Portugal Hiking & Wine Adventure

DAY 1

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

DAY 2

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

DAY 3

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

DAY 4

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

DAY 5

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)

DAY 6

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)

DAY 7

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