Our 5-Night Lisbon, Portugal Itinerary: Castles, Beaches & Day Trips
After finishing my solo five-night trip through Ireland, I flew to Lisbon to meet up with two friends for the next leg of our Europe adventure.
We spent five nights using Lisbon as our home base while exploring the city and taking day trips to Sintra, Colares, and Sesimbra. The trip ended up being the perfect mix of colorful palaces, historic castles, hidden beaches, amazing viewpoints, and great food.
I’ll admit, I’m usually more of a mountain and national park traveler than a city traveler, so I wasn’t sure what to expect. But Lisbon was an awesome city. Every neighborhood had its own personality, there were incredible viewpoints around almost every corner, and we were constantly stumbling across hidden cafés, gardens, and local spots that weren’t even on our itinerary.
If you’re planning your first trip to Portugal, I think five nights is a great amount of time. We were able to experience Lisbon’s highlights while still fitting in a few unforgettable day trips without feeling rushed.
The only issue was that it was very hot when we were there from August 19th to August 24th.
Here’s exactly how we spent our five nights in Portugal.
Portugal Itinerary at a Glance
| Day | Destination | Highlights |
|---|---|---|
| Day 1 | Lisbon | Belém Tower, Garden of the Empire Square, São Pedro de Alcântara Viewpoint |
| Day 2 | Sintra & Colares | Pena Palace, Quinta da Regaleira, Monserrate Palace, Azenhas do Mar |
| Day 3 | Sesimbra | Praia da Ribeira do Cavalo, Pink Street nightlife |
| Day 4 | Lisbon | Portuguese food, Ginjinha, exploring the city |
| Day 5 | Lisbon | São Jorge Castle, Sunset Sailing Tour |
| Day 6 | Departure | FlixBus to Madrid |
Trip Highlights
Belém Tower
A UNESCO World Heritage Site built in the 1500s, Belém Tower once protected Lisbon’s harbor and is one of the city’s most famous landmarks. Sitting right along the Tagus River, it’s a great place to start exploring Lisbon.
Pena Palace
Perched high above Sintra, Its bright yellow and red towers, colorful terraces, and panoramic views make it one of Portugal’s most iconic attractions.
Quinta da Regaleira
One of Sintra’s most unique estates, Quinta da Regaleira is known for its beautiful gardens, underground tunnels, hidden grottoes, and the famous Initiation Well.
Monserrate Palace
The mix of Gothic, Moorish, and Indian-inspired architecture surrounded by botanical gardens makes it feel completely different from the other palaces.
Praia da Ribeira do Cavalo
This tucked away beach near Sesimbra is famous for its crystal-clear turquoise water and cliffs. Whether you hike in or arrive by water taxi, it’s easily one of the most beautiful beaches we visited in Portugal.
São Jorge Castle
This medieval castle sits high above Lisbon and offers some of the best panoramic views of the city and the Tagus River. It ended up being my favorite castle of the entire trip.
Sunset Sailing Tour
Watching the sun set behind Belém Tower while sailing along the Tagus River with a glass of champagne was the perfect way to end our Portugal adventure.
Why We Chose This Itinerary
Since none of us had been to Portugal before, we wanted to experience more than just Lisbon.
Using Lisbon as our home base made it easy to take day trips to Sintra’s famous palaces, relax at one of Portugal’s most beautiful beaches in Sesimbra, and still have plenty of time to explore the city itself.
Looking back, I think this itinerary gave us a great balance of sightseeing, beach time, history, nightlife, and relaxing without trying to squeeze too much into one trip.
Day 1: Exploring Torre de Belém & Lisbon
After my solo trip through Ireland, I met up with my two friends at Lisbon Airport and we grabbed a taxi to our Airbnb on Rua de Santo Amaro. Our Airbnb was located in a central part of Lisbon in a quiet residential area.
Our two-bedroom Airbnb was in a good location for exploring the city and worked out to be very affordable once we split the cost between the three of us. We did have to take taxis every day to explore different areas.
The only downside? Dragging suitcases up what felt like a million flights of stairs to reach our third-floor apartment. If you’ve ever traveled through Europe with a large suitcase, you know the struggle.
After dropping off our bags, we took about a 15-minute taxi ride to Belém Tower (Torre de Belém). Built in the early 1500s, this UNESCO World Heritage Site once helped defend Lisbon’s harbor and welcomed ships arriving from Portugal’s Age of Discovery. Today, it’s one of Lisbon’s most recognizable landmarks.
The tower itself isn’t very large, so it usually takes around 30–45 minutes to explore.
Belém Tower Visitor Information
- Closed Mondays
- Adult tickets cost around €15
- Self-guided visit
- Allow about 30–45 minutes
After visiting the tower, we walked along the waterfront and came across a cute little tuk-tuk wine stand called Wine With a View. We ordered a couple glasses of wine, grabbed one of the chairs overlooking the river, and spent some time relaxing before continuing our walk.
