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Chris's Guide

Portugal.

Mainland. Azores. Madeira. Three very different places — one country.

The Overview

Portugal surprised me. Lisbon is walkable and pretty. The Azores has one of the best views I've ever seen. And, as someone who rarely revisits places, Madeira is somewhere I'd be interested in going back to.

Part One · Mainland Portugal

Lisbon, Sintra & the Algarve.

The Algarve is the main event. Note: Madeira and the Azores both require a separate flight — I flew Lisbon → Madeira → Azores.

Sintra castles Portugal
Stop 01

Sintra Castles

Sintra · 40 min from Lisbon

Worth a day trip. The Moorish castle is my favorite — old, weathered, great views. Palace of Pena is impressive but busy. Go early.

Moorish Castle Palace of Pena
Ponta da Piedade Algarve
Stop 02 · Algarve

Ponta da Piedade

Lagos · Algarve · Portugal

My favorite spot in the region. Golden sea stacks, turquoise grottos, clifftop paths that keep rewarding you. Park at the link and just wander. Praia do Camilo is a short walk away and equally beautiful.

Favorite in the Algarve Park Here
Marinha Beach Algarve
Stop 03 · Algarve

Marinha Beach Area

Lagoa · Algarve · Portugal

Beautiful clifftop viewpoints in every direction. Same move as Ponta da Piedade — park and walk the coastline.

Park Here
Benagil Cave Algarve
Stop 04 · Algarve

Benagil Cave

Benagil · Algarve · Portugal

Rent a kayak and paddle in. Little side caves to explore once you're inside. One of the more unique things I did on the coast.

Open in Maps

On Lisbon: I'm always chasing mountains, coastlines, and viewpoints, so cities rarely make my highlight reel. But Lisbon is enjoyable — it's clean, easy to walk, and has a charm that makes wandering around worthwhile.

Part Two · São Miguel, Azores · Requires a flight from Lisbon

The Azores.

I drove the entire island and thought most of it was fine. Then I got to Boca do Inferno.

Pico do Ferro Azores
Miradouro da Ponta do Sossego Azores
Worth Seeing

Around the Island

São Miguel · Azores

Pico do Ferro and Miradouro da Ponta do Sossego are both worth a quick stop if you're already exploring the island. Nice views, but neither were a highlight for me.

Pico do Ferro Ponta do Sossego
Boca do Inferno Azores
Top 5 Views in the World · #2

Boca do Inferno

São Miguel · Azores · Portugal

A collapsed volcanic crater opening to the ocean — water an impossible shade of blue, rimmed by black lava rock. I was blown away. Build your trip around this.

Open in Maps →
Part Three · Madeira · Requires a flight from Lisbon or Azores

Madeira.

One of the few places I'd actually go back to. Reminded me of Kauai. Skip the rental car — the tour infrastructure here is excellent. Just walk into the tourism offices around town and book the two tours below.

Boca do Risco hike Madeira
Tour 01

Boca do Risco Hike

Madeira · ~30€ · ~10km one way

Drop-off at the start, hike along the coast with a guide. One of the best hikes I've done. Relentless coastal views the entire way.

Trailhead →
Madeira island tour
Madeira island tour
Madeira island tour
Tour 02

Island Overview Tour

Madeira · Full day

Porto Moniz, Seixal, Lagoa Encantada (foggy trees — unreal), Lombo do Mouro, Miradouro da Terra Grande. Do this and Tour 01 and you've seen the island properly.

One thing I didn't do — Pico Ruivo hike. Genuinely disappointed I missed it. Highest peak on the island, views above the clouds. If you do it, let me know how it was.

More worth exploring.

Destination guides and honest takes from 39 countries and 44 U.S. states.

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