Portugal had been on my “list” for as long as I can remember. Maybe, even as a child, I felt connected to the exploring spirit of the country’s past. Now, about to celebrate a birthday that brought a new decade, it was time for me to find my adventure there.  I searched for “kayaking in Portugal.” Douro Kayak popped up and promised me gentle paddling, good food and plentiful wine. I signed up immediately.

I arrived to find Porto, where the trip begins, to be a warm, walking city with the historic center a UNESCO World Heritage Site. Ancient architecture fronted with colorful tiles and patterned sidewalks entice even the jaded into exploring on foot, despite the many hills. In this city where beauty surrounds, I spent my first night of our six day kayaking trip down the Douro in a drab, hermetically sealed tourist hotel. Perhaps it was chosen for the cost, rather than its charms.

Early the next morning, our group of nine walked to the Sao Bento train station to view the famous blue and white tile panoramas adorning the station walls, then boarded the Linha do Douro train to Pocinho, our first stop on the river. Little did we know that the short, yellow train would become our constant companion on the river, causing us to yell “Train!” every time it cheerily sped past our pod of kayaks.

This is not a strenuous trip, as kayaking trips go. Breakfasts are leisurely affairs, with no thought of early schedules. Each day, we would enjoy homemade bread, local cheeses and cured meats. Hard-boiled eggs, fresh jam and sweet butter rounded out our morning feasts. Despite overeating, we would load into the van and head to a nearby grassy or sandy spot to launch our kayaks.

The weather and river’s current conspired to make this an easy and glorious journey. We’d start by 9:30am or 10am and paddle past vineyards spanning across the Douro valley and clinging to hills far into the distance. Perfect lines of grape vines molded to every curve and terraced up every hill, creating stripes of green that changed intensity as the sun moved through its day. Traditionally the area has produced port, the region’s famous wine, but more and more the Quintas, or vineyards, are producing internationally recognized wines. The reds are increasing in popularity, with fertile soil and forgiving weather working together to create earthy reds.

On one morning, we stopped at the Quinta do Vesúvio, which was started by António Bernardo Ferreira I in the early 1800s and is now owned by the Symington family. The Quinta is credited with helping to develop the Upper Douro wine region and has been producing port for over 200 years. We paddled to a small boat launch, hidden by weeping willows at the base of the family home. Jack, our leader and owner of Douro Kayak Expeditions, arranged a private opportunity for us to wander through the estate’s gardens and to explore the original winery, where grapes have been crushed in the same granite vats for over 200 years.

The historic winery smelled fragrant and earthy as we stepped around the giant barrels of port.  At the end of the building, we found a table draped in a crisp, white cloth, with tasting glasses and two bottles of the Quinta do Vesúvio’s reserve port waiting for us to enjoy. Getting back in our kayaks, post-tasting, was a bit less graceful and our kayak lines were not quite as straight as we headed down the river towards lunch.

When the early September sun brought its full heat, late each morning, Jack turned into our “international man of mystery.” With full-length sleeves, gloves, wide brimmed hat, sunglasses, bandana tied at the neck, balaclava pulled over his face and a spray skirt engaged, there was not a piece of skin or identifying feature exposed. I wore a tank top.

I’d like to think we were fast paddlers, but really the Douro’s current was fast that week and it pushed us along at about 3 knots, without paddling. We ended each day’s journey an hour or two earlier than expected. This meant by lunch we were off the river enjoying family style platters of local clams, sardines and expertly grilled chicken. Salads with fresh tomatoes were a group favorite and we could never seem to get enough. Pitchers of wine and large mugs of beer arrived and were refilled, sometimes repeatedly.

Afternoons were free to explore the small villages where we slept. Our inns ranged from bed and breakfasts to idyllic inns with infinity pools. On the river, we felt remote, but the afternoons would bring small villages waiting to charm us. Many of the buildings were older than the United States. Some had survived and been maintained, while others were crumbling, often side by side.

Each day brought new views and new adventures. One day, we kayaked passed steep rock walls, a shocking change from the wide, rolling valleys we’d become accustomed. Just as we left the canyon walls, we floated into a ship lock, a man-made canyon. Our flotilla looked like little rubber toys, rafted together in a space built for cruise ships.  The lock closed behind us, water was released, and suddenly we were 108 feet lower on the river and the massive garage door in front of us opened. A tip for kayakers going through a lock for the first time, like I was, be sure to put your spray skirt on before paddling under the rising gate and its residual waterfall.

We were never hungry, yet we always found room for what the river shared with us. It became typical to see at least one of us with juice dripping from ripe figs or sweet oranges, warmed by the sun and picked along the river’s banks.

Our last day on the river brought us to Pinhao, a small, but bustling tourist town made popular by wine enthusiasts who use it as a base to explore the local vineyards. We tried to slow our progress as we neared the take-out point. None of us wanted the trip to end. Once the kayaks were loaded, we shared our last lunch together at a restaurant situated along the river. We raised our glasses in thanks to the Douro and then joined our little yellow train for our final ride back to Porto.

Josephine Parr is a freelance writer who is passionate about adventure travel, ethnic food, and a good glass of red wine. She has been published in The New York Times, AFAR magazine, Travel Age West, Town & Country, Runner’s World and other publications. She lives in New York City.