Six nights in mainland Portugal before or after a week on Sao Miguel

I recommend saving the best for last, São Miguel, Azores.

Sintra is worth 2 days if you blitz through all there is to see in Rick’s guidebook, and you will be plenty tired. Near the train station is Dom Pipas. I have eaten there twice and would say it is one of the best restaurants I have been to in Portugal. Just Quinta da Regaleira is worth an entire morning or afternoon. To make life easier, do Sintra in the beginning or middle of your stay on the mainland, meaning Lisbon. I aways rent a car, but the guidebook and others on the forum will attest how easy it is to get to Sintra without a car. No car is necessary in Lisbon. Uber and taxis are plentiful and low cost.

Lisbon could keep you busy for months, and again, the guidebook offers plenty to do with 4 days. I used and thoroughly enjoyed Eco Tuk Tours in Lisbon. They can pick you up and drop you off at your hotel for a few extra euros. You will have a blast whether taking a company designed tour or make your own suggestion. It is a nice morning option to get your bearings. Lisbon offers almost limitless things to see and do.

So regarding São Miguel. A week is a wonderful time frame to truly explore this island paradise. I promise that your entire group will be amazed at what awaits you there.

Please make sure to rent, at a minimum, a 7 passenger van that will accommodate your group and probably most, if not all, your luggage. If you need to put all the possible extra luggage in a taxi, it is only about 10 euros to anywhere in Ponta Delgada, if that is where you are staying, and then you have the van for the week. When you fly out, again, if you need the taxi for the luggage, it can easily be arranged for the same price.

Try to do at least 1 hike on the island. There are dozens to choose from, depending on your comfort level. September should have spectacular weather for any beach time, but know that the water is not very warm. Locals will certainly be in the water. Your sightseeing days options are immense, and the nights will be enchanting, especially wandering around Ponta Delgada. I will be doing all of this in late July and early August!

At the top of this Portugal forum, the webmaster wrote a post regarding Azores advice. There is a link to the freemium section of my Azores guidebook. It has plenty of information for the Azores portion of your trip. I am certain that the freemium will give you lots of stress reducing ideas and planning tools, and it really is FREE :-).

I hope your group has a memorable trip. Send me a private message if there is anything I can help with in planning.

Carl

Carl:

Thank you for your thoughtful, informative response. I do have some follow-up questions.

Regarding when to visit Sintra, why not at the end of our mainland stay? Here’s my thinking: Assuming we fly from Boston to Lisbon, we arrive at 10:15 am. On the assumption that we may want pre-check-in access to a rented apartment, it seems more economical to add the night before our arrival in Lisbon than in Sinatra (where our only desirable option may be a hotel). Also, we may not be ready to hit the ground running to tour Sinatra. Putting Sinatra at the end, rather than the middle, also means we only need to relocate / shift our luggage once.

Regarding visiting San Miguel after the mainland, this has been our thought. I’ve started to wonder, however, whether we’re better off with our long Air Azores flight being Boston-PDL. Going the other way adds at least an hour. On TAP we’ll fly Premium Economy. I’m concerned about seating comfort and stiff joints and backs.

Good questions!

Lisbon and the surrounding area could require intensive sightseeing. Sao Miguel is a slower paced, drive with no traffic, albeit the cows on the road, type of sightseeing. Many places are free and provided by Mother Nature, so they can be appreciated even at 8:00 pm on a September evening. You get to set your own schedule without worrying about crowds. The few time I have visited Sintra were extremely crowded. Even the shops, bakeries, and restaurants were jammed packet. Dom Pipas will be the exception, but make a reservation to be safe.

I always suggest to travelers who want to combine the Azores with the mainland to get the hustle and bustle completed at the beginning of the trip, which allows you to really savor the islands. And an outdoor thermal bath, or two, after Lisbon could be what the “doctor orders”.

Of course, go with what suits you better. You know better your expectations. Certainly the flight schedules can make an impact on this type of trip. Lisbon traffic can be a nightmare, and must be taken into consideration as to when to get to the airport. Lisbon airport itself has loooooong walking distances between check-in and the gates. For me, 3 hours is a minimum to be there.

For Ponta Delgada airport, returning your car is normally 1/2 hour or more, because you will complete the paperwork at the counter. If there is a line in front of you, the clock keeps ticking. The lines at the check-in counter can also be very long, depending on the number of flights soon departing.

Whatever you decide, it will be a fantastic trip.

Carl