The sweet spot of Portugal

With five trips to Portugal under my belt, I can honestly say I’ve covered most of the country — including the islands. There’s always more to explore (and I will!), but at this point, I feel confident in saying I have a strong grasp on what makes Portugal so special.

My first trip took me through the Azores, then up to Porto and down to the Algarve. Later, I sailed the Douro River on a Viking cruise. In October 2023, I joined my first Portugal FAM, and by April 2024 I was back again for a quick solo trip to Lisbon.

I’ve seen Portugal from just about every angle, but this most recent trip — where I drove from Porto down the coast and then through the Alentejo — was the one that really helped me define what I’d call the perfect route for travelers.

Whether you’ve already visited and want something more authentic and less touristy, or this is your first trip and you want a mix of city, beach, and countryside, this itinerary hits the sweet spot.

I like to think of it as the Perfect Portugal Triangle — the ideal blend of vibrant cities, coastal landscapes, and inland wine country. Yes… so much good wine.

Let's say you have a week in Portugal and want to fly in and out of Lisbon. This is my top suggested route to make the most of your time in the country while seeing so many sides of it. This is going to take you off the beaten path, avoiding some of the most touristy spots (looking at you Sintra!). However, I can promise, you will walk away having fallen in love with Portugal for the first time or all over again, if you are going back for more.

Why This Route Works (Especially for One-Week Trips)

If you have a week in Portugal and you’re flying in and out of Lisbon, here’s the timeline that makes the most sense:

Arrive in Lisbon, drive to Comporta
Spend 2 nights in Comporta
Drive to the northeastern Alentejo (Monsaraz area)
Spend 3 nights in Alentejo
Drive back to Lisbon
Spend 2 nights in Lisbon
Fly home

Tip: Depending on your interests (beach vs. wine country), you can easily swap this to 3 nights Comporta + 2 nights Alentejo. And if you can stretch the whole trip to nine nights, even better.

Seasonal Tip:
Everyone assumes summer is ideal. In reality?
Spring and early fall are the sweet spots.
Summer brings mosquitos to Comporta (a lot of them) and intense heat to Alentejo. Unless you enjoy melting, skip this route in July/August — I have another itinerary for that coming soon.

Stop 1: Comporta (2 Nights)

If you’re flying from the U.S., you’ll land in Lisbon early. Skip the temptation to explore immediately — grab your rental car and head south.

Comporta is often called the “Hamptons of Portugal.” In truth, it’s more of an aspiration than a reality right now. Yes, it’s growing quickly and attracting luxury investment, but for the moment, it's still quaint, a bit rustic, and the small coastal towns are still charming and a bit sleepy--exactly as you want them!

One important thing to know: Comporta’s grasslands and dunes are protected, so you won’t find hotels directly on the beach (at least for now). This is intentional — it keeps the coastline untouched and wild, with long stretches of soft sand and chic-but-casual beach clubs that everyone can enjoy and because there are no private beaches in Portugal, once you pick your spot, it’s yours for the day.

Where to Stay: Quinta da Comporta

Quinta da Comporta is the property I recommend over and over because it truly blends luxury with nature, wellness, sustainability, and understated style.

Think:

calming neutral tones, natural textures that slow-living aesthetic Portugal does so well
a beautiful infinity pool overlooking rice fields
a holistic spa with treatments inspired by local botanicals
yoga, wellness programs, and quiet spaces to unwind
farm-to-table dining that highlights simple, seasonal Portuguese flavors
bicycles for guests, curated experiences, and an easygoing rhythm that encourages rest

It’s elevated but relaxed. Whether it's time at the beach, in the spa or exploring coastal towns, you'll have enough time to get a taste of all Comporta has to offer.

Stop 2: The Alentejo (3 Nights)

From Comporta, head northeast toward the Alentejo — specifically the Monsaraz area.
On your way, be sure to stop in Corval, if you love authentic Portuguese pottery. This town is loaded with locally owned small pottery makers and you can add to your collection. You'll see these pieces sold in towns like Evora and Monsaraz, so if you miss it, you'll have another chance but know, buying it direct will stretch your money and let you buy more (chic math!).

