Heritage Site whose perfectly preserved medieval quarter is among the most enchanting in Europe. Along the way, you’ll experience the quiet rhythms of rural life, savor hearty local cuisine, and stay in exceptional accommodations that reflect the spirit of the land.
With manageable daily distances, rewarding climbs, and a wealth of cultural and natural highlights, this tour is ideal for cyclists seeking a slower pace and deeper connection with Spain’s lesser-known treasures. It’s not just a ride—it’s a journey through time, tradition, and truly unforgettable landscapes.
Oropesa
Cáceres
casual plus
moderate
56km / 34mi
5
Adolfo Suárez Madrid–Barajas Airport (MAD)
Adolfo Suárez Madrid–Barajas Airport (MAD)
Min. 2, Max. 10
Highlights
Stay in Historic Paradors
Rest each night in extraordinary accommodations, including medieval castles, former convents, and elegant manor houses. These unique hotels, several of which are classified as Paradors offer not only comfort but also a deep sense of place, immersing you in the history and architectural beauty of towns like Jarandilla, Plasencia, Trujillo, and Cáceres.
Itinerary
Brief Itinerary
Meals are indicated as B = Breakfast, L = Lunch, D = Dinner.
Listed hotels are subject to availability and may be replaced with similar alternatives of equal standard.
| Day | Place | casual_plus Inns | Meals | Distance | Activity |
|---|---|---|---|---|---|
| DAY 1 | Oropesa | Hotel Casa Platon Paramo | |||
| DAY 2 | Jarandilla de la Vera | Hotel Mirador de la Portilla (4-star) | B | 67km / 41mi | cycling |
| DAY 3 | Plasencia | Parador de Plasencia (4-star) | B | 67km / 41mi | cycling |
| DAY 4 | Monfragüe | Palacio Viejo de las Corchuelas (4-star) | B | 41km / 25mi | cycling |
| DAY 5 | Trujillo | Parador de Trujillo (4-star) | B | 48km / 30mi | cycling |
| DAY 6 | Cáceres | Hotel NH Palacio de Oquendo (4-star) | B | 55km / 34mi | cycling |
| DAY 7 | Cáceres | B |
Detailed Itinerary
Day 1: Oropesa
Welcome to Oropesa, a town that wears its history with pride.
As you arrive, you’ll notice its dramatic 15th-century castle rising above the rooftops—a perfect introduction to Extremadura’s rich heritage.
Take a leisurely stroll through the narrow, winding streets, admire the Renaissance palaces, and soak in the relaxed rhythm of local life. Enjoy a delicious meal at a traditional tavern as you prepare for the journey ahead.
Day 2: Jarandilla de la Vera
Today’s route leads you through peaceful Mediterranean woodland as you begin your gentle ascent toward the Sierra de Gredos.
The landscape is dotted with cork oaks, olive trees, and aromatic herbs. You’ll cycle through rural villages that seem frozen in time, where whitewashed houses cling to the hillsides and the rhythm of life moves slowly. The distant peaks grow closer as you roll toward Jarandilla de la Vera, where your reward is a stunning stay in a restored medieval castle—now a Parador.
Once a residence of Emperor Charles V, it’s now your luxurious base for the night. Enjoy a quiet evening in the gardens or dine like royalty in the historic dining room, savoring regional dishes and local wines as the castle walls glow with evening light.
Day 3: Plasencia
A beautiful day of cycling awaits as you continue through La Vera, a region famed for its paprika, chestnut groves, and spring-fed gorges.
You'll ride past stone villages surrounded by orchards and almond trees, all set against a backdrop of rugged peaks. Rolling hills guide you through the countryside, and quiet backroads take you further from the modern world.
As you reach Plasencia, the scenery shifts—this monumental town is a lively blend of old and new. Its double-walled old quarter holds Romanesque churches, Baroque mansions, and the grand cathedral complex.
Explore the Plaza Mayor or wander the arcaded streets to soak in the city’s noble past. Tonight, relax in another elegant Parador—this time housed in a former convent—where cloisters and courtyards welcome you after your day’s ride.
Day 4: Monfragüe
Leaving Plasencia behind, you head south through open countryside toward the jewel of Extremadura’s natural wonders: Monfragüe National Park. The terrain is gentler today, allowing you to ease into the rhythm of the ride.
Cork oak forests, granite outcrops, and open pastures accompany your journey, but it’s the wildlife that takes center stage. As you approach the park, keep your eyes on the sky—griffon vultures, black storks, and perhaps even the elusive Spanish imperial eagle soar above the cliffs.
Your stay tonight is in a tranquil country farm hotel surrounded by nature, the perfect place to disconnect. As evening falls, enjoy the sounds of crickets and birdsong, and take in the star-filled sky that Monfragüe is famous for. This is a night to savor the peaceful isolation and natural beauty of Extremadura.
Day 5: Trujillo
Today you leave the wild landscapes of Monfragüe and cycle through rolling dehesa—pastures shaded by oaks and scattered with cattle and pigs. This is classic Extremadura, where Iberian ham is king and ancient stone farmhouses dot the hills.
