10-Day Glorious Autumn Itinerary in Portugal: Porto, Lisbon & Sintra

Most likely you’ll have an early arrival on a not so restful overnight flight if coming from the USA, like we did. Treat yourself with a private pick up at the airport for a Lisbon to Porto Private Luxury Road Trip. First stop will be the Medieval Village of Obidos and the onto Nazare, a colorful fishing village.

The half hour nap is just what you’ll needed as you arrived in Obidos. In October FOLIO (International Literary Festival of Obidos) goes on, while in Summer there are art festivals. Walk through Passos de Calvario the town gate with blue tiled archways into the hilltop village; making your first stop for coffee and 130-year-old recipe cakes and breads still cooked in a wood-fired oven at Capinha d’Obidos.

Your stop here isn’t long, so walk around the market square and castle of Obidos at the top of the hill and meandered back down through blue painted walls of winding streets and steps to Church of Saint Mary to find a local crafts fair in the square where you’ll encounter a local artisan making hand-loomed pouches and bags. You’ll find hers and other artists work at ID Local Concept Store (Book Exchange) as well. Before heading back to the car, treat yourselves to ginga de Obidos (ginjinha – syrupy cherry liqueur often served in a chocolate cup) at Fabrica das Bombokas chocolates shop.

Riding along the scenic drive, arrive at Nazare Village, a colorful fishing village in central Portugal. The views from the Sitio on the top of the cliff looking down at Nazare is breathtaking. Feeling jetlag setting in, take a nap as your driver brings you into Porto.

Your home in Porto is the charming Casa da Companhia on the pedestrian landmark, R. das Flores. After resting and feeling refreshed, head out to explore before dinner. A lovely evening walk would be from Sao Bento Train Station to see the opulent interior of hand painted blue tiles and vibrant yellow ceiling and catching Igreja de Santo Antonio lit up in azure blue at night.

Tonight’s dinner is at Tascö with their inventive and delicious Mediterranean and Portuguese cuisine on the menu. If the bartender happens to be trying a recipe for a new cocktail that night, you can have the pleasure of giving him your suggestions, as you tweak the recipe together.

An after dinner walk to see the incredible view on Miradouro da Rua das Aldas of the Rio Douro River at night before falling asleep in your room with its own private secret garden.

Start the day off with a Private or Small Group Walking Tour. If you prefer to explore on your own, follow this route. Head out from your hotel after breakfast to Miradouro da Vitoria for a morning view over the city. Next, head over to Mosterio de Sao Bento da Vitoria and Igreja e Torre dos Clerigos with Clerigos tower where the climb to the top is well worth the view.

Livraria Lello is a must see for those who are big Harry Potter fans being that this intricate tiny book shop interior inspired the library from the series. Take a walk onto Av. dos Aliados which is the main city center avenue and pop into the McDonald's Imperial (claiming to be the most beautiful McDonald's in the world, but I may vote for the one in Paris on Champs Elysée instead. Peek in and vote for yourself.).

Making your way to Majestic Café where you can stop for a coffee and see the Belle Epoque-era interior. Heading up to Chapel of Souls, you'll walk along Rue Santa Catarina. This chapel has the most impressive blue tiled exterior, but not to be missed is the beautiful fountain in front at Praca de Gomes Texieria. On your way back on Rua Santa Caterina, stop off for a treat at Fábrica da Nata.

Lunch at Café Santiago for a Francesinhas seems like a very touristy thing to do, but it’s a colossal meat lovers’ sandwich that’s surprisingly attractive with its glistening sauce over the sunny egg yolk in the center. It is the official sandwich of Porto, after all. Come hungry or share. If you’re a vegetarian, please avoid! This isn’t the place for slow service or even efficient service. Know that waiting and being ignored and rushed may all be part of the experience.

After that lunch, you’ll want to nap, but let’s keep you walking because now it’s time to go sample some Portuguese wine by the river. Stroll to Porto Cathedral (Se do Porto) then take the winding streets down to the river front (Cais da Riberia). It’s lovely to spend the afternoon on either side of the river. Both sides offer incredible views and lovely places to have an afternoon libation. To enjoy the river on the water, take a 6 Bridges afternoon river cruise instead.

Walking along R. das Flores back to the hotel, stop at Claus Porto Perfume store for gorgeous handmade Portuguese soap. Shop at Typographia for not-so-ordinary souvenir -t-shirts of high quality and unique designs.

We’ve not talked about Pasteis de Natas yet. Delicious custardy egg tarts and an absolute must eat in Portugal. My favorites in Porto? Manteigaria (many locations in Lisbon as well) and Castro.

Dinner tonight is at eMotivo. This petite restaurant is helmed by a petite stupendous chef Sara Verde and her team of 2 serving an incredibly well priced tasting menu of traditional Portuguese flavors with contemporary finishes. Inviting and unpretentious.