For most, the Alentejo region is new to them.The ironic thing is, it's the biggest region of Portugal, covering over a third of the country and is truly the agricultural epicenter of Portugal. The name itself means "beyond the Tagus," and once you cross that threshold, you enter a landscape that feels worlds apart from the terraced vineyards of the Douro or the Atlantic drama of the Algarve. This region is known for its olive groves, cork trees and Iberian black pigs.

And wine lovers, this is your zone! The estates around Évora, Reguengos de Monsaraz, and Vidigueira have transformed the area into one of Portugal’s most exciting wine destinations, known especially for bold reds.

Where to Stay: São Lourenço do Barrocal

If there is one place I’d send anyone in Alentejo, it’s São Lourenço do Barrocal — no hesitation!

This 780-acre estate feels like stepping back in time in the most beautiful, intentional way. Once a working farm village, it’s been restored into a luxury countryside retreat where everything feels grounded and peaceful.

Expect:

a minimalist, farmhouse-meets-boutique aesthetic
stone buildings, open landscapes, and absolute quiet
organic gardens + seasonal cuisine
a Susanne Kaufmann spa
horseback riding, hiking, swimming, wine tastings
onsite stables, olive groves, and their own winery
thoughtful touches everywhere without anything feeling fussy

On our whirlwind research trip, we only stayed for one night and it was not enough. The grounds alone feel like you are stepping back in time and slowing down (for real)! The design, service and offerings are perfection and you will want/need time to breathe deep, get outside, and discover all this stunning property has to offer.

What to See in the Area

While you may choose to never leave the property (and I fully support that plan), if you do, there are spots worth going to:

Monsaraz

Namely the hilltop village of Monsaraz. A 15-minute drive from the property, this hilltop medieval village overlooks the Alqueva Lake and countryside below. Wander the cobblestone alleyways, explore tiny museums, step inside ornate churches, and soak in endless views. It’s small but incredibly charming. If you love history, you can get your fix here with the small museums and elaborate churches to better comprehend the history of the region and the strife between Spain and Portugal.

Day Trip Idea: Explore Wineries Nearby

Alentejo is full of top-tier estates — you can easily plan day trips for tastings if you want to dive deeper into the region’s wine scene.

Stop 3: Évora → Lisbon (2 Nights)

When it’s time to leave São Lourenço, head towards Lisbon — but not without stopping in Évora. Évora is the Alentejo's crown jewel—a UNESCO World Heritage city that rises from the plains like a time capsule of Portuguese history. Encircled by medieval walls, its historic center is a mesmerizing labyrinth of narrow cobblestone streets, whitewashed houses trimmed in yellow ochre, and squares that seem to exist outside of time.

From a remarkably preserved Roman temple to the University that is one of Portugal's oldest to the haunting Capela dos Ossos—the Chapel of Bones—decorated with the remains of some 5,000 monks, there are many reasons to stop in Evora. If it's shopping or dining, Evora has that too. Évora manages the rare feat of being both a living, working city and an architectural masterpiece, making it the perfect base for exploring the wider Alentejo region.

Evora is the perfect halfway point between Monsaraz and Lisbon. Leave mid-morning (because no one wants to rush out of Sâo Lourenco do Barrocal) and plan to land in Evora at lunch. Spend an hour or two and head to Lisbon.

Land in Lisbon, return your car and check into your hotel. From there, put your walking shoes on and hit the hilly, colorful streets of Portugal's captial. The energy and rhythm of the city will no doubt wake you up from the slower pace of Alentejo.

Tip: If you’re looking for the best things to do on your first visit, you can check out my Lisbon guide here and download my free Lisbon resource here.

final thoughts

While Portugal is a small country and you can cover a lot in a short amount of time, I would argue to say, it's not a country you want to rush. It's like a fine wine, meant to be enjoyed and savored with time. To me, Portugal is a country you fall in love with the first time and return to again and again to embrace all it has to offer.

A plan like this gives you the best of Portugal without feeling overly rushed, and it will feel like a true vacation. After all, isn't that the point of travel - to escape the hustle and rush of our every day lives?

Happy travels, friends!

Celebrate and Explore Portugal!

One Week in Portugal: The Best Route from Lisbon for Beaches and Wine

The sweet spot of Portugal

Why This Route Works (Especially for One-Week Trips)