Portugal 14-day itinerary: The dream two-week luxury adventure

If it’s your first time in Portugal you’ll want a two-week itinerary that explores the top bucket-list destinations. But since we’re not your average Portugal travel planner, we’ve given this 14-day trip plenty of Epic twists, meaning you’ll see the best sights while diving deeper, connecting with the locals, and experiencing a more adventurous side to these top destinations that few get to see.

From remote, sandy beaches and boho cabanas, to hilltop villages overlooking vast plains, to lesser-known backstreets in popular cities, this two-week Portugal trip gathers the local knowledge and expertise of our on-the-ground team in Portugal. 

If you want to plan your own Portugal bucket list itinerary, reach out to us at info@epic.travel and we’ll co-curate your dream trip.

The two-week Portugal itinerary at a glance

  • Days 1-2: Porto, Portugal’s buzzing historic capital. Explore two sides of the city and discover its landmarks with an architect.
  • Days 3-4: Douro Valley, the oldest demarcated wine region in the world. Visit a historic family-run estate.
  • Days 5-7: Alentejo countryside. Vast, empty desert-like plains broken up by cork trees and fortified hilltop towns. Dive into culture, meet artisans and producers, and float above in a hot air balloon.
  • Days 8-11: Coastal Alentejo. Discover endless white-sandy beaches dotted with trendy boho cabana beach restaurants. 
  • Days 12-14: Lisbon, the eclectic capital. This colorful city is a mix of old and new, historic and cosmopolitan.
Family

When to go:
April – November

Ideal trip length:
14 days

Adventure level:
Active adventure

Days 1-2: Porto, Portugal’s second city

Often referred to as the Invicta (never conquered) city, Porto has a proud legacy that you’ll feel from the moment you land. Its paradoxical character shows its heritage and cosmopolitan charm at once, and the best way to explore is on foot. After checking into your luxe townhouse-hotel – set on the same street as some of Porto’s trendiest hole-in-the-wall art galleries – step out to explore.

On the first afternoon, close to sunset, jump in a thrilling sidecar for a tour of the city with one of the best, funniest, and most knowledgeable guides around. Tired from the flight, this is the best way to explore the bucket-list sights of Porto (without having to walk everywhere).

After a good night’s sleep, experience Porto from a fresh perspective. That might mean exploring with a food tour that weaves together history, snacks, and storytelling. Or a half-day tour with a local architect, who will share masterpieces by two of Portugal’s most creative and visionary architects. Álvaro Siza Vieira and Eduardo Souto Moura have both been awarded the Pritzker Prize.

Towards dusk, the riverfront Ribeira neighbourhood calls. Beneath the skinny buildings covered in colourful tiles you’ll find dozens of terraces. It’s an ideal spot to kick back with a glass of Port wine while watching the rabelo boats cruise up and down the Douro River. After dark one evening, there’s nothing like a private concert at Porto’s famous Clerigos Tower.

We never plan the same trip twice. Reach out to have Epic curate your custom Portugal itinerary at info@epic.travel

Days 3-4: Douro Valley, the oldest demarcated wine region in the world. 

Rise early to set off for the breathtaking Douro Valley, a UNESCO World Heritage site and the world’s oldest demarcated wine region. This spectacular, steep landscape has been sculpted by human hands over centuries into the patchwork of vines you’ll see today.

Cruise along the snaking curves of the Douro River from Porto to Pinhão, stopping at a beautiful family-run quinta for a farm-to-table lunch. Feast on freshly baked bread, local cheeses, and cured meats paired with olive oil made at the same estate. The wine? Made here too, of course. After lunch, return to the river and continue upstream to the heart of the Douro Valley, where a luxurious estate and a plush bed await your arrival.

The following day, get your hands dirty when you follow a young winemaker for the day, learning about how the new generation is disrupting the industry. Enjoy an organic lunch of petiscos (Portugal’s answer to tapas) while tasting these new-age wines. Or set out to explore the land in a vintage car. Stop at a handful of wineries to taste the terroir and learn about how this is the birthplace of Port wine, and how wine barrels were once shipped downstream to Porto by boat to age by the humidity of the sea air.

Did you know that every Epic trip includes a 24/7 concierge service? It’s not an emergency number – it’s a personal contact of a person dedicated to making your stay easier and more pleasant.

