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Suggested Itineraries for 9 days in the Azores - Late May / Early June

We are planning a family vacation to the Azores from 5/25/19 - 6/2/19. There are 5 of us with 2 mobile seniors and 3 active young adults (in their 30’s). We’d appreciate some suggested itineraries. Here are some thoughts / parameters we have developed:

  • Since this is a “family” vacation we’d like to all stay together. What is the typical availability of Air BNB accommodations or hotels / inns with at least 2 bedrooms?
  • We’d like to see at least 2 islands, and potentially 3. — Is it practical to stay at the same place on one island and do day trips to other islands by ferry? — Which islands would you recommend and for how long on each island? Our current top 3 are Sao Miguel, Terceira, and Pico.
  • Do you recommend a car rental or booking tours.?

Thank you

Posted by
629 posts

9 days Azores Itinerary.

Set base in Sao Miguel as it is the biggest island in the Azores

São Miguel (5 full days)

Pico (3 full days) - Day Trips by ferry to Faial and Sao Jorge islands - 30 min ferry ride to each island from Pico

Terceira or Santa Maria Island (1 Full Day)

You can rent a car to explore Sao Miguel but the other islands, you can either book a tour or hire a personal driver to take you around the point of interests.

AirBnbs on Sao Miguel 5 Days stay:

Posted by
357 posts

I sent you a private message with a link to my Azores guide. It will have just about all you need to plan a great vacation in the Azores.

Be aware that the biggest feast in the Azores, Senhor Santo Cristo dos Milagres, takes place this year from May 24-30 in Ponta Delgada Azores. This means you want to get ALL your reservations done ASAP. There are lots of great places to stay with 2 bedrooms. You just need to research what type of property you are looking for.

I recommend Sao Miguel and Santa Maria with this amount of time.

Let me know if you need anything else.


Posted by
2 posts

Thank you for the information. During the Senhor Santo Cristo dos Milagres feast, will the entire island be "overrun" by tourists or will the people be concentrated in Ponta Delgada? Would we be likely to find it difficult getting to the many areas away from Punta Delgada, renting a car, or hiring a local guide?

Posted by
357 posts

You will be fine anywhere on the island, including Ponta Delgada. Some streets will be closed at different hours, and restaurants will be busier. Tourism in the Azores is honestly booming by Azorean standards, but anywhere you visit, at anytime during the year, will never be overrun.

Reservations are a must, because of the influx of returning Azoreans for this feast. Tourists don’t visit Sao Miguel because of this religious feast. The people visiting this feast will practically (99.9%) all have family ties to the islands. Add in a possible cruise ship or 2 with another 5,000-6,000 cruisers and it will be almost gridlock in Ponta Delgada during the day. My family who live in Ponta Delgada try to avoid driving in the city if more than one cruise ship is docked. Too many people are walking around slowing down traffic. Some of the roads are tiny, most of the “sidewalks” are tiny and nothing in size compared to Lisbon or the mainland. Drive a mile or so out of Ponta Delgada and you will have numerous options to pass your days, with many places all to yourself.

Your main issues will be getting your flights and hotel (or apartment) taken care of soon.
I really suggest a rental car reservation as well, while you are at it.

Watch a couple of YouTube videos of the feast to understand better. Everything else you need (I am optimistic) is in my guide.

Posted by
1 posts

Hi Carl,

Could I get a copy of the guide? The wife and I are flying into Lisbon in late August and are considering taking a few days to visit the Azores and relax as part of our trip.

Thank you!

Posted by
357 posts

Hi Bradley,

I sent the information in a private message. I hope you have an amazing trip!


Posted by
6 posts

Hi Carl! We are looking at going to the Azores mid-Sept, early October timeframe.

Can you kindly send along your guide?

Many thanks in advance and much appreciated!

Posted by
357 posts


I sent you the information in a private message. I hope you have a wonderful trip and enjoy the planning.