Head across the Douro River this morning after 10 AM to Vila Nova de Gaia and take a walk over the Ponte Luis I bridge. If you are walking on the upper bridge over the river, don’t forget to take in the view of both banks of the river. Overlooking everything in Gaia is Mosterio da Serra de Pilar. Walk up to this complex you’ll also find Jardim da Morro for a stunning expansive view of Porto.

Coming down from the monastery, take a ride on Teleferico de Gaia (Cable cars) that takes you 50 meters above port lodges and terracotta roofs along the river edge. Many of the port wine cellars require reservations for tastings. The world’s most prestigious port houses live here such as Taylor’s, Graham’s Cockburn’s etc. However, my absolute favorite was the small tasting room of Kopke Wine House, the oldest port wine house in Porto. Try some of their vintage reserves. A casual friendly tasting room was Quevedo with servers full of charm and enthusiasm to tell you all about their port and wines.

Walking through the street art-filled back streets towards WOW, a fairly new port and wine museum complex built atop of the hills, attached to Taylor’s Port is where I fell in love with Sogevinus Wine Shop – Santa Marinha with its starkly beautiful industrial concrete circular staircase leading to the tasting room with wall-to-wall ceiling height port barrels lining each side on the showroom floor below. Up at WOW Porto in October the Craft Beer Festival was going on. Lively crowds took a detour from learning all about Portuguese wines and port to sample the plethora of beer choices. Making your way to Taylor’s for another tasting but in the end, it’s the charming garden and roaming peacocks and roosters that will catch your attention.

Make your way back to Porto side of the river to visit Igreja de Santa Clara, then take a food tour at Mercado do Bolhao. You’ll wish you lived in Porto so you can buy yourself a lovely dinner to cook at home tonight with all it's beautiful fresh produce offerings, cured hams, tin fish, flowers and of course more wine.

For your last night in Porto head to Mito. This great restaurant serves up sharing options. The menu is divided into four sections of hot, cold, grilled, and sweet. Ordering from each section rather reminded me of listening to a symphony.

In the morning take an Uber to Foz do Douro Beach to see the crashing waves of the Atlantic Ocean. Find a seat at the beach front restaurant Praia da Luz for a front seat view of the beach. Make your way to The Casa de Serralves - a pink 1930's art deco mansion with a contemporary art museum and expansive garden grounds.

Back in the area near your hotel, have a simple tenderest steak sandwich at Pregar and then a nata at Castro a few doors down. Pick up your luggage and head to your high-speed Alfa Pendular train to Lisbon. The train takes 3 hours to arrive in Lisbon. The scenic ride on this clean and fast train can be bumpy as it winds through hills and valleys into Lisbon, and not recommended for those with motion sickness.

Arrive at Santa Apolonia Station and make your way to your hotel in Alfama Lisbon, where you’ll be calling Santiago de Alfama – Boutique Hotel home for a few days. (*For this itinerary, we opted to stay in 2 different hotels in 2 different areas in Lisbon, however, there is no need to move hotels. I love hotels, what can I say?)

Arriving late and hungry into Lisbon, make your way through the hilly winding streets of the Alfama area this evening to have dinner at Antiga Wine Bar. In this cozy locally owned wine bar, you’ll find the best wine experts help you select the wine that suits your palette. Their food is phenomenal also. The walk back to your hotel after dinner through winding stairs and alley ways, finding street art and hidden courtyards will remind you why you opted to spend a few nights nestled in this area of Lisbon.

If you’re an early riser, do try to catch the 28E historic tram for the whole loop. If you get up early and catch it before the commuters and tourists crowd to get on, you’ll have a wonderful ride through all the major tourist sites of Lisbon. It’s also just an experience in and of itself to be this close to the side walks that you can almost touch the walls from the windows. Do not actually stick your arms out while riding it though!

Get off at the stop for Castelo de S Jorge and spend some time visiting this incredible castle fort. From atop you’ll see all of Lisbon from Praca do Comercio to Parque Eduardo VII along Avenida da Liberdade. On one side of this main avenue in the valley, you’ll find Alfama hills, Baixa at the far end to the waterfront, and Barrio Alto y Chiado hills on the other side.

The best part of Alfama is just to wander the steep winding steps. You will go see Church of Sao Vicente de Flora, National Pantheon, and Lisbon Cathedral along the way. After passing Old Afama Square, take R. de Sao Pedro where you'll pass by a lot of restaurants which features Fado singers. Make sure to stop off at Ginja de Alfama for a taste of ginjinha liquor. Go to Prado Mercearia - great place to get a coffee, lunch, and some local organic souvenirs, resting up before you head from Alfama to the waterfront / Baixa.

At the Praca do Comercio you’ll see the waterfront and understand the wealth and the ambitions of the Portuguese empire during the late 18th century as they take to the seas to conquer the world.

