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Portugal with multi-families and toddlers. Looking for tips!

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My close friends and I had a successful European adventure together two years ago, when about ten of us trekked from Rome, to Capri, to Positano together and had an amazing experience. Now, we all just started our famiies and want to have a new adventure together in Portugal, probably May 2012, when our babies will be 8 months, 8 months, 11 months, 16 months, and 20 months (mine). (Yes, we've all been busy). Not everyone is yet convinced they will come, but so far we are planning for the whole group. We'll probably at least get three families in.

We realize our new approach will be more "slow travel" and that a true home base is needed- we thought Sintra would be just the place, as we can leisurely visit castles, beaches, and the city of Lisbon all from Sintra. We realize that our days will be organized around naps and childcare duties, but we can still plan a worthwhile trip even under these constraints.

My personal itinerary will likely be close to two weeks- fly into Porto (maybe spend the night or two), drive to the Douro for some relaxation and wine tastings, visit my aunt in the mountains for a couple of nights, then drive down to Sintra to meet up with the group for a week, with a stop in Coimbra (visit the children's park) to break up the drive. We'd fly home (to Providence) from Lisbon.

I've also been to Sintra/ Cascais/ Lisbon, so that makes it a little easier on the planning, but planning with a toddler is VERY different and I am looking for tips. For example, i remember the Moorish castle having some pretty dangerous heights and would not think it baby/toddler friendly at all. Can I get a small stroller through the Pena Palace, or would a baby carrier be necessary? Other plans I had in mind with the babe- day trip to Obidos, beach days at Guincho beach and Cascais, the Oceanario in Lisbon, museums and sights in Lisbon, etc. If anyone has had particular success (or even failure) with these places with your little ones, could you please chime in??

I've checked some other websites (Deliciousbaby and CiaoBambino) devoted specifically to traveling with babies and small children, but haven't seen any reports on Portugal. Any advice is welcome!

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