Arrive at any time, make your way to our hotel, and have the day free to wander around Lisbon. The two-week group will arrive in the evening, and we will all go out for dinner. The Portuguese have dinner late, usually no earlier than 8:00 pm, so let’s get ready for our relaxed late-mealtimes.

Alternatively, if you can arrive two days early, you can arrive in Seville on Thursday, see a little bit of Spain, watch a flamenco show at the birthplace of flamenco, cross into Portugal by zipline (yes!), and explore the beautiful Algarve region of Portugal for two days. That’s very easy to do, and not very expensive. Let us know if you are interested after you register, and we’ll guide you through it.

OVERNIGHT: EXE Saldanha or similar

MEALS: N/A

Today is Lisbon day! We will start the day with a guided 3-hour city tour where we will get to see the main areas of Baixa, Chiado, and Alfama. We will break for lunch at Time Out Market, and then have the rest of the day to explore the city on our own. We’ll aim to visit the beautiful Belém tower, the famous Pastéis de Belém pastry shop, and Jerónimos Monastery (cloister) with its gorgeous azulejos.

In the evening we’ll head to lively Bairro Alto for dinner and a Fado performance (traditional Portuguese music).

OVERNIGHT: EXE Saldanha or similar

MEALS: Breakfast

Today is castle day! And as a bonus we’ll throw in some ocean views and cliffs. We’ll start our day driving to Sintra, that misty, magical town where palaces perch on mountaintops.

First stop: Palácio da Pena, the candy-colored icon of Portugal. We’ll wander its terraces and courtyards with sweeping views over the Serra de Sintra.

Next: a short hop to the Moorish Castle. We’ll walk the ancient ramparts, feel the breeze, and soak in those “wow” panoramas across the forest to Pena and beyond.

We’ll grab a quick bite in town, then aim the van toward the coast. Welcome to the edge of Europe: Cabo da Roca, the westernmost point of the continent—raw cliffs, Atlantic swell, lighthouse vibes, and camera-happy views.

From there we slide down to coastal city of Cascais for a relaxed seaside stroll and a late lunch/coffee by the marina. A gelado (Portuguese gelato) is a must!

Back in Lisbon, we’ll cap the day at São Jorge Castle for golden-hour views over Alfama and the Tagus—Lisbon glowing under our feet. Then it’s dinner and a slow, happy walk home. Perfect day.

OVERNIGHT: EXE Saldanha or similar

MEALS: Breakfast

Today we get to visit the Alentejo region, known as the Tuscany of Portugal. Welcome to Évora, a UNESCO-listed beauty wrapped in medieval walls. We’ll wander the whitewashed lanes to the wonderfully eerie Capela dos Ossos, the Chapel of Bones (yes, it’s made with real bones, and yes, it’s fascinating). From there, a quick stroll lands us at the Roman Temple, where columns have been sunbathing since the 1st century.

Next up: the Cathedral of Évora.  We’ll pop inside and, if you’re up for it, climb to the rooftop for jaw-dropping views over tiled roofs and rolling countryside. Then we’ll drift toward Praça do Giraldo for lunch. Lunch is all about hearty local flavors: think migas à alentejana (rustic bread-and-garlic goodness, often served with pork), porco preto (black Iberian pig), açorda, or a simple grilled fish, followed by a convent sweet like sericaia (soft egg pudding). Simple, local, delicious.

In the afternoon we’ll go for a walk at Aqueduto da Água de Prata, followed by an Alentejo wine tasting. Remember, this is the Tuscany of Portugal; of course they have their own wine!

We’ll finish the day at Almendres Cromlech, Portugal’s largest megalithic site, before heading back to Lisbon in the evening, happy and full of Alentejo stories.

OVERNIGHT: EXE Saldanha or similar

MEALS: Breakfast

Today we say goodbye to Lisbon and head north along the Atlantic to Nazaré, home of Praia do Norte and those record-breaking, hold-your-breath monster waves. Peak season is October-April, so May is usually calmer, but if the swell gods align… damn! We’ll hike  up to Sítio for the clifftop views and walk out by the São Miguel Arcanjo lighthouse above Praia do Norte, prime lookout for whatever Poseidon decides to throw at us.

