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

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:

https://www.airbnb.com/rooms/14546162?location=S%C3%A3o%20Miguel%20Island%2C%20Portugal&adults=5&check_in=2019-05-25&check_out=2019-05-29&guests=1&s=A-Sye8V-

https://www.airbnb.com/rooms/30709456?location=S%C3%A3o%20Miguel%20Island%2C%20Portugal&adults=5&check_in=2019-05-25&check_out=2019-05-29&guests=1&s=A-Sye8V-

https://www.airbnb.com/rooms/5952443?location=S%C3%A3o%20Miguel%20Island%2C%20Portugal&adults=5&check_in=2019-05-25&check_out=2019-05-29&guests=1&s=A-Sye8V-

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.

Carl

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?

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.

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!
Bradley

Hi Bradley,

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

Carl

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!

scoutburke,

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

Carl

Thank you so much Carl for sending along the guide!!

Scout Burke

Hi Carl,
Would you please send me your information on the Azore Islands? We are planning to go to Portugal and would like to include some time exploring the Azores.

Rwilson2,

I just sent you a private message with the information. I hope you have a wonderful trip.

Carl

Carl-
Would you please send me your guide? It sounds like a great help to many. We are from Rhode Island too and headed to Sao Miguel for 8 days next week.
Thank you.

KDPtraveler,

I sent you the guide link in a private message. You are all set for Sao Miguel, the biggest island with the most to see and do. The weather should be excellent.

Carl

Hello Carl,
Is the weather in Oct.- Nov. still nice enough for swimming at the beaches?
Could you please send your travel guide as well? it would be greatly appreciated.
Thank you.

skilyanek,

Swimming is sometimes possible in those months, and many locals swim even into December. For me it would be too cold, but I am not much of an ocean swimmer even in the summer. Also, as the nine islands are spread out over a vast distance, Santa Maria (the southernmost island) would probably have the warmest water followed by Sao Miguel.

I sent you a private message with the link to my guide. I hope you enjoy it.

Carl

Hi Carl, can I please get a copy of your guide. Solo traveller to the Azores sometime between December and February... I'll definitely bring a raincoat.