Day-by-Day Itinerary
Settle into Cascais with a gentle exploration of the charming historic center, visiting the local market and getting oriented in this elegant coastal town.
Morning
Arrival and Mercado da Vila exploration
After arriving in Cascais, check into your accommodation and head to Mercado da Vila, the town's vibrant market housed in a beautiful historic building. Browse fresh produce, local cheeses, seafood, and artisanal products. It's the perfect introduction to Portuguese flavors and local life, with friendly vendors and authentic atmosphere.
2-3 hours
$15-25
Lunch
A casual seafood restaurant near the marina
Fresh Portuguese seafood
Mid-range
Afternoon
Citadel Art District and waterfront stroll
Explore the Citadel Art District, a beautifully restored fortress complex now housing galleries, studios, and cultural spaces. Wander through contemporary art exhibitions and craft workshops. Afterward, stroll along the picturesque waterfront promenade, watching fishing boats and enjoying the Atlantic breeze while getting your bearings in town.
2-3 hours
$0-10
Evening
Sunset dinner and evening walk
Dine at a traditional Portuguese restaurant in the
old town, then enjoy an evening stroll through the pedestrian streets and main square
Where to Stay Tonight
Cascais Historic Center (Mid-range hotel or guesthouse near the old town)
Central location provides easy access to restaurants, shops, and attractions while immersing you in local atmosphere
The Mercado da Vila is busiest on Saturday mornings when locals do their weekly shopping - arrive early for the best selection and most authentic experience
Day 1 Budget: $90-130
Discover Cascais' dramatic coastal features, from the thundering waves at Boca do Inferno to the peaceful Santa Marta lighthouse and beach.
Morning
Boca do Inferno exploration
Visit Boca do Inferno (Devil's Mouth), a stunning cliff formation where Atlantic waves crash dramatically into a rocky chasm. The name comes from the thunderous sound created by the sea. Walk along the clifftop pathways for spectacular views, photograph the natural arch, and feel the spray from powerful waves. The site is particularly impressive during high tide or after storms.
1-2 hours
$0
Lunch
A clifftop cafe with ocean views near the coastal path
Light Portuguese fare and pastries
Budget
Afternoon
Praia de Santa Marta and lighthouse visit
Spend the afternoon at
Praia de Santa Marta, a lovely small beach protected by the historic Santa Marta lighthouse. The lighthouse area offers beautiful views and photo opportunities. Relax on the golden sand, swim in the Atlantic, or explore the rocky tide pools. The beach has a local, relaxed atmosphere and is perfect for your first Portuguese beach experience.
3-4 hours
$5-10
Evening
Casual dinner and local atmosphere
Enjoy grilled fish at a neighborhood restaurant, followed by gelato while people-watching in the town center
Where to Stay Tonight
Cascais Historic Center (Same accommodation as Day 1)
Continuing your stay in the central area maintains convenience for exploring different parts of town
Visit Boca do Inferno in the late afternoon for the best light for photography and fewer tour groups
Day 2 Budget: $70-100
Immerse yourself in Cascais' artistic and maritime heritage through museums and historic houses that tell the town's story.
Morning
Casa das Histórias Paula Rego
Explore this striking contemporary museum dedicated to Portuguese-British artist Paula Rego. The distinctive red pyramidal building houses an impressive collection of her powerful figurative works, prints, and illustrations. The museum provides insight into one of Portugal's most important contemporary artists, with rotating exhibitions and a beautiful sculpture garden. Allow time to appreciate the unique architecture designed by Eduardo Souto de Moura.
2 hours
$5-8
Lunch
A garden cafe near the museum district
Mediterranean salads and sandwiches
Budget
Afternoon
Visit the
Santa Maria House Museum to understand Cascais' evolution from fishing village to royal resort. Then explore Palacete Seixas, a beautifully preserved early 20th-century mansion showcasing the Belle Époque lifestyle when Portuguese nobility summered in Cascais. The elegant interiors, period furnishings, and architectural details offer a glimpse into aristocratic life.
