Some outfits I wore:
Get ready to scroll. This is a LONG, photo and text-heavy post. This took me days to make, and yet I am still probably forgetting things, so I may update this if I think of anything I missed!
Earlier this month, I visited Portugal for the first time and loved it! I wanted to share everything we did, as I know many of you are planning trips there soon! We stayed in two areas: Cascais and Lisbon, so I'm splitting them into two separate guides. We also took a day trip to Sintra, and I'll create a separate guide for that as well. We spent 5 nights in Cascais and 3 nights in Lisbon. Additionally, there were two full days for travel, totaling 10 days.
Cascais, Portugal
Cascais is on the Atlantic coast, about 45 minutes outside of Lisbon. Cascais and the neighboring town of Estoril are referred to as the Portuguese Riviera. They are small resort towns with rich history and stunning scenery. This area began as a fishing town, but in the 19th century, the Portuguese royal family transformed it into their summer retreat. During WWII, Estoril was a gathering place for spies and is said to have inspired the creation of the James Bond character. You can make this a day trip from Lisbon, but we really enjoyed staying there as our home base for 5 nights. As much as I enjoyed Lisbon, I enjoyed Cascais more (though very different). Cascais had a lovely vacation atmosphere, featuring beaches, marinas, and plenty of excellent restaurants and shops. It felt incredibly safe, and everywhere was remarkably clean. I didn't bring anything of high value, but in hindsight, I could have brought my nice jewelry and designer bags without a single worry. Many aspects of the area reminded me of Southern California, such as the weather, palm trees, hotel pool areas, and the marina.
When planning, we also considered the Algarve and Comporta. We ultimately landed on Cascais due to its closer proximity to Sintra and Lisbon, but those are two other areas that you may want to consider!
Getting There
We flew Delta from Pittsburgh (PIT) to Lisbon (LIS) with a layover in New York (JFK). The transatlantic leg from JFK to LIS took about seven hours. Before the trip, I had seen plenty of horror stories on social media about Lisbon Airport, ranging from strikes and three-hour passport control waits to delayed or canceled flights and lost luggage. I’m happy to report that our experience was smooth from start to finish. The journey was long (we had a 6-hour layover at JFK), but there wasn’t a single hiccup. I also placed AirTags in all of our checked bags, which I highly recommend these days...you just never know! As for airlines, I find Delta to be a good choice for international travel, though we don't have a lot of choice flying out of Pittsburgh.
For the return trip to the U.S., it’s advised to arrive at Lisbon Airport at least three hours before your flight. We followed that, and while everything moved quickly, we still ended up with plenty of time (read: too much time) at the gate. Passport control took all of 20 minutes. One thing worth noting: after going through security (which was quick), you’ll pass through a food and shopping area before reaching passport control. This layout can be misleading. Some travelers linger in the shopping area until close to boarding time, only to discover a long passport control line between them and their gate. Even though we lucked out with short waits, I’d still recommend giving yourself extra time here, just in case.
Also, the VAT refund area is after security and right before the shopping/food area.
Overall, Lisbon Airport felt somewhat chaotic, despite having clear signage. Although it wasn’t a nightmare for us, it was definitely not my favorite airport to navigate, so it's best to build in extra time just to be safe.
We had pre-arranged our hotel in Cascais to pick us up in a sprinter van at the Lisbon airport, so my parents, husband, and I could all travel together in one car and also fit all our luggage. It was smooth and easy. The airport is about 15 minutes from the heart of Lisbon and about a 45-minute drive from Cascais.
There are trains that run between Lisbon and Cascais, and from what I've read, they are easy to use. However, we didn't use any public transportation while visiting, so I can't speak to that firsthand. We mostly walked and used Uber when necessary!
When to Visit
The general consensus seems to be June through early September. It's a resort, sailing, and beach town, so many of the activities are focused on warmer weather. The weather is mild year-round. It rarely dips below 50°F, and even the summers tend to be mild. We went from August 30 to September 8, and the weather was perfect. Slightly cool in the mornings, warm during the day, and a light sweater or wrap was needed in the evenings. Cascais was crowded on the weekends. We were there during their Festas do Mars, which was exciting and crowded. During the week, it was quieter but still lively. I'm personally someone who likes to visit places during their shoulder seasons, so it is easier to get desirable hotel and food reservations as well as to avoid large crowds. This really felt like the ideal time to visit.
Length of Stay
Our 5-night stay was perfect. We saw a lot and never got bored. In fact, I truly think we could have stayed another night to explore even more! I also think you could pack a lot in if you are just doing a day trip, and it would also be a fun weekend getaway from Lisbon. If you are visiting in the winter, a day-trip would probably be best. It all just depends on what type of trip you are looking for.
