Cycling through Portugal

Eleven cycling days. 374 miles to cover. Quiet backroads and villages to ride through. What a splendid way to see a country, I thought. Was I naïve to assume that this would be a relaxing vacation? Yes! Was I going to get a workout like no other? You better believe it! Did I have a clue what experiences I would face from this unique tour? Absolutely not!

The idea of the trip began to take form two years ago.  Enjoying dinner with friends (and maybe too many glasses of wine), our conversation turned to travel.  Sharing different adventures, my husband and I became intrigued by how our friend combined cycling with traveling.  I found this appealing.  Cycling in the open air, exposed to areas of the country few saw, backroads, village folks, aromatic fragrances from the bounty of the earth, was a more intimate and robust approach to the senses for a seasoned traveler.  I wasn’t going to analyze potential downsides.  It was something I hadn’t tried, and hey, I was active enough to handle an idyllic ride in the country.  Or was I?

Day 1 was a meet and greet and a leisurely tour day.  John, our tour guide, gathered our small group of eight riders together at the NH Collection Lisboa on Liberdade Avenue in Lisbon.  I was surprised to see that women outnumbered men, and even more surprised that most of us were well into our sixties and one couple pushing 70.  Later, I would marvel that “age” had nothing to do with physical ability.  These folks were beasts!  

We were whisked off in a comfortable van/bus to our starting point in Elvas, a medieval town at the far eastern end of Portugal.  We crossed the Tagus River over one of the longest bridges in the country. Olive trees and vineyards covered gentle rolling hills.  A grove of pine trees called Rock Pine reminded me of lollipops with their long trunks and thick, rounded tops.   In the distance, walled cities with castles stood atop piedmonts overlooking villages below.  Our lunch stop along the way was, in fact, inside one of these walled towns.   

Once in Elvas, we settled into our hotel and met our second tour guide, Luis (pronounced Luish.  European- Portuguese is a curious mix of sounds coming from Spanish, Islamic, and Germanic cultures all who occupied Portugal at one time or another).  An upbeat and gregarious man, he would school us in the history of Portugal throughout the tour. 

John and Luis were both bicycle experts and “fitted” each of us to our bikes. The height of the bike seats and handlebars were adjusted. A variety of peddles were available to choose and use for the bikes, and finally came the “test-drive.”

Clouds had formed while gearing up, so we grabbed our rain jackets just in case. A ten mile course was drawn out for us with chalk lines on the road, taking us through part of the town and into the countryside. I was introduced to riding over cobblestone while in town (which is common in medieval villages). This jaw-shaking, teeth-rattling, bike-vibrating experience had me trying to figure out the best way to navigate over this uneven surface. Peddling fast didn’t decrease the vibration. Peddling slower was better, but my muscles still got a “good massage,” as our guides put it.

Light rain began splattering my sunglasses halfway through our ride. Nature proceeded to moisten my face, and I hurriedly pulled the hood of my jacket over my helmet. I lightly pumped the brakes when I needed to slow down. I certainly didn’t want to spin out and crash on the slippery pavement. As I peddled faster to finish the course, I prayed that this wasn’t a sign of weather to come for the rest of the trip.

My husband and I faced a few glitches on our first ride.  We were in hill-country, and shifting gears was a challenge for Jim. Riding beside my girlfriend, I hadn’t noticed that he was no longer cycling with us.  We stopped, wondering if he got lost.  Eventually, he appeared over the crest of a hill.  He had popped the chain on his bike and had to reset it.

My issue was my butt. I had brought a padded cover from home, concerned that eleven days of biking would push my derriere (does anyone even use that word anymore?) to the limits. I found out that too much padding wasn’t necessarily a good thing. John had a handful of saddles for the bikes and found one that was “just right.” This mama bear’s bum was sensitive!

I found Elvas to be a picturesque town. It felt as if I had stepped back into time, surrounded by watchtowers, battlements, and city gates. Our evening involved a stroll with John and Luis through its narrow streets and beside its two sets of defending walls. Elvas stood like a sentinel, sitting above the brown and green landscape below, keeping its eye on nearby Spain.


We got an excellent overview of the town’s strategic location and learned that Elvas was the “key” for holding back Spanish invasions. The following day, we toured a bit more to see the town’s squares, contemplate tall, marble pillories used for torturing the accused (a bit unnerving), step into beautifully tiled interiors of gothic churches, and observe the five mile 16th century Amoreira Aqueduct.