2-3 hours
$8-12
Evening
Dinner and cultural evening
Dine at a restaurant featuring traditional Portuguese music, or attend a cultural event at the Citadel Art District if available
Where to Stay Tonight
Cascais Historic Center (Same accommodation)
Maintaining your base while exploring different aspects of Cascais culture
Many museums in Cascais offer free admission on Sunday mornings - plan accordingly to save money
Day 3 Budget: $75-110
Experience the raw beauty of the Atlantic at
Praia do Guincho, one of Portugal's most spectacular beaches, surrounded by dramatic dunes and cliffs.
Morning
Praia do Guincho beach day
Head to
Praia do Guincho, a stunning wide beach backed by dunes within Parque Natural de Sintra-Cascais. Famous for strong winds and powerful waves, it's a paradise for surfers, windsurfers, and kitesurfers. Even if you're not surfing, the wild beauty is captivating. Walk the extensive sandy beach, explore the dune systems, and enjoy the dramatic Atlantic scenery.
3-4 hours
$10-15
Rent surfboards or arrange lessons in advance during summer months
Lunch
A beachfront restaurant specializing in fresh seafood with ocean views
Grilled fish and seafood rice
Mid-range
Afternoon
Forte do Guincho and coastal exploration
Visit Forte do Guincho, a 17th-century fortress perched on rocks overlooking the beach. Walk around the exterior and enjoy panoramic coastal views. Continue exploring the rugged coastline, discovering hidden coves and dramatic rock formations. The area offers excellent photography opportunities with its wild, windswept landscape contrasting with the deep blue Atlantic.
2 hours
$0
Evening
Return to Cascais for relaxed evening
Light dinner at a casual spot in town, early night to rest after a day of sun and wind
Where to Stay Tonight
Cascais Historic Center (Same accommodation)
Central base remains convenient for various day trips and explorations
Guincho can be very windy - bring a windbreaker even on sunny days, and secure your belongings on the beach
Day 4 Budget: $85-120
Journey to Cape Roca, the westernmost point of continental Europe, for breathtaking clifftop views and dramatic Atlantic scenery.
Morning
Cape Roca visit
Travel to Cape Roca (Cabo da Roca), where Europe meets the Atlantic Ocean. Stand at the westernmost point of the European mainland, 140 meters above the crashing waves. The dramatic cliffs, lighthouse, and endless ocean views create an unforgettable experience. Visit the small information center and purchase a certificate commemorating your visit to this geographic milestone. The raw, windswept beauty is humbling and spectacular.
2-3 hours
$5-10
Lunch
A countryside restaurant on the return journey
Traditional Portuguese country cooking
Budget
Afternoon
Parque Natural de Sintra-Cascais exploration
Explore sections of Parque Natural de Sintra-Cascais, the protected natural park encompassing diverse landscapes from coastal cliffs to forested hills. Hike one of the marked trails through Mediterranean vegetation, spotting native plants and birds. The park offers numerous walking paths with varying difficulty levels, all showcasing the region's natural beauty and biodiversity.
2-3 hours
$0
Evening
Relaxed evening in Cascais
Sunset drinks at a waterfront bar, followed by dinner at a cozy tavern serving petiscos (Portuguese tapas)
Where to Stay Tonight
Cascais Historic Center (Same accommodation)
Maintaining your established base for convenience and familiarity
Cape Roca is often foggy in the morning - aim for late morning or afternoon visits for better visibility and dramatic light
Day 5 Budget: $70-95
Take a day trip to nearby Sintra to explore the enchanting Quinta da Regaleira, one of Portugal's most magical and mysterious estates.
Morning
Quinta da Regaleira exploration
Visit Quinta da Regaleira, an extraordinary estate featuring a romantic palace, elaborate gardens, mysterious grottoes, and the famous Initiation Well. Descend the spiral staircase into the moss-covered well, explore underground tunnels, discover hidden symbols and Masonic references throughout the property, and wander through lush gardens with fountains, lakes, and exotic plants. This UNESCO World Heritage site is truly magical.