Days 5-7: Alentejo countryside, space to slow down

Wave goodbye to the Douro Valley and watch as the landscape changes from verdant green to mountainous peaks to the vast, arid plains dotted with cork trees and olive groves. On the drive to the Alentejo, your private driver will make a scenic detour to reveal hidden schist stone villages tucked away in Serra da Estrela, continental Portugal’s highest mountain. It’s a side to Portugal that few have the chance to see, but reveals so much about the history, beauty, and people of this country.

By dusk you’ll reach a humble farmhouse estate in the Alentejo, a glorious place that is somehow both luxurious yet understated. Here amongst hectares of ancient oaks, vineyards, and horses, just breathe out and relax.

At dawn you’ll rise for a spectacular experience, setting off in a private hot air balloon to see the Alentejo region from above. As one of Portugal’s most remote areas, you’ll gain a sense of the vast, quietness as you float above the landscape. Return to earth for a well-earned breakfast before setting off for Monsaraz, a fortified hilltop village. Dive into history with a private guided tour, then pop to a nearby pottery village to join a hands-on workshop and take your own terracotta piece home.

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Days 8-11: Coastal Alentejo, a place to relax

Comporta Beach

After a few days inland, it’s time for the coast – and the golden sands of Comporta are calling. This luxurious yet wild stretch of coastline is the perfect beach destination for barefoot luxury. Sink your toes into the sands of some of Portugal’s most beautiful beaches and breathe out. Comporta is all about where you stay, so at Epic we source the best hotels and resorts within your budget.

Being on the sparsely populated Alentejo coast is all about slowing down. You want time to relax by the pool or head to the beach with a good book, but also to experience the best of the landscape. Riding horses on the beach at sunset is ideal. Trot through the verdant rice paddies, over wild pine-covered dunes, and onto an empty, hard-to-access strip of golden sand. With any luck, you’ll be the only people on the beach.

Use an afternoon to cruise along the coast of nearby Arrábida Natural Park, a secret verdant paradise where lush green hills meet the turquoise blues of the Atlantic. As you captain jets across the Sado Estuary, look out for the local dolphins. Or get active on the Costa Vicentina, where you’ll find 24 circular day hiking trails, or follow part of the famous coastal Fishermen’s Trail (and have someone collect you at the end).

Four or 14 days…. let Epic handle the details of your custom Portugal itinerary at info@epic.travel

Days 12-14: Lisbon, the eclectic capital. 

At last, Portugal’s colorful capital is calling. From Comporta it’s a short 75-minute private transfer to your 5-star hotel in the heart of the city. Drop your bags, then set off for a foodie experience. Either join a private Portuguese food tour, and snack across the capital, or meet a local chef at his exquisite downtown home and roll up your sleeves for a hands-on cooking class. 

Besides seeing the sights and backstreets of the city alongside locals – there are a handful of unmissable Lisbon experiences. At sunset there’s nowhere better to be than aboard a sailboat. Cruise the Tagus River at dusk taking in Lisbon’s landmarks (such as the São Jorge Castle and Torre de Belém) from the water. Follow it with dinner at a world-class restaurant doing modern takes on traditional cuisine. Don’t skip the chance to see fado live, a traditional music genre from Lisbon with a melancholic heart. We’d send you to a fantastic concert set within the echoing halls of Lisbon’s historic aqueduct. Goosebumps worthy indeed!

Finally, Sintra is one of Portugal’s most popular day trip destinations, but there’s an off-beat and adventurous way to explore. Tick off the famous palaces and castle of Sintra in a vintage off-road jeep. Connect with locals who know the Sintra-Cascais Natural Park like the back of their hands, exploring via dirt backroads and seeing Sintra without the crowds.

READ NEXT: Portugal 7-day itinerary: A week of family foodie and coastal fun

How we choose accommodation

Our philosophy is to avoid large chain hotels and to focus on distinctive places to stay defined by character and style. This could be a charming traditional quintas or herdades in Portugal’s wine regions, a boutique hotel that combines traditional Portuguese style with contemporary design, or a luxury hotel that offers all the facilities and service you might expect from a 5-star property. Epic can propose a range of accommodation options to suit your budget and style.

If you’re planning an adventure to Portugal in 2025 or beyond, we can plan your custom 14-day Portugal itinerary. Just reach out at info@epic.travel 

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