Where We Stayed
We stayed right outside of the town center, at the Grande Real Villa Italia hotel. We found it via Leading Hotels of the World. I look to LHW or iPrefer as my gauge for hotels. If I see a hotel on either list, I assume it's a good one. It hasn't failed me yet. Cascais doesn't have any chains like the Ritz, Four Seasons, St. Regis, etc.
Other properties we considered were The Farol, The Albatroz, The Intercontinental, and Palacio Estoril. After being there, I am so glad with our choice. We had drinks at the Farol, which was directly across from our hotel, and it was nice, but very modern and overall not my personal vibe. But if you like that vibe, it's ideally located. The location of the Intercontinental was fine, but not as ideal as Grande Real Villa Italia. We never made it over to the Albatroz. That was my first choice, but it was fully booked six months out. The Albatroz location is nice because it's on a beach. We ended up going to Palacio Estoril for drinks, which I'll discuss further in the eating and drinking section. However, the questionable reviews about the actual rooms were what ultimately deterred us. The lobby and outdoor area were stunning, though!
The Grande Real Villa Italia was ideally located. We had a gorgeous view of the ocean, situated outside the bustle of the town center, yet just an effortless 5-minute walk into town. We were about a block from the marina. We were able to walk everywhere. The only time we used Uber was when we went over to Palacio Estoril for drinks.
We booked the 'sea view retreat room,' so we were on the upper floors with a direct view of the ocean, a spacious balcony, and a large room. There are 120ish rooms in the entire hotel, but it didn't feel large at all. The pool area was gorgeous, and breakfast (included in the room rate) was lovely. The room was well-appointed, and the bathroom was spacious; however, some design details felt slightly dated, although not enough to deter me from staying here! It's a 5-star hotel, but it's just not on the same level as something like a St. Regis. Not that I expected it, but I was hoping for service similar to what we experienced at the Singer Palace in Rome. While the service was nice, it wasn't outstanding. Ultimately, though, we enjoyed where we stayed, and I recommend staying here.
They also have a gorgeous spa. We tried to make a massage reservation when we checked in, but they were fully booked. I would recommend booking ahead of time if possible.
Where To Eat and Drink
This restaurant is in a boutique hotel with a view of the Praia da Ribeira de Cascais, which is a small beach followed by a fishing pier. It looked like a restaurant you'd find in Italy and, no surprise, they served Italian food. You can't make a reservation for the outdoor terrace, but you can make a reservation and hope that a table will be available outdoors. We lucked out and were able to sit on the patio, which was lovely. They have an adorable bar if you want to check it out, just for a cocktail. The service was great and the food was delicious. The Ossobucco was my favorite dish, and we got profiteroles for dessert, which were the best I have ever had (better than any I had in Paris, even). Those profiteroles are now up there for the best dessert I've ever had, along with the Snowball in Hell from the Clark Cooke House in Newport, RI.
This is a very trendy, upscale restaurant that feels like you are tucked away in a secret garden. It was beautifully designed and had a very cozy feel. I ate a LOT of beef tartare on this trip, and this was my favorite. This is another restaurant that would be fun to visit just for drinks, even if you don't have time for a full meal.
This was the other evening we left open without a reservation. We had spent the afternoon on a sailboat, so we just wanted to go somewhere casual. We wandered into town and landed at this Italian restaurant. We sat outside, and it truly felt like we were in Rome. The food was excellent, but the truffle prosciutto pizza was a standout. I dressed up every night, but this was a more casual spot.
If you are looking for FUN, look no further than Izakaya. It's a tiny little restaurant, and there can't be more than 20ish seats, which are mostly made up of a wrap-around bar that looks into the kitchen. The place is dark, and there is music pumping from the speakers. My husband and I were jamming out the entire time to the fun playlist. So much so that I asked about the playlist because it was so fun and upbeat. Everyone asks, so they have a public Spotify playlist. It's so fun to listen to! The restaurant is bustling and hard to get into, so be sure to make a reservation. They specialize in Japanese street-style food. I would advise you to only go here if you have an adventurous palate and are OK with sharing food with the people you dine with. It's tapas-style, so you get a bunch of small plates served course by course. The menu is confusing, so the waiter offered to just bring out courses that he thinks we would enjoy. We had him do that, and it did not disappoint. The food was incredible. It was one of the most memorable meals I've ever had, as I was able to watch the chefs, jam out to the fun music, and enjoy the unique and delicious food.
