Portugal
Portugal is a captivating blend of historic charm, dramatic coastline, and vibrant culture, where cobblestone streets, tiled façades, and fresh Atlantic seafood define everyday life. From the golden cliffs of the Algarve to the soulful sounds of Fado in Lisbon, it offers warm hospitality and rich traditions.
| Day | Highlights | Overnight |
|---|---|---|
| Day 1 | This is the travel day. Getting to the airport and taking an overnight flight to Lisbon. | In flight |
| Day 2 | Arriving in Lisbon, renting car and driving to Sintra area. | Sintra |
| Day 3 | Tour Pena Palace, Moorish Castle & Montserrat Palace & Gardens. | Sintra |
| Day 4 | Quinta de Regaleira and Gardens, Cabo da Roca, Praia da Ursa. Beach | Sintra |
| Day 5 | Leave Sintra, Visit town of Obidos, Arrive in Porto. | Porto |
| Day 6 | Sights of Porto. | Porto |
| Day 7 | Leave Porto, visit town of Amarante, arrive in Duoro. | Duoro |
| Day 8 | Santuário de Nossa, visit to a winery. | Duoro |
| Day 9 | Leave Duoro area, stop in the town of Evora, arrive in Lux (Lagos area in the Algarve region). | Luz |
| Day 10 | Hike along the Seven Hanging Valleys Trail, Lunch at by the sea, explore Lagos. | Luz |
| Day 11 | Visit the Benagil Cave, explore the town of Faro. | Luz |
| Day 12 | Beach day at Praia do Camilo | Luz |
| Day 13 | Drive back to Lisbon, Visit Praca do Comercio, Pink Street, and cocktails on terrace. | Lisbon |
| Day 14 | Sights of Lisbon. Tram ride. Dinner and Fado show. | Lisbon |
| Day 15 | Free day in Lisbon; Belem Castle, visit to Pastéis de Belém. | Lisbon |
| Day 16 | Taxi to the airport, flight home. |
Day 1 - We flew overnight on a transatlantic flight to Lisbon, Portugal
Day 2 - Lisbon & Sintra
We begin the adventure by picking up a rental car at the airport, providing the freedom to explore the coast at your own pace. From there, we headed straight to Cascais for lunch, where a lively stretch of restaurants offers plenty of options on Yellow Street. After lunch, we took a short drive to Boca do Inferno, a dramatic coastal cliff formation where waves crash powerfully against the rocks, creating one of the region’s most iconic scenic spots. Afterwards we continued onward to our hotel. Vila Vitorino is a beautiful luxury chalet on the outskirts of Sintra. From the comfy beds, the delicious breakfast (with amazing coffee!), the welcoming living room where we can relax and helped ourselves to some liquors, the amazing gardens and pool, I can’t recommend this place enough. The only thing to note is that you do need a car and will need to drive to the nearby sights of Sintra and the coast.
Day 3 - Sintra
If there is one place in Portugal that feels like a fairytale, it’s Sintra. Today is all about vibrant colors, misty forests, and ancient stone.
Sintra’s narrow, winding roads aren’t for the faint of heart. Our best advice: Aim to park your car up at Pena Palace early. Not only does this secure your spot for the main event, but it sets you up for a stunning 20-minute walk over to the Moorish Castle later. It’s much easier to navigate on foot than trying to re-park mid-day!
You’ve likely seen the photos, but nothing prepares you for the vivid yellows and reds of Pena Palace in person. Perched on the highest peaks of the Sintra Mountains, this Romanticist castle looks like it was plucked straight from a dream. Spend your morning wandering the terraces—the views of the valley below are unparalleled. Note that it is timed entry tickets for Pena Palace and they are strictly enforced now. If you miss your time slot, you might not get in!
After the flamboyant energy of Pena, take the wooded path over to the Castelo dos Mouros (Moorish Castel). This 8th-century fortress feels like the "Great Wall of Portugal." Walking along the high stone ramparts gives you a rugged, historical contrast to the palace you just left.
To escape the biggest crowds, head over to Monserrate Palace and Gardens. It’s a masterpiece of Anglo-Saxon, Indian, and Arab architectural influences. The gardens are world-class, featuring exotic plants from every corner of the globe. It’s the perfect place to slow down and breathe in the forest air.
