Exploring Portugal: Lisbon to the Algarve

Walking the Alfama district of Lisbon, with its intricate network of historical trams

Portugal constitutes the southwestern most tip of Europe. A prime position for sunset viewing for sure, but also a sliver of land that offers rich culture (and equally rich cuisine), stunning architecture, dramatic cliffs, perfect beaches, genuinely nice people and extreme value.

JESSICA: I can’t quite say why we landed on a trip to Portugal. I had seen some gorgeous, pastel-painted photos of Lisbon, while a steady stream of Portugal articles and casual mentions had shaped the idea in Trevor’s head. When our Detroit neighbors, a husband-and-wife team, revealed that they loved the country so much they hoped to retire there, our decision was made. We had a window of time to plan a week-long European trip before a rush of work commitments (and a January-due baby) that would squash our ease of travel, so … Portugal it was!

TREVOR: Our initial research revealed three obvious regions ripe for travel within the country: Lisbon, the bustling capital city in central Portugal; Porto, another cultural hub, wine region and large city located in the northern part of the country; and the Algarve, the southernmost part of Portugal known for its cliff-carved beaches and relaxed vibe. Since we only had a week, we decided that our trip to begin in Lisbon (we found especially reasonable airfare flying Canada Air Rouge direct from Toronto) and end in the Algarve, a short two-and-a-half hour drive away, which we’d use a rental car to travel to. Porto would have to wait till next time.

A walk on our first evening in capitol city, Lisbon


J: Flights from Detroit to Lisbon ranged from $1,500 – $2,000 per person, which felt steep. It took a couple extra days of research, but we finally landed on a slightly less convenient – but far more frugal – option. We could drive to Toronto on a Wednesday evening and depart around midnight, and arrive home around 4 p.m. one week later for a cost savings of more than $1,000. If the decision had been mine alone, I would have scrapped the drive to Toronto or considered the train, but Trevor didn’t mind playing chauffeur. In hindsight, we both agreed that the drive from Detroit wasn’t nearly as painful as we imagined it might be.

Parking at the Toronto airport is a breeze. The airport itself if well kept with plenty of amenities and is a completely pleasant experience. Our only hiccup … the realization that Trevor’s passport was two days shy of preventing our trip entirely due to its expiration date. The amount of side eye given to him in this moment cannot be understated. (For the love, check your passport expiration dates, folks! And then check – and double check the policies surrounding expiration for entry and exit to the country you are traveling to as well as any others that you’ll stop into en route.)

The balcony view from the Hotel Santa Justa in the city’s historic downtown


J: We arrived in Lisbon early on Thursday morning and grabbed a cab at the airport to our hotel in the city’s “Baixa” or downtown district. Determining where to stay had been a task, but I was more than happy with the neighborhood. We used this article to help narrow our choices.

T: Hotel Santa Justa was located on the tiled streets near the Santa Justa Lift – a gothic elevator that folks ride to avoid walking the steep, winding streets lined with al fresco dining tables, shops and patisseries. Very central location. Because the prices were so reasonable, we upgraded our three nights at the hotel to a suite with a balcony (score!).

J: The hotel itself was simple but lovely. The service was above and beyond. We’d absolutely recommend staying there and doing whatever you can to ensure a room with a tiny but delightfully charming balcony. We opened the balcony doors in the morning to the sounds of forks and knives clinking on plates four floors beneath us. This was mixed with the melodies of meandering musicians, playing for spare change. It was exactly the European vibe that we’d been hoping for.

T: For three full days, we wandered around the city, soaking up the sights and sounds without much of a timeline at all. It felt right to let the city lead us.