Palacio Estoril
In 1969, the James Bond movie "Her Majesty's Secret Service" was filmed here. It's right next to the Casino Estoril. This resort is situated a bit further back from the coast, in its own secluded area. We took an Uber from our hotel to Palacio Estoril. The lobby and grounds were beautiful, and it was so fun to grab a drink in the 'famous' bar. They have a restaurant, but we were headed to Bougain later that evening. It was a charming hotel and definitely worth checking out!
While we waited for our boat to be ready, we stopped into one of the marina restaurants, Pateo Guinchom, and had a cocktail. I typically don't like Aperol Spritzes as they taste syrupy to me and remind me of shampoo. Is that weird? Probably. Anyway, I started to like Aperol Spritzes in Portugal! The marina had many high-end shops like Vilebrequin and many restaurants.
Activites
We did not know this was happening when we booked the trip, but boy, did we luck out! I believe this is an annual event, but I'm not entirely sure. It lasts for about a week in the center of Cascais town. There were food and drink trucks everywhere, a large stage overlooking the water, and many vendors selling crafts and other fun items. This made the town packed on the weekends, but in an entertaining way. We loved sampling different food trucks and trying some different cocktails. The musical headliner one night was Bárbara Bandeira. I still don't really know much about her, but she is a Portuguese pop star, and the crowd was dancing and singing along. In hindsight, if you could plan your trip to align with this festival, do it! This may sound so silly, but one of the highlights of the trip, at least for me, was walking home after dinner each night and visiting the Farturas food truck. It was 1.50 euros for a fried dough masterpiece... a mix between a funnel cake and a churro. Soooooo delicious. Many of the trucks were open during the day, so we would walk over if we were feeling peckish. I really enjoyed the bifana, a traditional Portuguese sandwich made with pork. We had one in Lisbon, too, but the one from the food truck in Cascais was much better. They had many stalls with Pasteis de Nata, which is a custard tart that is another Portuguese staple. We tried a few from different shops. They weren't my favorite, but I can see how they are popular!
Day Trips
Portugal is relatively small. There is so much to do and see, but you can cover a lot of ground if you'd like. Lisbon/Cascais is in the lower third of the country, but Porto is just a 3-hour drive away. We did a day trip to Sintra, which was only 25 minutes from Cascais. I'll do a separate post on just Sintra since it is so different than Cascais and Lisbon. There is also a wine country in the Douro Valley, so you could do a wine tasting day or even a few days. You could also make your way East over to Spain. Seville is just a 4-ish hour drive from Lisbon.
Boat Day
Since we stayed on the coast, and quite literally across the street from the Cascais Marina, we chartered a boat for the day. We had our hotel book the boat for us. However, when we went to the boat company to board, they told us they had no record of the reservation. It sounds like a big snafu, but Aquastart, the company we thought we were booked with, was *incredibly* accommodating. They got us a boat, a captain, and a mate within 30 minutes. Now, it wasn't the boat we had selected, but we were more than happy and thrilled at their willingness to rectify something that wasn't even their fault! All that to say, reach out to Aquastart (yourself) and make the booking. Bruno was the one we talked with at Aquastart and was a gem! In my opinion, this is a must. There was so much to see while being on the water. Captain Jonathan was fabulous, and we enjoyed the gorgeous weather, coastline views, and champagne! Aquastart offers a wide range of boat options, and the prices are incredibly reasonable. In fact, much less costly than I would have thought.
Walk around!
The entire area around Cascais is so walkable. From the charming azulejo tiles, the adorable shops featuring ceramics, linens, and more, and the restaurants and bars, there is so much to take in! Not to mention the gorgeous views of the ocean! There is a landmark called Boca do Inferno where the water comes through the rocks. It was right up the street from our hotel and also very cool to see from the sailboat! We also enjoyed wandering around Parque Marechal Carmona, which was right across from our hotel. It was a huge park with so much going on!
Golf
There are many golf courses in Portugal! My dad and husband played at Oitavos Dunes, just a 10-minute Uber ride from our hotel. They loved it! There is also the Estoril Golf Club, located near the Palacio Estoril hotel.
Go to the Beach
We actually didn't go to the beach. We are not big beach people, but there were quite a few in Cascais that we walked past, which were easily accessible and open to the public. The water is a bit chilly, and according to our boat captain, it is warmest in July and August, but even then, it's considered 'cold' for many people. Many people enjoy visiting this area to surf. When we arrived, the waves were huge and our driver told us that you have to be very careful because of the currents!
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