Next, we wandered through the beautiful Jardim da Praça do Império (Garden of the Empire Square), one of Lisbon’s largest formal gardens. It has fountains, flower beds, and walking paths.
Later that afternoon we headed over to Gin Lovers, where we enjoyed drinks outside before making our way to an amazing viewpoint in Lisbon.
São Pedro de Alcântara Viewpoint
This free viewpoint overlooks São Jorge Castle, the Tagus River, and much of downtown Lisbon. It’s one of the best panoramic viewpoints in the city and definitely worth adding to your itinerary.
You can reach it a few different ways:
- Walk up the steep cobblestone street from Praça dos Restauradores (about 7 minutes).
- Take Tram 24.
- Ride the historic Glória Funicular when it’s operating.
We finished the evening with wine at a cozy neighborhood wine bar before walking back to our Airbnb and enjoying another glass of wine from our tiny balcony while talking about everything we wanted to see over the next few days.
Day 2: Sintra’s Fairytale Palaces & Azenhas do Mar
Sintras Pena Palace
Day two was dedicated to exploring Sintra.
Although it’s possible to reach Sintra by train, we decided to split a taxi between the three of us. It took about an hour from Lisbon and was much quicker than using public transportation.
Our first stop was Pena Palace (Palácio Nacional da Pena).
Perched high on a hill overlooking Sintra, Pena Palace is one of Portugal’s most famous landmarks. Built during the 19th century, the colorful palace combines Romantic, Gothic, Moorish, and Renaissance architecture, making it feel like something straight out of a storybook.
I highly recommend purchasing your tickets online ahead of time since entry times often sell out. We spent some time exploring both the palace and the terraces overlooking the surrounding hills.
Unfortunately, it was incredibly hot during our visit, so we didn’t stay as long as we originally planned before hopping into a tuk-tuk for the short ride to our next stop.
Quinta da Regaleira
We hopped in a tuk-tuk for the short ride over to Quinta da Regaleira, one of the most unique estates in all of Portugal.
Unlike Pena Palace, Quinta da Regaleira feels mysterious.. The estate is filled with winding garden paths, hidden tunnels, caves, fountains, and the famous Initiation Well, a spiral staircase that descends deep underground and has become one of Sintra’s most photographed attractions.
The line to enter was pretty long so we decided to just see it from the outside and we didn’t actually go inside.
Monserrate Palace
After wandering around for a while, we caught another tuk-tuk to our final palace of the day—Monserrate Palace.
Monserrate Palace doesn’t get nearly as much attention as Pena Palace or Quinta da Regaleira, but I think it’s worth adding to your itinerary if you have the time. The architecture is a beautiful mix of Gothic, Moorish, and Indian influences, and the surrounding botanical gardens were much quieter than the other attractions we visited.
Azenhas do Mar in Colares
We took about a 20-minute taxi to Azenhas do Mar, a small coastal village perched dramatically on the cliffs overlooking the Atlantic Ocean.
We had dinner at Azenhas do Mar Restaurante, and I don’t think you could ask for a better setting. The restaurant sits right above the ocean with incredible views of the cliffs, crashing waves, and the natural ocean pool below.
After dinner, we walked down toward the coastline, ordered a few drinks, and relaxed on one of the outdoor lounge couches while watching the waves.
Miradouro das Azenhas do Mar for Sunset
Before heading back to Lisbon, we made one last stop at Miradouro das Azenhas do Mar for sunset. This viewpoint was walking distance from the Azenhas do Mar Restaurante.
Watching the sun slowly disappear over the Atlantic Ocean was the perfect way to end an already amazing day.
We finally caught a one hour taxi back to Lisbon, exhausted after a full day of exploring.
Day 3: Sesimbra & Pink Street
After two busy sightseeing days, we were ready for a beach day. We took about a one-hour taxi south to Sesimbra, a beautiful coastal town known for its beaches and seafood restaurants.
Our destination was Praia da Ribeira do Cavalo, one of the most beautiful beaches I visited during my time in Portugal.
Getting there is part of the adventure. The beach is tucked between steep cliffs and isn’t accessible by road. You have two options:
- Hike about 0.7 miles (30–45 minutes) down a steep, rocky trail.
- Take a water taxi from Sesimbra Harbor.
- Bring cash if you plan to book the water taxi in person at the port.
We decided to hike in. It definitely wasn’t the easiest hike, especially while carrying beach chairs, towels, drinks, and a cooler, but the views along the trail made it worthwhile. As soon as we reached the beach, we knew we’d made the right decision. The water was clear, surrounded by towering limestone cliffs that made it feel like a hidden paradise. Since there are no restaurants, bathrooms, lifeguards, or other facilities, be sure to bring everything you’ll need for the day.
