Matt and I traveled to the island of Madeira for Thanksgiving 2023. We previously traveled to Madeira over 9 years ago and absolutely loved it. However, this time I had a little anxiety. Think about how you feel the first time you return to a restaurant 10 years later that you recall absolutely loving. What if it isn’t as good? That is how I felt about this trip. Luckily, not only did it meet our expectations, but it exceeded them. This is now my favorite vacation Matt and I have ever taken together. Let me tell you why. Think of this post as more of a diary of our trip and a love letter to Madeira.

The Island

It is important to note that while having beautiful weather year-round, ocean and resorts; this is not a beach vacation. The island is rocky with beautiful flowers, scenery and architecture. You get an island vacation with European flair in one trip. It is warm enough to sun bath, but not too hot.

Funchal

Funchal is the capital of Madeira. It is a small Portuguese city with wonderful food, markets, and shops. It has also become a popular cruise port carrying passengers largely from the UK and Germany, but an occasional transatlantic cruise from the USA does arrive.

Hotel: Les Suites at the Cliff Bay

We stayed at the new Les Suites and the Cliff Bay, which is a new private section of the Cliff Bay hotel. We stayed at the regular Cliff Bay last time, but our gay hearts were attracted to a nicer and flashier section of the hotel with less people and fewer children! Review to come.

Trip Diary

Saturday 9/18

We arrived in Madeira from our overnight flight from Boston early Saturday morning. Our room was not ready, so we dropped off our luggage, showered in the spa and had lunch at the hotel. Once our room was ready, we relaxed until dinner. Dinner was at our favorite local and casual restaurant on the island, Chalet Vincente. The restaurant is just a short walk from the hotel that serves typical Madeiran fair of garlic bread, Beef on a stick and local fish such as Cod. It was as delicious as we remembered!

Sunday 9/19

Today was our romantic day. We slept in after a long day of travel and made our way to our wonderful hotel breakfast overlooking Funchal and the sea. After, Matt and I spent 3 hours at the spa receiving a couple’s massage, facial and a bath. It was heaven.

Dinner tonight was at the hotel restaurant, Avista for a private romantic dinner. Matt lost his wedding band a few months ago and I secretly procured him a new one that I planned on giving it to him sometime during the trip. Matt has had a tough year with medical issues, and he is thankfully doing better, so I decided to be cute and arranged making the dinner extra special. We haven’t had good photos of ourselves taken in a long time and I also regret that we never had our original proposal photographed. All we had from that intimate night was a crappy selfie on my original iPhone. I decided to hire a photographer to capture our beautiful dinner, take good photos of us, and be there to document my surprise proposal for another 10 years of marriage. It was a perfect evening and he even said Yes. I reminded Matt that I have now proposed to him twice and expect him to do the doing next time 😉.

Monday 9/20

Today we went for a long walk into Funchal and did some window shopping. After we spent some time by the pool and went upstairs later in the day for a latte’ with beautiful views. Dinner was at Forte. We went to Forte last time and it is always a treat. They have a package that includes a 5-course dinner, transfers to/from your hotel in a classic car and a beautiful table.

Tuesday 9/21

I swallowed my fear of heights as we took the cable car up to Monte. Monte towers above Funchal and is home to beautiful Japanese gardens. We strolled the gardens but opted not to take the sleigh ride down this time, but y’all should do it once! Dinner, we tried a Chef Guru Indian restaurant as we can’t really get that in Wells, Maine either and it was fabulous.

Wednesday 9/22

Today we left Funchal for the first time by hiring a wonderful driver to take us around the western part of the Island. Matt and I also saw some wonderful real-estate opportunities, but next time. We visited the following.

• Camara de Lobos, local fishing village where Winston Churchill enjoyed painting.
• Cabo Girao, a 580m glass lookout platform suspended over the sea cliff.
• Ribeira Brava is a quaint coastal town with a river flowing into the sea, shops, cafes & a small market line the seafront.
• Sao Vicente, a small municipality surrounded by lush forest valleys.
• Porto Moniz & volcanic pools

I cannot recommend this tour enough if you are ever on the island. I regret not doing something similar last time! Dinner was at Goya which was the best dinner we had on the island. The owner of the restaurant added us as friends on Facebook 10 years ago despite not eating there. Now that is marketing and it worked! The food was excellent.

Thursday 9/23

As we approached the end of our trip, we kept Thursday open to walk into Funchal again and go shopping. We spent a lot of time in our room relaxing as well. Dinner was at Mozart. Mozart offers a wonderful 3 course meal with live music. The owner dresses up like Mozart every night and is quite friendly. He also offered us a ride home in his classic car. It was a perfect way to spend Thanksgiving.

Friday 11/23

Our final full day in Madeira. A travel hack we do is always go for a couples massage on the last day of a week or longer vacation. We always have anxiety about packing, traveling, going home and returning to work that a moment at the spa helps extend the vacation. Otherwise, we had final drinks on the balcony and returned to Chalet Vincente for a final dinner.

We had such a wonderful time. It was a great balance of sightseeing, good food, relaxation and time together. It will always be our special place where we got engaged…. AGAIN! I hope this post motivates you to travel to this gem. In my two next post I will discuss how you can get here cheaply and where you should stay!

Bon Voyage,

Andrew