For dinner, try some delicious authentic Portuguese cuisine at Ribeirinha de Colares at this location. Dinner was highly enjoyed by all and very reasonably priced! This place is busy and I highly recommend making a reservations a few days in advance.
Day 4 - Sintra
Today we traded the mountaintop palaces for underground mysteries and the rugged Atlantic coastline.
Our first stop was Quinta da Regaleira, and let me tell you—this place is an absolute trip. It’s a gothic fever dream of hidden tunnels, grottoes, and symbolism. Check out the Initiation Well. It’s an inverted tower that sinks nine stories into the earth. Walking down that spiral staircase feels like stepping into a secret society ritual. Note that you definitely need to book your tickets in advance. It’s one of the most popular spots in Sintra, and for good reason.
From the forest, we drove toward the salt air of Cabo da Roca. This is the westernmost point of continental Europe—as the Portuguese poet Camões wrote, it’s "where the land ends and the sea begins." The best part? The views are completely free. The lighthouse standing against the backdrop of the crashing Atlantic is a sight you won't forget.
If you have the legs for it, the hike down to Praia da Ursa is worth every step. It’s widely considered one of the most beautiful beaches in the world, framed by massive "bear-shaped" sea stacks. If you prefer something a bit more accessible but equally dramatic, Praia da Adraga is just a short drive away. The rock arches and dark sand here make it feel like a movie set. Praia da Ursa is quite steep and rocky. It’s definitely "sneakers or hiking boots" territory—not flip-flops! Praia Grande, aka big beach, lives up to its name with an enormous expanse of golden sand. At one end, the jagged cliffs bear the imprints of dinosaur footprints. A lovely nearby spot for a lunch is O Croa.
We ended the day at Moinho Dom Quixote, a quirky, greenery-filled restaurant built into an old windmill. They don’t take reservations, so you’ll want to arrive early. Grab a seat on the terrace with a cocktail. Watching the sun dip below the horizon from this perch is the ultimate way to toast to your Sintra adventures.
Day 5 - Obidos & Porto
Our journey north began with a stop in the medieval walled village of Óbidos, just an hour from Sintra. Walking the ancient perimeter walls offers a great bird’s-eye view of the terracotta rooftops, but the real highlight is the local ritual: sipping Ginja (sour cherry liqueur) out of a decadent chocolate cup. We continued toward Porto with an optional detour through Aveiro, the "Venice of Portugal," to admire the colorful Moliceiro boats and grab lunch by the canals.
After arriving in Porto and checking into our Airbnb at 3:00 PM, we immediately set out on a walking tour starting at Liberdade Square. Porto is a visual feast; we marveled at the massive blue-tiled exterior of Igreja do Carmo, looked up at the 250-foot Clérigos Tower, and explored the stunning tiled cloisters of the Porto Cathedral. The interior of the Church of St. Francis was equally breathtaking with its intricate gold leaf, while the Vitória Viewpoint provided the perfect panoramic introduction to the Old Town.
As evening approached, we wound our way through the narrow, colorful streets of the Ribeira neighborhood down to the riverfront. Crossing the bridge to Vila Nova de Gaia is a must for the best sunset views of the city skyline. We capped off the day with a tasting in the world-renowned Port wine cellars and a drink at Terrace Lounge 360. If you're driving, the Alfândega Car Park offers a 48-hour ticket for €35, which is a lifesaver in this hilly, pedestrian-heavy city.
Day 6 - Porto
Porto’s charm is best discovered on foot, starting with a stroll down Santa Catarina Street, the city’s vibrant main shopping artery. While you’re there, step into the Belle Époque elegance of the Majestic Café, a historic landmark frequently cited as one of the most beautiful cafés in the world. Just a short walk away is the legendary Livraria Lello; this stunning Neo-Gothic bookshop charges an €8 entry fee, which is conveniently refunded if you purchase a book.
The artistry continues at the São Bento Train Station, where the vestibule is covered in magnificent azulejo tilework depicting scenes from Portuguese history. From there, head to Batalha Square to admire the 18th-century Batalha Palace before making your way down to the lively riverfront. For a different perspective of the city’s skyline, book a 6 Bridges Cruise from the Gaia side (approximately €15 for 50 minutes) and finish your afternoon at Jardim do Morro for the most iconic panoramic views in town. We capped off the evening with a dinner reservation at Rua Tapas e Music Bar, a spot known for its fantastic atmosphere and live performances.