Beginning our journey in this sturdy garrison would remind me that endurance and strength could achieve great things.  Something I would try to emulate in the days ahead.

Day 2. Before leaving Elvas, Luis discussed what to expect on our route as he handed out flyers with additional information. A series of towns and villages were along the way. Places for coffee stops and lunch were suggested for the day’s ride. Cycling ahead, Luis would mark our way with white arrows on the ground so we wouldn’t get lost. John would drive the support van, making sure that everyone was doing okay.

Vila Vicosa was our destination. It was a 20-mile ride that would ease us into the longer cycle days ahead. Riding at our own pace, Jim and I took off with our friends later in the day.

It was getting warm, with expected temperatures reaching the 80s. We peddled through the countryside, where olive trees and small vineyards dotted the dry grassland. A nagging sense of recognition came to mind. Had I had seen this landscape before? It was similar to California’s central valley, with its own olive groves and wineries. But here, cows peacefully grazed on yellow grass, and sheep baahed along the roadside.

The sun was getting stronger as it beat down on my shoulders. I relished the soft breeze as I coasted down gentle hills, veering around bends and then shifting gears to climb. I was happy to see that there were few automobiles on the road. Distracted by the sights, sounds, and smells of my new surroundings, I suddenly discovered that I was left alone on the road. To my chagrin, I couldn’t see my husband or our friends. I started to peddle faster but still couldn’t find the rest of my party. As I climbed another hill, I saw them in the distance waiting. I mistakenly thought I needed to pick up the pace cycling; however, later, that became a problem, tiring me faster, frustrating me more.

Arriving at Vila Vicosa around 1:30 p.m., we found our lodgings next to the stately Ducal Palace, built by the Dukes of Braganza. Our rooms were ready, and we quickly slipped out of our bike gear, opting for shorts and tee-shirts and headed down the street for lunch. Jim and I weren’t sure where to find good food, but fortunately, we saw a couple from our cycle group seated at an outdoor café thoroughly enjoying theirs. Waving us over, they were eating a Bufonte sandwich. The sandwich is a typical lunch in Portugal made with a tender slice of pork. Juices from the cooked pork flavored the freshly made bread. It was a great find!

Later, Jim and I took a stroll through town, noticing light pink marble used on the sidewalks, fountains, monuments, and benches. It gave the city a pristine feel. Marble quarries were nearby, and this type of marble was shipped worldwide, as we would later learn at a visit to one of these quarries. An imposing gothic church, Sao Bartolomeu, stood on one end of Vila Vicosa’s wide boulevard through town while a medieval castle flanked the other.

Vila Vicosa

A lush, tropical park offered a cooling reprieve from the sun. We took our time, strolling through it, noticing families enjoying their Sunday afternoon with children playing on swings. A bar and café encased in glass stood in the middle of the Park, dark and deserted, indefinitely closed. Had the pandemic left its footprint on this small eatery?

Day 3 was a longer ride, racking up some 34 miles to the castle town of Monsaraz, a walled city near the Spanish border.  Warm sunshine followed us.  The skies were clear, bright, and blue.  Actually, the prettiest blue I had ever seen in a mainland country.  Olive trees and vineyards continued to dot the landscape.  This time we paused to take pictures and found newly harvested cork trees along the way.  The number 1 was painted on the trunk of the trees, telling us the cork had been removed in 2021.  Cork was harvested every nine years, according to Luis.  By placing the last digit of the year on the tree, farmers could gauge when the next harvest would be.

The hills became more frequent and longer. The countryside was quiet. Fallow fields took up the landscape at times, creating an empty feeling. Crossing a small reservoir, we stopped for a moment with our friends, enjoying the solitude and catching our breath. Ducks chattered in the water. Rows of olive trees stood in the distance. Faraway farm houses stood silent.

At Montejuntos, a small village (really off the radar), our group of eight seemed to converge once again, stopping for lunch.  Two women in our group were the powerbrokers of cycling.  They had already finished their lunch and were heading out when we showed up.  The rest of us bought sandwiches and relaxed around outdoor tables and chairs.  A friendly stray dog joined our group.  He enjoyed our handouts.   

As we got closer to our next stop for the night, we pulled off the road to check out a couple of megalithic sites dating back 5000 years BCE. These sites, known as the Monsaraz Complex, held columns of single-cut rocks. One jutted some 20 feet upwards and weighed around 10 tons. How did this rock get here, and what was it used for? We can only guess its purpose. Along our travels through the Alentejo region, I would discover that Portugal had hundreds of these sites, some older than the more well-known Stonehenge.

