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10 Day trip to Portugal in mid-march

I'm planning a 10 day solo trip to Portugal sometime in the 2nd/3rd week of March however was curious to see if there are any recommendations or tips! I'm currently torn on flying from EWR to either Porto or Lisbon, however leaning towards Lisbon considering the places i want to visit. I'm thinking of this trip will primarily be historical & cultural exploration, hiking, checking out different cuisines and ending with some nice R&R.

Would the 10 days be enough for these locations?
Lisbon or Porto / Sintra / Obidos / Nazare / Madeira or Azore

Portugal Itinerary - 10 day [draft]

EWR [Newark] – LIS [Lisbon]

Day 1: Explore Lisbon

  • Food & wine tour / Bike tour?
  • Wander?
  • Sleep in Lisbon

Day 2: Explore Lisbon & Sintra

Day 3: Explore Sintra -> Obidos -> Nazare

Day 4: Lisbon -> Madeira

  • Checkout of Lisbon Hotel and check into Funchal hotel

Day 5 - 10: Madeira

Day 4 – 10 options:

  • Rent a car for the rest of the week in Funchal?
  • Funchal: Sunrise Hike from Pico do Arieiro to Pico Ruivo
  • Madeira Best of the West Day Tour
  • Madeira South Coast Full-Day Tour
  • PR 8 - Vereda da Ponta de São Lourenço
  • Sao Vicente exploration
  • Ponta do Sol exploration
  • End with a Spa?

Then again this all depends on weather and if my body will be too tired

Would it be better if i rent a car in Madeira rather than relying on full-day guided tours? For traveling the first days i was thinking of just utilizing trains or maybe bus would be bettter and cheaper.

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