Visit Time Out Market. It’s bustling and crowded. If patience is your middle name, then you’ll likely find yourself a seat in this busy food hall filled with tempting eateries, but after a brief visit, if you’re feeling overwhelmed as I was, grabbed a nata from Manteigaria and let the sugary treat give you comfort as you take an Uber to Museu de Marinha (Maritime museum in a 1500’s monastery) to learn more about the Portuguese history and see actual historic boats and ships.

One of the things to note in Portugal is just how slick the streets can become when it rains. These intricate beautifully laid mosaic tiles that make up the Portugal pavement can be downright dangerous when wet, adding to the steep hills. Museums are a great way to take shelter when the weather turns bad, which isn’t often during fall season. There is no shortage of great museums to go to.

Dinner tonight is at Taberna - Bairro do Avillez. In this gastronomic complex you can sample traditional cuisine presented in the form of petiscos (snacks) and main dishes.

Maybe Lisbon isn’t your first choice for shopping, but you’ll be surprised what unique items you can find while sightseeing. Starting from Praca dos Restauradores, you’ll find the Gloria funicular from below the hill. This colorful funicular will take you up to Miradouro de Sao Pedro de Alcantara vista point. Locals and tourists alike gather at this park enjoying the view, street performers, and drinks.

After that, you’ll move on to Church de Sao Roque (a 16th C. church where all carvings are covered in gold from Brazil). For your first shopping opportunity, go to Together Anna Westerlund, a local Portuguese designer who makes one of a kind jewelry of ceramic and gold on site. From there, you'll go to Carmo Convent ruins. From here go from the back of the Convent (Museu Arqueologico do Caromo) to the upper viewing platform of Elevador de Santa Justa (cross the walkway, and then line up to climb the wrought-iron staircase to the viewing platform) so you can up an personal to the 19th century elegant Neo-Gothic iron tower. This is far more fun then riding the actual historic elevator up from below.

Around the area along R. Garret Street are a few Lisbon shops worth checking out: Luvaria Ulisses for Portugese leather gloves and The Feeting Room for Portugese leather shoes. Try Alcoa, a beautiful coffee shop with traditional Portugese pastries - their custard filled cones are special!

Next stop is Livraria Bertrand - Chiado (the oldest bookstore in the world according to Guinness World Records). From here, visit Loja da Burel, a unique Portguese company that still makes all hand loomed scarves, art, and furniture pieces. A Vida Portuguesa showcases traditional high quality home products. Heading down to Rua Augusta look up to see Santa Justa Lift from below.

Dinner tonight is at Sála de João Sá. The chef here showcases contemporary cuisine using only organic Portuguese products for this luscious tasting menu feast where everything is incredible to look at and never quite tastes as you’d expect (in a good way). Wine paring is a must and a delight. When your tummy is beyond full on the delectable dessert, they bring you a selection of hand made chocolates to die for!

Before dinner, if you’d like to have a break from days of walking the hills of Portugal, try a spa treatment at the sublime The Beauty Bar at Santiago de Alfama.

For this itinerary, we opted to do a move during the middle of the stay in Lisbon to Four Seasons Ritz. The side of Parque Eduardo VII has a different feeling than the ancient charm of Alfama. This hotel offers the chic luxury of Avenida da Liberdade and the Principe Real area.

If you’d like to do the same, this morning you’ll be making the hotel move. After getting settled into your spacious room with a view of the park, grab brunch at the Veranda Restaurant in the hotel and sign up for a private Pilates class to stretch out all your tired muscles. Walking in Lisbon is challenging even for the fit and healthy.

Head to LX Factory via Uber. This industrial compound turned cafes, restaurants, shops, and artist studios houses a unique bookstore, Ler Devagar. This is a great area to spend a few hours wandering through. After, make your way to Basilica da Estrela. For anyone not suffering from acrophobia, you must make your way to the top of the roof for both the panoramic view of the surrounding area as well as the view of the church dome from within. It’s a great place to catch the sunset.

Dinner tonight is Cura at Four Seasons Ritz – a one Michelin star restaurant in this contemporary elegant environment.

Joinin a small group tour today for a tour to Sintra. After being picked up to join the group, you’ll be on our way to Cascais. This charming seaside town is now the premier luxury destination of the Lisbon coastline. You’ll find a historic center with lavish villas and an imposing fort. However, I loved the Pestana Cidadela Cacais Hotel in the Pousada & Art District. The incredible modern art installation in the lobby alone is worth the short visit.
Next, you’ll reach Cabo da Roca, a cape that is the westernmost point in Europe. You will arrive to see this mystical place where the lighthouse is often covered by fog while wind whip through your hair as you try to capture a perfect photo.

