When I set out to explore a new destination I do a lot of research, collect loads for personal recommendations from locals and travelers who have been there before and then create a loose itinerary. Emphasis on loose though, because it could all change in a second on any given day. That’s the beauty of having it “together.” You can run on a plan but know enough about the destination to switch it up spontaneously when the mood or opportunity strikes. So here’s the rough sketch of our plans. No promises we will stick to the plan though.
Arrive in Lisbon Friday morning and head to town to check in before meeting Summer and Ivan. Spend the morning wandering the Bairro Alto and Chiado, the city’s bohemian district. Grab a late lunch at the market before joining a bike tour of Belem to spot the Cristo Rei statue, see the Ponte 25 de Abril and taste a famous Pastel de Belem. Enjoy a relaxing dinner at Artis in Bairro Alto before exploring the local nightlife.
Get up and head to Alfama to shop the flea markets, Feira da Ladra. It’s best to arrive early to beat the heat and get the best deals. Eat lunch at one of the nearby restuarants and wander Alfama. The best way to explore this neighborhood is to get lost down its winding streets. Freshen up before eating dinner at an authentic Portuguese restaurant in entrecampo with locals followed by dessert at an underground bakery, a late night drive around the city and port wine.
Wake up early for breakfast before saying goodbye to Ivan. Explore the lesser known parts of the city and fall in love with its seven hills on an nontraditional jeep tour or spend the morning in Sintra (I’ve received so many recs to make this day trip from Lisbon). After a late lunch, catch the train to Lagos. Settle into our new surroundings by exploring the town and maybe even a nearby beach on foot.
Rent a car and head west to see the wild and windy west coast of Portugal. Stop in the southwestern most point of Portugal, Sagres for stunning views and dramatic scenery before heading north towards Aljezur and Odeceixe. Stop at the Praia do Amado along the way to trek Carrapateira, ending at Praia da Bordeira. Return to Lagos for dinner and some rest before an exciting day tomorrow.
Wake up early to eat a hearty breakfast before heading off to day one of surf school. After a day of salt and sun, we will head back to town to meet Sophie, fresh in from Lisbon. Catch a sunset on beach with limestone stacks or explore Lagos nightlife if we have enough energy.
Hopefully by day two of surf school we will be catching more waves than mouthfuls of water. We will hang at some local beaches to get a feel for the surf culture in the Algarve. Afterwards we may recenter with a yoga practice or relax with a massage before grabbing dinner in town.
After an early breakfast we will head straight to the beach and wander aimlessly among the iconic limestone rock stacks and caves lining the southern coast of Portugal. In the late afternoon, I will bid Summer and Sophie farewell before heading back to Lisbon for one last night. Finish off the trip with a Fado performance.
Depart Lisbon on a morning flight heading back for Chicago (because my travels aren’t over yet). Summer and Sophie will spend another day or two in Lagos before returning to Lisbon to catch the Saint Anthony festivities (basically Lisbon’s Mardi Gras)!!
Lisbon free walking tours
Belem bike tour
Guide to Alfama
Portugal train schedule
Sintra day trip
Book a dinner in Lisbon with the locals
Lisbon jeep tour of seven hills
Things to do in Algarve
Surf school in Lagos
Where to find the best beaches in Algarve