Breakfast from Confeiteria Nacional, just down the block from our hotel

T: A few of our recommendations, in no particular order:


  • Patisseries: The city is full of historic patisseries (or bakeries) overflowing with decadent breakfast foods. I blame Jess being pregnant, but we started each morning with a trip to one of them for a box of pastries in bed. We hit up the Confeiteria Nacional, which was near our hotel and founded in 1829. You’ll find out soon enough that the Pastel de nata is a must-try in Portugal. An egg custard cup, Jess tells me. Our favorite version was the “secret recipe” that’s served warm at Pasteis de Belem and topped with cinnamon; expect a line unless you go late in the evening like we did. Only three monks at a time knew the recipe for centuries.
  • Café Culture: The slow-it-down mentality that pervades Europe is the perfect way to ease into vacation mode. The city is full of streetside cafes serving up espressos (or “bica,” – learn how the locals order coffee here) and stopping into one or three throughout the day for a cuppa or even a small pour beer just feels appropriate. PS: Drinking on the streets is legal in Lisbon! Grab a beer or Aperol Spritz to go.
  • Tapas: Our meals mainly consisted of tapa-style servings of rich meats and cheeses alongside with seafood like octopus or fresh-grilled sardines. Not a ton of vegetables in Portugal. Most evenings, we’d pop into two or three wine bars or restaurants between 8 p.m. and midnight. In Lisbon, we loved the Old Pharmacy Wine Bar in the Borreio Alto neighborhood for drinks and tableside cooked sausage, and also Meson Adaluz for a host of tapas alongside its stair-step lounge seating and laid back vibe.
  • Time Out Market: One of the most well-known stops in the city, this market is a busy one, offering up a bevy of food stalls. You can walk here from the historic district for an easy lunch or dinner. Take the path closest to the water to avoid an unnecessarily hilly route.
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Lisbon’s Time Out Market – a collection of innovative food stalls in a beer hall type setting

J: And what to once you’ve gorged yourself on pastries and beer?


  • Tuk Tuk Tour: These open-air, engine powered rickshaws aren’t known for their smooth rides, but they are a fun way to get around the city. We hopped onto a few during our trip, but what I wish we’d have done is started our first day with a one- or two-hour tuk-tuk tour of the neighborhoods to simply get our bearing and scope out the area.
  • Alfama: One of the oldest districts in Lisbon, Alfama is a spider web of steep, winding streets that are as picturesque as they are difficult to navigate. Spend a morning walking around while the streets are still silent and soak up the views (folks sleep in around here).
  • Sunset Sail: We booked a sunset sailboat tour one day in advance using AirBnB Experiences. Our boat held up to 10 guests and our sail lasted two hours, heading up the river from Belem toward the historic district and back, with our captains pointing out landmarks and providing tidbits on the city’s history along the way. For around $50 a person, it was a perfect way to spend the evening. Another perk of visiting the marina where most of these tours depart is the chance to see the Monument to the Discoveries up close. It’s a beautiful structure right on the water that celebrates the visionaries that departed Portugal in search of new lands (Magellan, Vasco da Gama, etc.).
  • Cabaret: One of the coolest experiences we had. Go to Becco Cabaret Gourmet, a dinner-and-a-show experience tucked two restaurants deep in Bairro Alto. We purchased tickets in advance for the Friday evening show and tasting menu. It’s pricey, but features experimental and delicious foods from one of the top chefs in Lisbon. And, if you’re into entertainment that’s a bit snarky and sexy, this is it.
  • Tram 28: One of the city’s iconic tram paths is taken by Tram 28. It’s nearly always crammed, so head out first thing in the morning to avoid long lines. On it, you’ll see IG-worthy views of the twisty streets and a sampling of all that the city has to offer.
  • LX Factory: Named “LX” because it’s shorthand for Lisbon, this retrofitted industrial complex is now a busy hub of restaurants and shops. Spend an evening there, arriving earlier to check out the shops and street art before settling into a drink or two before a late dinner.
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Monument to the Discoveries, along the river and near our sunset sail departure
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Enjoying the sail; we booked our sunset cruise with locals through AirBnB Experiences
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The highly Instagrammable bookstore at LX Factory

J: Before leaving Lisbon, we had one logistical to-do, which was to pick up our rental car for our Sunday departure. I reserved a vehicle from the one downtown rental location that I could find to avoid a trip back to the airport. But when we arrived at the Avis counter, just a few blocks from our hotel, we found a line that was depressingly long. We waited for over an hour, and my only tip – because I can’t think of any others – would be to arrive first thing in the morning for your pick up to avoid the late morning rush around hotel check-out time.

