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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, a solo trip through the gorgeous countries of Portugal and Spain.

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: Flying to Lisbon

My flight into Lisbon was hectic and eventful and included a speed sprint through Toronto Pearson International thanks to delays during the first leg.

Related: Need help prepping for your Eurotrip? Use this packing list to make sure you have everything you need. 

Day 2: Exploring the best of Lisbon

After arriving in Lisbon, I took 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 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. (Note that as of Dec. 2017, this Baixa-Chiado only has private rooms and the dorm-style hostel has moved a few blocks away.)

I thought I would just walk around downtown that afternoon, 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).

At night I 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 in to see if I could squeeze in at the bar. Queuing like a school child is not recommended if you’re alone. Drinking lots of vinho verdo is very much recommended.

Related: Only have one day in Lisbon? Check out this guide to make the most of your day. 

Day 3: The outskirts of Lisbon

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: Exploring the whimsical fantasy land that is Sintra

Sintra! You cannot leave the Lisbon area without a trip to this magical place. You can use the same public transit card you got for the metro 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.

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.

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.

By the time I got back to Lisbon, it was something like 10:30 p.m. and I was starving. But I’d held off on eating more than a pastry (or two) in Sintra because I’d heard about an amazingly delicious and cheap local spot in downtown Lisbon 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 ten. Cash only.

Day 5: Belem and Cascais

Belem is one of the other popular day trips from Lisbon and is actually more like a suburb that you can take a quick half-day trip to, not nearly as far as Sintra. The tram I’d been planning to take 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 main draw of Belem (other than those egg tarts) is Jeronimos Monastery. It 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.

After getting back to Lisbon and freshening up, I went out for dinner and ended up crashing a Spanish bachelor party as one does and then spent the rest of the night on a hostel-hosted pub crawl where I met more Spanish friends. It was a very Spanish night in Lisbon indeed.

Related: Need a more detailed Lisbon itinerary? Check out this 3-day guide. 

Day 6: Down south to the Algarve

I knew I’d only have time for one other spot in Lisbon, so I 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.

Note: Praia da Rocha’s hostel options are quite limited. Hostel beds were around $48 a night, while the 4-star Jupiter Algarve was $70 a night for a room with a double bed. I’d highly recommend splurging here, especially if you’re traveling with a partner.

Day 7: In search of Benagil

The other key reason I’d chosen Praia da Rocha besides the fact it was a small, walkable town was that it 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 Praia de Benagil, so it was a convenient choice to go together. (Want to visit Praia de Benagil without a car like I did? Find biking directions here!)

Unfortunately, they weren’t renting kayaks at Praia de Benagil 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 fantastical cave we had come so far to see. So no photos from me, but check out this Praia de Benagil guide from someone who was a little more prepared for the visit than I was.

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.

Day 8: Portugal and Spain

As much as hated leaving the relaxing seashores of the Algarve, I was also excited to get to Spain. To do so, 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 (it was a bus from a different company).

Upon arriving in Seville, I was a little confused, so I walked the 30ish minutes to my hostel instead of taking public transit, and in that time I heard more English than I had my entire week in Portugal.

Day 9: Seville’s greatest hits

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.

I then spent the evening with my new friend Guga (the bachelor from that party I crashed 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: Exploring Seville by foot

Triana is a cute neighborhood across the river from Seville proper. There I spent a morning looking at cool tile art and having awkward interactions while 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.

Day 11: The White Villages 

One place I knew I wanted to explore but 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.

By the time we got back to Seville I was pretty pooped, but I was also excited for that night. 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 though 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 past midnight, as folks tend to be out in public squares and parks well into the early hours.

Day 12: Onward to Granada

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. I also decided to visit the bullring 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.

Day 13: The jewels of Granada

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. Tip: Please, please book your Alhambra tickets in advance. And give yourself more time and better directions than I did to get there ahead of your scheduled Nasrid Palace entry time.

Day 14: Headed to Spain’s capital

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?

Once I arrived in Madrid by bus and dropped off my stuff at the hostel, I headed out to hang out with Marta, one of the Spanish friends I’d met 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: All of Madrid in one day

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.

Related: Got more time in the Madrid area? Segovia makes for a fantastic day trip from Spain’s capital. 

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.

Day 16: Bye Portugal and Spain!

And with that, my time in Madrid was over and I headed out to the airport at the break of dawn. Until next time, Portugal and Spain!

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