International Travel, Itineraries & Trip Planning

P.S. 2016 – Solo Tripping Portugal and Spain

September 2016

My dreams of Lisbon led me to the city last fall. From there, I made my way to the southern coast of Portugal, across the border to Seville, and then Granada and finally Madrid.

It was my first 100% solo trip in countries where I don’t speak the language. I’ve done domestic trips alone and legs of international ones by myself, but never a full trip. Solo tripping is not for everyone, but I’m quiet content with amusing myself and exploring new places on my own, so it was a wondrous experience. Two weeks of whatever I felt like when I felt like it. Crashing bachelor parties, taking the train to the next town over to explore, biking through the Algarve, eating so many free tapas, and making new friends along the way.

Here’s my general itinerary and some tips and suggestions, but I highly urge you not to follow it. The best part of solo tripping is doing whatever you want whenever you want to!

Length: 16 days, including flights 

Budget: $1200-$1400 (my flight was just under $600 but free with credit card points, so this trip cost me less than $800) 

Lodging type: all hostels save for one 4-star hotel courtesy of credit card points 

Travelers: solo 

Day 1

– Fly to Lisbon (included a speed sprint through Toronto Pearson International thanks to delays during the first leg)

Day 2

– Arrive in Lisbon and take the metro into town. Tip: you’ll need cash to buy a metro pass unless you have a Portuguese credit or debit card.

– Located just above the Baixa-Chiado metro stop in the center of the city, the Lisbon Poet’s Hostel is probably my most favorite hostel ever. It’s clean, well-appointed, and spacious (even in my 6-person dorm!), with an incredibly nice staff and fun dinners and activities.

– Explore downtown Lisbon. I thought I would just walk around but after lunch I ended up going to almost all of the main sights on my list, including:

  • Santa Justa Lift, this random elevator in the middle of the city. The long line and steep price drove me to go elsewhere for city views.
  • Praca Rossio, a fun square to grab a drink or just sit and people watch.
  • Praca do Comerico, another great people watching spot. You can also see the 24 de abril bridge (aka Golden Gate twin) from here if you walk to the water’s edge.
  • Castelo de Sao Jorge. As it’s located on the highest of Lisbon’s 7 hills, it’s got a gorgeous view for sunsets.
  • Se de Lisboa. I’ve been to too many cathedrals and churches to count, but this one was worth exploring (plus it was a reprieve from the heat).

– Hit up a fado spot to hear this yearning, soulful Portuguese musical tradition. Tasca do Chico (Rua Diário de Notícias 39) has fado Monday and Wednesday nights starting at 9, but get there early as the place is small and they will absolutely close the door on those in line. I was only able to sneak in because I was solo and walked right in to see if I could squeeze in at the bar. Queuing like a school child not recommended if you’re alone. Drinking lots of vinho verdo recommended.

Lisbon street art

Day 3

– I started my day with a free Moorish quarters walking tour offered through my hostel. The highlight was some fun street art we saw, but unfortunately the guide wasn’t amazing. Tip: do your own walking tour and look for signs that say “miradouro” for the best viewpoints in town, or join one of the free daily tours offered by various tourism agencies.


– I spent the rest of my day walking around, ducking into landmarks I’d missed or chatting up store owners as I shopped, before hitting up the hipster LX Factory outside of town. (My opinion: okay to miss.)

Day 4

– Sintra! You cannot leave the Lisbon area without a trip to this magical place. You can use the same public transit card to take the regional train to Sintra.

– The fantastical Pena Palace is a must. Its colorful and whimsical architecture still brings a smile to my face anytime I think of it.

Pena palace

Tip: Avoid the costly restaurants and time-consuming crowds. Instead, bring your own lunch and take a stroll through Pena Park and find a spot there to picnic.

Pena Park

– The Moorish Castle is a nice walk and the National Palace is interesting if you have the time, but my second favorite spot in Sintra is the less-visited Quinta da Regaleria. This gorgeous estate is also super romantic should you be in town with a special someone.

Quinta da Regaleria
Quinta da Regaleria

– I’d heard about an amazingly delicious and cheap local spot called Restaurante Cerqueira (Calçada de Santana nº49). The family-run spot serves up huge meals with friendly service. My apps, entree, dessert, and half a bottle of wine was only 8 euros. I felt so bad given how much I had consumed I left a 10. Cash only.

Day 5

– The tram to Belem was delayed so I found a Swiss couple and split a cab with them. We went to famous Pasteis de Belem to get pasteis de nata (Portuguese egg tarts) and I was reminded of how much more we Americans eat when each of them only got one. 😶

– The Jeronimos Monastery was fascinating and informative, but I was feeling less landmarks and more nature, so instead of exploring other parts of Belem, I found my way to a regional train stop and made my way to the beach town of Cascais. Food, booze, paddleboarding, tanning galore. Tip: restaurants in Portugal will generally bring out pâté, olives, cheeses, or some other small bites. You’re only charged for them if you eat them, so if you’d rather refrain, just ask them to take it away.

Sardines in Lisbon

– After getting back to Lisbon and freshening up, I went out for dinner and ended up crashing a Spanish bachelor party. And then spent most of the rest of the right on a pub crawl where I met more Spanish friends. It was a very Spanish night in Lisbon indeed.

Day 6

– I’d booked an Eva bus to go down to Praia da Rocha, a resort town that dies down as soon as the summer crowd leaves. I’d wanted some peace and rejuvenation and hence had skipped larger Algarve towns like Lagos and Faro. There was a lot of food, sun, sand, and relaxation upon arrival.