Day 7 - Douro Valley
After one last morning soaking in Porto’s atmosphere, we left its granite-lined streets behind and headed toward the rolling, terraced hills of the Douro Valley. On the way, we paused in the charming town of Amarante for a relaxed stroll and lunch before continuing on to Quinta das Susandas, where we settled in for a two-night stay.
The journey into the valley is an experience all its own, with winding roads opening onto vineyard-covered slopes at every turn. Arriving at our hotel in the heart of wine country, the city’s hum gave way to the gentle rustle of grapevines—an idyllic setting to sip a glass of local Port as the sun slipped behind the hills.
Quinta das Susandas is a small, family-run wine estate tucked into the hills of Portugal’s Douro Valley, offering a quiet, intimate alternative to the region’s larger vineyard properties. Surrounded by terraced vines and sweeping valley views, it feels more like staying at a countryside home than a traditional hotel.
For dinner our hotel host recommend a small family run restaurant, Tasca do Zéquinha, which was so good we decided to go there the second night as well. It’s located in the nearby town of São Nicolau which offers great views of the Douro Valley and the charming town..
Day 8 - Douro Valley
We began with a visit to the Santuário de Nossa Senhora dos Remédios. Even if you aren't religious, the monumental baroque staircase—with its nine landings, ornate fountains, and blue-and-white tiling—is a breathtaking architectural feat.
From the spiritual, we moved to the viticultural with a visit to Quinta do Panascal. This estate is one of the most prestigious in the region, and walking through the vineyards offers a real sense of the "heroic viticulture" required to grow grapes on such steep, rugged terrain. After a tasting of their world-class Fonseca Ports, we hit the road for a beautiful drive on the N222 between Peso da Régua and Pinhão. This stretch of pavement hugs the river so closely you can almost touch the water, winding through the heart of the UNESCO World Heritage landscape.
Day 9 - Evora, Luz - in the Algarve
We hit the road early, checking out of the Douro at 8:00 AM for the long trek south. The landscape shifted dramatically during the 4.5-hour drive as the lush, terraced vineyards of the north gave way to the sun-baked cork forests and rolling plains of the Alentejo region. We pulled into Évorajust in time for lunch. This ancient museum-city is a UNESCO World Heritage site, and wandering through its whitewashed streets leads you straight to the hauntingly beautiful Roman Temple (often called the Temple of Diana). If you're looking for something even older, a quick detour to the Almendres Cromlech reveals a mysterious circle of prehistoric standing stones that rivals Stonehenge in age.
After our brief dive into history, we settled in for the final 2.5-hour leg of the journey to the Algarve, checking into our Airbnb in Luz and strolled the waterfront in Luz and settled in for dinner. We choose Luz because it was close to the touristy popular Lagos, but quieter.
Dinner by the waterfront in Praia da Luz is relaxed and quietly atmospheric. Tables sit just steps from the sand, with the sound of waves in the background and cliffs glowing in the evening light. Meals are simple and fresh—grilled fish, clams, or cataplana—paired with chilled local wine. As the sun sets, the promenade lights come on and the mood softens into an unhurried evening of conversation, sea air, and lingering over good food.
Day 10 - Algarve
We kicked things off at 8:00 AM to beat the midday heat, starting the Seven Hanging Valleys Trail at the world-renowned Praia da Marinha. This 3.5 km moderate hike is a continuous highlights reel of golden limestone cliffs, hidden sea caves, and turquoise sinkholes. Every bend in the path reveals a new, dramatic perspective of the Atlantic carving into the coastline.
After working up an appetite, we made our way to Boneca Beach Restaurant & Bar. Tucked into the rocks, it’s an incredible spot to refuel while listening to the waves. We took some time to explore the nearby caves, which feel like secret chambers accessible only by the sea. To wrap up the day, we headed into Lagos. The old town is a charming maze of cobblestone streets, traditional tiled houses, and lively plazas—perfect for a slow evening of shopping and people-watching.
Day 11 - Algarve
A perfect blend of natural wonder and historic charm. We kicked things off with a 10:00 AM boat trip to the Benagil Cave, an absolute bucket-list experience. Seeing the "Algar de Benagil" from the water is the only way to truly appreciate the scale of its massive sea dome and the iconic "eye" in the ceiling that floods the cave with golden light. It felt like being inside a natural cathedral carved entirely by the waves.
