The alarm rang at the very displeasing 7:30am, but I had no choice as I was to be picked up at 8:30am for my day tour exploring the Douro wine region. I had booked a seat on an 8 person private tour so I made my way to the meeting point and was soon greeted by our guide, Vasco.

The Mercedes van was already full of the other guests – 3 older women from just outside of London, a couple from Italy and soon to round out with a couple from Germany. Vasco declared us his family today and as Papa he would make sure we were taken care of.

We were soon out of the city and on the way to our first stop (“not a gas station, I promise”) Vasco explained that the city of Amarante was known for two things – a 13th century church on the river and a pastry modeled after the fact that the town was home to the Patron Saint of fertility.

We took our snaps and soon climbed back into the van to make our way up and over the mountain that led to the Douro Valley, stopping at the top for some breathtaking views.

Near just on the other side of the mountain was our first winery (Quinta) where we would also have lunch – Quinta do Santa Julia. We greeted and led through a very pretty garden which overlooked the valley below.

We were led into the cellar where a table had been set up for our tastings. Our cheerful host explained the winery had been in the family for 8 generations and featured both wine and port.

The massive oak barrels, she explained, had to be cleaned every couple of years. The process involves climbing into the barrel through a small entryway and then can stand up inside. They have to wait an hour for the alcohol fumes to subside and even with that, the person doing the scrubbing has to stop every hour to avoid the toxic fumes and has a spotter outside of the barrel to ensure they are ok. It’s a laborious task that can take up to 3 days to complete.

We sampled their white, reserva red and a vintage port (a designation that can only happen on a particularly good year but no more than 3 per decade.) All 3 were quite good and after finishing we were escorted to the adjoining kitchen for our lunch.

The three course meal consisted of a very tasty vegetable soup, a hearty beef stew and a local egg tart. Simple but satisfying. I decided to add a glass of their 20 year old Tawny port for an aperitif, which was superb.

We made our way now down to the river across a bridge that had been designed by Gustavo Eiffel’s firm (yes that Eiffel) and to our next destination, an hour cruise along the Douro River. Our very friendly captain explained the river was brown because of all of the recent heavy rain the region had been experiencing.

He offered us a shot of a port that friends of his had made recently – not bad – and pointed out the now familiar looking boats which, back in the day, were using to transport the port wine barrels to Porto, which would take about 3-4 days to get there. However, due to going against the currents, it would take 3-4 weeks to get back due to the currents and required mules to help pull the boats through.

He also explained that the orange trees that dotted the landscape weren’t for eating but rather to attract the bugs away from the grape vines. Also, if we saw a terrace without any vines, that means the landowner had given up making wine, which happened a lot after a devastating wave of pylloxera wiped out most of the vines in the 1870s, causing some to believe the land was cursed.

We said goodbye to the captain and headed to our final stop – Quinta do Beijo (kiss) which was a much smaller producer. Our guide, Cara, was just delightful, combining deep knowledge with genuine hilarity.

She explained that all wine produced there was done the old fashioned way, with their feet. The whole winery gets involved as well as friends and neighbors. Like Julia, they have both wine and port. Sara noted that their port is what they used to be known for but that about 10 years ago started making wine as well.

The barrel on the left was 187 years old and used for their tawny ports. She was also proud of their vintage white port, which she said was not to be mixed “I will murder you if I see you do that!” and gave us some to try. It was a bit too sweet for my tastes but not bad.

Like at Julia, Sara covered the cleaning process of the barrels but went further by showing us a sample of what they have to remove. The ridges are crystallized sugar which will eventually throw off the balance of the wines so need to be cleared every couple of years or so.

Sara then said it was our time in the barrel and had each of us, after showing us the proper technique to go in head first and twist, go inside. I thought there was NFW I could possibly fit but amazingly I did and could even stand completely upright. After a couple of minutes, she showed me how to reverse the process to get out “like birthing a baby” and as I twisted my way she kept saying “push! push!” When I finally freed myself she exclaimed “it’s a very big boy!”

I ended up buying a couple of bottles of their very interesting rose and headed back to the van one more time. Most of the “family” was now asleep but I chatted with Vasco the entire ride home learning even more about Portuguese history both ancient and current. He eventually dropped me off, and I thanked him profusely for being such a great guide.

After a brief respite, I ventured out for dinner. Given my long day, I picked somewhere very close to my place. Scarlett was a mere 2 blocks up from me, and the menu had intrigued me earlier. I needed to use the bathroom and was escorted into the very cool lobby of what turned out to be the attached hotel.

One of the starter that had caught my attention earlier was a beetroot “tartare” with crackers and dill. It truly did taste a tartare, with the diced roasted beets mimicking the usual beef and the familiar flavors, just without the egg as it was a vegan dish.

I decided to stay on the vegetarian tip and ordered another meatless starter – Shroom Wings. It consisted of oyster mushrooms, shaped into “wings” and deep fried. The thick mushrooms were not greasy at all and nicely seasoned. The kicker though was the absolutely perfect remoulade. Delicious.

The long day had finally taken its toll on me so I declined dessert and made the quick walk back to my penthouse. Tomorrow was supposed to be cold and rainy, which would be perfect weather for some tawny port tastings.