4 Days in Lisbon: The Perfect Winter Escape (for first-timers & returners)

Nana Guerreiro
Sep 4
3 min read

Winter is coming… and that’s great news if you're planning a getaway to Lisbon.

Mild weather, fewer crowds, warm pastries, golden light over terracotta rooftops — Portugal’s capital is the perfect destination for a long weekend. Whether it’s your first time or your fifth, we’ve got you covered with classic highlights and hidden gems. Let’s plan those 4 days right.

Day 1 – Lisbon’s Timeless Charm: Alfama, Baixa, and a Tram Ride

Start your Lisbon journey with a deep dive into its soul:

Alfama: Wander the narrow streets of the oldest district. Let yourself get lost, stop at a local café, and catch the scent of grilled sardines.
Sé Cathedral & Miradouros: Visit the cathedral, then climb to Miradouro de Santa Luzia or Portas do Sol for picture-perfect views.
Baixa & Praça do Comércio: Head downtown for elegant squares, shopping, and a stroll along the river.
Ride Tram 28: Yes, it’s touristy. Yes, it’s iconic. Jump on board and enjoy the vintage ride.

📝 Pro tip for winter: Grab a hot ginjinha (cherry liqueur) near Rossio Square — it warms the soul.

Day 2 – Belém & Beyond: A Day of Monuments and Custard Tarts

No trip to Lisbon is complete without visiting Belém.

Jerónimos Monastery: A UNESCO wonder with intricate Manueline architecture.
Belém Tower & Discoveries Monument: Take a scenic walk along the river to these iconic landmarks.
Pastéis de Belém: Need we say more? Yes, the line is worth it.
MAAT or Berardo Museum: For art lovers, there’s contemporary inspiration right nearby.

Optional stop: Head across the river to Cristo Rei for a panoramic view of Lisbon from the opposite bank. In winter light, the photos are stunning.

Day 3 – Cascais & the Coast: A Seaside Escape

Hop on a train (or join my tour!) and head to Cascais, just 40 minutes away:

Boca do Inferno: Watch waves crash into the rocky cliffs — dramatic even on calmer days.
Cascais old town: Stylish, relaxed, with great food and charming streets.
Guincho Beach: Windswept, wild, and beautiful even in winter. A great spot for photos and a coastal walk.

🧥 It’s winter, so bring a windbreaker, but don’t worry — it rarely gets truly cold!

Day 4 – For the Returners: Off the Beaten Path

If you’ve done the classics and want something more authentic…

Option A: Évora Day Trip

Head east to Alentejo’s crown jewel:

Roman Temple
Chapel of Bones (*“We bones that here are…” you’ll see.)
Quiet streets and local wine.Évora is a UNESCO World Heritage Site and feels like stepping into a history book — without the crowds.

Option B: Setúbal & Arrábida

For nature and food lovers:

Explore the Arrábida Natural Park: dramatic cliffs, blue waters, and peaceful beaches.
Lunch in Setúbal: seafood heaven (try choco frito!)
Stop by a vineyard for a winter wine tasting (we're in Moscatel country here).

🚐 Want to relax and enjoy without thinking about logistics? I’ll drive, guide, and fill the day with local stories.

Winter Bonus Tips

Light is gold. Winter light in Lisbon is soft and photogenic — ideal for photos.
Crowds are low. You can actually enjoy places like Jerónimos or Tram 28 without waiting in line forever.
Hotels are more affordable, and restaurants are easier to book.

Let me show you around - Day tours from Lisbon

Whether it’s your first time in Portugal or your tenth, spring is the season to fall in love with this country. And I’d love to be your local guide, driver, and storyteller.

Planning a trip doesn’t have to be overwhelming.

Sintra & Cascais Tour: Palaces, gardens, ocean views, and pastel de travesseiro? Say less. I’ll guide you through Pena Palace, Quinta da Regaleira, and we’ll end the day by the sea.
Fátima, Nazaré & Óbidos: Spiritual peace, monster waves, and medieval charm in one perfect day. You won't regret it.
Évora & the Cork Trees: History, wine, and a side of something unexpected.
Setúbal - Palmela: Wine, views, and the stunning Arrábida coastline — with dolphins if we’re lucky. It’s the kind of day that makes you fall in love with Portugal all over again.
Remember: I can also take you on a Lisbon half day tour — quick, fun, and packed with hidden gems only a local would know

With Portugal Journeys With Peppe, all you have to do is show up ready to smile, eat, explore, and maybe dance a little.

My Fleet

No matter your group size or travel style, I’ve got the wheels to match — from comfy SUVs to spacious minibuses and a full-size bus for the party people. Let’s ride in comfort and style!