A Guide to Visiting Pena Palace & Quinta da Regaleira in Sintra, Portugal

If there is one place in Portugal that feels straight out of a fairytale, it is Sintra. Nestled in the hills just outside Lisbon, this charming town is home to two of the most magical landmarks: Pena Palace and Quinta da Regaleira.

We recently explored both during our latest trip to Portugal, where our shoes are expertly handcrafted, and it was pure magic — colorful, steep, a little chaotic, and completely unforgettable.

1. Start Early and Prepare for Hills

Sintra is built on a series of steep, winding roads surrounded by lush greenery. Arrive early to beat the crowds and plan to walk a lot. Comfortable shoes are a must. We wore our Paisley Sneakers and walked over six miles exploring the palaces and gardens. No blisters, no discomfort, just effortless comfort and style.

Tip: Bring water, start early, and know that it is hilly but worth every step.

2. Pena Palace: A Kaleidoscope of Color

Perched high above Sintra, Pena Palace looks like something out of a dream. Its vivid yellow and red towers and sweeping views over the Atlantic coast make it one of Portugal’s most iconic sights.

Get your tickets ahead of time and be punctual. Entry times are enforced, and the lines can be long. Taking an Uber or taxi up to the entrance is the easiest way to avoid the steep uphill walk.

Once you arrive, take your time wandering through the terraces and gardens — every corner reveals a new detail, from intricate tiles to romantic viewpoints overlooking the town below.

Joyasol Insider Tip: If you can, visit during the shoulder seasons of spring or fall. It is cooler, less crowded, and more enjoyable. In summer, it can get very hot and packed with tourists.

3. Quinta da Regaleira: Mystical and Mysterious

Just a short drive from Pena Palace (or about a 45 minute walk if you are up for a hike like we were) Quinta da Regaleira feels like stepping into another world. This romantic estate is filled with underground tunnels, mossy fountains, and secret passageways that make you feel as though you have wandered into a storybook.

Do not miss the famous Initiation Well, a spiral staircase descending deep into the earth. It is mesmerizing and symbolic, representing a journey into self-discovery and rebirth.

Exploring every pathway and hidden corner feels magical. You will want time to get lost in the gardens, listen to the sound of running water, and take in the beauty of nature surrounding you.

Tip: Buy tickets in advance for this one too and bring water. The walkways are steep, and the estate is large, so give yourself at least a couple of hours to explore.

4. Where to Eat and Recharge

After a morning of exploring, stop by Tascantiga, a cozy spot serving traditional Portuguese tapas and local wine. For something sweet, grab a pastel de nata from Piriquita, a legendary bakery that has been delighting visitors since 1862.

If you have time, stop by one of the small cafés tucked along Sintra’s winding streets and enjoy a coffee while people-watching. It is a charming way to end your day before heading back to Lisbon.

5. Make It a Day Trip or Stay the Night

Sintra is an easy 40 minute train or Uber ride from Lisbon, but if time allows, stay overnight. The town has a completely different feel once the day-trippers leave. The streets quiet down, the fog settles over the hills, and the palaces glow softly at dusk — it is an experience you will never forget.

We stayed in nearby Cascais, which was only about a half hour Uber ride. Another top Portugal destination that we'll write a blog post on soon. 

Final Thoughts

Sintra is one of those rare places that captures both your imagination and your heart. Between the vivid colors of Pena Palace and the mystery of Quinta da Regaleira, every moment feels cinematic.

It is a reminder that the best experiences often lie just beyond your comfort zone — and that the right shoes can make all the difference. Our Paisley Sneakers, handcrafted in Portugal, carried us through more than six miles of hills, cobblestones, and palace grounds without a single blister or ounce of discomfort.

So go ahead. Take the trip. Wander a little farther. Step out of your comfort zone and into a fairytale.