Hi! It feels good to be writing a message on here again and means we are finally planning a fun trip I've had so much success with advice from these boards in the past, so here goes...

I am planning a vacation in Europe summer-ish 2011, with my husband and our 4-year old son, who is a great traveler. Timeframe is open but I'm thinking we'll make the trip about 7-10 days in length, and we can go pretty much any month, though I'd prefer it not to be stifling hot. From what I've read, I've narrowed it down to Portugal at this point. There is so much information out there so I'm just looking for basic itinerary/city suggestions so I can plan from there. Budget is very flexible. There is a chance another family would join us, in which case that would probably limit us in choices more, but that's unknown at this point. We'd be traveling from the US. Here's what I know:

1. would love a great beach for a few days
2. the Azores look intriguing
3. we're not complicated - not so much into the whole "tourist" thing as much as just getting a great experience. I'd much rather enjoy the day in a casual fashion as opposed to cramming in every major attraction.
4. would like to do whale watching
5. a chartered yacht/sail sounds great
6. and as a sidenote, our 4-year old son would greatly love anything medieval - castles, etc

Suggestions on cities/locales? Also unsure re: transportation, i.e. if renting a car is a good option. I'm familiar with driving in Europe... well, at least Ireland.

Thanks!

Hi jumper

Have you considered the Algarve? We spent a week in a villa with pool down there a couple of years ago - and it's beautiful. Plenty of fabulous sandy beaches and even a sprinkling of castles - very layed back. We took a day out and drove up to Lisbon, staying overnight (your son would love Sintra) - that was easily do-able. And, from the Algarve, we drove to Seville, Spain for a couple of nights, before returning to the Algarve to fly home to the UK. The Alcázar of Seville is stunning.

I think you need to see the azores as being "outside" of Portugal as is Madeira. I loved the azores and it is worth surfing this site to read about that area (I think I loaded my visit report a few years ago).

Tavira on the South East is a lovely town with great beaches off shore (out side the lagoon)

Lisbon itself is great and there is a trireme (or what ever it was called in the medieval period) still in the boat yard or Arsenal. Lisbon is surrounded by the Duke of Wellington's lines of defence against the evil French.

If you want Modern European beach holidays at their worst goWest of Faro , however if you keep going West you will find a national park along the coast to Lisbon.

If you want another city to visit then Porto is interesting , if a little beaten down, and is connected by a good train service.

Roads are good and while the locals are pretty stupid at driving generally we are talking the sensible side of the Belgians or Italians. Weater avoid July and August unless sure of the westerly breeze

If it were me and I could fly from the states I'd look at the Azores, such nice friendly people and little crime, our whale watching there was wonderful. The Azores weather varies daily

If you are traveling from Boston (or Toronto) then SATA International will sell you a ticket to Lisbon with Azores stopover. Ponta Delgada is only 4.5-5 hrs from Boston. Otherwise it's a two hr flight from Lisbon. On our trip we were in Lisbon, visited Sintra (lots of castles) and Praia Rocha (Portimao) in Algarve. Very positive impressions of the whole trip. My trip report with some pixs is here http://harryk.hostzi.com/TripReport.html

Some of the pousadas are medieval castles. Maybe you can spend a night in 1 of those, if it's within your itinerary. We'll be staying in the one in Obidos a week from today!

See www.pousadas.pt

Thanks everyone, this gives me a great start. I am on the thought-process of doing a multi-leg flight approach, starting with 2-3 days in Azores (Ponta Delgada) then heading to Lisbon (or reversed). I wish the Sata flight website would give you the "flexible date" option on the multi-city flights since the few random dates I've plugged in don't seem to be available. But, we'll see, just time consuming to figure out. So that's where I'm at right now. I read about the Algarves and other than fabulous beaches, am not sure about much to do there with a child?

Algarve is is big on golf and aqua parks so may be dull for a 4 year old.

Yes, SATA website is not pulling correct schedule for 2011 and that's multi-city is failing. You can contact [email protected] if you have specific dates in mind. Their prices change daily. However return look up works. I randomly checked June 2011; then operate 1 stop flights on Tue, Fri & Sat from BOS to LIS. PDL to LIS and vise verso is daily; more than one per day. Toronto has non-stops to Lisbon and Porto

In Portimao (where we stayed) I would suggest dolphin boat trip for kids (as long as ocean is calm). Also there are water parks with some rides suitable for younger children. Buses from water park companies pick and drop off for free. Beach in Alvor is better for children; no steps and calmer water.

To jumper22

Multi city fare look up on sata.pt started to work (I tested BOS-PDL-LIS-BOS in Jun 2011)

THe Algarve (we have been at least 4 times)would be a great home base, especially with a child. Lots of European tourists in the summer and can be quite crowded, but easy going. We got an apartment at Villa Moura and rented a car. You can visit a lot of little towns inland from there, also go to Sagres, which has some of the most spectacular ocean seens we have ever seen...

As for us (we leave in a week) we are now more interested in the north country, Douro valley and north of that. While it is a small country, one must account for traffic, time being lost LOL etc..Just don't do what many do...try to see too much in too short of time. I'd vote for the Algarve (if you get a 'self catered' apartment, you can stroll to the beach...lots of play grounds and even an amusement park, if I remember correctly.

I'm just back from Portugal - we started in Lisbon, went as far east as Evora, and saw Sintra, Obidos, Alcobaca, Tomar, and Coimbra, before relaxing in the Douro valley for a few days and ending the trip in Porto. If I had it to do over again, I'd spend a week in Porto/Douro valley. The rest was nice, and I'm glad I went, but we really didn't relax until we got to the wine country.

We drove (after Lisbon), and it was not the horror I had come to expect given so many of the posts. Roads are well-marked and generally in good-to-excellent repair.

One strange fun-fact not mentioned heretofore regarding Portugal: the beds are hard. You've been warned!