Before retirement begins: Take the trip you’ll talk about for years — four weeks in the Azores

24 Sep Before retirement begins: Take the trip you’ll talk about for years — four weeks in the Azores

There comes a point when travel starts to mean something different.

For a couple approaching retirement, the idea of rushing through ten cities in fourteen days can lose some of its appeal. Instead, you may find yourself wanting more time, more freedom and destinations where the journey itself feels like a glimpse of the lifestyle ahead.

For that kind of trip, consider somewhere many Australians have heard little about: the Azores.

Sitting in the middle of the Atlantic Ocean, the Azores are an autonomous region of Portugal made up of nine volcanic islands. Think crater lakes, hydrangea-lined country roads, thermal springs, tiny fishing villages, vineyards growing between walls of black volcanic rock and an ocean where whales and dolphins are never far away. 

For couples nearing retirement, it offers something particularly appealing: adventure without having to rough it.

A Different Kind of Four-Week Holiday

Rather than trying to see all nine islands, give yourself permission to travel slowly.

Begin with around ten days on São Miguel, the largest island. Hire a car, but resist the temptation to plan every hour. Drive to the spectacular crater lakes around Sete Cidades, walk coastal trails and spend an afternoon soaking tired muscles in the geothermal waters around Furnas.

The volcanic landscape is one of the defining characteristics of the Azores. Across the archipelago you’ll find calderas, crater lakes, fumaroles, volcanic caves and thermal springs — constant reminders that these islands were created by extraordinary geological forces. 

This is also the place to begin enjoying Portuguese island life: long lunches, locally caught seafood, cheeses, fresh bread and a glass of wine without needing to be anywhere afterwards.

Then Go Island Hopping

For your second week, fly or ferry to Pico and Faial.

Pico is dominated by the immense cone of Mount Pico, Portugal’s highest mountain. Serious walkers can tackle more demanding trails, while those looking for something gentler can explore the coastline, vineyards and small villages.

Across the water, Faial offers the colourful marina town of Horta and easy access to some of the Atlantic’s most memorable wildlife experiences.

The Azores are regarded as an exceptional destination for whale and dolphin watching. More than 20 cetacean species have been recorded around the islands, including both resident and migrating species. 

Imagine reaching retirement knowing that one of your last big holidays before finishing work involved watching whales surface beside a boat in the middle of the Atlantic.

Save Time for the Quiet Islands

For the third week, consider São Jorge, with its dramatic cliffs and coastal fajãs, or venture further west to Flores, an island of waterfalls, green mountains and tiny settlements.

Walking is one of the great pleasures of travelling through the Azores. The official trail network extends across the islands, allowing travellers to choose everything from relatively easy walks to more demanding adventures. 

And there is plenty to do beyond hiking. The islands offer kayaking, diving, cycling, canyoning, horse riding, sailing and birdwatching, making it easy to mix active days with slower ones. 

Make the Final Week About Doing Less

Spend your final week back on São Miguel.

Book beautiful accommodation overlooking the ocean. Revisit a favourite restaurant. Have a thermal bath in the morning. Walk in the afternoon. Sit somewhere with a bottle of Portuguese wine and start discussing what retirement might actually look like.

Because perhaps that’s the real reason for taking a trip like this.

Approaching retirement isn’t simply about finishing work. It’s about deciding what you’re going to do with something you’ve spent decades wishing you had more of: time.

Four weeks in the Azores allows you to experiment with travelling more slowly, staying longer and waking up without needing to rush.

It may be a holiday.

But it could also be a very good preview of the next chapter of your life.

If this article has inspired you to think about your unique situation and, more importantly, what you and your family are going through right now, please get in touch with your advice professional.

This information does not consider any person’s objectives, financial situation, or needs. Before making a decision, you should consider whether it is appropriate in light of your particular objectives, financial situation, or needs.

(Feedsy Exclusive)