3-4 hours
$12-15
Book tickets online in advance, especially during high season, to avoid long queues
Lunch
A traditional restaurant in Sintra's historic center
Portuguese classics and famous Sintra pastries
Mid-range
Afternoon
Sintra town exploration
Wander through Sintra's charming historic center, a UNESCO World Heritage site. Browse artisan shops, visit local bakeries to try travesseiros and queijadas (traditional Sintra sweets), and explore the narrow cobblestone streets. The romantic, fairy-tale atmosphere of this mountain town provides a perfect complement to the morning's palace visit.
2-3 hours
$10-20
Evening
Return to Cascais for dinner
Celebrate your Sintra adventure with a special dinner at an upscale restaurant in Cascais
Where to Stay Tonight
Cascais Historic Center (Same accommodation)
Easy return to your Cascais base after a full day of Sintra exploration
Wear comfortable shoes with good grip - Quinta da Regaleira involves climbing stairs, exploring caves, and walking on sometimes slippery stone surfaces
Day 6 Budget: $95-140
Discover multiple beaches along the Cascais coastline, from family-friendly coves to dramatic Atlantic shores, with historic fortresses standing guard.
Morning
Start at
Praia da Parede, a popular local beach with golden sand and good facilities. The beach is backed by colorful houses and offers a authentic neighborhood atmosphere. Then walk to
Praia da Arriba, a smaller, more secluded beach nestled between cliffs. Both beaches provide excellent swimming conditions and showcase different aspects of Cascais' coastal character.
3 hours
$5-10
Lunch
A beachside cafe with outdoor seating
Grilled sardines and salads
Budget
Afternoon
Forte da Crismina and Farol do Cabo Raso
Visit Forte da Crismina, a coastal fortress offering panoramic ocean views and insight into the region's defensive history. Continue to Farol do Cabo Raso, a picturesque lighthouse standing on dramatic cliffs. The area around the lighthouse provides stunning coastal vistas and excellent sunset viewing opportunities. Walk the clifftop paths and enjoy the rugged Atlantic scenery.
2-3 hours
$0
Evening
Sunset and dinner celebration
Watch the sunset from the coastal promenade, then enjoy a celebratory dinner marking your first week in Cascais
Where to Stay Tonight
Cascais Historic Center (Same accommodation)
Continuing your comfortable established base in central Cascais
The coastal walk between beaches is beautiful but can be challenging in places - wear appropriate footwear and bring water
Day 7 Budget: $65-90
Explore the rural side of the Cascais region, discovering vineyards and experiencing the agricultural heritage of the area.
Morning
Vineyards Trail exploration
Hike or cycle the Vineyards Trail, a scenic route through the wine-growing areas near Cascais. The trail winds through traditional vineyards, offering insights into local viticulture and stunning countryside views. Learn about the region's wine production history and enjoy the peaceful rural landscape, a refreshing contrast to coastal attractions. The route is well-marked and suitable for various fitness levels.
3-4 hours
$5-10
Lunch
A rural tavern serving farm-to-table Portuguese cuisine
Hearty regional dishes and local wine
Mid-range
Afternoon
Casa Sommer visit and relaxation
Visit Casa Sommer, a historic property that showcases the architectural and cultural heritage of the region. Spend time exploring the grounds and understanding the area's development. Afterward, enjoy a leisurely afternoon relaxing in Cascais, perhaps visiting a local spa or simply unwinding at a park or cafe, recovering from your active morning.
2-3 hours
$5-8
Evening
Casual evening in town
Explore a different neighborhood for dinner, trying a restaurant you haven't visited yet
Where to Stay Tonight
Cascais Historic Center (Same accommodation)
Your established home base continues to provide convenience and comfort
Bring a reusable water bottle for the Vineyards Trail - there are limited facilities along the route
Day 8 Budget: $75-105
Dedicate a day to deeper exploration of Cascais' artistic and architectural treasures, revisiting favorites and discovering new details.