Megaliths by Monsaraz

Wine vineyards became abundant again. I was excited to see that we would be staying at a sprawling, low-lying hotel that overlooked them.  It was an oasis in the sometimes-stark agricultural landscape.  Above the property soared Monsaraz, its severe ramparts proclaiming a position of power and immobility. We would be driven up to its protective walls to enjoy what I felt was the reason for a vacation, to relax, try local wines, and feast on a fabulous dinner.

Walking with our cycle group through one of Monsaraz’s four main openings, I was delighted to see that the ancient cobblestone roads were free from automobiles.  This absence of modern trappings gave me a mild sense of what it could be like living in a walled city. We strolled past the ever-present whitewashed buildings with their red-tiled roofs to the castle ruins.   Climbing stone stairs, we were given a brief history of the structure.  A circular interior with amphitheater seating caused us to wonder what this part of the castle was used for.  In the recent past, bullfighting had been one of them.  Today, it is used for concerts.    

Our guides were “in the know” with a wine expert at Ervideira Winery. The Ervideira wine shop was perched high within the walls of Monsaraz, with a birds-eye view of the surrounding landscape.  Patchwork farm fields spread out below us.  A large body of water, the Alqueva reservoir, spanned across both Portuguese and Spanish territory.  In the golden light of the late afternoon sun, our wine tasting took us on a journey through refreshing whites, garnet-colored reds, and burgundy ports.  Enthusiasm swelled among our group, and soon the guys were busy locating bottles online to have them shipped home! 

We later ate at Sabores de Monsaraz Restaurante, famous for its traditional Portuguese food. Platters of appetizers came out with olives, bread, cured meats and cheeses, farm-to-table salads, scrambled eggs and sausage, very tender Black pork, rich soups, and incredibly decadent desserts. We sat outside in the twilight and gazed upon the distant reservoir below and the floating walled city above. It was a great ending to a magical night.

The walled city and castle town of Monsaraz

Day 4 had us cycling 43 miles to the town of Evora. There was going to be an elevation gain of 1500 feet. The numbers didn’t mean anything until I started feeling the burn in my muscles just before lunchtime. Hills and an intermittent headwind caused me to cycle harder. When I reached our lunch stop in Senhora de Machede, I was done for the day. I hitched a ride in our support van, leaving my husband and friends to continue. I never appreciated the comfort of a vehicle more as I watched the rest of the cyclists peddle onward, their shirts billowing in the wind.

My vacation had turned into an exercise-cation.  And honestly, I was starting to have my doubts.  As the slowest cyclist, I felt like I needed to peddle harder to keep up.  That alone had its downside.  My breathing became more labored.  My muscles tensed, and I still ended up cycling alone while my husband went merrily on his way.  I felt like screaming, HELLO???  EARTH TO MAJOR TOM!!! Aren’t we supposed to be cycling together?  But I feared that wouldn’t even get his attention.  He was definitely in his own world.  I needed to say something, but at the moment I was too annoyed.

Evora was our first two-night stay on a tour schedule that I hadn’t thought about. Fast-paced, vigorous, more work than I realized, I was ready for a break. I suspect everyone else was, too, as folks quickly disappeared into their rooms, and as I watched my husband collapse in bed, falling asleep for a short afternoon nap.

Day 5. Today was considered a “rest day” with an optional bike ride if desired (It goes without saying what my choice was). Our ceaselessly energetic Luis had gathered the group together to walk by some of the more popular sights upon our arrival. With a list in mind, I was ready to explore this enchanting walled town in greater depth.

With a well-deserved late morning, we met up with our friends for lunch. We didn’t have a restaurant in mind but hoped to find a local place away from tourist driven establishments. Searching through the narrow, cobblestone streets, we happened upon a tiny restaurant hidden off the beaten track. It was the real deal. My girlfriend had to resort to her Spanish to convey our interest in dining there (seating was limited), and later my husband deferred to sign language when asking for another beer. The proprietor welcomed us in with friendly, excited gestures.

The kitchen was open to the dining area, and we watched with fascination as our hostess, waitress, and cook all wrapped up in one served us a delicious Portuguese meal.  O balcao at Number 4, known for its tapas e petiscos tradicional alentejana, became another great experience to Portuguese food. 

After lunch, we walked past whitewashed buildings built side by side to the Chapel of Bones. Paying a small entrance fee, we entered the most disturbing yet fascinating room Christendom had built. Why was such a macabre room created? It was surreal to see human bones in such numbers (an estimated 5000), covering walls, columns, and ceilings. An ominous announcement is carved into the chapel entrance proclaiming, “we the bones that are here for yours, we are waiting.”

