Sintra & Cascais Day Tour: Pena Palace, Regaleira, Cabo da Roca

Summary

Private Sintra and Cascais Tour with Pena Palace & Ocean Views

You’ll walk through fairytale palaces in Sintra, explore mysterious gardens at Regaleira, feel Atlantic winds at Cabo da Roca, hear waves crash at Boca do Inferno, then unwind with fresh seafood in lively Cascais—all in one relaxed day with private transport.

What’s the experience like?

The air up in Sintra always feels a bit cooler—maybe it’s the thick forest or just the altitude, but you’ll notice it as soon as we step off the van. Our guide, João, met us right by the entrance to Palácio da Pena. The palace sits high on a rocky peak—second highest in the Serra de Sintra—and honestly, it looks like something out of a storybook with its mix of bright colors and odd towers. We wandered through the gardens first; I kept catching whiffs of wet moss and wildflowers after last night’s rain. João pointed out Cruz Alta above us (it’s at 528 meters), which apparently is the only spot higher than where we stood. Photos here just don’t do justice to how wide the views stretch—on clear days you can see all the way to Lisbon.

Quinta da Regaleira is just a short drive downhill, tucked behind old stone walls and shaded by massive trees. The place feels secretive—there are winding paths, hidden tunnels, even a well that spirals deep underground (João called it an “initiation well”—something about old Masonic rituals). The gardens are wild but somehow still neat; I spotted a couple of frogs near one of the little lakes. The palace itself mixes all sorts of styles—bits of Gothic arches next to Renaissance windows—and was built in the early 1900s when Portugal still had a king.

After lunch (we grabbed sandwiches from a tiny café near Sintra’s center—try the queijadas if you’ve got a sweet tooth), we headed west toward Cabo da Roca. Wind picks up here; you’ll want a jacket even if it’s sunny. Standing at what Camões called “where land ends and sea begins,” you really get that sense of being at Europe’s edge—the cliffs drop straight down to crashing waves below. There’s an old lighthouse from 1758 still working away, and our guide mentioned some rare plants grow around here that botanists come to study.

On our way to Cascais, we stopped at Boca do Inferno—a spot where waves slam into jagged cliffs and spray shoots up through a collapsed cave. It’s loud, almost hypnotic if you stand there long enough. Locals say sunsets here are unreal, but even mid-afternoon it felt dramatic.

Cascais itself is lively—a mix of families strolling along the marina and surfers heading for the beach. We ended our day with grilled fish at one of those seaside restaurants where tables spill onto the sidewalk. The smell of saltwater never really leaves your nose here. If seafood isn’t your thing, there are plenty of other options too; Cascais has something for every taste and budget.

Step-by-step itinerary

Day 1 — Sintra and Cascais Highlights

• Visit Pena National Palace
• Explore Quinta da Regaleira
• See Cabo da Roca
• Visit Boca do Inferno cliffs
• Enjoy Cascais beaches and cuisine

Top questions

Is this tour suitable for families with young kids?

Yes! Kids love exploring the palaces and gardens. We have infant seats available and strollers/prams fit easily in our vehicles.

Are entrance tickets included?

No, tickets for attractions like Pena Palace or Quinta da Regaleira aren’t included so you can choose what you want to visit inside.

How accessible is this tour for people with mobility needs?

The vehicle is wheelchair accessible and service animals are welcome. Some palace areas have steps or uneven ground but most main paths are manageable.

What should I bring?

A light jacket (it gets windy at Cabo da Roca), comfy shoes for walking, camera or phone for photos—and maybe some cash for snacks or souvenirs.

What’s included

This tour covers private transportation in an air-conditioned vehicle with WiFi onboard. We provide specialized infant seats on request and can accommodate wheelchairs or strollers easily. All ages and fitness levels welcome!