Sintra & Cascais Private Tour: Palaces, Coast & Dinosaur Tracks

Summary

Explore Sintra’s Palaces, Cascais Coast & Ancient Footprints

You’ll get picked up in Lisbon and whisked away to Sintra’s palaces, secret gardens, and dramatic coastlines—all with a local guide who knows every shortcut and story. Taste regional treats, stand at Europe’s edge at Cabo da Roca, explore Cascais’ beaches, and touch ancient dinosaur footprints most visitors miss.

What’s the experience like?

We kicked off the day with a smooth pick-up right at our hotel in Lisbon—no scrambling for trains or buses. Our guide, João, was already waiting with a comfy van (Wi-Fi on board, which was handy for sharing photos). The drive up to Sintra felt quick; mist hung over the hills and you could smell eucalyptus as we wound through the forest roads. João pointed out old tram tracks—apparently they still run on weekends if you’re curious.

Pena Palace looked like something out of a storybook. We decided to spend extra time wandering the gardens—almost 200 acres of winding paths and little streams. There were trees from Japan and Australia mixed in with Portuguese oaks. I grabbed a pastel de nata at the palace café while watching clouds drift below us. If you want to go inside the palace itself, João can help skip some of the lines (trust me, it gets busy after 10am).

Next up was Quinta da Regaleira. The gardens here are wild—caves, secret tunnels, tiny towers everywhere. The Initiation Well is spooky but fascinating; walking down those spiral steps feels like stepping into another world. João explained all the Masonic symbols carved into the stones—he really knows his stuff.

Lunch was in Sintra’s historic center at a spot João recommended (I went for grilled octopus; my friend tried bacalhau). We sampled queijadas and ginjinha from a tiny bakery where the owner chatted about her family’s recipes. The town itself is full of little shops selling cork bags and ceramics—easy to lose track of time here.

After lunch we stopped by Monserrate Palace—a quieter spot with Moorish arches and crazy botanical gardens. Then it was off to Cabo da Roca, Europe’s westernmost point. Windy doesn’t even begin to cover it! You can see waves crashing far below and there’s this salty tang in the air that sticks with you.

Cascais came next—a seaside town that feels both fancy and laid-back at once. We walked along the marina where fishermen were mending nets beside sleek yachts. At Boca do Inferno, waves thundered into a huge cave—the sound echoes across the cliffs when there’s a swell rolling in.

The real surprise? Dinosaur footprints right on the beach near Cascais! João knew exactly where to find them—huge prints pressed into stone, more than 70 million years old. It’s wild thinking about what used to walk these shores long before us.

Step-by-step itinerary

Day 1 — Explore Sintra's Palaces and Gardens

• Visit Pena Palace gardens and palace
• Explore Castle of the Moors
• Tour Quinta da Regaleira and Initiation Well
• Lunch and stroll in Sintra historical center
• Visit Monserrate Palace and botanic gardens

Day 2 — Coastal Sights and Cascais Town

• Wine tasting visit
• Visit Cabo da Roca, westernmost point
• Explore Cascais villa and town
• Visit Mercado da Vila in Cascais
• See Boca do Inferno cave

Top questions

Is this tour suitable for families with kids?

Absolutely! The tour is flexible—we’ve had families with strollers and even grandparents join in comfortably. There are plenty of stops for snacks or bathroom breaks too.

Can we customize which palaces or sites we visit?

Yes! You decide how long you want at each stop or if you want to skip any places altogether. Just let your guide know your preferences on the day.

Are tickets to attractions included?

No, entrance fees aren’t included so you can choose which sites you want to enter—but your guide will help arrange tickets quickly so you don’t waste time in line.

What should I bring?

I’d suggest comfy shoes (lots of walking), a light jacket (Sintra can be cool even in summer), sunscreen for Cabo da Roca/Cascais, and maybe some cash for small shops or bakeries.

What’s included

Your own private van with Wi-Fi and AC; friendly local guide/driver; pick-up/drop-off wherever suits you in Lisbon; tasting of regional sweets and drinks; flexible schedule—you set the pace! Wheelchair accessible options available too.