One of Europe’s most underrated destinations, Portugal is becoming increasingly popular with tourists looking for an easy and affordable summer escape. While Lisbon is a thriving cultural center, Portugal also offers plenty of options for relaxation, from lush wineries in the north to pristine beaches in the south. I recently spent a week with a good friend of mine exploring and enjoying this beautiful country.
First Stop: Porto

View of the Cais de Gaia
Porto (or Oporto) is the second largest city in Lisbon, situated in the northern part of the country. Famous for its port wine production, Porto is also the gateway to the Duoro Valley, a world heritage site.
From New York, we were able to fly directly from Newark to Porto on TAP Portugal Airline. While in the city for two days, we stayed at the Premium Porto Downtown, which was a lovely and affordable boutique hotel well situated for exploring the city.
Our favorite moments in Porto:
- Sipping vinho verde in a cafe along the Cais de Ribeira (our favorite: Casal Garcia)
- Following in JK Rowling’s footsteps at Livraria Lello & Irmao (a beautiful bookstore rumored to be an inspiration for Hogwarts)
- Wandering the cobblestone streets and admiring the architecture of the Clerigos Tower, Porto Cathedral, and Palacio de Bolsa
- Sampling port wine at the tasting rooms along the Cais de Gaia
Day Trip: Duoro Valley
While the city was just beautiful, the absolute highlight of the trip was the full day tour we took to the Duoro Valley.

The town of Pinhao in the Duoro Valley
About an hour and a half drive from downtown Porto is the town of Pinhao in the heart of the Duoro Valley. Our tour included lunch in town with traditional Portuguese fare, tasting at two different wine estates (1 with regular Duoro wine and 1 focused on port wine), and a river cruise on a traditional Portuguese riverboat. Not only was the scenery stunning, but we also learned a ton about Portuguese culture, history and wine from our very knowledgeable guide.
Next Stop: Lisbon

Panorama of Lisbon perched at the Castelo de Sao Jorge
Just a three-hour train ride from Porto, sits Lisbon, Portugal’s capital and cultural center. The city is extremely reminiscent of San Francisco, from its hilly streets, to its cable cars, to the 25th of April Bridge, which mirrors the Golden Gate.
Where to Stay
In Lisbon, we stayed at the Memmo Alfama, a boutique hotel located in the heart of Alfama, Lisbon’s historic district. The accommodations were comfortable and modern, the free breakfast was fresh and delicious, and the rooftop dipping pool was the perfect break on a hot summer afternoon.
Lisbon Highlights:
- Castelo de Sao Jorge – A Moorish castle set on a hilltop in Alfama; panoramic city views
- Rua Augusta – Lisbon’s main pedestrian street with plentiful shops & cafes
- Praca do Comercio – Waterfront square; served as the port of entry to the city
- Minibar – Our best meal in Portugal! Make reservations in advance and order the tasting menu.
- Park Bar – a rooftop bar on the top of a Parking Garage in Bairro Alto
- Belem Tower – a 16th century fortress in Belem
- Monument of the Discoveries – a stunning monument which pays homage to Portugal’s rich exploratory history
- Pasteis de Belem – home of the original custard tart! You will find these mini custard tarts all over Portugal, but the original version at this Belem bakery is hands down the best. Worth the wait, they are served warm with cinnamon and powdered sugar.
Day Trip: Sintra
While there is plenty to see in Lisbon, a day trip to Sintra and Cascais is well worth it. Sintra is an adorable little hillside town about 30 minutes from Lisbon, home to the Pena Palace, King Ferdinand II’s summer home, which offers daily tours.

Pena National Palace in Sintra
And Cascais, only about 15-20 minutes from Lisbon, is a popular seaside getaway for Lisbon residents.
Last Stop: The Algarve

Private beach at the Vilalara Thalassa Resort
For the last stop on our Portuguese tour, we rented a car and drove 2.5 hours from Lisbon to The Algarve, Portugal’s beach region. We checked into the Vilalara Thalassa Resort, a 5-star luxury resort in the heart of the Algarve region. While we enjoyed exploring the Algarve region including a drive to The End of the World, swimming at Praia dona Ana in Lagos, and enjoying the nightlife in Albufeira, the best part of our three days here was relaxing at our resort! We spent plenty of time enjoying the private beach and buffet breakfasts. And not to be missed, is a small boat tour along the coastline to explore the Algarve’s famous caves and azure waters.