Sintra Private Convertible Wine Tour: Colares Winery & Cascais

Summary

Convertible Wine Tasting Tour from Lisbon to Sintra & Cascais

If you want to explore Sintra and Cascais in style—plus taste rare Portuguese wines—this private convertible tour is for you. Local guides, hidden spots, and real flavors make it special.

What’s the experience like?

Right after our guide picked us up at our Lisbon apartment, we cruised out in a shiny convertible with the top down—felt like a movie. The salty air hit us as we drove along the coast, and you could actually see where the Tagus River spills into the Atlantic. There’s this spot where the water changes color, and if you’re lucky, you’ll catch fishermen casting lines right off the rocks. Our guide, Miguel, pointed out a tiny café near Campo de Ourique Market where locals grab their morning bica—wish we’d had time to stop.

We rolled through Cascais, which still has that old fishing village vibe even though it’s pretty lively now. There’s a marina packed with boats and a little bakery on the corner selling warm pastéis de nata. Free time here meant wandering the narrow streets, watching surfers haul boards down to the sand, and hearing gulls squabble over crumbs. The sun was already warming up by mid-morning, so we ducked into the shade whenever we could.

Driving through Sintra-Cascais Natural Park, we stopped at a beach I’d never heard of—windy, with kitesurfers zipping across the waves and the smell of grilled sardines drifting from a shack nearby. At Cabo da Roca, it gets blustery; you can stand right at the edge of Europe and see nothing but ocean and sky. There’s a stone marker there, and if you squint, you’ll spot wildflowers clinging to the cliffs.

The real highlight? The Colares winery. It’s Portugal’s oldest, tucked away behind stone walls and run by folks who know their stuff. We tasted two DOC Colares wines and a 15-year-old Ramisco—earthy, almost salty from the sea air. The enologist explained how their vines grow in sandy soil, which is rare. You can actually feel the coolness in the cellar, even on a hot day.

Lunch was in Sintra’s historic center—UNESCO-listed, all pastel buildings and cobbled lanes. Our guide suggested a spot for grilled octopus (can’t remember the name, but it had blue tiles everywhere). Afterward, we picked which palace to visit based on what was less crowded—Miguel checked his phone for updates so we could skip the lines. By late afternoon, we were back in Lisbon, sun-tired but happy.

Step-by-step itinerary

Day 1 — Coastal and Wine Tour in Sintra Region

• Hotel pickup and coastal sightseeing
• Visit WWII spy gathering site
• Explore Cascais fishing village
• Sightseeing at Sintra-Cascais Natural Park beach
• Visit Cabo da Roca westernmost point
• Tour oldest winery with wine tasting
• Lunch in Sintra UNESCO Heritage center
• Visit Sintra palace
• Drop off at hotel or meeting point

Top questions

Is this Sintra wine tour suitable for beginners or non-wine experts?

Absolutely! The enologist explains everything in simple terms, and you can just enjoy the tasting—no prior knowledge needed.

Can you pick us up from our Airbnb in Lisbon?

Yes, pick-up and drop-off are available from hotels, Airbnbs, or meeting points in Lisbon or Cascais.

Are vegetarian options available for lunch in Sintra?

Yes, there are several restaurants with vegetarian dishes—your guide can recommend some good ones in the historic center.

What should I wear for this tour?

Comfortable clothes and layers—Sintra can be cooler than Lisbon, especially near the coast. Sunglasses and sunscreen help too!

What’s included

This tour includes private transportation in a convertible car with a local guide, bottled water, entry and tasting at Adega Cooperativa de Colares (with three wines), and pick-up/drop-off in Lisbon or Cascais. Lunch isn’t included, but your guide will help you find great local spots.