Self-Guided Sintra and Cascais in Luxury Food and Hike Tour

Tour type

Self-Guided

at your own pace

Hiking days

5 days

Total hiking distance

58 km

~12 km/day

Level

moderate

Start / End

Santa Cruz

ends Cascais

Group size

2–12

participants

Accommodation

Premiere Inns (5★)

Best season

Apr – May, Sep – Oct

This premium journey through the Sintra-Cascais region combines scenic hiking with refined comfort and memorable culinary experiences. Beginning in Santa Cruz, the route introduces you to Portugal’s dramatic Atlantic coastline, where cliffs, beaches, and historic villages create a constantly changing backdrop.

As the days progress, you move south along the coast, passing through picturesque locations such as Azenhas do Mar and Praia Grande before heading inland to Sintra. In Sintra, forest trails lead to iconic landmarks like Pena Palace and the Moorish Castle, set within a UNESCO-listed landscape. The experience is elevated by carefully selected accommodations and distinctive dining, including a Michelin-starred restaurant.

The journey continues through coastal and countryside paths before ending in Cascais, a lively seaside town. Blending nature, culture, and gastronomy, this itinerary offers a well-rounded and more refined take on a classic hiking route.

Highlights

Cape Roca : Europe's Westernmost Point

Stand at the dramatic westernmost point of continental Europe, where sweeping ocean vistas and rugged cliffs create an unforgettable natural spectacle along the stunning Sintra coastline.

UNESCO World Heritage Sintra

Explore the magical hilltop town of Sintra, discovering architectural treasures like the vibrant Pena Palace and ancient Moorish Castle set within mystical forest landscapes recognized by UNESCO.

Michelin-Starred Culinary Excellence

Elevate your evenings with exceptional dining at a Michelin-starred restaurant, where Portuguese gastronomy is reimagined through passion and artistry in an unforgettable gastronomic celebration.

Royal Heritage Retreat in Sintra at 5★ Valverde Sintra Palácio de Seteais

Stay at the 5★ Valverde Sintra Palácio de Seteais, an elegant palace hotel offering regal architecture, panoramic views, and timeless luxury.

7 Days from $3,995

Free cancellation · Up to 60 days before group departure

Itinerary

Brief Itinerary

Day	Place	premiere Inns	Meals	Distance	Activity
01	Santa Cruz	Areias do Seixo (5 Star)	B,D	-
02	Santa Cruz	Areias do Seixo (5 Star)	B	8 km / 5 mi	hiking
03	Sintra	Valverde Sintra Palácio de Seteais (5 Star)	B, D	10 km / 6 mi	hiking
04	Sintra	Valverde Sintra Palácio de Seteais (5 Star)	B	13 km / 8 mi	hiking
05	Guincho	Fortaleza do Guincho (5 Star)	B, D	10 km / 6 mi	hiking
06	Cascais	Farol Hotel (5 Star)	B, D	17 km / 11 mi	hiking
07	Cascais	-	-	-

Meals: B = Breakfast · L = Lunch · D = Dinner

Listed hotels are subject to availability and may be replaced with similar alternatives.

Detailed Itinerary

Day 1: Santa Cruz

Welcome to Portugal. Upon arrival, you are transferred from Lisbon to Santa Cruz, where your journey begins along the Atlantic coast. After settling into your accommodation, a welcome briefing introduces the itinerary and highlights of the days ahead. Santa Cruz offers a peaceful coastal setting, with dunes and ocean views creating a relaxed atmosphere.

You have time to explore the surroundings or simply unwind at your hotel. The location, set close to the sea, provides an ideal introduction to the region’s natural beauty and refined character, setting the tone for the days to come.

Meals: B,D

Accommodation: Areias do Seixo (5 Star)

Day 2: Santa Cruz

Your day begins with a short transfer to Vimeiro, a village known for its historical significance during the Napoleonic invasions. From here, the trail follows the Alcabrichel River as it gradually leads toward the coast. You pass through a scenic valley before reaching Porto Novo beach, once an important fishing port.

As you continue south, the landscape opens to reveal a series of striking beaches along the Atlantic coastline. The route combines history, river landscapes, and coastal scenery before returning to Santa Cruz, where you can relax and enjoy the surroundings.

Meals: B

Hiking Distance: 8 km / 5 mi

Accommodation: Areias do Seixo (5 Star)

Day 3: Sintra

After a transfer to Magoito, your hike begins along a dramatic stretch of coastline marked by cliffs and sandy beaches. The route takes you through coastal villages, including Azenhas do Mar, known for its striking position overlooking the ocean. A viewpoint here offers expansive views of the Sintra coastline.