Morning
Dom Luis I Foundation
Explore the Dom Luis I Foundation, a cultural institution housed in a beautiful historic building. The foundation hosts art exhibitions, cultural events, and educational programs. Spend time appreciating the collections and the elegant architecture of the building itself. The foundation often features contemporary Portuguese artists alongside historical works, providing a comprehensive view of Portuguese artistic achievement.
2 hours
$5-8
Lunch
A bistro in the cultural district
Contemporary Portuguese fusion
Mid-range
Afternoon
Citadel Art District revisit and
Santa Maria exploration
Return to the Citadel Art District for a more thorough exploration, visiting galleries you may have missed initially. Engage with local artists in their studios and browse unique crafts. Then explore the
Santa Maria area, discovering its historic churches, traditional architecture, and neighborhood character. Take time to photograph architectural details and absorb the local atmosphere.
3 hours
$10-15
Evening
Cultural evening experience
Attend a concert, art opening, or cultural event if available, or enjoy a sophisticated dinner at a restaurant known for innovative cuisine
Where to Stay Tonight
Cascais Historic Center (Same accommodation)
Maintaining your comfortable established base
Check the Citadel Art District's event calendar online - many galleries host opening receptions with free wine and the opportunity to meet artists
Day 9 Budget: $80-115
An active day combining water sports, hiking, and outdoor exploration in the beautiful natural settings around Cascais.
Morning
Water sports at
Praia do Guincho
Return to
Praia do Guincho for water sports activities. Try surfing, windsurfing, or kitesurfing with lessons from local schools, or simply bodyboard in the waves. The consistent winds and waves make this one of Europe's premier spots for wind sports. Even beginners can enjoy the experience with proper instruction, and watching skilled athletes is entertaining in itself.
3-4 hours
$40-60
Book surf or windsurf lessons in advance, especially during summer weekends
Lunch
A casual beach bar with healthy options
Smoothies, salads, and grilled fish
Budget
Afternoon
Parque Natural de Sintra-Cascais hiking
Hike a different section of Parque Natural de Sintra-Cascais, exploring inland trails through pine forests and Mediterranean scrubland. Choose a moderate trail that offers views of both mountains and ocean. The park's diverse ecosystems provide excellent opportunities for nature photography and wildlife spotting. Enjoy the peaceful natural environment away from coastal crowds.
2-3 hours
$0
Evening
Recovery and relaxation
After an active day, enjoy a restorative meal with plenty of protein, followed by an early evening to rest
Where to Stay Tonight
Cascais Historic Center (Same accommodation)
Your familiar base provides comfort after an active adventure day
Pack a small backpack with sunscreen, water, snacks, and a light jacket - weather can change quickly between beach and forest
Day 10 Budget: $90-125
Discover quieter corners of Cascais, exploring less-visited beaches and neighborhoods where locals spend their time.
Morning
Local neighborhood exploration
Venture into residential neighborhoods away from the tourist center. Visit local bakeries where residents buy their morning pastries, browse neighborhood markets, and observe daily Portuguese life. Walk through parks where families gather and discover small plazas with neighborhood cafes. This authentic experience reveals the real character of Cascais beyond its resort reputation.
2-3 hours
$5-10
Lunch
A family-run neighborhood restaurant frequented by locals
Daily specials and home-style Portuguese cooking
Budget
Afternoon
Quiet beach time and coastal walks
Find a quieter stretch of beach or cove that you haven't visited yet. Spend a peaceful afternoon swimming, reading, or simply relaxing by the Atlantic. Take leisurely walks along less-traveled sections of the coastal path, discovering your own favorite spots. This slower-paced afternoon allows for reflection on your journey and genuine relaxation.
3-4 hours
$5
Evening
Authentic local dining
Dine at a no-frills local restaurant where you might be the only tourist, experiencing genuine Portuguese hospitality
Where to Stay Tonight
Cascais Historic Center (Same accommodation)
Your established base remains convenient as you explore different aspects of local life
Ask your accommodation host for their personal favorite local spots - they often know hidden gems that don't appear in guidebooks
Day 11 Budget: $60-85
Return to Sintra for a second day trip, exploring additional palaces and viewpoints in this magical mountain town.