You’ll arrive in Sintra, a town that is up on the hills of Serra de Sintra and is hidden by majestic pine trees as your driver takes the winding road up. First thing you’ll see is the Sintra Palace hovering over the main town square. But the highlight of Sintra is Quinta da Regaleira. Your guide will walk you through this UNESCO World Heritage 16th century private Renaissance style manor and gardens full of mystery, gothic details, gargoles and towers.

Your last stop is the Park & National Palace of Pena. You have the choice of visiting the interior of the Palace of just walk the grounds. This colorful hilltop castle is most beautiful from the exterior but the walls present a stunning view of the surrounding gardens.
You’ll be returned to your hotel area.

Tonight’s dinner is at the gastronomic delight that is Boubou's. This family-owned restaurant is well loved by travelers and locals, with casual refined dining, open kitchen, and a lovely private courtyard. There’s a sense of “I’m just happy to be here” upon arriving and greeted with charming friendliness.

This morning, you’ll head out to Museu Nacional do Azulejo to get familiar with these famous decorative blue tiles that define Portugal. This museum is in a 16th century monastery with stunning chapel.

After you’ll head to the waterfront and take the Cacilhas - Cais do Sodre ferry across the Tagus River. Once across, have lunch at Ponto Final by the water for fresh seafood and a relaxing view of the river. It is also a great place just to sip wine in the early afternoon. It does get busy, but the wait isn’t usually too long unless it’s on a weekend. Take a walk at your leisure in Almada and Cacilhas.

Dinner tonight is at Suba. This is absolutely one of my favorite places in Lisbon. If the weather is nice, arrive earlier than your reservation and have your pre-dinner cocktail on the rooftop. You won’t want to miss their view. The cocktails are delicious as well. If it’s cold, they’ll offer you blankets and turn the heaters on to keep you warm. The incredible sunset seen here is worth a little chill or wind.

Suba is in Verride Palacio de Santa Catarina hotel. It is a converted palace and worth walking around the hotel itself to see the architecture. After your drinks, the staff will guide you down one flight of stairs to the restaurant. Whether you order the tasting menu or a la cart, you’ll be treated with surprise courses between the main courses. I’m going to give one hint on the surprise but will say no more – the flower box! There’s not one patron at the restaurant whose eyes didn’t light up when this was presented. The staff was delighted to see everyone’s reactions. This is elegant, fine and fun dining at it’s best!

This morning, head out early by Uber to Pasteis de Belem for breakfast of nata and coffee at the original natas pastry bakery. Tummy full, you’ll head over to Mosteiro Jeronimos. At 9:30 AM Paroquia de Santa Maria de Belem opens and you can first enter the park and purchase the tickets for Mosterio Jeronimos and Igreja de Santa Maria de Belem (both officially open at 10 AM). Because there is a long line to wait for the tickets followed by another line to wait to get in, alternatively, you can purchase pre-timed tickets in advance. The finest stone carvings in the monastery are along the exterior at the southern doorway into the church. However, visiting the interior of this incredible monastery is a must. The interior courtyard is astonishingly beautiful.

After that Torre de Belem. This is also a very busy attraction, so do pre-book timed tickets. This 16th century fortification was the main port of entry and departure for Portuguese explorers. Like the monastery the stone carvings are spectacular. The tower allows you to visit each level and each presents a different vantage point of the Tagus River. Take a scenic walk along the river to the imposing Padrao dos Descobrimentos monument.

Lunch is a highlight here for me. I cannot tell you how much I loved O’Frade. It’s predominantly a circular bar seating set-up inside with some outdoor seating. This is one restaurant where no matter how lovely the weather, I highly recommend you grab a seat at the bar. Make a reservation even for lunch. It gets super busy. Order a variety of petiscos to share but save a little room for the duck rice dish. Let them suggest some wine paring by the glass for you based on what you ordered. Sitting around the bar, you’ll see your delicious dishes being prepared.

After lunch, visit the National Coach Museum. This gem of a museum showcases the finest collection of carriages in the world.

Another scenic stretch along the river front, is Doca de Belem to MAAT. Time permitting, it’s a nice to visit.

As today is your last day in Lisbon, after returning from Belem via Uber, head to Embaixada, a 19th century palace turned shopping mall and a lovely Gin bar featuring Portuguese designers, brands, and gin of course! This ex-private palace turned shopping paradise is a gem to explore. The bartender at Gin Lovers Bar & Restaurant will give you a tour of the plethora of gin varieties they produce and make you a delightful cocktail. Take a walk back to your hotel on Praca do Principe Real, stopping at 21 PR Concept Store.

Have dinner at Oficio tonight. They define their menu as “atypical tasco”. This informal modern restaurant takes traditional Portuguese cuisine perfect for sharing and gives it a modern global twist with excellent cooking techniques.

If you’re up for a beautiful evening walk, take Av. Da Liberade back to your hotel and see this grand center of Lisbon lit up at night as you say goodbye to this beautiful city.