Day 1 – Madeira: Double Red Eye to Paradise
Prelude
Hello friends! I’m back again for a 10 day European adventure – this time taking us to the beautiful island of Madeira, Portugal! Let me start by saying that the past 2 weeks have been an absolute whirlwind and I was beyond ready to be on vacation. Monday morning I flew to San Francisco for our team on site, took the red eye home Friday night so I could make it to my dad’s 60th birthday party, then flew back to San Francisco Monday morning for our company on site, only to take the red eye home again Wednesday night. I landed back in Jersey Thursday at 7am for a quick “layover” at home and will be heading back to EWR in about 10 hours for our flight to Madeira. I showered, took a quick 3 hour power nap until noon, moved some items from my work carry on to my checked bag (pre-packing for this trip was essential) and now I am finishing packing my suitcase for my second red eye flight to Madeira, Portugal. WOOF.
It’s been a LOT of travel, more than I ever would’ve asked for but I’m honestly not as tired as I thought I would be so that’s a good sign and I hope I pass out on the plane tonight. For the record, flying to San Francisco 2x was not originally part of the plan when we booked our trip to Madeira. I started a new job this past May and found out about the on sites then. My dad’s birthday and Portugal were already booked and I was determined to make it all happen without missing the opportunity to meet my new team members in person (we’re a remote company) or altering any of my personal plans for work. Mission accomplished.
After my 10 hour layover at home, we drove back to the airport, arrived at 6:30pm and hit the United lounge to grab some food & drinks until it was time to board our flight. Overall the flight was smooth except the kid behind me kept kicking my seat occasionally. I used to have this issue as a child when I flew, so while it’s utterly annoying I also understand that they can’t control it. Somehow I managed to sleep for a few hours and watched Avengers Civil War on the plane in between.
Day 1
Olá! We landed in Madeira at 9am, quickly got through customs, and went to the Budget Car rental line to pick up our car. I don’t really have a preference when it comes to car rental companies – I usually just book whichever one has a deal running through Expedia and with an 80% or more satisfactory rating, but I was very happy we didn’t book through SIXT (which I almost did) because they had a VERY long line and only 2 reps working.
Our car was a tiny but mighty white SEAT Ibiza rental – roomy enough for the 2 of us and fit our luggage (1 medium checked bag each) in the trunk and back seat. We hopped in the car and set our destination to our hotel.

The island of Madeira is much more built up than I had anticipated, or at least the area that we passed on the drive from the airport to the hotel was. After a 25 minute drive we arrived at The Cliff Bay Hotel, a stunning property tucked away from the main town of Funchal with panoramic views of the ocean.
Our room wasn’t ready yet, so we decided to walk & get a quick bite since breakfast at the hotel had already ended. It seemed that most nearby cafes/restaurants either didn’t offer breakfast or opened later, so we ended up at Beerhouse – a spot by the marina and shared a steak sandwich, fries, and Stelios had a local IPA. Not the first meal I would’ve have chosen just landing in Madeira, but I was famished and they are known for their steak here so it was fine.



By 12pm we walked back to the hotel to change and head to the pool to lay out and go for a swim. The pool was warmer than expected but we both felt refreshed laying out on the lounge chairs that were naturally shaded by the surrounding palm trees. Once 2pm rolled around we got access to our room to unpack and get settled in.







After a quick shower and change, We decided to walk into town and explore. It was about a 30 minute walk to the downtown of Funchal which to us was a perfect stroll to and from our hotel. Once you reach the old town of Funchal there is a large section where the streets are closed off with lots of restaurants and shops. We walked into Old Town Funchal where I had a few restaurant recs saved in my phone and we grabbed an outdoor table at Taberna Ruel.




Steli ordered a glass of red and I got a glass of the house white, both were very good. Then the waiter brought out a selection of the catch of the day fish which was quite impressive. We decided to order the bolo de caco (madeiran bread), Greek salad, the octopus, and black scabbard fish with banana (a classic Madeiran dish and delicacy). The bread was served hot in a bag and while the photo does not make it look appetizing, the inside of the bread was filled with garlic and butter and was so delicious. The overall winner of the night however was the scabbard fish with banana – it melted in our mouths and was the perfect combination of salty and sweet. We also shared the cheesecake taberna style for dessert but it had a cherry filling which was too sweet for my palate.






After dinner we continued to explore the old town of Funchal and heard music in the distance so naturally we followed it. We stumbled upon a beautiful overlook with an outdoor bar with tables and people spilling into the street, hanging out, socializing and some were dancing. The DJ was playing outside the bar in the street and was mixing with actual records, a lost art in America.





We went inside Barreirinha Bar Café and ordered 2 ponchas for 4 euros each (poncha is a local Madeiran drink that usually contains rum, honey, and lemon or orange juice). The bar put a 2€ deposit on our card until we returned the cups which I thought was funny (I forgot to take a pic). Unfortunately the poncha was not for me & I thought it tasted like medicine (apparently it can be used for medicinal purposes) but I had to try it! After hanging out for an hour or so it was 10:30pm and we started our walk back to the hotel and were in bed by 11:30pm. Overall a nice relaxing and easy day to the start of our Madeiran adventure.