At mainland Europe’s western edge lies one of its lesser-known gems—a land of wild coasts and broad beaches, lush forests and terraced vineyards, and cities whose cobbled streets tell long histories. Experience the charms of Portugal as you hike and kayak in the wine country of the Douro Valley and sample fine ports in enchanting Porto. Explore Moorish castles in Lisbon and Sintra, and trace the beaches and cliffs that line the Atlantic to the continent’s westernmost point.

Trip Highlights

  • Explore three UNESCO World Heritage sites on foot: historic Porto, the Douro wine region, and the former royal resort town of Sintra.

  • Hike along coastal beaches and cliffs to Cabo da Roca, the westernmost point of continental Europe.

  • Kayak the Douro River, breaking to relax on secluded beaches only accessible by boat.

  • Discover the cobblestone lanes and colorful neighborhoods of Lisbon, and venture into its Moorish castle.

Activity Level: Easy and Moderate

We will hike 3 to 6 hours per day (3 to 5 miles) mostly on level trails but with some steeper grades at times. During hikes, vehicle support is provided at various points along the way, and participants always have the option to rest a day and ride to the next hotel. There is 1 day of optional kayaking, maximum 4 hours.


Itinerary - 8 Days

Day 1 — Porto, Portugal
Arrive in Porto and settle into our hotel in the city center. After lunch, head out on foot to explore the narrow streets of the historic old town. Take in views across the Douro River from Praça da Ribeira, and walk along the riverfront spanned by iron bridges. Gather for a welcome dinner tonight. Crowne Plaza Porto (L,D)


Day 2 — Pinhao/Douro Valley
Travel by train to Pinhão, following the Douro River into the terraced vineyards of the stunning Douro Valley, where some of Portugal’s best wines and ports are produced. This afternoon, set out on a hike through these rolling landscapes, climbing from the river’s edge into the hills and taking in a vista of striped slopes and the meandering river below. (5 miles hiking, 4 hours) 
Quinta do Portal (B,L,D)


Day 3 — Douro Valley
Board a rabelo, a traditional wooden cargo boat native to the region, and glide up the Douro to its junction with the Tua River. Kayak back down to Pinhão, paddling past charming port wine estates and pausing for a swim or a snack at sandy beaches only accessible by boat. Enjoy a final hike through the region’s vineyards capped off by a wine tasting. (7–8 miles paddling, 4 hours; 3-4 miles hiking, 3 hours) Quinta do Portal (B,L,D)


Day 4 — Porto
Return to Porto, stopping en route to learn more about the region’s culture at the Museu do Douro. Then stroll formal gardens on a visit to the Casa de Mateus, an ornate manor house that exemplifies Portuguese baroque architecture. Arrive back in Porto, and later this afternoon, cross the river to visit a port wine cellar where we’ll sample the city’s most famous export.  Crowne Plaza Porto (B,L,D)


Day 5 — Lisbon
The next day, travel to Lisbon, Portugal’s capital set on seven hills at the mouth of the Tejo River. After settling in, climb the steep cobblestoned streets of the historic Alfama neighborhood, explore multicultural Mouraria, and take in the view from the ramparts of São Jorge Castle — a Moorish stronghold that presides over the city. (4–5 miles hiking, 4–5 hours)  Tivoli Liberdade Lisbon (B,L,D)


Day 6 — Cabo da Roca/Sintra
Follow the Atlantic coast from Lisbon to Guincho Beach, a wide, wild swath of surf and dunes backed by gorgeous cliffs. This is the starting point for our coastal hike to Cabo da Roca — the westernmost point of continental Europe. From the beach, climb up to the Abano Fortress and then continue up to the cliff tops, passing secluded coves and valleys on the way to the Cabo da Roca lighthouse. Our home for the night is the historic town of Sintra, nestled amid lush hills at the edge of a vast nature reserve that stretches all the way to the coast. (5 miles hiking, 5–6 hours)


Day 7 — Sintra/Lisbon
Beautiful Sintra was a favorite haunt of Lord Byron and European royalty, but the Celts and the Moors made it here first. Pastel churches and manor houses line the cobbled roads here, and palaces and castles loom among the misty forests. Our hike today begins in the old town with visits to landmarks such as Santa Maria Church, the former home of Hans Christian Andersen. Then ascend to the hilltop Castle of the Moors whose serpentine stone ramparts twist along the ridge, offering a fantastic view of Sintra’s crown jewel: the Palacio da Pena, perched on a neighboring peak. Designed by King Fernando II, this 19th-century Romanticist castle is a whimsical patchwork of turrets and domes overlooking luxuriant gardens. Continue there on foot, exploring the park paths and touring the opulent palace interiors. Return to Lisbon for a final dinner together tonight. (4–5 miles hiking, 5–6 hours)  Tivoli Liberdade Lisbon (B,L,D)


Day 8 — Lisbon
After breakfast, transfer to the airport for your flight home. (B)



Pricing starts at $5,000 per person, double occupancy. For a single room, add $600.
International airfare to Porto and return from Lisbon is not included in the cost.

Group Size: 8–16


Solo Travelers

Accommodations (hotels, tents and cruise cabins) are based on double occupancy. If you prefer single accommodations, and if such are available, you can pay a single supplement fee. If you are traveling alone and wish to share accommodations, we can assign a roommate of the same gender. If there is no one with whom you can share, a single supplement fee will apply.

See special terms and conditions for this adventure.

Portugal Hiking Adventure

Learn More

Group or Custom Journeys

Starting at $5,000 Per Person