Portugal Hiking & Wine Adventure

“Drinking good wine with good food in good company is one of life’s most civilized pleasures.”

Michael Broadbent

From gorgeous palaces to faded manors, from lush forests to breathtaking cliffs and pristine sandy beaches, what’s not to love about Portugal? We meander through one of Europe’s oldest nations, exploring historically charming Sintra to sun-kissed Lagos, hiking in national parks, vineyards, historic sites, and coastlines, and stopping to sample cheese, olive oil, seafood, and of course, wine!

Portugal is well-known for its superbly crafted wine. Due to its magical combination of the right soil, with the right climate, and the right grapes,  just a taste of a Portuguese wine makes it easy for even the most casual wine drinker to see why they have been heavily exported and traded for hundreds of years.

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Trip Favorite Moments & Reviews

“Very hard to say, there were so many, but if I had to choose one, it would be the coastal hike on the first day. Great scenery, amazing wild flowers, challenging hike, and of course, beer and wine at the end!”

George K.

“I loved the wineries, restaurants, and seeing so much of southern Portugal. It was so special to meet some of the winery owners and hear the winery’s story from them such as our visit to Pera-Grave. I surprised myself by how much I loved Portugal.”

Lisa T.


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Past Traveler Tour Rating

4.89/5 stars

Trip Highlights

  • Hike through Portugal’s stunning landscape, from lakes and forests to sand dunes and beaches.
  • Explore delicious Portuguese wines at several winery visits and wine-paired meals.
  • Enjoy incredible cuisine including fresh seafood and delectable olive oil.

Bom dia! We meet this morning at our hotel in the fairytale-esque town of Sintra. This UNESCO World heritage cultural landscape contains a stunning diversity – from lakes and forests to sand dunes and beaches. The area is a testament to the harmonious coexistence between man and nature displayed through pristine manor houses and embellished gardens nestled throughout, unique examples of old world Portuguese and British colonial affluence. On the way to our introductory hike overlooking the wild Atlantic, we'll stop at the beautiful Monserrate Palace and walk around its glorious gardens before we depart for the coast.  We'll also stop at a hole-in-the-wall bakery to pick up a little something to tuck in our daypacks for lunch and perhaps nibble on some delightful pasteis de nata – delicious custard pastries. Our hike today (you can choose one of two options) stretches along the coast, high above the crashing waves of the Atlantic, on trails hidden among the coastal flora from Cabo Roca, the western-most point of continental Europe, all the way to Praia da Adraga.  Returning to Sintra this afternoon, you'll have the option to visit the exquisite Pena Palace high above the town – an amalgamation of different design styles and influences, which range from North African to medieval gothic.  Dinner tonight will be at a tiny adega where we will have an introduction to Portugese wines and be surrounded by musicians playing Fado music, a melancholy style that has its origins in Portugal.
Activity: you have the option of a one hour hike on a winding coastal trail of dirt and rocks, or extending for a total of two+ hours on coastal trails that have significant ups and downs


Today we leave Sintra behind and head into the Setúbal region of Portugal, with Palmela as our destination. Once a fortress and now a small town, Palmela has quiet streets and mountainous panoramic views. On our way, we shuttle south over the longest river in the Iberian Peninsula, the Tejo. We’ll stop in the aristocratic town of Azeitao and tour the historic wine cellars of Jose Maria da Fonseca, the oldest wine house in Portugal. We sample several wines and then allow you to explore and have lunch on your own in town. Next, we are off to hike a portion of the Rota Moinhos (windmills path) in the Arrábida Natural Park. The trail owes its name to several traditional windmills which can be seen along the way and passes by the ruins of a fortified settlement from the Copper Age. Panoramic views include the region’s mountain ranges, Palmela Castle (our destination for the evening) and the Tejo River estuary. Before dinner, you'll have the option to learn all about (and of course, sample) the Moscatels of the area before enjoying a memorable tapas dinner at a local taverna only a few steps from our hotel.
Activity: hiking two to three hours on rolling dirt road roads and a ridgetop trail


Today is one of our “winiest” days of the tour! This morning we'll walk through town, downhill to the base of Palmela. Although the coffee in Portugal is more than adequate to wake one up, nothing says "vacation" quite like a morning wine tasting!  And Quinta do Piloto is happy to oblige us. Afterwards we’ll drive into the mountains of Portugal and the heart of the Alentejo wine region, to the remarkable private wine estate of Monte da Ravasqueira, where you can stretch your legs again with a nature hike around the estate after our wine-paired estate lunch.  From there, it is on to the bustling walled city of Evora, a UNESCO world heritage site and the capital of the Alentejo region.  You'll have a bit of time to relax before Francisco leads everyone on a short historical walking tour (including a visit to the Chapel of Bones!) of the winding cobbled streets prior to our dinner at a lovely farm-to-table dinner in the heart of old town.
Activity: hiking up to six kilometers on rolling dirt roads and paths inside a vineyard + city walk of approximately one hour


