Last chance availability on popular trips: Browse here


Lisbon & Sintra In Style

8 Days & 7 Nights
  • Treat yourself to 5-star hotels bursting with character
  • Discover the regal palaces, castles and monasteries of Sintra
  • Feast on mouth-watering food at the seaside town of Cascais
  • Spectacular clifftop trails, wild beaches and dramatic views
  • Take in the history and nightlife of Portugal’s vibrant capital, Lisbon
Walk through the Sintra-Cascais Natural Park, from the rugged Atlantic coast at Santa Cruz to the much-loved seaside town of Cascais. Begin your journey on Portugal's 'Silver Coast' before moving south to the mystical wooded trails of Sintra, renowned for its exquisite palaces, castles, monasteries, and lush tropical gardens. Continue on clifftop trails to the much-loved seaside town of Cascais, taking in the dramatic views and feasting on fresh seafood and wine along the way, before finishing at Portugal's vibrant capital city, Lisbon. Portugal is never short on fascinating culture and spellbinding beauty, and to enhance your experience, we've hand-selected 5-star hotels bursting with character; from a clifftop eco-conscious beach retreat overlooking the Atlantic Ocean, to an 18th century palace hidden in the mountainside.
Easily accessible from Lisbon, this tour offers easy to moderately graded coastal trails through a variety of coastal and inland landscapes on a mixture of paved and forest trails, clifftop coastal paths and quiet country paths. There are some significant elevations gains in the Sintra hills, but nothing too challenging. Please note that the trail near Cabo da Roca lighthouse can be sandy, which may slow you down. This is a multi-centre walking holiday with 5 days of walking, so there will be a private transfer most days to the start-point of your walk. We also include a private transfer from Lisbon Airport to your first hotel, to ensure you're fully relaxed at the start of your holiday. The circular walk in Sintra can be shortened should you wish to have more time to relax on this day. Stay overnight in 5-star hotels bursting with character, perfect for those who would like to treat themselves with luxurious accommodation at the end of their hike, whilst taking in lots of historical and cultural highlights.

Tour Type:

In Style | After a day of exciting adventures and soaking up unbeatable scenery, retreat to stylish accommodations and unwind with fine food and wine. This trip type is for those who like sophisticated places to stay and are looking for active routes but still want the holiday to feel special.


Multi Centre Walking | With a mix of loop and point-to-point walks stay 2 or 3 nights in one place which offers the chance to slow down and really explore a destination.

This trip is suitable for:

Solo Travellers

As a guide, we would suggest that the minimum age of traveler this tour would be suitable for is: 12 Years

Ideal if you have an interest in:

  • Foodie
  • Wine
  • Coastal Walking

Activity Level & Terrain

This trip is graded ‘easy to moderate’ overall and includes daily walks of 8-18km. It is suitable for most people that are in good physical fitness. The route follows a mixture of gravel trails, sandy coastal trails, forest and clifftop paths and the maximum accumulative elevation gain in a day is 430m, and the maximum accumulative elevation loss in a day is 543m. On days where you walk along clifftop coastal paths, it can feel exposed so if you suffer from vertigo, you may wish to miss those walks. The terrain can also be quite challenging here, with steep sections of bare dirt. You may wish to use walking poles here. We recommend training ahead of this tour, by walking some daily walks of similar daily distances to your planned itinerary.


As the navigation on this tour is fairly straightforward, it does not have turn-by-turn directions. It will be necessary to use the Macs Adventure Smartphone App. Simply download the app for offline use and follow the route on your phone with the assurance that you will be able to find your way, even without turn-by-turn directions. The route is way-marked in places and not in others. Several trails have way-marks on the ground, so please do keep your eye out for these. 


Your holiday includes accommodation in characterful 5-star hotels, starting with a luxurious eco-conscious beach retreat in Santa Cruz, with an infinity pool overlooking the Atlantic Ocean. In Sintra, you'll be treated like royalty in what was an 18th century palace hidden in the mountainside, and in Cascais you'll be staying in a 19th century aristocrat mansion, perched on an outcrop of rock above the ocean. Finish with a contemporary hotel on Lisbon's most elegant avenue, renowned for their award-winning spa and rooftop bar. All hotels are unique in their own way, capturing the essence of their location.

You can add on extra nights in any of the overnight locations. 

Single Rooms 

If you require single rooms we would be happy to accommodate you although there is a single room supplement payable. 


A breakfast will be provided at your accommodation every morning. A dinner is also included on your first night in Sintra (Day 3). For meals that aren't included, there are options to dine out in most of the towns and villages. The food in Portugal is fantastic, famous for it’s codfish dish Bacelhau a bras amongst many other fresh seafood dishes, and the Sintra region in particular is home to the delicious pastry treat, Queijada de Sintra, as well as the mouth-watering Colares wine.

Lunches aren't included, but you can find small stores in which to purchase items for a picnic lunch, or some of your accommodations can make a picnic lunch if you ask in advance. In your route notes we give advice on where you can eat/pick up lunch.

