Exploring the Azores: A Week in São Miguel, Pico and Faial

Fly into Ponta Delgada on São Miguel Island and obtain a rental car from the airport. Check into a hotel near the city center and grab a quick coffee or bite to eat at INTZ 48. Be sure to check that they are open first as their hours can be a bit erratic.

Head to the nearby Augusto Arruda Pineapple Plantation for a self-guided tour of the grounds and taste of all things pineapple. Azorean pineapples are grown in whitewashed greenhouses and can take up to two years to mature before being hand-harvested. While much smaller than other varieties, they are mighty in flavor with a uniquely sweet and slightly acidic finish. They have frankly ruined all other pineapples for me, so be sure to give them a try and check out the wonderful onsite gift shop before you leave.

Spend the rest of your day exploring the cobblestone streets of Ponta Delgada. Later in the evening, make your way to Reserva for an excellent meal of tapas and wine before turning in for the night.

Start your day with breakfast at your hotel and then drive about 40 minutes west towards the famous crater lakes of Sete Cidades. If you’re up for a bit of exercise, walk the Mata do Canário trail that runs along the caldera’s rim and down towards the village. The full hike is approximately 7.5 miles long and can take about 4–5 hours, so plan accordingly. You can also opt for a shorter walk or make a beeline towards one of the many lookout points, such as the Miradouro do Cerrado das Freiras, to enjoy the gorgeous views.

Take your time on the return trip to Ponta Delgada, as there are many photo-worthy scenic stops along the way. Relax for a bit and then try to catch a fado show or other performance at the Teatro Micaelanse or Coliseu Micaelanse.

Explore more of the island by driving about 30 minutes northeast to the small, but charming tea estate of Porto Formoso. Watch their short video on local tea production and enjoy a tasting before exploring the lovely gardens and grounds.

Continue to the much larger Gorreana estate, which is the oldest tea factory still operating in Europe. Here, you can observe the production process first-hand and spend a bit of time in their bustling gift shop and café. You are also welcome to freely roam about their hillside tea fields. Simply cross the street, wander into the emerald-green rows of shrubs and follow one of two post-marked trails. The views from here are really quite stunning and should not be missed.

Once you’re fully caffeinated and ready to go, carry on to the small spa town of Furnas. Head straight to the Terra Nostra Garden Hotel and indulge in a relaxing treatment or massage. Afterwards, walk across the bridge into the Terra Nostra Garden to enjoy its hot thermal pool and beautiful gardens. Upon your return to the hotel, enjoy a top-notch cocktail at The Gardener Bar & Terrace or consider staying for dinner at the TN Restaurant.

Return to Ponta Delgada and make the most of your final evening on São Miguel. If you’re a wine lover, be sure to pop into the A Vinha Garrafeira wine shop for a great selection of Azorean and Portuguese wines. The owner is wonderful and can help you select a bottle or two.

Head to the airport to return your rental car and make the short 55-minute flight over to Pico Island. Obtain another rental car. Although be sure to book way ahead if you need an automatic, as Pico is fairly small and most of the cars happen to be manual.

Check into your hotel and spend the day exploring Madalena and the surrounding area. I recommend staying at the Azores Wine Company, which is both a winery and small boutique hotel set back amid a rocky expanse of vineyards. All of the vineyards on Pico are truly unique in that they are surrounded by man-made currais, or walls made of volcanic rock. These walls protect the vines from the wind and salty ocean spray while also retaining heat. They are truly unlike any vineyards that I have seen anywhere else and have been classified as a UNESCO World Heritage Site.

Another option is to visit the vineyards in nearby Lajido, where you can take a lovely walk from the picturesque Moinho do Frade windmill to the ocean beyond. You can then head to the Museo de Vinho for a brief history of winemaking in Pico. Learn about the only three varieties that qualify for the Protected Designation of Origin (PDO): Arinto dos Acores, Terrantez do Pico and Verdelho. The museum unfortunately does not offer tastings, but you can make your way to the local wine cooperative, Ilha do Pico Coop Vitivinicola to try these varieties from a number of different producers.

End your day with a gourmet wine-pairing dinner at the Azores Wine Company restaurant. You can choose from one of four different tasting menus depending on how many courses you would like to enjoy. It is a special and well-executed experience in a simply beautiful space.

Get an early start to the day and tackle the ascent to the top of Portugal’s highest mountain, Mount Pico. This is not an easy hike and should only be considered by those willing and physically able to reach the peak, which sits at an altitude of 7,713 feet. You can and should go with a guide as parts of the trail are difficult to follow and there are a good number of slippery spots on the way back down. I highly recommend booking ahead with atiPICO and squirreling away a bevy of snacks as the journey is about six to eight hours round trip. Don’t worry though, the views from the top are absolutely magnificent and are more than worth the hard work!

If climbing a mountain is not your thing, head south to Lajes and go on a whale-watching excursion. Afterwards, explore the town and pop by the Aromas & Sabores Pastelaria for some delicious baked goods.

End your day with a casual dinner overlooking the ocean at Cella Bar and get some well-deserved rest!

Take the morning ferry along with your rental car as long as the company from whom you rented permits it. Head from Madalena over to Horta and spend the day exploring the beautiful island of Faial. The latter is only five miles from Pico and it’s a fairly quick and painless 30-minute crossing.

Make a beeline for the oh-so-tasty Ah Boca Santa eatery, which is located in a cute little food market in Horta, and order up…everything is amazing!

Start your driving tour of Faial by heading north of Horta towards the Espalamaca, where there is a great viewpoint of the town. Carry on to the must-stop Caldeira do Cabeco Gordo and walk through the short pedestrian tunnel to enjoy the views. There is also a well-marked rim trail if you are up for a walk.

When you’ve had enough exercise, backtrack just slightly before proceeding towards the Ribeira Funda. While this area admittedly does not have the best roads, it does have spectacular fields full of hedgerows of hydrangeas that extend down to the ocean below. Be sure to take some photos and then proceed to the Capelinhos Volcano Interpretative Centre. This otherworldly location was the site of a volcanic eruption in 1957-1958 and is worth exploring. Be sure to climb to the top of the lighthouse after you have exhausted the museum. If you’re up for a swim, walk or drive a few minutes down to the Porto do Comprido swimming “pool” and take a refreshing dip in the ocean.

Hop back in your car and return to Horta. If they are open, you can stop by the charming Capelo Centro Do Artesanato on your way and peruse their selection of locally made crafts. Once in town, enjoy a casual dinner at the popular Peter Café Sport before catching an evening ferry back to Pico for the night.

Enjoy a final morning in the Azores before flying back to Ponta Delgada to catch your flight home. Be sure to carefully back any bottles of wine or other souvenirs that you may have procured during your stay.