You may hear the roosters crowing as daylight approaches.  Just ignore them, as today is your opportunity to sleep in a bit!  You'll have some free time to explore Evora this morning, lounge at the pool, or perhaps arrange for a spa treatment at our hotel.  We'll depart later this morning.  Our first stop is one of our favorite places in Portugal: the tiny and picturesque medieval village of Monsaraz – complete with a hilltop castle that offers a lovely view of the entire Alqueva reservoir valley.  If you peer closely, you can see Spain, right across the water!. We'll offer a short historical walk of Monsaraz and encourage you to visit the tiny tasting room at Ervideira before we depart for a five-course wine-paired lunch at Herdade do Esporão, one of the most prestigious wine estates in Portugal, located on an extraordinary landscape surrounding a lake which serves as a sanctuary for local wildlife.  Afterwards, the group can decide if they want to hike around the lake before returning to Evora for the evening. Tonight's dinner is on your own.
Activity: optional mostly flat walk around the lake inside a vineyard, which will take approximately an hour and a half


If Portugal hasn’t impressed you yet, today will surely be the day. From the mountains to the beach we go, of course with a very sophisticated pit stop along the way. Our journey today takes us through the Alentejo plains into the Southern region of Algarve and its historic town of Lagos.  Our trail starts at the Alvor lagoon and takes us west to the stunning beach of Meia Praia. This area is known for its delicious clams. Those who wish can walk all the way to the hotel along the beach, stopping for lunch at any of the many great seafood restaurants. Our lodging for the next two nights is centrally located on the marina, giving everyone the option to shop, relax or wander the afternoon away as they please. We will visit the Monte do Além Organic winery for a tasting before we walk to dinner and if you so choose, some more great Algarve wine.
Activity: easy walk along lagoon and Meia Praia beach (approximately 4K) and an additional optional 2K into town (with the opportunity to swim)


Today is the kind of day dreams are made of. We meet in the morning and take a fun local bus ride out to Praia da Luz for seaside walk back to Lagos. For those who prefer an easier walk, we will peer over cliffs that give way to secluded beaches. Those who care to get their feet wet can engage in the more challenging ambling and will have the liberty to explore as they please, descending and ascending the rocky pathways. We recommend stopping for a seafood lunch by the ocean before returning to our hotel in Lagos.  We will have time to freshen up before walking to a nearby wine shop for a Port wine tasting prior to a multi-course gastronomic farewell dinner at our hotel.
Activity: seaside cliff trail hike of approximately 3K/one hour with the opportunity to extend another 5K/2 hours (and the opportunity to swim)


This morning we rest our feet and take a sweet boat tour along the coast and into the famous caves of Ponta da Piedade. After visiting the caves and regaining our land legs, you can walk to the nearby Lagos castle wall and old town before checking out of the hotel and saying our farewells. You can choose to take a train (or fly) back to Lisbon, or extend your time in this wonderful city or places nearby, which we highly recommend.
Activity: One- to two-hour boat ride to the caves, with the opportunity to swim from the boat

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Trip Accommodations


This hotel is centrally located and offers contemporary comfort and quiet seclusion, making it a perfect spot to relax after a long day of hiking.


The town of Palmela is centered around a fortified castle and nestled at the foothills of the Arrabida Mountain Range. Our hotel is next to the castle and is a former hospital dating back to the 1600s. It offers panoramic views of the village and surrounding countryside.


This five-star spa hotel resides under an ancient aqueduct right on the edge of the narrow, winding streets of the old town.


The perfect place to end our trip! This chic hotel overlooks the Lagos Marina and houses and an excellent restaurant. If you don't feel like walking, you can relax in their rooftop pool!

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Arrival & Departure

We meet you in Sintra (30 minutes west of Lisbon) in the morning, on the first day of the trip. We recommend arriving the day prior to explore Lisbon (the wonderful capital city) or Sintra and cushion any potential travel delays. The main airport in Lisbon (airport code LIS) is located only 15 minutes from downtown. Our tour ends in Lagos. From here, you can return by train to Lisbon, or extend your travels. We will provide more information on transportation in the Pre-Departure Packet.

What's Included
  • A Zephyr guide accompanies each trip, with a second added as necessary.
  • Double occupancy lodging is included. If you are traveling solo, we will match you with another traveler of the same gender. However, you may pay a single supplement to have your own room.
  • All dinners (except one night, in Evora, when we have a filling and rather late lunch), two lunches, and all breakfasts are included. Gratuity for these meals is also included. In general, we leave one dinner and most lunches open so that you have time to explore and enjoy the local flavors en route.
  • All your transportation is included once you meet your guides on the first day.
  • All group activities are included, including wine tastings and entrance fees.
  • NOT INCLUDED One dinner, beverages, desserts, most lunches, gratuities to your guides, personal expenses, and travel to and from the destination.

You can expect an average temperature of 65 degrees with a high of 70 in May.  They will also be coming out of their wetter season so it may rain, but most likely only for a day or two.

Hiking Conditions

Our walks will vary between well-beaten gravel paths to cobblestone streets to some rocky ascents and descents, please bring good shoes and walking sticks. We will let you know ahead of time what to expect on each trail as well as if there are alternate routes.

Changes to Your Itinerary

While everything under “What is Included” will remain the same, the actual restaurants, hotels, and activities listed in our itineraries are subject to modifications. Changes that are out of our control are common – a restaurant closes or loses its awesome chef, a winery changes its visiting hours, a hotel gets remodeled, a road or trail undergoes construction. You are entrusting us to create an outstanding vacation for you and so it is possible we may take the liberty of making necessary changes (even at the last minute, during the guides’ scout trip) to the itinerary that will improve your overall trip experience. If there is any one experience that is going to make or break your trip, please discuss this with us in advance! We will attempt to keep our website itinerary as current as possible and communicate any major changes with you in the weeks prior to the tour.

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