After spending the entire afternoon relaxing on the beach, none of us had any interest in hiking back up the steep trail. Luckily, a water taxi pulled up around 5:30 p.m., and we happily paid for the ride back to Sesimbra Harbor.
I definitely recommend doing it this way if you’re visiting—hike down for the adventure, then save your legs and take the boat back.
Once back in Sesimbra, we grabbed ice cream and wandered along the waterfront before heading back to Lisbon to get ready for our night out.
Night Life on Pink Street
That evening we visited Pink Street, one of Lisbon’s most popular nightlife areas.
The once ordinary street has been painted bright pink and is lined with bars, restaurants, live music, and colorful umbrellas hanging overhead.
We ended up at O Bom, O Mau e o Vilão, where we spent the rest of the night enjoying cocktails, dancing, and soaking up the fun atmosphere until around 2 a.m.
Day 4: A Slow Day Exploring Lisbon
After our late night on Pink Street, we took things much slower. Around lunchtime, we headed to Eating Bear, where one of my friends wanted to try some traditional Portuguese dishes.
I’ll be honest…the Portuguese food that we ordered wasn’t for me.
We ordered several local dishes to share, and while my friends enjoyed them, I couldn’t really get into it. I ended up grabbing a burger later that day instead, which was much more my style. The rest of the afternoon was completely unplanned. We wandered through Lisbon’s winding streets, stopping whenever something caught our attention.
One stop I definitely recommend is Ginjinha do Carmo, where we tried ginjinha, Portugal’s famous sour cherry liqueur served in a small shot glass. It’s sweet, smooth, and worth trying at least once while you’re in Lisbon.
We also spent some time relaxing near Chafariz do Carmo, a historic fountain tucked into one of Lisbon’s charming squares. Sometimes it’s nice to have a day without a strict itinerary, and this ended up being exactly that.
While my two friends went back out that evening, I decided to stay in and get some much-needed sleep before our final day.
Day 5: São Jorge Castle & A Sunset Sail
For our last full day in Portugal, we visited São Jorge Castle (Castelo de São Jorge).
Originally built by the Moors during the 11th century, the medieval fortress sits on Lisbon’s highest hill and offers panoramic views over the city and the Tagus River. Out of all the castles and palaces we visited during the trip, this one ended up being my favorite. I loved walking along the old stone walls, exploring the grounds, and taking in the views from every angle. If you’re only planning to visit one castle while in Lisbon, I’d make it this one.
That evening, we booked a sunset sailing cruise along the Tagus River from 6:30–8:30 p.m., and it couldn’t have been a better way to end our trip. As the sun started setting, we sailed past many of Lisbon’s most famous landmarks, including Belém Tower and the 25 de Abril Bridge.
The crew provided blankets once the temperature started cooling off, and there was plenty of champagne as we relaxed at the front of the sailboat watching the sky turn shades of orange and pink. Seeing the sun set behind Belém Tower from the water was easily one of the highlights of the trip.
After the cruise, we had dinner near the marina before heading back to our Airbnb to pack for the next morning.
Day 6: On to Madrid
The next morning, it was time to say goodbye to Portugal.
Instead of flying, I hopped on an eight-hour FlixBus to Madrid to continue the final two nights of my Europe trip before heading home to San Diego.
Portugal Overall
Looking back, I think five nights was the perfect amount of time for a first trip to Portugal.
Using Lisbon as our home base allowed us to experience so much more than just the city itself. We explored colorful palaces in Sintra, wandered through medieval castles, found one of the most beautiful hidden beaches I’ve ever visited, watched sunsets over the Atlantic Ocean, and ended the trip sailing along the Tagus River with a glass of champagne in hand.
As someone who usually prefers mountains and national parks over cities, I honestly didn’t expect Lisbon to become one of my favorite European cities—but it completely surprised me. Every neighborhood felt different, the viewpoints were incredible, and there always seemed to be another hidden street, garden, or café waiting to be discovered.
If you’re planning your first visit to Portugal, I highly recommend combining Lisbon with a few nearby day trips. Together, Sintra, Colares, and Sesimbra made this a well-rounded city trip and it’s a destination I’d happily return to someday.
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I am thinking of visiting Lisbon, so I appreciate the descriptions you provided. I was wondering how much the sunset sail cost per person? I definitely will visit the Arzenos do Mar restaurant for the view! Did you happen to notice any nice hotels by the port?
Hi, the sailboat tour was $40 USD per person. Keep in mind the Azenhas do Mar restaurant is around a one hour drive from Lisbon but it was worth it especially if you combine it with a stop in Sintra. A nice hotel right near the port is The Editory Riverside Santa Apolonia Hotel and another option a little further is Verride Palacio Santa Catarina which has great views.