The Chapel of Bones

The Se or Evora Cathedral is another “must-see” while visiting the ancient city. Its 14th-century sculpted Apostles that wrap around the soaring main entrance set the stage for what is inside. Vaulted ceilings, gilded altars, dark paintings that span large sections of the walls, along with its access to a rooftop that gives a 360-degree view of the town and its surrounding area, is well worth a visit.

Evora Cathedral
Rooftop view from the Evora Cathedral

We later wandered around the main square in Evora with its enormous marble fountain. Shops and restaurants encircle the plaza. Nearby, Rua 5 de Outubro is lined on both sides with colorful pottery, cork made into things I never thought of (a bikini is one of them. I can’t help wonder if the suit helps you float?) and clothing stores. It is a shopper’s haven!

Finally, we finished the day watching the sunset against a soaring Roman Temple, seemingly out of place in a medieval city but lasting evidence of Roman occupation.

Roman Temple

As we walked back to our hotel, we followed the Aqueduto da Agua de Prata an elevated aqueduct system. On yesterday’s tour with Luis, his words resonated. Townspeople who couldn’t afford housing, built shelters under the soaring arches. Designated as public property, the aqueduct was free space. Houses, some abandoned, still stood there. I couldn’t help think of our own public spaces and the tent cities that exist today.

Day 6. We rode on bike paths out of Evora. Traffic was heavy as the city’s surrounding area was the hustle and bustle of new urban growth. Today entailed a long flat stretch along Highway 254 with a tight shoulder. This route was one of two roadways heavy with traffic, and I wasn’t thrilled riding alongside semi-trucks that hauled both produce and pigs to market!

Jim became more vigilant riding with me and said later that riding behind me gave him concern, as it looked like a semi, was cutting me off the road. I was okay, but the sooner we turned off the highway, the better.

We had another sunny, relatively calm day. Eventually, we veered off onto country roads where cycling became less stressful, but steep hills waited. I decided to “tough it out” on the first half of our scheduled 58-mile route. By lunchtime, I was ready to enjoy another comfortable ride in the van. A valley was coming up on the route with a long haul up a hill. I had biked a respectable 34 ¾ miles so far. The rest of the group was all in for the challenge.

Driving ahead of the cyclists, John parked the van to take video with his drone. It was a great perspective to see the action from the air as I temporarily manned the device, getting a brief tutorial. As the cyclists appeared John took over and followed their progress through the lush valley before the dreaded hill I had declined to bike up.

Tonight’s lodgings were on a cork farm turned into a hotel. Tucked in off the road, we drove on a dirt road before reaching the establishment. It was a peaceful setting with long, low ranch-style buildings turned into rooms. A common area was built at one end where meals were served. A pool, tennis courts, and jacuzzi were available. I headed for the pool to relax my aching muscles.

Cork Farm

Our group were the only guests that night, and we were generously waited on by David, the owner, and his staff. David was so kind that I felt comfortable practicing my Portuguese on him. I said, “Prazer em conhecer voce”. Which means, “It’s a pleasure to meet you.” In his perfect English, he replied, “Almost Portuguese,” with a teasing smile. Was my pronunciation that bad? Later I found out that I was speaking Brazilian Portuguese. My language App offered only one Portuguese language. It deferred to the more widely used South American version.

The night sky was incredible. With no street lights, the Milky Way glowed above our heads. In a campfire-like setting, our guides, who we began to realize were multi-talented, pulled out their guitar and ukulele and led us in nostalgic songs….. I did my best. It wasn’t muchhallelujah…. I’ll stand right here before the Lord of song… hallelujah could have been my mantra.

I didn’t know there was so much talent in our group!

Day 7 and 8 were going to be spent in the town of Vila Nova de Milfontes or Milfontes for short. We had finally crossed the easternmost border of Portugal, reaching the Atlantic coast. Climbing out of the agricultural Alentejo region, we were in for a final big push up steep hills to get to the coastal area. I looked at our daily flyer with information written about our ride. When I saw the graph of elevation changes, I thought, OOH, HELL NO! Where did anyone believe that cycling up Mt Everest was enjoyable? On closer examination, John, who was driving the van, suggested that after kilometer 22 on the route, I would find it more manageable.

