Sintra, Cabo da Roca & Cascais: Small group tour with guide

Summary

Sintra’s palaces, wild Atlantic cliffs & Cascais by small group tour

You’ll wander Sintra’s magical gardens, taste local pastries in old town bakeries, stand above crashing waves at Cabo da Roca, and end your day exploring Cascais—all with a friendly local guide who knows every shortcut and story. It’s a mix of fairytale palaces, wild Atlantic air, and small moments you’ll remember long after the trip.

What’s the experience like?

The first thing I noticed in Sintra was the way the air smelled—kind of sweet and mossy, almost like old stone after rain. We’d barely stepped off at the train station when our guide, Joana, waved us over with this big grin and a “Bom dia!” that made me feel like we were meeting an old friend instead of starting a day trip from Lisbon. She handed out pastel-colored tickets for Pena Palace and warned us about the uphill walk (“Don’t worry, it’s worth it—I promise!”). She was right. The path wound through gardens that felt half-wild, half-fairy tale; I kept brushing past ferns and catching flashes of yellow and red through the trees. At one point, a peacock just strutted across our path like he owned the place. I didn’t expect that.

Pena Palace itself is almost too much to take in—tiles everywhere, towers popping up at odd angles, and these views that make you stop talking for a second. Joana pointed out the Moorish Castle on another hilltop (“That one’s older than Portugal itself,” she said), but honestly I was still thinking about how cold the stone felt under my hand on the terrace. After wandering back down into Sintra’s old town (cobblestones are no joke), we tried queijadas and travesseiros from this bakery where the woman behind the counter winked when I tried to order in Portuguese—probably butchered it but she seemed amused.

We didn’t go inside every palace—just quick stops for photos at Monserrate and the National Palace—but then we drove out past Colares vineyards toward Cabo da Roca. The wind there is something else; salty and sharp, it gets into your sleeves no matter what you’re wearing. Standing on those cliffs looking out at nothing but Atlantic blue…well, you get quiet for a minute. Joana said locals come here to clear their heads or just watch storms roll in. I can see why.

The drive along Guincho Beach toward Cascais was all wild grass and crashing waves—I kept trying to snap photos but they never looked quite right compared to being there. We stopped at Boca do Inferno (the “Mouth of Hell”—which sounds dramatic but actually just means big waves smashing into rocks) before rolling into Cascais. Some people stayed to wander around; I grabbed a coffee by the bay and watched kids chasing pigeons until it was time for the train back. It wasn’t perfect—my shoes got soaked at one point—but I still think about that view from Cabo da Roca when things get noisy back home.

Step-by-step itinerary

Day 1 — Explore Sintra and Pena Palace

• Visit Pena Palace Park and Terraces
• View Moorish Castle
• Visit Sintra Old Town and try local treats
• View National Palace of Sintra
• Visit Quinta da Regaleira
• Pass through Natural Park
• View Monserrate Palace

Day 2 — Cabo da Roca and Cascais Coast

• Photo stop at Cabo da Roca
• Drive along coastal road including Guincho Beach
• Visit Boca do Inferno
• Arrive and explore Cascais bay

Top questions

How long does this Sintra, Cabo da Roca & Cascais tour last?

The tour covers all highlights in one day as a small group experience.

Is pickup included for this day trip from Lisbon?

Pickup is included at Sintra Train Station; drop-off is at Cascais Train Station.

Are entrance fees to Pena Palace or Quinta da Regaleira included?

No, admission fees (up to 10–12 € each) are not included in the price.

Is lunch provided during the tour?

No lunch is provided but there’s time in Sintra old town to buy pastries or snacks.

How many people are in each group?

The maximum group size is 8 people per booking.

Is this tour suitable for children or infants?

Yes, infants can join using prams or strollers; infant seats are available if needed.

Do we visit inside all palaces?

You’ll visit inside Pena Palace park/terraces and Quinta da Regaleira; other palaces are seen from outside or specific viewpoints.

What should I wear for this tour?

Comfortable walking shoes are recommended due to cobblestones and some uphill paths.

What’s included

Your day includes pickup at Sintra Train Station with a friendly local guide who also drives between stops; sightseeing through Sintra’s palaces (with entry possible at Pena Palace park/terraces and Quinta da Regaleira), scenic drives past Colares vineyards to Cabo da Roca cliffs, photo stops along Guincho Beach and Boca do Inferno, plus drop-off at Cascais Train Station—all local taxes and fuel covered so you can just focus on exploring.