What to Do and What to Pack: Cascais, Portugal in the Fall

I spent a few days in Cascais a couple October’s ago, and it turned out to be exactly the break I needed. I went mainly for a yoga retreat but made time to explore the town and slow down. Here’s what I loved, what I’d do again, and some tips if you’re planning a trip.

Salty Pelican Yoga Retreat

The main reason for my trip was The Salty Pelican Yoga & Surf Retreat. Mornings started with yoga by the ocean, which set the tone for the day. Evenings were restorative sessions that were the perfect reset before dinner.

The retreat offered surfing too, but I skipped it and spent that time relaxing, journaling, or heading out for a walk. The space felt welcoming and casual, and it was easy to connect with other travelers. If you’re looking for a place to reset, this is a great option. I met a couple of wonderful people that were both there for the yoga and the surfing, and we had such a fun time bopping around the town together. Ubers were our friend but there was so much to do in town and just getting to know each other at the retreat. I made friends from the Netherlands, Germany, Norway and more, and I am lucky to still keep in touch with a few of them still.

Exploring Cascais

When I wasn’t at the retreat, I explored Cascais. The town is small and easy to walk around, which made it perfect for slow mornings and afternoons without an agenda.

Some of my favorite stops:

• Santa Marta Lighthouse – A quiet spot with great views of the harbor.

• Boca do Inferno – Waves crash dramatically against the cliffs here. Go around sunset for the best light. This was the most insane sunset I have ever seen and the pictures do not do it justice but its a start.

• Praia do Guincho – A wide, windy beach that’s great for a long walk.

Cascais has plenty of little shops, cafes, and tiled streets that are fun to just wander through.

Food Recommendations (With my allergies)

Finding safe food is usually stressful when I travel, but Cascais had some great options:

• Roots Café – Cozy spot near the train station with gluten-free and vegan options.

• Cozinha por Mim Gluten Free – 100% gluten-free bakery and restaurant. I grabbed pastries and take-away meals here a few times.

• House of Wonders – A colorful café with clearly marked gluten-free choices.

• Greenwish – Plant-based café with smoothie bowls, salads, and gluten-free desserts.

Having a handful of reliable spots meant I could actually enjoy eating out without worry.

Day Trip to Sintra

Cascais is just a short train ride from Sintra, which is an absolute must if you have even a day to spare. Sintra feels like stepping into a fairy tale—palaces, castles, and rolling hills everywhere you look.

Highlights I visited:

• Pena Palace – Brightly colored and perched on a hill, it’s impossible not to stop and stare.

• Quinta da Regaleira – The gardens, tunnels, and whimsical towers are perfect for wandering. I spent hours exploring and kept discovering new nooks.

• Sintra town center – Small streets lined with cafés and shops. It’s touristy but worth a quick walk to grab a coffee and enjoy the atmosphere.

If you’re only doing a day trip, I recommend starting early, picking 1–2 main sites, and leaving time to wander the town itself. The train back to Cascais is easy and relaxing after a full day of exploring.

What to Pack for October

The weather in October was mild—warm during the day but cooler in the mornings and evenings. Here’s what worked well:

• Light layers (sweaters, long-sleeve shirts, a light cardigan)

• Comfortable sneakers for walking on cobblestones and palace gardens

• Light jacket for evenings or coastal breezes. This was necessary for the morning walks to the pier to do yoga.

• Sunglasses and sunscreen

• One or two casual-but-nice outfits for dinner. It was a lot dressier than I anticipated so Im glad I had a few pieces but should have packed more mix and match than just my leopard print silk skirt and a black tee!

Boca do Inferno Sunset

Here are the Top 10 Things to do in Cascais to plan your trip:

1. Explore the Historic Centre
   Start by wandering the heart of Cascais. The cobblestone streets are lined with boutique shops, cafés, and pastel-colored buildings. It’s the perfect area to get lost for a few hours, pop into a local shop, or grab a coffee and watch the world go by.

2. Visit Boca do Inferno
   This dramatic cliffside spot is one of Cascais’ most famous natural attractions. Waves crash into the sea cave with a surprising roar, creating a striking spectacle. It’s especially beautiful at sunset, and it’s a quick walk from the town center.

3. Relax at Praia da Rainha
   This small, sheltered beach is perfect for a calm morning or afternoon. The water is clear, the sand is soft, and the atmosphere is relaxed—ideal if you want a little downtime away from the town’s buzz.

4. Walk the Cascais to Estoril Promenade
   A 2.3 km coastal path connects Cascais to Estoril. Along the way, you’ll pass beaches, gardens, and charming villas. It’s a peaceful walk with plenty of photo opportunities and a great way to stretch your legs after a yoga session.

5. Explore the Museu Condes de Castro Guimarães
   This neo-Gothic mansion-turned-museum houses art, archaeological finds, and a beautiful library. It’s a glimpse into Cascais’ aristocratic past and offers some quiet time in a stunning, historical setting.

6. Discover Casa das Histórias Paula Rego
   This small museum is dedicated to the works of one of Portugal’s most celebrated artists, Paula Rego. The exhibits are fascinating, often whimsical or bold, and the building itself is architecturally interesting.

7. Visit Santa Marta Lighthouse & Museum
   Located right by the water, this lighthouse is a quick stop but worth it for history buffs and anyone who loves a scenic coastal view. The small museum inside explains Cascais’ maritime history and is easy to explore in 30–45 minutes.

8. Tour the Citadel of Cascais
   This historic fortress now hosts art galleries, shops, and a few restaurants. Walking through the Citadel gives you a sense of the town’s past while offering plenty of modern touches, from exhibitions to ocean views.

9. Take a Boat Ride from Cascais Marina
   For a different perspective of the coast, take a short boat ride from the marina. Options range from traditional sailboats to eco-friendly electric tours. Seeing the cliffs, beaches, and town from the water is a peaceful way to spend an hour or two.

10. Take a Day Trip to Sintra
    Just a short train ride from Cascais, Sintra is a must-do. The town is dotted with fairy-tale palaces and historic estates, including Pena Palace and Quinta da Regaleira. Even just one day allows you to explore the main sites and wander the charming streets of Sintra town center.

This trip reminded me how much a change of pace helps. Yoga twice a day, long walks, a day trip to Sintra, and lots of gluten free option made it easy to relax. October is a great time to visit Cascais—fewer crowds, comfortable weather, and a calm atmosphere.

Anyone headed there soon?

Love, M