Sintra to Cascais Walking Tour

Day 1 Arrive

Your tour begins in Sintra, where you’ll be welcomed at your pleasant family-run hotel, just outside the historic town center.

After you’ve settled in, enjoy views of Sintra and the surrounding rolling hills from the hotel’s peaceful terrace and perhaps set out on a little walk to acquaint yourself with the whimsical town.
Overnight Location: Hotel in Sintra
Distance: None
Meals: None

Day 2 Explore the Sintra Palaces

Prepare to be awe-struck, as today’s walk will introduce the former summer getaways of Portugal’s royals and nobility.

Up first, a steep ascent leads you to the Castelo de Mouro (eighth to twelfth-century), an impressive Moorish castle that lords over Sintra, built strategically on a rocky outcrop. Next, you’ll explore the Palacio da Pena, followed by the Palacio Nacional.

You may find yourself in a daze of luxury following the palace visits, so enjoy some fresh air as you explore the vast palace grounds, home to remarkable gardens. A final descent via Vila Sasseti will guide you back into the center of town.
Overnight Location: Hotel in Sintra
Distance: 4.5 hours, 9km, 150m of ascent, 400m of descent
Meals: Breakfast

Day 3 Convento dos Capuchos and Azoia

This morning, following a short transfer, you’ll kick off the day with a visit to the Convento dos Capuchos. In this sixteenth-century Franciscan monastery, you’ll appreciate the tranquillity of the serene setting.

Next, you’ll navigate magical Mediterranean woodlands leading you to a final descent to Azoia. From Azoia, catch the bus back to Sintra.
Overnight Location: Hotel in Sintra
Distance: 5 hours, 11.5km, 425m of ascent, 500m of descent
Meals: Breakfast

Day 4 Explore the Sintra Manor Houses

Like so many other countries in Europe, the nineteenth and twentieth centuries in Portugal were influenced by the sweeping winds of the Romantic era. Today, you’ll see this fact on full display as you explore the luxurious interiors of some of Sintra’s romantical style mansions, built by nobles and the wealthiest merchants. Some of the homes are still occupied by residents today, while others have been converted into super-luxe hotels.
Overnight Location: Hotel in Sintra
Distance: 3 hours, 4.5km
Meals: Breakfast

Day 5 Walk Northbound to Arribas via Azenha do Mar

Say farewell to the wealth and romance of Sintra this morning as you head north through sprawling fields, vineyards, and pine forests toward the dramatic coast.

Reaching the pretty fishing village of Azenha do Mar, you’ll join the GR-11, taking it south to your seaside hotel in Colares. Enjoy a dip in the hotel’s gigantic saltwater pool to top off an exciting day on foot.
Overnight Location: Hotel in Colares
Distance: 5 hours, 15km, 225m of ascent, 485m of descent
Meals: Breakfast

Day 6 Praia Grande Loop

Set out from your hotel this morning, joining the long-distance walking path GR-11, also known as Costa Atlantica. The gorgeous coastal path will guide you south as you trace ancient fishermen’s trails until you reach the village of Ulgueira.

The trail continues, granting you beautiful views of the Cabo de Roca and the beach-lined coast as you continue the loop back to Praia Grande, via the village of Almoçageme.
Overnight Location: Hotel in Colares
Distance: 4 hours, 11km, 50m of ascent, 650m of descent
Meals: Breakfast

Day 7 Bound for Cascais

Your final day of walking begins with a transfer to Azoia, inviting you to pick up the GR-11 again and follow it along the coast. On the way, you’ll encounter the seventeenth-century fortress of Fortaleza de Guincho, which has since been converted into a luxury hotel.

You have the option to end today’s walk after 8 kilometres, taking a bus to Cascais instead of walking the full 17.5-kilometre route.

Once in Cascais, enjoy this lively beach town, where you’ll have no trouble finding a suitable spot for tonight’s farewell dinner and drinks!
Overnight Location: Hotel in Cascais
Distance: 5 hours, 17.5km, 275m of ascent, 475m of descent
Meals: Breakfast

Day 8 Depart

This morning, your walking tour comes to an end. Check out of the hotel and head to the airport to depart.
Overnight Location: None
Distance: None
Meals: Breakfast