Lisbon, Sintra and Azores

Respectfully, I'm questioning how realistic your plan is. Sorry, I know this is not what you want to hear.

Your trip ("9 nights") is quite short for any trip to mainland Portugal (I assume you are coming from North America; please correct me if that's not the case). Painfully short, if you are going to and from the Azores via Lisbon, in the middle of it, and honestly I'd be concerned about your ratio of time spent "getting there" to time spent "being there." Start by counting your days and nights -- and your actual, usable, full non-travel days -- carefully (and be honest with yourself). Don't count any day that you are on a plane as a usable day for sightseeing or activities, that's a travel day.

Where are you coming from? If you are flying from North America to Lisbon, no matter what time your flight arrives, your arrival day will probably not be good for much since you will be jetlagged and exhausted from lack of sleep on the flight over (if that's the case, you would actually be better off pushing on to São Miguel that same day, since it's going to be a wash anyway). The day you fly from Lisbon to São Miguel will be mostly consumed by flying and getting settled (the flight itself isn't terribly long, but hotel check-out/check-in, airport tasks, getting oriented, etc. will consume most of the day). Same for the day you fly back to Lisbon. Same for the day you fly home from Lisbon.

If you are arriving in Lisbon from some other place in Europe, and this is part of a larger trip, then you should fly all the way to São Miguel that day, rather than stopping for a day/half day in Lisbon; you would gain at least a little time that way.

Do the math...your trip is going to lose many days to flights, leaving you short on full, non-travel days on the ground to enjoy the places you've come so far to see. Looks like you'll end up with just 4 full days on São Miguel (the day you arrive from Lisbon, the day you fly back to Lisbon won't be very useful for sightseeing and activities), one full day in Lisbon on the way in, and "half a day" (how does that work?) on the way out (if your "day count" has already excluded every day you are on a flight, please correct me).

São Miguel is beautiful and worth more time than you will have (I was there for 7 full days last year and we didn't get to all the things we wanted to see and do; we wished we had 10 days there). So is Lisbon for that matter (maybe you have been there already and seen it all?).

Given how little time you have, I would probably do Sintra as a day trip on your single full day in Lisbon (or just stay in LIsbon itself for your single full day there and enjoy it). Remember, every time you pick up and change locations, even if it's someplace relatively close and does not involve a flight, you still spend half a day with all the tasks you need to do. You can't realistically do Sintra on your "half day" in Lisbon.

Is there any way you can extend your trip? I think your plan is way too heavy on days "in-transit" and without enough days "being there."

Personally, I have found that when I notice my itinerary includes "half a day here, half a day there" I eventually have to admit to myself that I have sliced things too thin, and it's time to re-examine my plan. The "half day self-deception" is a strong indicator (to me at least) that I'm trying too hard to stretch time, and it's time for me to step back and re-evaluate my plan. YMMV but I'd suggest you take a hard look at your plan to see if it's really going to give you a trip you will enjoy.

Sorry if that's not what you wanted to hear. I hope it's helpful and you have a great trip whatever you decide to do.

Thank you David. This is very insightful and I appreciate your candidness very much! We are coming from North America and cannot extend the trip (spring break for the young people). After planning to be in Portugal the entire time we decided it would be worth a bit of a "rushed" trip to add São Miguel. We may come to regret the planning on this trip - if so, we will just have to come back. :) Thank you again!

I had a feeling this might be a "spring break" trip constrained by school calendars.

You know, there are direct flights from several cities in North America to the Azores (check TAP, SATA, and even United Airlines). Service tends to be highly "seasonal" so options in March may be extremely limited. But if you can manage it (even if it required a domestic connection before the Azores flight) it could work out so much better for you (your trip is short, but what looks most problematic is that you're going by way of Lisbon, with all those stops). If you can skip the detour to mainland Europe, then you get a full week (all non-travel days) in the Azores, without that long detour to Lisbon, and the extra days you gain would make a big difference. (Lisbon is wonderful, an underappreciated gem, but save it for another trip when you can do the mainland justice.)

I would try hard to get a flight direct from North America to Ponta Delgada.

You probably already know this, but the Azores get a lot of rain, year round (I was there in late August and most of September; it rained almost every day). In March, I would expect pretty dynamic weather (that is, expect the weather to change multiple times during the day, and be ready for the possibility of lots of rain). It may be the most "wet" place I've ever been (and I live in a famously wet place, have been to many rain forests and jungles). You'll see lots of green. It's beautiful, but be prepared for "interesting" weather.

BTW, I just checked: although United does have a nonstop between Newark and Ponta Delgada, it's summer only, so won't work for you in March.

Good news: SATA (also known as Air Azores) flies year round between New York (JFK) and Ponta Delgada. Their schedule is reduced in the "off season" when you are going, but in March they still fly 2X per week (JFK to PDL outbound on Fridays and Saturdays; returning PDL to JFK on Thursdays and Saturdays); service frequency increases to 5 days per week during the last week of March and 6 days per week in summer.

SATA is a codeshare partner with TAP (which is a member of Star Alliance) so (if New York isn't convenient for you) you could probably book a domestic leg to get you to JFK to catch the SATA nonstop to Ponta Delgada, all on one ticket. SATA also flies from Boston and Toronto in March (I did not look at those schedules). SATA flights can be surprisingly inexpensive.

I'd take a serious look at this option. Consider skipping the detour to Lisbon; that nonstop from JFK to PDL could get you almost a full week on the ground on São Miguel. It would also spare you the long schlepp of flying all the way to mainland Europe, then turning around and flying 1/3 of the way back across the Atlantic just to reach your destination, and arriving feeling like you've been through an ordeal just to get there.

That sounds like a much better experience to me. Hope this helps. If you have specific questions about the Azores, feel free to PM me. There's also an excellent resource listed in the Portugal forum here (see Carl's Guide to the Azores), which I highly recommend.

Have fun and good luck.

Super helpful and I will look into these direct options. Thank you again for all the assistance/advice - much appreciated!

We did a similar trip over 14 days but also spent a couple of days in Evora. With such a tight schedule, maybe head to Sao Miguel as your first stop and then stay in Lisbon doing a day trip to Sintra.

We arrived late so stayed at the airport Melia hotel (nice, not expensive and 5 min walk from front doors of airport) before early flight to Sao Miguel. We had 4 nights (3.5 days) there with our base being in a central location in Ponta Delgada. Spent the day of arrival in town which is totally walkable. A car was a timesaver and we explored the entire island over 3 days. We even had time the last morning to wander the town before our flight. We figured we would need to go back to spend time there and explore the other islands.

Lisbon serves a few days minimum and Sintra can be done in full day trip starting with first train out.

I agree with the other suggestions - try to minimize the half days and travel days. Went early June and had rain on Sao Miguel but it was beautiful. There are a lot of great restaurants in Ponta Delgada - the favorite was Rotas - vegetarian but even the meat eaters really enjoyed it - went there twice for dinner - reservations needed otherwise a long wait. Enjoy your trip!