Sightseeing Portugal

Lisbon

Lisbon offers coastal beauty and lovely vistas with quick day trips to the seaside town Cascais or the forested village of Sintra. Note: while the Alfama neighborhood is quintessential Lisbon, I'd recommend against staying there. Its winding streets and alleys are impossible to navigate and it's really difficult to get anywhere else in the city.

Rocco

Very cool cocktail bar and restaurant in central Lisbon (an easy walk from the train station to Cascais).

Casa do Alentejo

A good old-school Portuguese restaurant specializing in dishes from Portugal's interior (Allison's favorite: porco alentejana). The restaurant is inside an old Moorish mansion.

Cascais

Cascais is a beautiful, easily walkable community 45 mins by train from downtown Lisbon. It makes a good alternative to the big city of Lisbon, if you want to be nearby but not *in* the city. If you have a car you can also easily drive the gorgeous coastline to Cabo da Roca, Ursa beach and beyond.

Westlight Cascais Chalet

Wonderful hotel right in the heart of Cascais with beautiful balcony views.

Taberna Clandestina Cascais

Great food and cocktails right in Cascais' eat-street.

Cabo da Roca

Ursa Beach

Evora

Evora is a museum-city with roots dating back to roman times. It is the best example of classic Portuguese history as it was spared the 1755 earthquake that leveled Lisbon.

Fialho

An excellent restaurant serving traditional regional Alentejo cuisine with old-school waitstaff formality. The food is excellent as is the service, just don't expect them to smile.

Enoteca Cartuxa

Cartuxa winery's in-town restaurant. Relaxed, delicious and great waitstaff who speak perfect English. It's an easy and tasty lunch or dinner option.

Parque Natural da Arrábida

Portugal's version of California Hwy 1 and Big Sur. Beautiful drive and gorgeous beaches. Plenty of hiking.

Senhora do Cabo Meco

Quaint bed and breakfast near Sesimbra and Arrabida park.

Onda Azul

Excellent seafood at this unpretentious beach restaurant. Go. Eat.

Bacalhoa Winery

$15 for a wine "tasting" will get you 6 essentially full glasses of great wine. Bring snacks!

Nazaré

Beautiful, low-key fishing village with a huge beach, stunning cliffs and a great overall vibe.

Iris Apartment

Great stay right off the beach with easy street parking. The host, Osvaldo, speaks excellent English and is a great guide to the small village.

Tomar

Tomar is former seat of the Order of the Knights Templar and is a charming little town with the impressive Convent of Christ, one of the chief works of the Portuguese Renaissance. It is an easy drive from Nazare.

Lagos

The Algarve is famous for its beaches, with good reason. Lagos is our favorite base for exploring the region. Lucky for you, it'll be before high season, so you'll have most of the beaches to yourselves.

Sunrays kitchen

Incredible breakfast just outside the old-town part of Lagos and near a number of AirBnB apartments.

Vila Nova de Milfontes

Milfontes is where the Portuguese go for holiday. It's a beautiful beach town off-the-beaten-path of international tourists and yet still relatively en-route to the Algarve.

Porto

Porto sits atop the banks of the Douro River and is the birthplace of port wine. The city offers remarkable architecture and day trips--by boat or train--up the river to the stunning terraced vineyards of the Douro Valley. Be sure to cross the river to Vila de Nova Gaia and tour the port wine houses.

Padaria Ribeiro

THE MOST AMAZING GINGER CARROT CAKE. EAT IT AND LIVE, DAMNIT, LIVE!

Pinhão

The Douro Valley is stunning. The terraced wineries and dramatic river banks are definitely worth a day trip or, better yet, renting a car and experiencing the whole area. Note: Northern Portugal gets a lot of rain in the winter and May might still be wet. That said, there are a lot of gorgeous wine lodges where the weather won't matter.