In the afternoon we shifted gears to explore the Faro Old Town (Cidade Velha). Entering through the grand Arco da Vila, we were instantly transported away from the modern bustle into a peaceful maze of cobblestone streets and whitewashed buildings shaded by orange trees. It was the perfect afternoon for a slow walk, admiring the medieval walls and the quiet, historic atmosphere that makes Faro such a unique, soulful gem on the coast.
Day 12 - Algarve
Golden cliffs and turquoise waters define the Algarve. We spent the morning beach-hopping between two of the region's most picturesque spots: Praia do Camilo, which you reach by descending a long, winding set of wooden stairs, and Praia Dona Ana, where the towering cliffs protect a calm, crystal-clear bay. For those looking for more than a tan, kayaking is a popular way to explore the coastline and hidden grottoes from here.
Continuing south, we reached the spectacular Ponta da Piedade. This headland is a labyrinth of sea arches, grottoes, and hidden coves carved out of the ochre-colored limestone. Whether you walk the cliff-top paths or take a small boat down into the water-level caves, the scenery is absolutely world-class. We finished our day around back in the Lagos old town, wandering through the historic plazas and soaking up the vibrant evening energy of the downtown streets.
Day 13 - Lisbon
We bid farewell to the Algarve and made the drive north to the vibrant capital. First arriving at the airport to return the car and take a taxi to our apartment in Lisbon. Once settled, we wasted no time diving into the city’s electric atmosphere, starting at the grand Praça do Comércio. This massive, sun-drenched plaza serves as Lisbon’s front door to the Tagus River; standing between the yellow Pombaline buildings with the Rua Augusta Arch behind you, you really get a sense of the city's regal history.
From the riverfront, we made our way to the famous Pink Street in Cais do Sodré. Once a gritty maritime district, this neon-pink stretch of pavement is now one of the most photographed spots in the city, lined with eclectic bars and cafes that hum with energy. We capped off our first Lisbon evening at Terraço Chill-Out Limão, a rooftop bar perched atop the H10 Duque de Loulé. With its charming blue-and-white tiles and intimate atmosphere, it offered a spectacular panoramic view of the city’s red rooftops as the sun began to set.
Day 14 - Lisbon
We fully embraced the steep hills and historic soul of Lisbon. We started the morning with the quintessential city experience: a ride on Tram 28. This vintage yellow streetcar clatters and squeaks through the narrowest streets of the Alfama and Baixa districts, offering a "hold on for your life" tour that feels like a trip back in time.
From the tram, we climbed even higher to the Castle of São Jorge. Wandering the ancient fortifications and pine-shaded courtyards of this Moorish castle provides a breathtaking 360-degree view of the city and the river. Of course, Lisbon is the city of miradouros (viewpoints), so we spent the rest of the afternoon hopping between them. Miradouro da Graça offered a perfect, relaxed spot to see the castle from a different angle, while the terrace at Miradouro de Santa Luzia.
Visiting Lisbon isn’t complete without an evening of live Fado. Tucked into candlelit taverns in neighborhoods like Alfama or Bairro Alto, the music feels intimate and deeply emotional. As singers pour out stories of longing and nostalgia, the room falls silent, creating a powerful, unforgettable connection to the soul of Portugal.
Day 15 - Lisbon
From Lisbon, getting to Belém is easy—just hop on the tram or train along the river for a short, scenic ride. Once there, start with a stop at Pastéis de Belém to try the city’s most famous pastel de nata, served warm with a dusting of cinnamon. Then take a stroll along the waterfront to admire landmarks like the Jerónimos Monastery and the iconic Belém Tower, often referred to as Belém’s castle, standing proudly by the river. Finish off the trip at one of the many restaurants back in Lisbon.
Day 16 - Lisbon - Home
The end of an adventure through Portugal. It began in the lush hills of Sintra, where fairytale palaces and misty forests set a magical tone, before heading north to the vibrant riverside city of Porto. From there, the route slowed into the terraced vineyards of the Douro Valley, offering quiet beauty and world-class wine. The trip then shifted south to the sun-soaked cliffs and beaches of the Algarve, where coastal views and relaxed seaside towns took over. It all concluded in Lisbon, a city rich in history and atmosphere—perfect for reflecting on a journey that captured the many sides of the country.
Time to leave and take a taxi to the airport to embark on the return trip home.