Continuing onward, you reach Praia das Maçãs, a small village set beside a wide sandy beach. The journey concludes at Praia Grande, where the coastal scenery remains impressive. From here, a transfer takes you inland to Sintra, where the atmosphere shifts from coastal to historic.

Meals: B, D

Hiking Distance: 10 km / 6 mi

Accommodation: Valverde Sintra Palácio de Seteais (5 Star)

Day 4: Sintra

Today focuses on exploring the hills above Sintra, a UNESCO World Heritage site rich in history and architectural heritage. The trails wind through forested paths and elevated viewpoints, revealing castles, palaces, and historic estates. Key highlights include Pena Palace, known for its distinctive design, and the Moorish Castle, offering wide views across the region.

The combination of natural beauty and historical landmarks creates a varied and engaging day. Returning to Sintra village, you can enjoy its charming streets and atmosphere, adding a cultural dimension to the hiking experience.

Elevation Gained : +400m/+300m

Meals: B

Hiking Distance: 13 km / 8 mi

Accommodation: Valverde Sintra Palácio de Seteais (5 Star)

Day 5: Guincho

A transfer brings you to Peninha, one of the highest points in the Sintra mountains. From here, the route descends toward the coast, offering sweeping views of the surrounding landscape. The trail passes through forested paths before opening to expansive coastal scenery. As you approach the Atlantic, the terrain alternates between beaches and rugged coastline.

Historical elements appear along the way, reflecting the region’s past as a defensive line for Lisbon. The day concludes near Guincho Beach, with the option to continue along the coast and pass Boca do Inferno before reaching your accommodation.

Meals: B, D

Hiking Distance: 10 km / 6 mi

Accommodation: Fortaleza do Guincho (5 Star)

Day 6: Cascais

Today’s route shifts from the coastline into the countryside, offering a different perspective of the region. The trail leads toward Quinta do Pisão, an area known for its natural beauty, with forests, meadows, and streams creating a peaceful setting. As you continue, the landscape opens into rolling hills and vineyard surroundings, providing a quieter and more rural experience.

Gradually, the route transitions back toward the coast, leading into Cascais. This lively town offers a contrast to the day’s tranquility, with vibrant streets and coastal charm marking the final stage of the journey.

Meals: B, D

Hiking Distance: 17 km / 11 mi

Accommodation: Farol Hotel (5 Star)

Day 7: Cascais

Your incredible Sintra-Cascais journey concludes today. A transfer to Lisbon will be arranged according to your schedule and preferences. Consider extending your adventure by staying an extra night in Cascais, exploring another captivating Portuguese city, or adding additional hiking days to continue discovering Portugal's stunning nature trails.

Meals: -

Ready to plan your adventure? Download a print-ready detailed itinerary.

Accommodation

Each accommodation has been thoughtfully selected to ensure an exceptional and memorable experience for guests. Should the listed hotel be unavailable, we will ensure an alternative of similar quality.

Essential Info

Inclusions

Lodging

All hotels as mentioned in the tour details or similar (subject to availability).

Luggage Transfer

Transportation of luggage from one hotel to another.

Airport Pickup

Enjoy a hassle-free group airport pickup to start your journey. Available only on the tour start date.

Airport Drop

Enjoy a hassle-free group airport drop to finish your journey. Available only on the tour end date.

Meals

Meals as per itinerary. Guests are given the opportunity to dine on their own so that they discover a location independently.

Additional Inclusions

PRE DEPARTURE INFORMATION PACK. (Travel Check list, General Travel Information about Portugal)
6 NIGHTS LODGING (Breakfast included)
DINNER Included at the hotel on Day1, Day3, Day5 & Day6 (drinks excluded)
WELCOME BRIEFING
DIGITAL INFORMATION BOOK made available before Tour start (Daily Information, Daily Maps, Restaurant recommendations, etc.)
LOCAL SUPPORT NUMBER (Contact us during the Tour if you need assistance)
NAVIGATION APP
ARRIVAL TRANSFER from Lisbon to first Hotel
DEPARTURE TRANSFER from last Hotel to Lisbon
LUGGAGE TRANSFER from Hotel to Hotel on every day of the Tour

Exclusions

Beverages

Beverages such as alcohol, tea, coffee, juice at a hotel or restaurant.

Gratuity

Gratuities for your guide team are not included in the trip price.

Start

Santa Cruz

Finish

Cascais

Fly-In

Lisbon Portela Airport (LIS)

Fly-Out

Lisbon Portela Airport (LIS)

ARRIVAL

Your tour begins in Santa Cruz, with the nearest airport being Lisbon Humberto Delgado Airport (LIS). Upon arrival, a transfer is included from Lisbon to your hotel in Santa Cruz, taking approximately 1 hour and 30 minutes. This ensures a smooth and comfortable start without the need to arrange local transport.