Day 7

– The other key reason I’d chosen Praia da Rocha was because it was a small, walkable town that was also close enough to Praia de Benagil, my #1 wish list in the Algarve. While renting a bike to get me there, I met Claudi from Germany. We had both planned on biking solo over to Benagil, so it was a convenient choice to go together. (Biking directions here.)

– Unfortunately they weren’t renting kayaks that day, so we had to leave all our stuff on the beach (gasp! I know, it took a little convincing for me too) and swim out to the cave. So no photos from me, Google it instead.

– We also visited Praia da Marinha before heading back, our 27-mile ride cut short by a flat tire I got about 2 miles outside of town.

Praia da Marinha
Praia da Marinha at sunset

Day 8

– To get myself to Spain, I had to first get myself to the nearby town of Portimao. The local bus is fairly easy to navigate, just make sure to bring the correct change. The bigger issue was the ALSA bus. It took me a bit to find the right stop for my route, and I almost got on the wrong bus at one point (different company).

– I was a little confused upon arriving in Seville so I walked ~30 min to my hostel instead of taking public transit. In that time I heard more English than I had my entire week in Portugal.

Day 9

– I made sure to purchase my Alcazar tickets ahead of time to avoid the lines and had a blast exploring the place. And then I got a little ambitious and did the Seville Cathedral and Church of El Salvador that day as well. Tip: Buy your ticket for the cathedral at Iglesia del Salvador and visit that first because it’s a combined ticket and they have way shorter lines than the cathedral.

Seville Alcazar
Having some extra fun at the Alzacar, an UNESCO World Heritage Site


Seville Alcazar gardens
The gardens of the Alcazar

– I spent the evening with my new friend Guga (the bachelor from that party in Lisbon!) and his friends at their local favorite Boedga Antonio Romero (Calle Antonia Diaz 19), learning to eat my last meal of the day well past 10 p.m.

Day 10

– Triana is a cute neighborhood across the river from Seville proper, where I spent a morning realizing that maybe I should’ve learned some spoken Spanish before my trip. (I did this for Cuba!)

– The rest of the day was heavy on walking as well as I explored the lush Maria Luisa Park and the expansive Plaza de Espana.

In Plaza de Espana

Day 11

– One place I’d wanted to explore but knew I couldn’t do on my own without renting a car was the white villages of Andalusia. And so I begrudgingly booked a tour and headed out to the land of olive trees, white houses, and gorgeous views. If I had more time, I would’ve stayed overnight in Ronda. My tour only had us there for 70 minutes, which meant I was working up a sweat going all over town.

Zahara de la Sierra
Zahara de la Sierra
Ronda gorge
Ronda’s scenic gorge

– I was super lucky to have been in town for Bienal de Flamenco, the biannual flamenco festival. It’s not heavily frequented by regular tourists, but flamenco lovers from around the world come to Seville for it every other year. I knew I wanted to see these performances versus the typical tourist show. Tickets go fast so I wasn’t able to get the shows I wanted but was able to snag one for a late show just outside of Seville proper. Seville was amazingly safe, even at night, as folks tend to be out in public squares and parks well into the early hours.

Day 12

– I had some time before my bus to Granada so I went to buy sweets made by nuns, drink orange wine, and eat more tapas.

Yemas Seville nuns
This is how you buy sweets from nuns. Money in, yemas out.
Tapas and vino naranja
Tapas and vino naranja

– I also decided to visit the bull ring after much contemplation. It was an interestingly and culturally educational experience, though I don’t think I’ll be at a bullfight anytime soon.

– In Granada, I made sure to stay in Albaicin, the old Moorish neighborhood. With my hostel mates, we explored the city’s various viewpoints and Sacromonte, the neighboring district of gypsies and cave dwellers. We chatted and had tea in one of these caves, an experience that reiterated to me how minimalist one can live, and of the hardships faced by immigrants and refugees around the world.

Granada Alhambra

Day 13

– Having had that poor random walking tour experience in Lisbon, I made sure to join a more organized free walking tour in Granada. Our guide was very knowledgeable and funny and provided a lot of interesting tidbits.

– Once I broke off from the group, I was led astray by Google Maps and almost missed my Nasrid Palace entry time at the Alhambra. Good thing these San Francisco hills have trained me to walk up hills at record speeds. I then spent the rest of the time wandering around the Alhambra grounds until closing time, stopping to read my book whenever I got tired of walking.

Day 14

– I’d had somewhat of a late night chasing street art and free tapas the evening before, so I took the next morning easy with a slow and sweet breakfast of Spanish churros. Who doesn’t like chocolate for breakfast?

Seville street art

Spanish churros

– Once I arrived in Madrid by bus and dropped off my stuff at the hostel, I headed out to hang out with Marta, whom I’d met during my time in Lisbon. There’s something about sitting around with Spaniards drinking tinto de verano and trying things like fried pig ears that made my first night in Madrid extraordinary.

Day 15

– I knew I only had one day in Madrid (but it wasn’t economical to fly home from Granada), so I wanted to make the most of it. I got up relatively early and started a heck of a day of walking. First was Parque del Retiro, which you could really spend an entire day relaxing in. Then I checked out some viewpoints before joining a hostel-offered walking tour that led us through various Madrid highlights.

Parque del Retiro Madrid

– On that tour I met Jordan and Cory, two fresh grads who’d moved to Spain to teach English and were exploring Europe for the first time. We spent the rest of the day chasing good food and sunsets, with a spectacular stop at the Temple of Debod, an ancient Egyptian temple that had been gifted by the Egyptian government as a thank you for Spanish help during the late 1960s floods.

Temple of Debod, Madrid

Day 16

– And with that, my time in Madrid was over and I headed out to the airport at the break of dawn.

Until next time!

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