The ride is gentle and meditative, with long stretches of countryside between tiny villages. Your destination is Trujillo, a magnificent town of conquistadors and explorers, crowned by a hilltop castle and bursting with charm. Its vast Plaza Mayor is one of the finest in Spain, surrounded by Renaissance palaces and stately homes.
Tonight, you’ll stay in yet another Parador, this one housed in a former convent, with cloisters and quiet courtyards offering a peaceful retreat. Take time to explore the cobbled lanes and soak in the golden light that bathes the sandstone walls of this unforgettable town.
Day 6: Cáceres
Your final full day of cycling takes you through open landscapes dotted with stone walls, dry fields, and evergreen holm oaks. It’s a peaceful and reflective ride, where the only traffic might be a flock of sheep crossing your path.
Gradually, the countryside gives way to signs of the city, and soon you’re entering the magnificent city of Cáceres—your journey’s end. A UNESCO World Heritage Site, Cáceres boasts one of the best-preserved medieval quarters in Europe. Its maze of cobbled streets, Moorish towers, and Gothic palaces feels like a journey back in time.
Celebrate your arrival with a walk through the old town, perhaps enjoying a final meal of Extremaduran specialties—like roast lamb or migas—paired with a glass of local wine. You've earned it.
Day 7: Cáceres
After breakfast, you can depart at your leisure or stay on to explore more of Cáceres and its surroundings. If you’re not quite ready to say goodbye, consider an extra night in this remarkable city.
Alternatively, you can consider crossing the border into Estremoz in Portugal which is located only 148kms (90mi) away, and combine this tour with our Guided Alentejo to Algarve Castles and Beaches Bike Tour.
Ready to plan your adventure? Download a print-ready detailed itinerary.
Dates and Prices
Single Supplement
From US $360
E-Bike Upgrade
From US $180
Couldn't find a trip with convenient dates?
Open your date as a join-in tour or customize further as a private one.
Essential Info
Inclusions
LODGING
All hotels as mentioned in the tour details or similar (subject to availability).
trip leader
Expert Trip Leader(s) who look after your every need and add meaning to your vacation.
bike
Immaculately maintained bike with helmet, suited to a terrain.
shuttle
A Van support follows the group of riders and carries all belongings.
meals
Meals as per itinerary. Guests are given the opportunity to dine on their own so that they discover a location independently.
refreshments
Refreshments and mineral water while cycling.
entrance
Entrance fees to most of the monuments and temples.
Exclusions
Airport pickup and drop
We recommend to book direclty from airport or hotel.
Beverages
Beverages such as alcohol, tea, coffee, juice at a hotel or restaurant.
Gratuity
Gratuities for your guide team are not included in the trip price.
Bikes
When you have a road and the thrill of a journey ahead of you, it’s imperative to have a good bike to enjoy it. Our fleet majorly consist of the below bikes as a part of this tour. However, sometimes due to height or availability constraints, we may provide a different but similar quality bike.
Kross or similar
Included in your trip price
Ortler Bozen Performance Wave or similar
Available at a surcharge
Ortler E-Montana 400 or similar
Available at a surcharge
Arrival & Departure Details
Arrival
Your tour begins in Oropesa de Toledo. The nearest international airport is the Madrid-Barajas International Airport (MAD).
From Madrid, you can take the train operated by Renfe that runs from the Atocha station in Madrid to Oropesa de Toledo. The journey takes 1 hour 45 minutes. To get to the Atocha station from the Madrid airport, you can take the Cercanias Line C1 or C10 from the T4 termina.
Bus service is also available from Madrid to Oropesa. The bus journey takes around 2 hours 30 minutes.
You can also take a cab directly from the airport to Oropesa de Toledo if you so desire.
Departure
Your tour ends in Caceres. Caceres is equidistant from both Madrid and Lisbon.
The nearest major international airport is once again the Madrid airport, located 250 km (155 miles) northeast of Cáceres.
There is train service from the Caceres train station to the Madrid-Chamartín-Clara Campoamor Station. The journey takes a little over 3 hours. Bus service is also available. You can also take a cab from Caceres to Madrid.
For those who wish to fly, the Badajoz Airport (BJZ) located 76 km (47 miles) southwest of Cáceres is the nearest domestic airport with flights to Madrid and Barcelona.
The Lisbon Portela Airport (LIS) is located 250 km (155 miles) west of Caceres.
Weather
Cycling in Extremadura from Oropesa to Cáceres is best enjoyed during spring (March to June) and autumn (September to November), when temperatures are mild and the landscapes are at their most vibrant.
Spring brings blooming wildflowers, lush greenery, and comfortable daytime highs ranging from 18°C to 25°C (64°F to 77°F). Autumn offers golden light, harvest colors, and pleasantly warm days, perfect for long rides through the countryside.
Summers can be intensely hot, especially inland, making cycling more strenuous. Rain is generally scarce, so you can expect mostly dry conditions, especially in spring. These seasons offer ideal weather for a relaxed, scenic tour.
January
Offseason
February
Offseason
March
Offseason
April
Good
May
Best
June
Good
July
Offseason
August
Offseason
September
Best
October
Best
November
Mixed
December
Offseason
Best
Good
Mixed
Offseason
What to Pack
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 (personal gloves are ideal).