Morning
Sintra palace exploration
Visit one or more of Sintra's other spectacular palaces. Explore the colorful Pena Palace perched high on the mountain, the romantic Monserrate Palace with its exotic gardens, or the medieval National Palace in the town center. Each palace offers unique architecture, historical significance, and stunning views. The fairy-tale quality of these royal residences makes Sintra truly unforgettable.
3-4 hours
$15-25
Pre-book palace tickets online to skip queues; consider a combination ticket if visiting multiple sites
Lunch
A mountain-view restaurant with terrace seating
Portuguese cuisine with panoramic views
Mid-range
Afternoon
Sintra scenic viewpoints and gardens
Explore Sintra's beautiful gardens and seek out scenic viewpoints overlooking the Atlantic and countryside. Visit public gardens, walk forest trails, and discover hidden corners of this UNESCO World Heritage landscape. The combination of natural beauty and romantic architecture creates an enchanting atmosphere perfect for photography and contemplation.
2-3 hours
$5-10
Evening
Return to Cascais for farewell dinner
Enjoy a special farewell dinner at one of Cascais' finest restaurants, celebrating your two weeks in Portugal
Where to Stay Tonight
Cascais Historic Center (Same accommodation)
Final nights in your comfortable established base
Sintra can be very crowded - start early in the morning to beat tour groups and enjoy a more peaceful experience
Day 12 Budget: $100-145
Revisit your favorite spots, shop for souvenirs, and savor final moments in Cascais before departure.
Morning
Revisit favorite locations
Return to your favorite beach, viewpoint, or neighborhood from your two weeks. Take time to soak in the atmosphere one last time, capture final photographs, and perhaps discover details you missed on first visits. This morning is about savoring the places and experiences that resonated most with you during your stay.
2-3 hours
$0-5
Lunch
Return to your favorite restaurant from the trip
Whatever you've been craving most
Mid-range
Afternoon
Souvenir shopping and Mercado da Vila
Shop for authentic Portuguese souvenirs, including ceramics, textiles, cork products, and local foods to bring home. Return to Mercado da Vila to purchase gourmet items like Portuguese olive oil, tinned fish, local honey, and artisanal products. Browse shops in the historic center for handcrafted items and traditional goods that will remind you of your Cascais experience.
2-3 hours
$30-80
Evening
Farewell sunset and dinner
Watch your final Cascais sunset from the waterfront, then enjoy a memorable farewell dinner at a restaurant with ocean views
Where to Stay Tonight
Cascais Historic Center (Same accommodation)
Final night in your home away from home
Portuguese ceramics and cork products make excellent gifts - they're lightweight, authentic, and represent traditional Portuguese craftsmanship
Day 13 Budget: $95-150
Final morning in Cascais before departing, with time for last-minute activities depending on your flight schedule.
Morning
Leisurely final breakfast and packing
Enjoy a relaxed final breakfast at a favorite cafe, savoring Portuguese coffee and pastries one last time. Pack your souvenirs carefully, take a final stroll through the streets of Cascais, and perhaps visit the beach for one last glimpse of the Atlantic. Reflect on two wonderful weeks of coastal beauty, cultural discoveries, and Portuguese hospitality.
2-3 hours
$10-15
Lunch
Light meal before departure, or at Lisbon airport depending on timing
Portuguese favorites for the journey
Budget
Afternoon
Departure to Lisbon and airport
Travel from Cascais to Lisbon airport for your departure flight. The journey takes approximately 45 minutes to an hour depending on your transportation choice. If time permits before your flight, you might briefly explore Lisbon's Belém district near the airport, famous for its monuments and the original pastéis de nata bakery.
Variable
$10-40
Book airport transfer in advance or allow extra time if using public transportation
Evening
Departure
Depart with memories of two perfect weeks on the Portuguese coast
Where to Stay Tonight
N/A (Departure day)
End of journey
Keep some euros for airport purchases and tips - and save room in your luggage for last-minute pastéis de nata!
Day 14 Budget: $50-80