A Luxury 14-Day Itinerary Through Portugal: From Lisbon to the Alentejo
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Portugal is one of those destinations that effortlessly blends history, flavor, charm, and natural beauty—and it does so in a way that never feels forced. From the electric energy of Lisbon’s tiled hillsides to the quiet, sun-drenched landscapes of the Alentejo, it’s a place that rewards both relaxed wandering and carefully planned experiences. That’s why, as a luxury travel advisor with over 10 years of experience (and someone who’s personally fallen for Portugal), this is one of my favorite countries to design longer, slower itineraries.
Whether you want to plan the best way to spend two weeks in Portugal or you’re researching direct flights from the USA to Lisbon, this guide will give you a curated look at how I might structure a 14-day Portugal itinerary—one that’s immersive, well-paced, and elevated with insider access throughout. These aren’t just “highlights of Portugal;” they’re experiences that can be woven into a trip that feels tailored to your preferences, pace, and passions.
And while these suggestions are some of my favorites, there are a million ways to plan a memorable trip to Portugal based on what you are hoping for. Reach out to my team today to talk about how we can personally curate your trip to Portugal.
5 Days in Lisbon
I recommend starting your trip with five nights in Lisbon, where you'll find the best international flight options and an incredible mix of culture, food, and coastal charm. Lisbon’s airport (LIS) is Portugal’s largest and best-connected, offering nonstop flights from major U.S. cities like New York (JFK), Boston (BOS), Washington D.C. (IAD), Miami (MIA), and Chicago (ORD). Most nonstop flights range from 6.5 to 8 hours, making it one of the most accessible European destinations from the East Coast and Midwest.
Use your first day to settle in—but don’t waste it entirely. One of my favorite ways to start a Lisbon stay is with a private vintage sidecar tour through the city’s winding neighborhoods. Lisbon is built on seven very steep hills, and walking around on day one (especially jet-lagged!) can be exhausting. This tour gives you a feel for the layout of the city and stops at some of the best miradouros (viewpoints) without the sore feet. When you work with a travel advisor like me, I make sure your tours are guided by people who are both deeply local and incredibly attentive.
On day two, lace up your walking shoes and dive into Lisbon’s food scene with a guided food tour. I always say that eating is one of the best ways to understand a place—and Lisbon is full of culinary surprises, from custard tarts (pastel de nata) and codfish cakes to traditional liqueurs like ginjinha (made from sour cherries). The best guides will not only introduce you to local dishes and markets but also share stories behind the food; about the families who run the bakeries, the colonial history behind certain spices, and the modern chefs reimagining old flavors.
Your third day is perfect for a day trip to Sintra, a romantic hilltop town filled with palaces and gardens that feel like something out of a fairytale. Getting around Sintra is not easy, as most of the major sites are far apart, and it’s very hilly. I always work with my clients to figure out their ideal plan for getting around Sintra, whether that is through the ease of hiring a private driver (and guide) or a little more thrilling tuk-tuk. Some adventurous and active travelers like to mountain bike or hike around the town.
One experience I love to arrange (and my personal favorite) is a luxury picnic overlooking the grounds of Pena Palace or the cliffs near Monserrate…an elegant and peaceful moment far from the crowds to soak in the experience while also giving your feet a break.
Back in Lisbon, consider spending your fourth day taking a cooking class. You can opt for a full savory menu, like seafood cataplana or caldo verde, or a pastel de nata workshop if you’re craving something sweet and fun. It’s a hands-on way to take a little piece of Portugal home with you, and a travel advisor like me can connect you with chefs who offer intimate, personalized classes.
For your final day in Lisbon, I love pairing two experiences: a private tram ride through the city’s historic quarters (yes, we can rent one just for you!) and a tile-painting class where you create your own hand-painted azulejo tile. These are both iconic parts of Portuguese culture, and experiencing them in a personal, unrushed way is something you’ll never forget.
3 Days in the Algarve
From Lisbon, head south to the Algarve, Portugal’s southern coast. Dramatic cliffs, golden beaches, and laid-back lifestyle offer a different vibe of Portuguese life. But if you’re expecting Caribbean-style beachfront resorts, think again. The coastline is rugged and elevated, which means many properties are perched on cliffs with sweeping ocean views. It’s also one of Portugal’s destinations for surfing, and during some times of the year it can be windier.
You can take a scenic train ride or arrange a private transfer—either way, it’s about three hours trip from Lisbon. Some clients prefer to stay directly on the coast, but my personal favorite resorts are tucked away slightly inland—still just a 15- to 20-minute drive from the sea, but with a more boutique, local feel. These countryside properties often have award-winning restaurants, on-site spas, and peaceful settings that feel worlds away from the busier beach towns.
When planning itineraries for my clients, this leg of the trip is about recharging and relaxing. Trust me, after 5 days walking Lisbon, you’ll want it. On your first day in the Algarve, settle in and relax by the pool, stroll through a nearby village, or enjoy a massage at the resort spa.
Then your second day is for exploring the coastline by boat. I always recommend chartering a private boat to see the famous sea caves—especially Benagil Cave, which is one of the most photographed spots in the Algarve. With a private captain, you can avoid the crowds, explore lesser-known caves, and even stop to swim if the weather’s right.
On your third day, dive deeper into the region’s culture. Visit a cork factory to see how Portugal’s most iconic export is made, or explore one of the charming whitewashed towns like Silves or Ferragudo. I also love pairing this with a wine tasting and lunch at a local winery. Even though Portugal’s wines are still somewhat under the radar internationally, they are incredible and unique, and Portuguese wineries are proud to share their wine and food culture with you.
4 Days in the Alentejo Countryside
After your coastal escape, head north and inland to one of Portugal’s most magical (and underrated) regions: the Alentejo, home to one of my favorite hotels in Europe: São Lourenço do Barrocal. This luxury estate is tucked into the countryside near Monsaraz, and is one of those rare hotels where the property itself becomes the destination.
Image from São Lourenço do Barrocal
Spread across a 2,000-acre estate, the hotel blends understated luxury with a deep connection to the land. You’ll find olive groves, vineyards, horseback trails, and even ancient Roman ruins on site. Whether you’re sipping estate-made wines, biking through the fields, or indulging in treatments at the Susanne Kaufmann spa, every moment here invites you to slow down.
For one of your days, explore Monsaraz, a nearby medieval village that’s as charming and historic as they come. I love arranging sunset picnics here overlooking Alqueva Lake. Rustic bread, local cheese, and crisp white wine as the light glows golden across the horizon…it’s a perfect way to wrap up your last few days in Portugal.
The beauty of spending several nights in the Alentejo is that you truly get to rest and reflect before the trip ends, with stress-free access to nearby sights and experiences. I always tell clients to leave at least one day completely open with no plans. Just permission to wander, nap, or repeat a favorite activity. The region encourages this kind of stillness, and it’s one of the reasons my clients say this portion of the trip stays with them the longest.
To get home, it’s about a 2-hour drive back to Lisbon from the Alentejo, which makes it easy to plan around your departure flight. Most travelers don’t need to overnight in Lisbon again, unless you have a very early flight. Either way, I’ll make sure your transfer is timed perfectly so you can end your trip with ease.
14 days in Portugal won't be enough
Portugal is full of the kinds of experiences that travelers remember forever, and this 14-day itinerary is one of my favorites because it blends city, coast, and countryside in a way that feels balanced and immersive. You’ll taste, explore, relax, and connect—with the culture, with your surroundings, and with the people you meet along the way.
When you work with a luxury travel advisor like me, I make sure every detail is taken care of: from restaurant reservations and private guides to room upgrades and exclusive experiences you won’t find in a Google search. If you’re dreaming of Portugal and want it done right, I’d love to help you plan something extraordinary.
Ready to plan your perfect island escape? Let’s design the ultimate luxury beach trip that’s tailored to you.
Whitney Shindelar
Undiscovered Sunsets was a long time in the making, even if I myself didn’t realize it. During my time at the University of Northern Iowa, I studied abroad in New Zealand. Upon graduating, I bought a one-way ticket to France, lived with a French family and studied with classmates from Turkey, China, Russia, Germany, Italy, and everywhere in between. In 2010 I began teaching English as a foreign language. This job quickly took me to China, where English teachers were in high demand and within three years, I began working in a 5-star hotel, speaking Mandarin throughout most of my day. In total, I lived abroad for 7 years.
I consider Undiscovered Sunsets to be the perfect mélange of my personal experience traveling the world and my professional experience working in the hospitality industry.
I look forward to designing your next adventure!