  • 7 nights in 5-star boutique hotels
  • All breakfasts and 1 dinner
  • Door-to-door baggage transfer as per itinerary
  • Arrival transfer from Lisbon Airport to Santa Cruz
  • Detailed Information Pack
  • GPX tracks and access to our smartphone app
  • 24/7 telephone support from our UK office
  • Private transfers mentioned in the itinerary
  • Departure transfer on the final day
  • Travel insurance (required)
  • Lunches and dinners not mentioned in the itinerary
  • Drinks and snacks
  • Personal equipment
  • Entrance fees to monuments
  • City taxes - up to 3 EUR per person per night, payable locally in cash
  • Additional nights before, during and after the walk
  • Departure transfer on the final day

When To Go

You can start this walking tour on any day of the week from January through to June , and then from September through to December, subject to availability. Sintra offers great weather most of the year round but the months of July and August can get very hot and doesn't make for enjoyable walking. Both spring and autumn offer excellent conditions for walking. Average temperatures range from 10-15°C (70°F) in the winter to 25-30 °C (77 °F) in the summer months. The inland regions are always slightly cooler than Lisbon and Cascais due to the higher elevations.

Getting to the Start

Lisbon Airport is easily accessed by direct flights from across the UK, Europe and several cities in the US. Major airlines who fly there include American Airlines, TAP, British Airways, Easyjet and Ryanair amongst others.

If you are travelling to Lisbon from elsewhere in Portugal or Spain, it is also easily accessed by rail. View rail timetables at the Comboios de Portugal website.  

A private transfer will be waiting for you to take you to your first hotel in Santa Cruz.

Getting from the End

Transfers are not included on the final day. It is very easy to get from yourhotel in Lisbon to the Airport by public transport. 

Luggage Transfer

Your bags will be transferred from your accommodation as per your itinerary and moved onto your next overnight accommodation, giving you the freedom to walk each day with just a day pack. We ask you to limit your luggage to one bag of up to 20kg per person. Please ensure that you do not bring more than one bag of 20kg as if this occurs, you may be asked to pay an additional fee for an extra bag.

General Information

The distances and ascents/descents are approximations of the recommended routes. 


Please be prepared by packing all necessary items. Your information pack has a detailed equipment list, which includes standard walking gear such as good walking boots or shoes, warm and waterproof clothes for the cooler months and lightweight clothing for summer, and a day pack.

Travel Insurance

It is a requirement of booking this tour with Macs Adventure that you have suitable travel insurance which covers you for the activity and emergency evacuation and hospital care.

How far in advance do I need to book?
What equipment do I need?
What happens if I can't walk a stage?
How fit do I need to be?
When is the best time of year?


Day 1 Arrive Lisbon; transfer to Santa Cruz Day 2 Walk from Vimeiro back to Santa Cruz 5 miles / 8 km Day 3 Walk from Colares to Sintra 8 miles / 13 km Day 4 Circular Sintra hike 7.5 miles / 12 km Day 5 Walk from Capuchos to Praia Grande; transfer to Cascais 9 miles / 15 km Day 6 Walk from Peninha Sanctuary back to Cascais 11 miles / 18 km Day 7 Transfer to Lisbon; free time to explore the city Day 8 Departure

Blog Articles

You May Also Like

  • In Style
    Type In Style
    8 Days 7 Nights

    0 Reviews
    Douro Valley In Style
    Explore a side of the Douro Valley where fewer tourists venture, with walks finishing at wineries.
    • Elegant wine hotels boasting spectacular views
    • Sumptuous food and wine at historic wineries
    • Walks through vineyards, olive groves and villages
    From $4,175.00
  • Slower Adventures
    Type Slower Adventures
    7 Days 6 Nights
    Walking Sintra to Cascais
    Walk through the Sintra-Cascais Natural Park, and discover palaces, castles and monasteries.
    • Walk through the Sintra-Cascais Natural Park
    • The colourful UNESCO World Heritage Site of Sintra
    • Stay in boutique hotels and charming guesthouses
    From $1,195.00
  • In Style
    Type In Style
    9 Days 8 Nights
    Walking the Catalan Coast in Style
    Walk on quiet trails between traditional Catalan villages, staying in stylish boutique hotels.
    • Stay in boutique hotels along the Catalan coast.
    • Llafranc, former haunt of Salvador Dali.
    • Wine tasting at the country house of Bell-lloc.
    From $2,290.00

The Macs Way

  • Tried & Tested Adventures Tried & Tested Adventures
  • Freedom Freedom
  • Book with Confidence Book with Confidence
  • Expertise Expertise
  • Positive Impact Positive Impact
Built with our expert knowledge, to suit you.
  • Knowledgeable and helpful specialist trip planners
  • Wide variety of tours to suit all interests and experience levels
  • Start on any date that suits you
  • Choose your ideal trip length and difficulty
  • Range of accommodation comfort levels
  • Choice of trip styles
Authentic adventure travel experiences on your own terms
  • Choose your own travel companions
  • Walk, cycle and explore at your own pace
  • Make your own decisions
  • Choose your own path
  • Indulge your passions
Feel secure in making the right choice for your precious adventure time
  • 18,000+ unbiased trip & service reviews
  • Feefo Platinum Award 2023
  • 25,000+ travelers trust us each year
  • As featured in the Guardian, Times, Nat Geo Traveler
  • Founder owned & operated since 2003
  • 100+ passionate team members across the US, UK & Europe
You can be confident that every detail of your journey has been expertly planned
  • Carefully planned adventures
  • Quality, hand-picked accommodations
  • Seamless and reliable arrangements
  • Comprehensive trip information & insider tips
  • Detailed maps, route notes and mobile GPS app
  • Helpful 24/7 support should you need it
Travel the right way and make a positive impact
  • Travel responsibly
  • Explore off the beaten track
  • Support locally owned businesses
  • Engage with local communities
  • Minimize your impact
  • Maximize the benefit of your travel
  • Challenge yourself & grow
$ - USD - US Dollar
Country/Region name: