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Lisbon/Algarve April 2026 5 day itinerary

My son and I are traveling to Portugal in April for 1 week. We are planning possibly 3 days in Algarve and 2 or 3 days Lisbon/Cascias. In Algarve, where is the best location to stay if we want to kayak the caves, hike and see the surfers. Should we pick just one city or possible do 2 different city stays? Also, what about a night in Cascias or should we just stay in Lisbon and do day trips from there to Sintra/Cascias?

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Are you familiar with the Seven Hanging Valleys Trail? You can kayak and hike on this one. Best place to sleep is Carvoeiro or Praia da Marinha/Benagil. April is not surfing season in the Algarve.
Sleep in Lisbon and do a day trip to Sintra, however, you need four nights alone to enjoy Lisbon’s old towns. No need to visit Cascais if you’re going to the Algarve.

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I have heard of the Seven Hanging Valleys and that is part of the plan while there. Do you recommend booking excursions ahead of time or can we book a kayaking or boat trip once there? What about Faro or Lagos?
I was thinking one day in the town of Lisbon would be enough thinking it will just be another big city. But, definitely want to see Peña Castle, National Palace and a monastery. This is a surprise birthday trip from my son and I have never done research or anything on Portugal and it can get a little overwhelming.

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The Seven Hanging Valleys Trail is a self-guided walking trail that doesn’t require a booking. Boat Tours to Benagil Cave can be made through tour operators i.e.: https://www.getyourguide.com/lagoa-l90069/seven-hanging-valleys-t493215/ and https://acoupledaystravel.com/how-to-hike-the-seven-hanging-valleys-trail/.
Download Rick Steves app on your phone before leaving home and take his Lisbon City Walk. Make sure you get an early start the day you visit Sintra.