After our ocean fix, we’ll roll inland to storybook Óbidos, a tiny walled town that looks straight off a movie set: cobblestone lanes, whitewashed houses trimmed in blue and yellow, flowered balconies, and medieval walls you can actually walk. We’ll wander the Porta da Vila gate with its blue-and-white azulejos, peek into the little shops, maybe find the church-turned-bookstore (Livraria de Santiago), and of course try a shot of ginja (sour cherry liqueur) in a chocolate cup, because yes.

And tonight… we sleep like royals: inside Óbidos Castle. Sunset from the ramparts, a slow dinner in town, and a moonlit stroll along the walls if you’re up for it. Medieval adventure unlocked!

OVERNIGHT: Óbidos Castle

MEALS: Breakfast

From castle walls to mountain peaks! We’ll roll out toward Serra da Estrela, The Alps of Portugal, with granite cliffs, mirror-calm lagoons, and big-sky views for days.

First goal: Torre (mainland Portugal’s highest point, 6538 ft.). We’ll wander the summit area for those 360° panoramas and snap the “top of Portugal” photo. If the weather plays nice, it’s crystal clear; if it’s moody, it’s dramatic. Win-win.

We’ll descend into the Zêzere Glacier Valley, a stunning U-shaped valley carved by ancient ice. Think sweeping curves, granite walls, and green meadows. We’ll stop at Covão d’Ametade, a little slice of magic with boardwalks, streams, and perfect picnic vibes. An easy wander and lots of photo ops.

From there, we head to Poço do Inferno, a pretty waterfall tucked in the forest near our final stop.

This is dairy country, so yes: Queijo da Serra tasting is on the menu (plus requeijão with honey). Simple, local, delicious.

We’ll finish the day in Manteigas, a cozy mountain town right in the heart of the park. Stroll the lanes, breathe that alpine air, and enjoy a hearty mountain dinner. Sleep comes easy up here.

OVERNIGHT: Vila Galé Serra da Estrela or similar

MEALS: Breakfast

We’ll leave our mountain hideaway and aim for Coimbra, one of the oldest university towns in the world, perched above the Mondego River.

In Coimbra we’ll wander the historic hilltop: the University of Coimbra (the Harvard of Portugal) courtyards, the baroque Joanina Library (pure art), the Sé Velha (Old Cathedral), and a stroll through narrow lanes where fado echoes from tiny cafés. Quick coffee, quick photos, big smiles.

Next, we roll to Aveiro, the charming canal town nicknamed the “Venice of Portugal.” We’ll hop on a colorful moliceiro boat to glide past Art Nouveau façades and the salt pans, then sweeten the day with ovos moles, the local pastry specialty. Before heading out, we’ll slip out to Costa Nova for a peek at the candy-striped beach houses. Postcard material, guaranteed.

From there it’s a smooth coastal hop to Porto. We’ll check in, freshen up, and head into town for our first taste of Portugal’s northern soul: ribeira views, azulejo-covered churches, and maybe a francesinha or fresh seafood for dinner.

OVERNIGHT: Holiday Inn Express Porto Boavista by IHG or similar

MEALS: Breakfast

Today is Porto day! We’ll start with a guided 3-hour city tour where we will see Sé do Porto (Cathedral), São Bento station and its famous azulejos, Avenida dos Aliados and Rua das Flores, Livraria Lello, and Ribeira quarter. Then we take a break for a scenic lunch at Ribeira riverfront. After lunch, we will finish conquering the city on our own and cross the Ponte de Dom Luís I, do a Port wine tasting in Gaia, visit Igreja de São Francisco, and if time allows, go on a Douro River cruise.

We’ll wrap the night back in the Ribeira with Porto twinkling across the Douro. Perfect Porto day.

OVERNIGHT: Holiday Inn Express Porto Boavista by IHG or similar

MEALS: Breakfast

Well, the time has come to say “adeus”, or better yet, just “ate logo” (see you soon) to beautiful Portugal. Those of us continuing on to the Azores will leave in the morning, and those of us coming back home can leave at any time.

OVERNIGHT: N/A

MEALS: Breakfast