- Brightly colored cycling jerseys or synthetic T-shirts for visibility.
- Synthetic cycling socks.
- Sunglasses with UV protection.
- Personal helmet (recommended even though provided).
- Personal saddle (optional for added comfort).
- Rain jacket or windbreaker.
- Cycling water bottle (to reduce plastic waste).
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 (if traveling in winter).
- Comfortable footwear for non-cycling time.
- Bring a compact rain jacket in case of sudden weather changes.
- Ethnic or modest clothing for exploring towns and temples.
Other Necessities
- Toiletries: Basic hygiene essentials, including insect/mosquito repellent and sunscreen.
- Hand sanitizer and wet wipes.
- Plug socket adaptor.
- Binoculars for wildlife spotting or desert landscapes.
Pro Tips
- Pack light but plan for the varying temperatures: warm days, chilly evenings, and desert winds.
- Use brightly colored clothing for visibility on roads.
- Pack light to leave room for shopping.
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.
Visa Information
Before venturing on your adventure, make sure you're equipped with essential travel advice, including security updates, local laws, and crucial passport and visa information. Start by visiting the official government website of your home country for accurate and reliable guidance:
- UK Residents: Stay informed by reviewing the Foreign, Commonwealth & Development Office (FCDO) Travel Advice.
- US Residents: Access vital travel tips and updates through the US Department of State Travel Advice.
- Australian Residents: Plan ahead with the latest updates on the Smart Traveller website.
- Canadian Residents: Find comprehensive travel and visa guidance on the Government of Canada's Travel Advice and Advisories.
- New Zealand Residents: Get practical travel advice on the New Zealand SafeTravel website
- Residents of Other Countries: Check with your government or local consulate for tailored travel advice and requirements.
Note: Passport and visa regulations can change at any time. Stay proactive by checking for the latest updates to ensure a smooth and stress-free journey.
Insurance
Medical insurance that covers medical costs in case of an accident during the trip is mandatory to participate in our tours.
We recommend to purchase adequate travel insurance in order to participate in our tours and 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 (including Covid-19), and personal liability—travel with greater peace of mind.
Can I use my credit card insurance?
Yes, as long as it meets our requirements and provides adequate coverage. Ensure you have an emergency contact number and policy number available.
When should I buy travel insurance?
Purchase travel insurance as soon as you've paid in full or booked your flights.
Is proof of travel insurance required?
Yes. You must provide your insurer's name, policy number, and emergency contact via our reservation form. This is mandatory. If you cannot provide proof, you’ll need to purchase insurance before traveling with us.
Does Art of Bicycle Trips sell travel insurance?
We do not sell travel insurance directly, as we believe our customers should have the freedom to choose a policy that best suits their needs. However, we recommend Insured Nomads as a great starting point.
Frequently Asked Questions
We provide an app-based navigation system that can also be used offline. You can download the app to your phone in advance, and we will share the login details ahead of your trip. Since the app works offline, it helps conserve your phone's battery during use.
For minor issues like punctures, the guests are provided with a self-repair kit, which includes tire levers, a spare tube, a patch kit, and a pump, allowing riders to fix the problem themselves. Self-guided riders are expected to be independent in handling these minor problems. While there are some bike shops along the route, they are limited. If you are unsure about how to repair a puncture, we recommend considering a guided or van-supported trip instead.
For major mechanical failures, such as a cable break, the guests can contact the emergency support number provided. The support team will help coordinate a solution, which could include dispatching a local mechanic, suggesting a nearby bicycle shop for repairs, or sending a vehicle to pick up the rider. Please note that all support services will be provided on a chargeable basis, and assistance may take time, so we advise being prepared for potential delays.
We provide 24/7 emergency support by phone for any medical emergencies during the tour. Our team will assist in coordinating medical care, guiding you to the nearest healthcare facility, and ensuring you receive the necessary support. The national emergency system is reliable and effective, and in the event of a serious accident, contacting them is highly recommended. However, due to our distance from certain areas, response times may be longer. We strongly recommend having appropriate travel insurance, and we will do everything we can to ensure your safety and well-being during an emergency.
The fitness level required for each trip is indicated by the "level" of the tour, which in turn is mentioned on each tour page right next to the price and the trip duration.
Easy: The terrain is mostly flat with a few gentle climbs.
Moderate: The terrain is either mostly flat or consists of rolling hills with a few challenging climbs. There could also be a few days with longer riding distances of up to 75 kms (45 miles)
Difficult: The terrain is mostly hilly with strong elevation gains and/or has long days on the bike. Such trips are recommended for intermediate to advanced cyclists.
Please note that we usually bike around 4-5 hours per day irrespective of the level of the trip.
You can exchange currency at the airport itself, or at ATMs in larger cities. Most commercial establishments will accept international credit cards for payments, though its good to carry some local currency with you at all times.
The meeting time on Day 1 is mentioned in your travel planner shared with you. You can arrive either on the morning of Day 1 depending on the meeting time, or book a pre-tour night to arrive a day earlier.
For answers to broader questions, please visit our Comprehensive FAQs section.