With a few minor hills, I found myself coasting down a scenic tree-studded, winding road. We had entered the Alentejo Coastal Region. Balmy, sunny weather followed us. Most of the gang had converged in Santiago do Cacem to view a windmill turned into a museum and pick up some snacks. The city has hilltop castles, lush tropical vegetation and distant ocean views. Its colorful buildings and lively atmosphere made it a destination that I would like to explore further someday.

As the landscape flattened out into straw-covered fields, I saw the blue- grey Atlantic growing closer in front of me. We turned onto the only road along the coast. It was the last stretch of the ride before entering Milfontes. Traffic became busier, and again I couldn’t get off this road fast enough. There was no shoulder, and even though cars were courteous, the larger trucks had a schedule to keep and moved past us without barely giving us space. That said, for most of the trip, the roads were safe and quiet, but these stretches unnerved me.

Milfontes is a beach town with beautiful murals painted on walls, lots of beach activities from boating to paddleboarding, both golden sand beaches and dramatic coastline cliffs, and friendly folks who were so helpful. I can’t help put in a plug for Alento, a restaurant on Mainstreet that we enjoyed during our second night. Researching restaurants on TripAdvisor, this place had stellar ratings, and they were well deserved. I asked Luis if he could call ahead and get a reservation for our party of four, and I’m glad I did! When we arrived, we watched the waiter turn people away. They were sold out for the night!

Vila Nova de Milfontes

Days 9, 10 & 11. We entered into the Costa Vicentina National Park. We would stay in the Park for the rest of our cycle trip. The coastline became more dramatic with sheer cliffs, hidden coves with emerald-colored water, and vast golden dunes. This part of the trip was optional, adding more cycle days while in Portugal. Even though I was new to this kind of “marathon” cycling, I’m glad Jim and I hopped on board and cycled the entire trip with our friends. Portugal’s southern coastline shouldn’t be missed.

Cycling through beach towns, up to lighthouses, and into hidden abandoned villages turned into resort destinations was a pleasure to discover. Jim and I had finally found our rhythm cycling together, leaving the rest of the group to power ahead while we played in the ocean, climbed sand dunes, and enjoyed a beer with locals. The coast had an entirely different vibe. We seemed to have left the medieval past behind. Modern homes and businesses dominated the landscape. Coastal trails with avid hikers carrying backpacks appeared. We watched surfers enjoy some of the best waves along Portugal’s coast.


We lodged near Zambujeira do Mar which has a great boardwalk following the coast. It is perched high along the top of the cliffs with a newly paved blacktop road going into town. Set back from the cliffs, one had to walk on wooden walkways to see the ocean below( a view of this area is in the YouTube video at the end of this post).

Our evenings were filled with live Fado music performed by Luis’s friends. We tried our hand in the culinary arts as we prepared a dish for dinner one night. We lived like villagers, where abandoned houses were turned into lodgings. We cycled to the End of the World according to ancient perceptions at the time. Finally, in the modern, sleek styling beach resort town of Sagres, we finished our tour.

The End of the World

Touring a country on a bicycle was a vigorous trip. We were on the move(literally)every day. Our guides were amazing. Packing up our luggage, stowing away bikes when I was too tired, keeping our bikes in tiptop condition each day, observing our skills and ready to assist, taking us to top-notch eateries and bars, and entertaining us was no small feat. The group developed an easy camaraderie. We joked and encouraged. We bought drinks and gave toasts at dinner time. And watched out for each other when someone was stopped along the road. I won’t forget this trip for a very long time.

Travel Information:

COVID is still causing hassles across borders.  Policies were fluid during our stay in Portugal.  Masks were mandated until October 1, 2021, but businesses still wanted folks to wear them.

Portugal requires a Passenger Locator Card filed 3 days before entry into the country. I have provided the link Keep in mind that rules are changing. Always check the embassy site for current requirements.

At Customs, I was asked if I had been vaccinated, but I didn’t have to show my card. Hotels and restaurants never asked for the card however some hotels wanted to see our COVID test.

A COVID test was required before exiting the country and getting back into the United States.  We had our results posted on our smartphones.  Some of us had our results printed out at our hotels.

We used EXPERIENCEPLUS for our cycle tour.  Lodgings and meals were provided in the package.

We took UNITED AIRLINES, which changed our flight twice before we left for Portugal.  We spent hours on the phone sorting out the scheduling mess that they would create.  But once on the flight, the staff was helpful and courteous.

Most businesses were open in Portugal, but I would advise making reservations at restaurants.  They were limiting the number of folks inside.

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