Surrounded by woodlands, the town of Monchique perches on the slopes of the Sierra de Monchique, a stunning mountain range in the northwestern Algarve. Punctuated by dazzling white buildings, a pretty square and flourishing growth — picture bougainvillea spilling above walls and along, steep, cobbled walkways — the settlement of some 2,500 people is picture perfect. Despite its obvious beauty, my friend and I are more concerned than impressed. We are arriving to begin a self-guided cycling trip and all we can see are hills. It is October, the weather has turned unseasonably hot and did I mention that we are not young — we are fit, but, alas, perhaps a tad past our prime. The itinerary on the website described this trip as “moderate” with “undulating terrain” but in the detailed description we received when picked up at the airport, we notice there are more than a few “steep climbs.” As we settle into Bica Boa, a small inn (known as an Albergaria here) tucked into greenery, my friend Margo and I joke about the unknown that is always an aspect of a self-guided trip. We were kibitzing with our innkeeper, Susan Cassidy, a charming Irish woman, who introduced us to Medronho — think schnapps only stronger. (It seems Monchique is famous for producing the best of this fiery liqueur.) Although Susan confirms that her backyard is known for its challenging cycling and hiking, we look over our map and feel confident that the next day’s 28.5-kilometre trip is not daunting — perhaps this is the effect of Medronho. However, the unknown looms. A word about self-guided vacations: This mode of holiday hearkens back to early backpacking trips but with appealing modifications. You enjoy the freedom of independence (you aren’t part of a tour group), coupled with the convenience of having luggage moved to pre-booked accommodations and some meals have also been arranged. You are provided with map and directions for each day’s journey and an emergency contact is usually available. Bikes and often helmets are provided. On this trip, booked through World Expeditions, we were on 24-speed, B’Win bikes with amazing gel seats that we both found very comfortable. For many of us, self-guided is the best of holiday worlds — I’ve cycled and hiked in many countries and found you are pretty well guaranteed an adventure. For example, it is not unusual to get lost, which means mingling with the locals, an appealing aspect — I’ve been invited for tea, had my bike transported in the back of a truck when I was way off track and picnicked in delightful places like coffee plantations and vineyards on my travels. While it’s convenient that some meals on a self-guided trip are arranged, other times you wander a new locale to suss out the hot spots. It’s a terrific meld of convenience and adventure and Portugal didn’t let us down. The first day we swooped out of Monchique — all downhill — through verdant valleys where brilliant blue morning glories covered shrubs and the bases of lofty trees. Through some small towns where men gathered on benches and children waved as we passed — still downhill — until we left the main road to follow a rural, mountainous route. We pedalled a forested countryside where we overlooked vast valleys and saw few signs of life. Take Fornalha, a hamlet mentioned in our directions. We hoped for a shady square, maybe a java break. Nada. Fornalha consisted of eight buildings; we saw three people and dozens of cats.

While the scenery was spectacular, the weather was unbearably hot. The forecast I had checked before leaving Canada had promised temperatures in the mid-20s. We were pedalling — OK, we walked a few hills as well — in steamy heat that we later found had hit 34C. Two and a half hours later, we arrived in the small town of Alferce that had slightly more activity. We breezed into a sleepy town square where three men sat on a bench, they looked at us surprised, perhaps wondering why we weren’t in a kitchen wearing aprons. Bougainvillea draped beside clothes drying on a line and all was peaceful. We had our picnic lunch in the shade and decided the afternoon cycle would probably be easier. And it was. Although mostly uphill back to Monchique, it was breathtakingly lovely. Along the paved road, we were often in the shade of huge eucalyptus trees — I would defy an artist to capture the richness of their bark. Occasionally the red-tiled roof of a luxurious estate could be seen and we passed tiny pastel-hued buildings clustered near the road; there are hole-in-the-wall restaurants and bars always filled with men, it seemed. We are in low-gear mode, lots of time to enjoy our surroundings and then we spot picturesque Monchique, across the valley. In no time, we were lounging and eating ice cream in the shady plaza. We chat with two young men on a cycling trip, although their English was limited, we understood “too many hills” and “too hot” and we heartily agree. Later, we sit on the deck of cheerful Bica Boa and look across the valley to the mountain range we had cycled. While we had taken a pass on the extra eight kilometres that would have taken us up Mount Foia, the Algarve’s highest peak, we toasted our day and wondered what the tomorrows would bring. Despite the gradual two-kilometre uphill as we leave Monchique, day two provides a blissful morning cycle. Who wouldn’t love this forested landscape where we see few people and villages but kilometres of untouched greenery and occasionally a few shacks and burgeoning gardens. Apples, plums, pomegranates, lemons, limes, berries and grapes all thrive here. We stop at the village of Selao where the only sign of life is two men barbecuing sardines. The fish, a staple of the Portuguese diet, smelled and looked delicious and the two gnarly-faced locals invited us, in the universal language of sign, into the minuscule bar. Four men and us; we all smile, salute each other, they raise glasses of beer, we sip cold juice before we head back out in the blinding sunlight. On this day we are travelling west toward the coast and after this pit stop, we zoom along an enjoyable, undulating route; at times we would come around a bend and a glorious fragrance of sweet flowers filled the air. A perfumery, we wondered but we kept pedalling. However there were challenges ahead as by midday we were on a butt-aching secondary road for about five kilometres (our daily rides are between 28 and 50 kilometres) before another steep climb, then veering off the road to follow a rocky trail that was fringed by wilderness and a few pretty farms. Eventually, we arrive at a busy, main highway with a huge sign welcoming us to the Algarve, and suddenly, everything looks brighter.

It may be the brilliance of the blue sky — the temperature is still in the 30s — or the fact we can smell the ocean — but we pedal into the town of Odeceixe with big grins on our faces. Since it is past the hectic tourist season, this precious town with pastel buildings and narrow, winding streets is beyond sleepy. We spend a pleasant two nights at Casa de Celeste — a tidy, small hotel where our innkeeper, tiny Celeste, speaks no English but smiles continuously. The next day we had several cycling options, all easy circular routes that returned us to Odeceixe — one leads to what could easily be described as one of the world’s best beaches. There is a lot to be said for approaching these illustrious sites by bike — you arrive to feel the ocean breeze on your sweaty body and you can’t help but gasp at the curvature of sand bounded by rocky headlands at each end. Although it is October, the beach is dotted with sun worshippers and we join them, dipping toes into a not-too-cold Atlantic. As well as the astounding beach and cute town, my Odeceixe memory is of meeting Maria. When Margo had a flat tire near the edge of town, chubby, cheerful Maria appeared out of nowhere. In this case, we had difficulty changing it and Maria was eager to be of assistance, offering her cellular phone so we could call the bike company but also asking many questions about the trip we were on. As we waited while Walter, our bike guy, arrived to assist us, Maria assured us we could have stayed in her hotel. She pointed us to the best restaurant, owned by her son, and later that evening, she called us into a maze of shops with some nicer-than-usual mementoes. After two nights in Odeceixe we cycled down the coast; exploring the western shoreline of Portugal we were treated to many spectacular sights. A memorable one was Amado Beach, where surf pounded a frothy white and daredevil surfers played. This was day four and most of it was spent on quiet country roads. We were happy to land in Sagres, where our ultra-modern hotel overlooked one of the many famed Algarve beaches. For many, this is what the Algarve is all about: the perfect curvatures of sand in picturesque fishing villages that have been transformed into tourist havens. Again, the benefit of biking — the next few days we followed routes that led us off the main roads to little-known beaches tucked off the main roads. Although it was October, we swam in the Atlantic, ate fresh fish and walked the warm sand to view the sunsets.