Sintra – Cascais Walking Holidays

Located just a short distance from Lisbon, Sintra was a popular summer residence for Portuguese rulers and nobility between the 15thand 19thcenturies. They have left a cultural landscape of extravagant palaces, manor houses and gardens which form a fascinating UNESCO world heritage site. This walking holiday combines the richness of Sintra’s extravagant and exquisite cultural monuments, with peaceful and scenic walks in the Sintra Hills, and the rugged and dramatic Atlantic coastline, where the coastal trail leads you to the most westerly point of the European continent.

View over Pena Palace, Sintra
Nights
7 to 7 Nights
Distance
46.8 to 46.8 miles
Location
Southern Portugal
Difficulty
Easy to Moderate
Season
Jan to Dec
Price from
£1035

Highlights

Discover Sintra’s Extravagant Culture & Dramatic Atlantic Coast

Prominent national monuments including the unmissable Palacio de Pena, a beautiful example of Romanticism architecture, idyllic Castelo dos Mouros and the Palacio Nacional
Captivating and mystical gardens of Quinta da Regaleira
Beautiful Parque Natural de Sintra with its wild and rugged Atlantic coastline and opportunity to visit the austere Convento dos Capuchos convent
Cabo da Roca, the most westerly point of mainland Europe
Bustling coastal town of Cascais
Savour locally sourced, traditional Portuguese cuisine
High standard, historic accommodations
From £1035 per person
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Why Choose Our Sintra-Cascais Walking Holiday?

Walking the Sintra and Cascais landscape is an open window into the past, following routes designed to explore the area’s foremost historical and cultural sites. Discover Sintra’s fascinating sights in the morning, before joining hiking routes out into the area’s peaceful surrounding woodland and rural landscapes later on in the day. Starting in the vibrant town of Sintra, discover the town’s extravagant palaces, gardens and manor houses, with the latter half of the walking holiday located on the breathtaking Atlantic coastline, reaching Azenhas do Mar and the fisherman’s town of Cascais – just one hour away from Lisbon by public transport.

Cabo_da_Roca_Sintra-Cascais_Natural_Park_Portugal

The Path

Exploring the castles, palaces and manor houses of Sintra in the morning, you'll find even, well-defined footpaths around the town's palace grounds and surrounding hillsides. As you make your way out into the more rural areas in the afternoon, you follow a more shaded route, under the canopy of the forest along slightly more rugged dirt trails and woodland paths that lead out of the town's historic centre. A combination of circular walks, and sections that follow the established "Costa Atlántica" make up the coastal sections at the end of the itinerary. These routes that lead out of the hillsides to the coast take you through the Sintra-Cascais National Park, a landscape of vibrant colours, beaches and secluded coves.

The footpaths you follow are well way-marked with some steep ascents/descents, designed to accommodate around 4-5 hours walking each day, allowing ample time to experience the traditionally relaxed Portuguese lifestyle in the communities, towns and villages you stay in.

Sintra Walking Holiday Map

The Accommodation

Sintra Accommodation

Choose Your Walk

Our Sintra-Cascais Itineraries

Sintra to Cascais

45.5 miles (73.2 km)

Key Information

  • 7 nights’ accommodation on a bed and breakfast basis
  • Luggage transfers
  • Personal transfers where indicated in the programme as a standard arrangement
  • Walk Pack, to include Road Book (route notes/mapping) including directions to your accommodation and destination information.
  • A Sintra Cascais Nature Park map
  • Access to a Travel App

Price Does Not Include

  • Packed lunches (own arrangements)
  • Evening meals (own arrangements). Available in local restaurant or in-house.
  • Travel to Sintra/travel from Cascais.

Customise your trip?

We can organise additional nights/rest days, as well as transport options. Please contact us to discuss how we can help you with your specific requirements.

Sintra-Cascais Client Reviews

5/5 based on 8 reviews

"I would recommend Celtic Trails to a friend. They are better than other companies. All accommodations were 5/5."

Bruce Dodd
April 2025

"Everything you provided and arranged for us was excellent. This was our 4th walk with you and given our current physical limitation was probably the best walk you had for us."

Ronald Myers, Florida, USA
October 2024

"This is our 9th Walk with Celtic Trails! Walking with Celtic, has given us the opportunity to see parts of the UK and Europe up close, away from the crowds - we can enjoy the walk always knowing we have comfortable accommodations & good food at the end of each day."

Carol & Andy, San Francisco
May 2024

"Detailed & helpful in every way. Although we did not have any trouble (missed connections, etc.), we felt confident that we could contact you if we needed your help. The trust factor matters a lot!"

S. Wilson
May 2023

"Well organised tour with relevant information about what I could see and visit. West Highland Way next."

M.I.Eszter
April 2023

"This is our third trip with Celtic Trails. They are well organised, excellent communication and information, interesting and varied walking, very nice accommodation, local providers dependable. This is a wonderful way to experience a country and its cul"

Bob & Suzanne Fox
May 2022

"I haven't felt this good in a while - both in body and spirit. The feeling of connection to the land was overwhelming. The people were incredibly warm and friendly. Did I mention the wonderful hospitality and food? A tough choice between Portugal and Tuscany. May yet do Tuscany with this company."

A. Headburg
March 2019

"Thoroughly enjoyed the experience - shall book with you again. Thank you."

M. Brown
December 2018

Hand-Picked Accommodation: Comfort Along the Way

We seek out the best accommodation of its type available

Sintra Accommodation

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Customise your trip?

We can organise additional nights/rest days, as well as transport options. Please contact us to discuss how we can help you with your specific requirements.

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