Portugal Hiking 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 first 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 5-mile 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 a short walk away and feature classic Portuguese flavors.

Easier Route: 8 km (5 miles) on a winding, tree-lined trail of dirt and rocks (310 ft elevation)
Main Route:  8 km (5 miles) on coastal trails that have significant ups and downs (950 ft. elevation)

DAY 2

After breakfast, we’ll depart Sintra and make our way to the coast for today’s hike. We’ll be dropped off at Praia do Guincho to begin our walk along the shoreline toward Cascais. This stretch of trail follows the Atlantic with wide-open views, salty breezes, and the option to continue a bit farther to Tamariz Beach for those who want to extend the day. We’ll break for lunch at Casa da Guia, perched above the water, or in Cascais itself, where cafés and fresh seafood abound. This afternoon, our local guide Francisco will lead us on a walking tour of Cascais, sharing stories of its transformation from a fishing village into a coastal retreat. You’ll then have some free time to dip your toes in the sand, wander the narrow streets, or simply relax at a café before we gather for dinner together at Emma, filled with fresh seafood and delicious Portuguese classics. Afterward, we’ll head back to Sintra to rest up for the next day.

Main Route: A 9.5 km (5.9 miles) coastal hike (65 ft elevation)
Extension: Continue 1.7 km (1 mile) towards Tamariz Beach

DAY 3

This morning, after breakfast, we say goodbye to Sintra and set our sights on the south. On the way to Lagos, we’ll stop for a hike through the Arrábida Natural Park, following the Rota dos Moinhos—the windmill route. Starting from Quinta de Alcube, we’ll wind our way along rolling hills and vineyards, passing traditional windmills as we make our way toward the historic town of Palmela. The hike will take about 2–3 hours, with time to enjoy the views and soak in the countryside. Lunch is on your own today, with options like dining at Bobo da Corte inside Palmela Castle—where the views stretch for miles—or at Quinta do Piloto, a family-owned winery right at the end of the trail. Afterward, we’ll continue south, crossing the mountains, weaving past cork oak forests, and arriving at the Algarve coast. By evening, we’ll settle into Lagos, our home for the next several nights, and come together for dinner at a local favorite.

Main Route: 10.9 km (6.8 miles) hike on rolling dirt roads and a ridgetop trail (557 ft elevation)

DAY 4

We meet in the morning and take a fun local bus ride out to Praia da Luz for a seaside walk back to Lagos along the Algarve’s golden coast. After a short bus ride to Praia da Luz, we’ll follow the shoreline back toward Lagos. The first stretch—about 3 km to Porto do Mós—takes roughly an hour, with an option to continue another 5 km (two hours) along dramatic cliffs and coves all the way into town. Bring a towel and swimsuit if you’d like to pause for a dip, and a little pocket money for a seaside lunch—our top pick is O Camilo, a restaurant perched above the ocean with unbeatable views. The afternoon is yours to enjoy at your own pace: wander Lagos’ cobbled streets, head to the beach, or simply relax at the hotel’s rooftop pool. In the evening, we’ll regroup for a port tasting led by Francisco, who will guide us through the distinct styles of White, Ruby, and Tawny port. Dinner tonight is on your own, perfect for exploring more of Lagos’ old town or revisiting a favorite spot.

Main Route: An 8 km (5 miles) seaside hike from Praia da Luz to Lagos (1,125 ft elevation)

DAY 5

This morning, we set off for a short transfer to Praia do Vale da Lama, where our day begins with a spectacular coastal walk back to Lagos. The trail starts along the quiet wetlands of the Ria de Alvor, home to oyster nurseries that thrive in the tidal flats. As we make our way west, the landscape opens up to long stretches of golden sand and turquoise waters. Along the way, we’ll pass a handful of beach bars where you can stop for a cool drink, a light snack, lunch on your own or to soak in the ocean breeze. With wide-open views of the Atlantic and the waves rolling in beside us, today’s hike is a sun-drenched, toes-in-the-sand kind of adventure. In the afternoon, you'll have some time to explore more of the coast, like Praia Dona Ana and Praia do Camilo beaches, which are close by, if you’re craving a dip in the sea. This evening, we’ll regroup for another wonderful local dinner together!

Main Route: 5 km (3.1 mile) hike along sand and boardwalk with optional swimming and free afternoon in town

DAY 6

After breakfast at our hotel, we set out for a scenic transfer to the Barragem da Bravura, a peaceful reservoir tucked into the rolling hills above the Algarve coast. Surrounded by eucalyptus groves and oak trees, the area feels worlds away from the bustling seaside towns. From here, we lace up for today’s hike—a winding route that keeps us off the main roads and instead follows quiet country trails back toward Lagos. Expect a mix of shaded woodland paths, open fields dotted with wildflowers, and the occasional sweeping view down toward the sea. Midday, we’ll pause in the charming town of Bensafrim for a well-deserved lunch. You can opt to tuck into a hearty local dish at a café or carry provisions for a trailside picnic before finishing the hike into Lagos. This evening, we’ll set out on foot for dinner. We'll enjoy a sunset stroll along the lagoon and Meia Praia beach to Por do Sol Restaurante, a laid-back seaside spot serving up fresh flavors just steps from the sand and cheers to a great hiking trip with new friends!

Main Route: 13.8 km (8.6 mile) hike from trees down to the coast (410 feet elevation)

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 wander back to the hotel on your own