After reaching your accommodation, you will have time to settle in and attend a welcome briefing outlining the journey ahead. If you prefer to arrive independently, taxis and private transfers are available from the airport.

DEPARTURE Your tour concludes in Cascais. A transfer from your hotel in Cascais to Lisbon is included, taking around 45 minutes, providing a convenient connection to Lisbon Humberto Delgado Airport (LIS) for your onward journey. Depending on your departure schedule, you may also choose to extend your stay in Cascais or Lisbon. For independent arrangements, taxis and public transport options are easily accessible from Cascais.

The best time to enjoy this tour is during spring and autumn, when the weather is mild and ideal for hiking. From March to May and September to November, temperatures typically range between 15°C to 25°C (59°F to 77°F), offering comfortable conditions for walking. Summer months can be warmer, with temperatures around 25°C to 30°C (77°F to 86°F), though coastal breezes provide some relief.

Winter is cooler and wetter, with temperatures around 10°C to 15°C (50°F to 59°F), and occasional rain may affect trail conditions, especially along coastal and forest paths.

January

Offseason

February

Offseason

March

Good

April

Best

May

Best

June

Good

July

Mixed

August

Mixed

September

Best

October

Best

November

Good

December

Offseason

Best

Good

Mixed

Offseason

Packing wisely ensures comfort and safety on your hiking adventure. This list covers essential hiking gear, clothing, and travel items to help you handle varied terrain and weather conditions.

Recommended Hiking Clothes & Gear

Lightweight hiking shoes or boots with good traction.
Moisture-wicking base layers and breathable hiking shirts.
Quick-dry hiking pants or shorts.
Light fleece or down jacket for cooler temperatures.
Waterproof and windproof shell jacket.
Sun hat and sunglasses with UV protection.
Hiking poles if you prefer extra support on uneven terrain.
Small daypack with hydration system or water bottles.
Headlamp or small flashlight.
Light gloves and a beanie for early mornings or higher altitudes.

Clothing

Layered clothing for temperature changes throughout the day.
Full-sleeved tops for sun and insect protection.
Comfortable evening wear for lodges or inns.
Compact rain jacket for unpredictable weather.
Extra socks, preferably synthetic or wool.

Other Necessities

Basic first-aid kit with personal medication.
Sunscreen, lip balm, and insect repellent.
Reusable water bottle or hydration bladder.
Snacks like trail mix, nuts, or energy bars.
Plug adaptor and power bank for charging devices.

Pro Tips

Pack light. You'll appreciate it on the trail.
Break in your shoes before the trip to avoid blisters.
Keep rain gear easy to access in your daypack.

Luggage

Please limit your luggage to one medium-sized suitcase and one daypack. Mark your luggage clearly with your name, address, and phone number.

Before venturing on your adventure, make sure you're equipped with essential travel advice, including security updates, local laws, and crucial passport and visa information. Start by visiting the official government website of your home country for accurate and reliable guidance:

UK Residents: Foreign, Commonwealth & Development Office Travel Advice.
US Residents: US Department of State Travel Advice.
Australian Residents: Smartraveller.
Canadian Residents: Government of Canada Travel Advice and Advisories.
New Zealand Residents: SafeTravel.
Residents of Other Countries: Check with your government or local consulate for tailored travel advice and requirements.

Note: Passport and visa regulations can change at any time. Check for updates close to departure to avoid last-minute issues.

Medical insurance that covers medical costs in case of an accident during the trip is mandatory to participate in our tours.

We recommend purchasing adequate travel insurance to protect yourself from unforeseen events. Our experience shows that guests who purchase travel insurance, including coverage for all activities on the itinerary, trip cancellation, interruption, delay, baggage damage, loss or theft, personal accident, death and repatriation costs, medical and emergency expenses, and personal liability, travel with greater peace of mind.

Is proof of medical insurance required?

Yes. You must provide your insurer's name, policy number, and emergency contact through our reservation form. If you cannot provide proof, you'll need to purchase insurance before traveling with us.

Can I use my credit card insurance?

Yes, as long as it meets our requirements and provides adequate coverage. Keep your emergency contact number and policy number accessible while traveling.

When should I buy travel insurance?

Purchase travel insurance as soon as you've paid in full or booked your flights.

Does Art of Bicycle Trips sell travel insurance?

We do not sell travel insurance directly. We recommend comparing policies and choosing the one that best fits your needs. A useful place to start is Insured Nomads.