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Walking up the facade of Pena Palace in Sintra


T: As soon as we’d grabbed the keys to our rental car, we made our way toward Sintra. About 40 minutes outside of Lisbon. Enough people had advised a stop in the village known for its “sub-division” of mountaintop castles.

J: We purchased tickets to visit Pena Palace, the most picturesque of the castles, the day before online to avoid waiting on site. Before we headed up toward the palace itself, we stopped in the village of Sintra. A charming collection of cafes, restaurants and shops. We could have easily spent a full afternoon perusing the town, and then hiking the trails from castle to castle (which I’d recommend, if you can!), but our time was limited. If you’re driving your own vehicle, be prepared for a bit of a twisty ride toward Pena Palace. Parking is scarce and you’ll want to use the Waze app to ensure you’re headed the right way if you’re not already following a long line of traffic.

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Trevor walking the Pena Palace castle perimeter, or “The Wall Walk”

T: Walking up toward Pena Palace revealed a castle more colorful and cliche than Excalibur on the Vegas Strip. An intricately carved stone façade, painted in shades of blue, red and bright yellow. And, crazy ass works of art. I mean crazy.

J: Our tickets provided access into the castle as well. We waited in a short line to walk the guided pathway through the ancient rooms (no photos allowed unfortunately). If I could plan our visit over again, I would have given us an entire, un-rushed day in Sintra and maybe even considered staying the night.

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The architectural detail at the entry to Pena Palace
The front door to our Lagos AirBnB
A side street view of Lagos’ slightly gritty but adorable downtown district


T: A two-and-a-half-hour drive over the 25th of April suspension bridge and through the desert gets you to the Algarve region. If you’re looking for a quieter beach experience, consider staying in Sagres. If you’d prefer the late-night crowd with a walkable, downtown vibe, find yourself a rental in Lagos. Or, if you’re more the resort type that’s okay with a suburban feel, steer toward Alvor. No matter where you stay, here’s what we know: the beaches everywhere are breathtaking. Our AirBnB was located in Lagos’ historic district, within walking distance to dozens of restaurants, shops and bars. The location was perfect. Be prepared to park your car a few blocks away. The streets are impossibly narrow, windy and nearly all one-way. It’s a confusing – and according to front passenger Jess, anxiety-inducing – web, especially when your cell phone navigation can’t keep up.

Praia do Camilo beach in Lagos, one of the region’s most picturesque (and popular!)

J: For a full tour of the AirBnB, check out our Instagram “Portugal” story. It was a modern but charming two-story row house with a private rooftop plunge pool. Awesome.

Historic downtown views of Lagos from our AirBnB rooftop


  • Beliche Beach, Sagres: 40 minutes from Lagos, Sagres moves at a bit slower pace, offering up less crowded and bigger (more naked) beaches. We headed to Beliche Beach, a double cove stretch of sand between towering cliffs with gentle waves and plenty of room to stretch out. A bonus is the cliff-hugging restaurant that’s open during till sunset serving up drinks and fresh grilled sardines. Beach chaises and umbrellas were also available for rent during our visit.
  • Sunset at the Southwestern Tip of Europe: As dusk settles over the Lighthouse of Cabo de Sao Vincente outside of Sagres, hundreds of folks park along the road and make the rocky walk to the coastal cliffs to catch the sunset. This is the southwestern most point in Europe and it makes for a scenic setting as the sun dips into the Atlantic each evening. Bring a jacket; it gets chilly! We stopped into A Sagres Restaurant on our way out of town for dinner; ordering up the seafood pasta for two. Delish.
  • Praia do Camilo, Lagos: One of the most picturesque beaches in Lagos, the beauty of Camilo Beach is only rivaled by the crazy crowdedness that it incites. Plan to arrive early (say, 9:30 a.m.) to grab a parking spot and carve out a sandy space for your towels and belongings. There’s a tunnel through the rocky cliffs that will lead you to a slightly less crowded second alcove of the beach that’s worth checking out. A small shack near the bottom of the many, many stairs down sells cold sodas, waters and snorkeling rentals.
  • Tres Irmaos Beach, Alvor: For two Euros per day, you can park at this beach, about 30 minutes outside of Lagos in the opposite direction of Sagres. It’s a long and big beach that connects at one end to several smaller beach alcoves, each featuring sweet cliffside restaurants that overlook the waves. We spent an afternoon here; walking from beach to beach and taking in the sunset.
  • Belmar Spa & Beach Resort: Just because we didn’t stay at a resort didn’t mean I wasn’t going to find a way to spa ;) We booked massages at Lagos’ Belmar Spa & Beach Resort (pre-natal massage for me, deep tissue massage for him). Would absolutely recommend a visit if you’re looking for relaxation (my masseuse, Sarah, was amazing!).
A hidden alcove at Tres Irmaos Beach in Alvor
Beliche Beach in Sagres, Portugal
The rocky coastline at Beliche Beach in Sagres
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“Side streets” views on the way from Lisbon to Lagos


T: We booked our last night in Portugal near the airport in Lisbon, which meant that we could take the long way back from the Algarve, skipping the expressway and instead, hugging the coast and stopping at several of the beaches along the way.

The drive was primarily back roads and along the way, we swung into a few spots that proved entirely worthwhile.

Portugal surfer friendly beach south of Lisbon
The walk down to Praia do Amado and it’s deep stretch of surfer-friendly beach
Odeceixe Beach in Portugal
The long walk down to the pretty (and tide-changing) Odeceixe Beach


  • Praia do Amado: A huge beach stocked full of surfing schools, we found easy parking in the beach lot and grabbed lunch at a food truck near the top of the stairs toward the sand. Wavy, but not too windy, this was a stunning stop. (We could have stayed much longer, but we wanted to leave time for other stops.)
  • Odeceixe: A small hillside town that winds down to an especially deep and shallow-water beach. Find a parking spot (it was packed when we arrived mid-day) and make the long trek down to the water. You can grab lunch along the way. The tide changes quickly at this spot, where a lazy river wraps around the beach itself. You can wade pretty far out before it gets deep.
  • Porto Covo: For dinner, we swung into Porto Covo, an idyllic little coastal town with plenty of food and shopping options. It features lots of rocky cliffs to watch the sunset. The town charmed Jess especially. In fact, it didn’t take her long to spy O Lugar, a bed-and-breakfast that we wished we’d known about in advance. If we could re-do it, we might have spent our last night there, opting to head out bright and early for the trek into Lisbon to catch our flight.
An overhead look at Beliche Beach in Sagres, Portugal
An overhead look at Sagres’ Beliche Beach (note, it’s nude friendly!)


  • If you’re looking for budget friendly European destination, Portugal is a great find. Food is inexpensive and lodging – especially hostels – are a song. Mass transit is also a steal and is readily available.
  • Rent a small car. We were tempted to reserve an SUV for our checked-luggage stowing. But, in hindsight, I’d take the smallest vehicle they’d give us to accommodate the narrow, winding streets. (Make note, most vehicles available for rent are manual transmission cars. You’ll pay far more for an automatic transmission car.)
  • Ladies, bring flat shoes! With rubber soles. The tiled streets are notoriously slippery and even in my flat sandals – completely sober – walking up and down the streets was tricky.

*Actual travel date: September 2019

Lagos' Belmar Spa and Beach Resort, Portugal
Belmar Beach & Spa Resort, where we holed up for our massages in Lagos
A walk along the Porto Covo coast in Portugal
A walk along the Porto Covo coast in Portugal
Sunset along the coast of Porto Covo, Portugal
Sunset along the coast of Porto Covo, Portugal, on our last evening of the trip 

4 thoughts on “Exploring Portugal: Lisbon to the Algarve”

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